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Lipton's fiduciary responsibility is to best represent and advocate in support of his client's interests. Our lengthy website contains a Table of Contents with many links. Not only do CEOs get theirs, but , when they do wrong, Shareholders foot the bill. All five sharks bit. Taxpayers and shareholders, meanwhile, who had nothing to do with the problems, are left holding the bag. Archived from the original on 29 December A seven-year-old female named Jin Yi died in in a zoo in Zhengzhou , China, after showing symptoms of gastroenteritis and respiratory disease.

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Equity Asset Class Size: Multi-Cap Asset Class Style: Consumer Discretionaries Sector Specific: North America Region Specific: Historical Trading Data 1 Month Avg. Realtime Rating Summary The adjacent table gives investors an individual Realtime Rating for IBUY on several different metrics, including liquidity, expenses, performance, volatility, dividend, concentration of holdings in addition to an overall rating.

Compare to another ETF. Filings Data as of: Year to Date Return. Year to Date Fund Flow. Brought to You by Mitre Media. Bollinger Brands Lower Bollinger 10 Day: Download the fact sheet PDF. Icahn on his own. The Delaware court's increased scrutiny of possible conflicts comes amid rising complaints, and more lawsuits, criticizing buyout deals for allegedly enriching corporate executives at the expense of the shareholders.

In the current buyout craze, many buyout firms retain the management by offering rich pay packages and a stake in the newly private entity.

These deals are being challenged in the courts by shareholders who allege that they are getting a meager payout for the company. They say boards are accepting deals based on factors other than the best-available price. In addition, shareholders are accusing boards of running into the friendly arms of private-equity buyers to escape activist hedge funds, who are trying to oust them through proxy battles.

In the case of Topps, the New York producer of trading cards, collectibles and candy, shareholders have accused the board of breaching its duties to get the highest price for the company Strine warned in his Topps opinion. Not only do CEOs get theirs, but , when they do wrong, Shareholders foot the bill. Once again, shareholders are shouldering the costs of unethical behavior they had nothing to do with.

Hill and Richard W. Painter, professors at the University of Minnesota Law School. In 'Better Bankers, Better Banks,' they argue for making financial executives personally liable for a portion of any fines and fraud-based judgments a bank enters into, including legal settlements.

Hill said in an interview. If that's the case, bad CEOs are able to hang on to their jobs long after they should be driven out. In a new study titled Pay for Failure: Few of the plans, for example, required that the company's performance be measured against its industry peers.

It's a matter of mutual back-scratching, as another recent study confirmed. The authors are John K. They found that companies paying CEOs excessive amounts also pay directors excessive amounts. Companies that pay too much also tend to perform worse than their peers. Kozlowski was exceptionally extravagant with company money, Mr. Campriello showed jurors an expense report Mr. John Fort submitted for his attendance at a single three-day board meeting.

Campriello asked 'This is the way we traveled,' Mr. Permitting extravagant expenses is the morale equivalent of bribery. Raines received salary, bonus and other compensation last year However, Fannie Mae is not a person. The Broadcom Corporation … shareholders are being asked to vote on a company proposal to increase by 12 million the number of shares authorized for grants under its stock incentive plan. In addition, a 'yes' vote will expand the types of stock awards that the company can offer executives and employees, as well as grant the compensation committee the right to reprice underwater options at any time.

This objectionable repricing practice removes the risk for executives and employees that outside shareholders incur when their stock falls. Had the proposed plan been in place last year, it would have cost shareholders an amount equal to about 75 percent of the company's revenue, the firm said.

Berman had until 29 February been affiliated with a law firm that served as outside counsel to the Company and had since 1 March been engaged by the Company to render legal, regulatory and other professional services.

Berman was a director of Tyco until December 5, From March 1, through July 31, , Mr. Berman was engaged to render legal and other services. During this period, Tyco compensated Mr. Berman with health benefits, secretarial assistance, a cell phone and electronic security services for his homes. Weingarten said the two clashed over several issues, including the amount of Tyco business sent to Kramer Levin for which Berman received referral fees. Dennis Kozlowski , Tyco's former chief executive, and were not approved by the board or disclosed in filings with the United States Securities and Exchange Commission.

He also has drawn fire from critics for having business ties to Disney in the past while sitting on the board. Those payments ended two years ago amid an outcry from corporate governance experts.

Independence of new chairman, who had sided with Eisner, is called into question. Mitchell, 70, … who has little business experience, said … yesterday that he had no desire to play the corporate strategist, as many chairmen do.

Instead, he sees his main job as negotiating among factions of unhappy investors, other board members and Michael D. Eisner, the chief executive who lost the chairman's title in the wake of a resounding no-confidence vote at the company's shareholder meeting on Wednesday.

Mitchell's appointment is not sitting well with many of the investors … nor with corporate governance experts. They complained that not only does Mr. Mitchell have negligible corporate experience, but they say he is too closely allied to Mr. Eisner and his appointment does little to address investor discontent with Mr. Eisner's management of the company.

Mitchell takes umbrage at the notion he is beholden to Mr. He said he had only had three social dinners with Mr. Eisner actually approached Mr.

Mitchell in to gauge his interest in joining Disney as president. Mitchell said because the decision was made only on Wednesday, the duties of the job had not been completely defined. But he said the setup and his lack of business experience should not impede his ability to oversee Mr. The most beholden Directors may live in states of denial. And that has prompted some governance experts and investment fund officials to question his sincerity toward reform and sensitivity to appearances.

Their concern is that directors may have competing loyalties between the shareholders they are supposed to serve and the executives who put them on the payroll. Sidhu has … become a national force in community banking by repeatedly triumphing over rebellious directors and shareholders.

Sidhu has excluded directors from important deal deliberations or waits until the last minute to brief them. Some investors say his public statements about acquisition plans are misleading. Sidhu has a board of supportive directors who have scant banking experience, are compensated unusually well and, in some cases, enjoy access to Sovereign loans and business opportunities.

While that's more than directors at similar banks get, Sovereign justifies the pay by noting that its directors meet 14 times a year, five more times than its peer average. Sovereign has had business dealings with and made increasing loans to its directors in recent years. Sovereign added that the Troilo leases all have been at market rates. Troilo didn't return calls.

Troilo so he could buy a Lawrenceville, N. To help secure the loan, Mr. Troilo used another Sovereign-mortgaged property, in Pennsylvania , that he also rented to the bank. The Monday filing said Mr. Troilo's bid was better because it included 'no financing, inspection or due diligence' conditions. Was Sovereign concerned that its building could not withstand "inspection or due diligence"?

Upon what objective criteria was that decision made and by whom? But, after all, it is just another instance of Shareholder assets being considered as chump change! The bank offers no relevant disclosure about the loans, including terms, interest rates or performance.

Relational Investors discovered the full extent of them only by cross-referencing Sovereign's Securities and Exchange Commission filings with records at the Office of Thrift Supervision. Sovereign says the SEC filings excluded credit extensions that haven't been drawn down.

Since , however, Sovereign's filings have included no specific figures, just vague reassurances. Wall Street is skeptical that a three-year turnaround plan will work, and Fitch has cut its bond rating to triple C, which is low even for junk bonds.

So far this year it is down another 27 percent. But there is little pain at the top. But there is no mention of internal equity -- of the justice of paying a lot to bosses when workers and investors are suffering. Perhaps board members think they deserve an increase because their past stock grants keep losing value. They face tricky choices in deciding how much to challenge year-old Mr. Mozilo, who co-founded the company 38 years ago. Countrywide's nonemployee directors collect fees, shares that they must hold for at least a year, and perks that include health insurance and spousal travel, according to the latest proxy statement.

The pay range is above median total compensation for directors of the largest U. Countrywide said directors review their compensation annually with the help of an independent pay consultant Countrywide rewards board members so well that 'at some point, you cross the line between paying for services provided and a very lucrative thing where board members aren't going to challenge management,' says Mark Reilly, a partner at 3C, Compensation Consulting Consortium.

Corporate Library has long argued that Countrywide's board has done a poor job of designing Mr. Mozilo's pay package, guaranteeing him too much compensation regardless of performance. The consultants urged directors to slim his hefty contract, partly by revamping his annual bonus formula Directors kept the formula and decided to replace the consultancy Snyder , 75, is Countrywide's lead director. Institutional shareholders who have tried to engage the Countrywide board on issues like Mr.

Mozilo's pay say that Mr. Snyder, who has been a board member since , prevents such dialogues from occurring. One complaint was that he does not share letters from stockholders with other members of the board. Charles Prince , for instance, who stepped down under fire as Citigroup Inc. The rules are in place to allow boards to retain an appropriate mix of retired and active executives and push out members who no longer have the time for outside directorships because of more demanding new jobs.

Still, many governance watchers and veteran directors say boards rarely accept a resignation after a member loses a CEO spot—no matter the reason.

Another former chief who kept a directorship is Richard Syron , ousted as head of Freddie Mac in when the U. He recently received a warning that he may face civil action from the Securities and Exchange Commission as part of its investigation into whether Freddie Mac properly disclosed its exposure to subprime loans.

Syron held a board seat, rejected his offer to resign. Syron didn't have to defend his actions to fellow board members. To be sure, boards occasionally drop a member after leaving a CEO post under fire. Advanced Micro Devices Inc. AMD declined to comment.

I just could not resist the temptation. The devil made me do it. The other dude done it. It was my poor upbringing. Then, there is reciprocal back scratching. It would be so embarrassing at the country club to encounter a removed former fellow Director. Additional conflicts of interest are caused by the existence of a Director clique. No one wants a wild card. It's not surprising that their objective is to get along. Statistical analyses can go just so far in detecting links between Directors.

For directors, it is simply bad form to nitpick over a couple of million dollars with another member of the club, particularly one who helps set director fees or serves on the compensation committee of other corporations. Even legendary investor Warren E. Buffett was not immune to the collegiality. He recently wrote to the Shareholders of Berkshire Hathaway Inc.

A certain social atmosphere presides in boardrooms where it becomes impolitic to challenge the chief executive, he wrote. Buffett is reputed to be the best of the best! Thus, Shareholders have no reason to expect better representation from any other Director. Buffet, the best of the best, found it necessary to ask a subordinate multiple times about a sizable transaction and walked away without getting the "details. Was he suspicious when he had to ask a second time? What about the third time?

Did the subordinate still retain his job? Is there a letter of reprimand in the file? What does the subordinate say he communicated to Buffet? Why was the questioning of Buffet not done under oath? Well, since he was questioned by regulators, if the truth not be told, there is always the obstruction of justice route.

Hopefully, Buffet does better where he serves in the capacity of a corporate Director. After his talk with Mr. Ferguson wrote an e-mail to Joseph Brandon, then General Re executive vice president, describing the conversation with Mr. Buffet, saying that he asked Mr. Buffet whether the deal was proper. Ferguson reported that Mr. Buffet said the deal was proper, but not by a large margin. Buffet told regulators that didn't happen. Buffet told regulators that he asked Mr.

Brandon several times whether General Re's accounting on the deal was okay, but didn't learn details. Did Ferguson want to know? If not, why not?

Was a copy of the email transmitted to Buffet when it was written? Did Buffet read it and not respond? When did Buffet first question Brandon? What triggered the question? If Brandon was not answering Buffet, perhaps Buffet could have asked his external auditors?

On the other hand, if one is suspicious, why alert the external auditors to look carefully at what might be a minefield? Perhaps the issue of a Director's fiduciary duty to Shareholders was lost in an ethical haze?

He stated, in part, "I've sat on enough boards and audit committees to understand the kind of culture of seduction that characterizes many boards.

It's a game that many CEOs played and played well by seducing their boards with perks and private attention and contributions to favorite philanthropies, and meetings that were short on substance and long on fluff.

The boards became willing accomplices. And it's part of the American personality to go along and become more fraternal rather than more vigilant. Levitt did all that board sitting before From to , as Chairman of the SEC, what did he do or attempt to do to cure the specific problem? Also, it appears that Mr. Levitt is claiming that it would be un-American to require Directors to be vigilant on behalf of Shareholders.

Directors who served at failed companies may rate a red badge of courage and additional opportunities to employ their varied talents. In some cases, however, companies have stopped passing on this information in proxy materials distributed to shareholders…. But what about the directors of companies like Enron, WorldCom, Adelphia Communications, Global Crossing, Waste Management, Tyco International and others who oversaw the implosion of hundreds of billions in market capitalization?

In many cases, they got better jobs. But many companies don't make it easy for shareholders to find out where their directors have been. Sprint Nextel 's biography for William E. Conway , for instance, mentions nothing about his stint at Enron.

Thornton of Goldman Sachs Group Ford's, someone with whom he shares several friends and even more interests. Thornton was appointed to the Ford board at the recommendation of the company's chief executive and chairman The lawsuit … said the chief executive and chairman, William Clay Ford Jr. The suit said Mr. Ford's acceptance of the shares was a 'usurpation of an opportunity that belonged to the company' After shareholders complained in late , the company formed a committee that concluded that Mr.

Ford had not acted improperly. Ford's purchase in May of , shares of Goldman Sachs, the largest allocation to an individual, drew attention after a lawyer for Ford shareholders wrote to the company's board, demanding an investigation. The shareholders demanded that Mr. Ford return any profits and pay damages to the company for the lost investment opportunity. Ford bought the shares, Goldman's co-chief operating officer, John Thornton, sat on Ford's board.

Ford had no significant say in the awarding of investment banking business. They also said … that Mr. Ford had a long personal banking relationship with the firm. Ford probably claimed a tax deduction for his charitable donation. And, how does one determine that "no wrongdoing had occurred"? Ford did not violate the non-existent policy. Therefore, "no wrongdoing had occurred. In some cases, 10 percent or more of all donations went to these organizations.

Companies, directors and non-profits routinely stress the importance of philanthropy and say the donations don't affect board members' independence. Critics, however, say big donations can create a clubby atmosphere that may make directors less likely to aggressively challenge management. Although foundations detail their donations in annual tax filings with the Internal Revenue Service, companies are not required to disclose most non-profit affiliations of their directors, making it problematic for investors to know the full extent of such connections.

Farmer , the 87 year old chairman of the company Farmers, who are members of the board, along with other directors The coming-together will be at a town in Georgia where the main attraction is a 'gentleman's club' exclusive enough to garner members by invitation only. Augusta National Golf Club, which openly and proudly discriminates against women, will produce its Masters Golf Tournament with considerable help from the masters of corporate America. It also makes a mockery of board independence, now required to protect stockholders and the public from cronyism in financial dealings.

The cronyism that perpetuates gender bias against employees is every bit as harmful, and ought to be stopped just as forcefully. At nearly all other companies, a simple majority will do. Purcell will color their judgment in any way. Indeed, Morgan Stanley bankers, not to mention the dissident executives, have accused the board of coddling him. It is packed with former chief executives, many from the Chicago area, where Mr. Some have golfed together; others have worked for one another.

First, there is the Kraft connection. Miles, the chairman of the nominating committee and … recruited two former executives who worked for him at Kraft in the mid's: Then there is the McKinsey connection. Four directors were partners at McKinsey, the management consulting firm, as was Mr. And finally, there is the fact that a number of directors, notably Mr. Miles, serve together on boards at other companies.

Miles, for example, serves on six boards, including that of the AMR Corporation, where he serves alongside Mr. Brennan also serves on six boards, and Charles F. Brennan during his battle with shareholders. Miles and Kraft on its merger with Philip Morris, and he is now advising the independent directors at Morgan Stanley on a range of matters, including their strategy for dealing with their antagonists.

One point made by the retired executives is that until recently, no director - including Mr. Purcell - had ever operated a line of business for a securities firm. That set Morgan Stanley apart from nearly every other Wall Street firm. Partners have fiduciary duties to one another. So much for the concept that BODs have undivided loyalty to represent the interests of Shareholders!

Who is watching the supposed watchdogs of Management? Do conflicts of interest disappear if they are disclosed to Shareholders who have no effective means to remedy the situation?

Purcell, their first call for help when to the superlawyer Martin Lipton. Lipton quickly donned a number of other legal hats - advising the board, Mr. Purcell and the company itself on tactics, legalities and, most controversially, severance pay to departing executives. Purcell stepped down, a compensation specialist at Wachtell, Adam D. Chinn, in tandem with the board's compensation committee, draft the controversial severance packages that awarded Mr.

Chinn's reputation for cobbling together generous severance awards for departing chief executives is such that the contracts are known as Chinn-ups. As a result of these payouts, the board has been sued by shareholders and received irate letters from institutional investors who have decried the packages as a violation of the very governance practices Mr.

Lipton was hired to improve. Purcell's leadership, many Morgan Stanley executives were never quite clear about Mr. Several said they frequently asked each other: Was he advising the board? The answer, people close to the board said, is that Mr. Lipton was, first and foremost, an adviser to the board. When it became clear that Mr. Purcell would depart, he hired his own lawyer to negotiate.

While the very best governance practices would argue for the hiring of separate counsel on the compensation packages, time and confidentiality considerations led the board to stick with Wachtell. Lipton for being an apologist for corporate management, that assertion misses the point - that Mr. Lipton's fiduciary responsibility is to best represent and advocate in support of his client's interests.

If Lipton represented only the BOD and, thus, the Shareholders, his fiduciary duty was to get the executive to leave for the lowest amount. It is fair to assume that he, at the least, did not discourage the BOD from appointing Chinn while knowing that he Chinn does Chinn-ups. Lipton and Chinn are members of the same law firm. Lipton probably benefits from each fee Chinn earns for the firm. The BOD tries to justify its act of hiring Chinn by claiming "time and confidentiality" considerations.

Does Lipton's rolodex contain the name of at least one competent non-Wachtell attorney who has a reputation for being parsimonious when dealing with executive payoffs? Couldn't Lipton have asked Chinn for a referral? Did the BOD not know that attorneys, even non-Wachtell attorneys, have a duty to maintain confidentiality? Purcell decided he should step down….

The tale serves as a caution for boards in an era when their role in corporate governance is drawing more scrutiny. The damage from delay when directors fail to spread their antennae widely is especially great at a Wall Street securities firm like Morgan Stanley, where the most valuable assets can walk out the door and never return.

At a mid-March board meeting, Laura D'Andrea Tyson , a former Clinton administration economic official who is dean of the London Business School , said directors should take the criticism of Mr. Purcell's record more seriously. Tyson, calling her comment inappropriate … The board took steps to interview more employees. Knight, the director who had clashed with Ms. Purcell and didn't see any reason to discuss the matter since the board had already decided on it….

The attempt to cut off debate bothered some other directors, people familiar with the meeting say. Knight and Zumwinkel left, the discussion turned more freewheeling. Knight's conduct is reminiscent of that of a school yard bully who made it to the big time. Institutional Shareholders do much "discussing an effort to out the directions," but, when push came to shove, they faded. Knight and Zumwinkel, who should be their first targets, need not lose any sleep.

Bostock , had a family connection to a hedge fund that does business with the firm. They generally worry that the indirect connections can impair the directors' abilities to serve as independent advocates for shareholder interests. Is this what is meant by "the ties that bind"? If this is what Morgan Stanley does when it is under a corporate governance microscope, imagine what might occur when the spot light turns elsewhere business as usual. Yet during that time, the company's stock has slid 12 percent while shares of its archrival, Lowe's , have climbed percent.

Why would a company award a chief executive that much money at a time when the company's shareholders are arguably faring far less well? Two of those members have ties to Mr. Nardelli's former employer, General Electric. Nardelli's lawyer in negotiating his own salary. And three either sat on other boards with Home Depot's influential lead director, Kenneth G. Langone , or were former executives at companies with significant business relationships with Mr.

In addition, five of the six members of the compensation committee are active or former chief executives, including one whose compensation dwarfs Mr. Governance experts say people who are or have been in the top job have a harder time saying no to the salary demands of fellow chief executives. Moreover, chief executives indirectly benefit from one another's pay increases because compensation packages are often based on surveys detailing what their peers are earning. To its critics, the panel exemplifies the close personal and professional ties among board members and executives at many companies — ties that can make it harder for a board to restrain executive pay.

They say this can occur even though all of a board's compensation committee members technically meet the legal definition of independent, as is the case at Home Depot. Langone's circle of friends and associates… [T]he Home Depot board decided … Mr. Nardelli, who had no retail experience, should become CEO. Nardelli might not hit one of the few performance goals the board had set to cause payment of a long-term incentive plan, the board lowered the goalposts….

More than a dozen U. Several factors are spurring such appointments, recruiters and management consultants say. Boards are quicker to fire poorly performing CEOs, often before potential internal successors are ready for the job.

Many of these companies have deep-seated problems, making it harder to recruit outsiders. And increasingly, there's a deep pool of outside executives in the boardroom.

They contend that a chief chosen from the board signals cronyism and weak succession planning. A director's comfort with a colleague obscures 'a clear view of the individual's suitability to be a successful CEO,' says Richard Breeden, an activist investor and former chairman of the Securities and Exchange Commission. Franks , the former chief of the Public Broadcasting System and the publisher of a Spanish newspaper would seem to have nothing in common — except for one thing.

They all sit on the board of Bank of America. But as they and 13 of their colleagues meet Wednesday to discuss how to steer the bank through its troubled merger with Merrill Lynch, they are likely to be united by something else: Their shareholder scrutiny has also turned an unusual spotlight on the oversight role played by the board members, many of whom were picked by Mr. Lewis from several companies that the bank, based in Charlotte , N. Bank of America's board is an eclectic group, and it will grow larger this week when it adds three members from the board of Merrill.

The bank's two most powerful directors, O. Spangler , are close to Mr. Lewis's predecessor, Hugh L. Lewis, only two people on the board — the former chief of FleetBoston and a former senior executive of MBNA — have roots in banking. While Wall Street is rife with tales of bank and brokerage directors who deferred to executives seeking faster growth through ever-riskier business, Bank of America's shareholder advocates have grown increasingly concerned about the board's ability to understand financial risks and rein in managers.

While critics charge that Bank of America's board has been little more than a rubber stamp in the empire-building campaign of Mr. Lewis, others describe it as independent and willing to push back against the chief executive.

Its members are expected to vote Wednesday on the addition of three directors from Merrill Lynch Their approval would raise the number of board members to 20, and would tighten the web that already binds many of the board's current representatives. Yet some board members are connected in other ways that reveal strong cross-pollinations with other company boards.

Nothing could get the attention of Directors more than the prospect of being held personally accountable for their lack of diligence in performing their duties to Shareholders. Board members also acknowledge they are struggling to rein in bloated executive compensation, but are counting on investors to lead the cause to knock it down.

Those conclusions aren't a decade old, but are part of a recent survey from the consulting firm PricewaterhouseCoopers and the Corporate Board Member magazine , which culled responses of more than 1, directors at U.

Directors still don't have as much control over corporate dealings that many believe is needed to curb supersized compensation. While more boards are independent of management, there are still plenty of cases of directors using flawed judgment or kowtowing to demanding executives who are pushing their own agendas. Part of the problem, it seems, is that boards are still controlled by CEOs, with 50 percent of directors surveyed saying that board leadership flows from the company's top executive who is also board chairman.

Those individuals, therefore, set the agenda as well as the flow of information at board meetings and among members. In the area of compensation, two-thirds of responding directors believe that U.

Separately, a third believe that stockholders are the group most likely to get pay pared down. But it is hard to reduce pay when the directors themselves don't know how much they've even agreed to pay executives.

Less than half of those surveyed said their boards use tally sheets to add up total compensation, and about one in five directors said that they didn't know what the CEO would collect if he or she is terminated, retires or should there be a change in control.

Among the bigger shockers in these filings are the tallies showing how much money executives will cart away if they are terminated or agree to a merger. Buried in these figures is one of the most contentious items in all of payland: Michael Kesner , principal at Deloitte Consulting in Chicago said, 'Boards are now just getting a sense of how big that number is. If directors are surprised by gross-ups, you can imagine how stockholders will react.

And given how ubiquitous gross-ups are -- surveys say 75 percent of chief executives have such arrangements with their companies -- the shocks could be far and wide. Training the spotlight on gross-ups may help stamp them out.

As long as they were kept under wraps, directors didn't have to justify them to angry shareholders. Six days later, its chief executive, E.

Underlying the situation at Merrill is the nagging question of what a Wall Street board is expected to know about complex financial markets where asset values can shift drastically and where many directors are not in the business of managing trillion-dollar balance sheets — or perhaps have little experience in doing so.

Directors should know what independent risk controls are in place, who is overseeing that function After every market crisis Case law, lawyers say, has affirmed that directors have to be informed and make sure that obvious red flags are not ignored. There were certainly some red flags waving in front of directors.

One issue should have been the revolving door of talent in the upper echelons of the firm And, like everyone else, directors knew about the bank's very public shift into riskier business areas, which until this summer were delivering handsome profits. Merrill had become the top issuer of collateralized debt obligations in the marketplace, and its profitability soared; fixed-income revenue in the second quarter was up percent. According to some analysts, the billion-dollar size of those profits — and the soaring return on equity — should have caused directors to ask whether the risks being taken to generate higher profits warranted better controls.

Analysts say that directors should have asked about the exposures and, more important, what might happen to those exposures under various financial scenarios, including a collapse of the mortgage market. In July, when credit markets worsened and Merrill faced escalating losses Merrill's potential losses did not reflect the heavy levels that they ultimately reached in October.

Management realized that there was a structural problem, and Merrill announced on Sept. Extracorporeal treatments are recommended in severe overdoses. Metformin may be quantified in blood, plasma, or serum to monitor therapy, confirm a diagnosis of poisoning, or assist in a forensic death investigation.

Chromatographic techniques are commonly employed. The H 2 -receptor antagonist cimetidine causes an increase in the plasma concentration of metformin by reducing clearance of metformin by the kidneys; [91] both metformin and cimetidine are cleared from the body by tubular secretion , and both, particularly the cationic positively charged form of cimetidine, may compete for the same transport mechanism.

Metformin also interacts with anticholinergic medications, due to their effect on gastric motility. Anticholinergic drugs reduce gastric motility, prolonging the time drugs spend in the gastrointestinal tract. This impairment may lead to more metformin being absorbed than without the presence of an anticholinergic drug, thereby increasing the concentration of metformin in the plasma and increasing the risk for adverse effects. Metformin's main effect is to decrease liver glucose production.

Metformin decreases high blood sugar , primarily by suppressing liver glucose production hepatic gluconeogenesis. Multiple potential mechanisms of action have been proposed, including; inhibition of the mitochondrial respiratory chain complex I , activation of AMP-activated protein kinase AMPK , inhibition of glucagon-induced elevation of cyclic adenosine monophosphate cAMP with reduced activation of protein kinase A PKA , inhibition of mitochondrial glycerophosphate dehydrogenase , and an effect on gut microbiota.

Activation of AMPK was required for metformin's inhibitory effect on liver glucose production. In addition to suppressing hepatic glucose production, metformin increases insulin sensitivity, enhances peripheral glucose uptake by inducing the phosphorylation of GLUT4 enhancer factor , decreases insulin-induced suppression of fatty acid oxidation , [] and decreases absorption of glucose from the gastrointestinal tract.

Increased peripheral use of glucose may be due to improved insulin binding to insulin receptors. AMPK probably also plays a role in increased peripheral insulin sensitivity, as metformin administration increases AMPK activity in skeletal muscle. The usual synthesis of metformin, originally described in , involves the one-pot reaction of dimethylamine hydrochloride and 2-cyanoguanidine over heat.

According to the procedure described in the Aron patent, [] and the Pharmaceutical Manufacturing Encyclopedia , [] equimolar amounts of dimethylamine and 2-cyanoguanidine are dissolved in toluene with cooling to make a concentrated solution, and an equimolar amount of hydrogen chloride is slowly added.

Steady state is usually reached in one or two days. Metformin has acid dissociation constant values pKa of 2. The metformin pKa values make metformin a stronger base than most other basic medications with less than 0. Furthermore, the lipid solubility of the nonionized species is slight as shown by its low logP value log 10 of the distribution coefficient of the nonionized form between octanol and water of These chemical parameters indicate low lipophilicity and, consequently, rapid passive diffusion of metformin through cell membranes is unlikely.

As a result of its low lipid solubility it requires the transporter SLC22A1 in order for it to enter cells. More lipophilic derivatives of metformin are presently under investigation with the aim of producing prodrugs with superior oral absorption than metformin.

Metformin is not metabolized. It is cleared from the body by tubular secretion and excreted unchanged in the urine; metformin is undetectable in blood plasma within 24 hours of a single oral dose. The biguanide class of antidiabetic medications, which also includes the withdrawn agents phenformin and buformin , originates from the French lilac or goat's rue Galega officinalis , a plant used in folk medicine for several centuries. Metformin was first described in the scientific literature in , by Emil Werner and James Bell, as a product in the synthesis of N , N -dimethylguanidine.

Interest in metformin resumed at the end of the s. In , metformin, unlike some other similar compounds, was found not to decrease blood pressure and heart rate in animals. Garcia [] used metformin he named it Fluamine to treat influenza; he noted the medication "lowered the blood sugar to minimum physiological limit" and was not toxic. Garcia believed metformin to have bacteriostatic , antiviral , antimalarial , antipyretic and analgesic actions.

Instead he observed antiviral effects in humans. French diabetologist Jean Sterne studied the antihyperglycemic properties of galegine , an alkaloid isolated from Galega officinalis , which is related in structure to metformin and had seen brief use as an antidiabetic before the synthalins were developed.

Sterne was the first to try metformin on humans for the treatment of diabetes; he coined the name "Glucophage" glucose eater for the medication and published his results in Metformin became available in the British National Formulary in It was sold in the UK by a small Aron subsidiary called Rona. Broad interest in metformin was not rekindled until the withdrawal of the other biguanides in the s. Metformin was approved in Canada in , [] but did not receive approval by the U.

Liquid metformin is sold under the name Riomet in India. Metformin IR immediate release is available in , , and mg tablets. All of these are available as generic medications in the U.

Metformin SR slow release or XR extended release was introduced in It is available in , , and mg strengths, mainly to counteract common gastrointestinal side effects, as well as to increase compliance by reducing pill burden. No difference in effectiveness exists between the two preparations. When used for type 2 diabetes, metformin is often prescribed in combination with other medications.

Several are available as fixed-dose combinations , to reduce pill burden and simplify administration. A combination of metformin and rosiglitazone was released in and sold as Avandamet by GlaxoSmithKline. By it had become the most popular metformin combination. In , the stock of Avandamet was removed from the market, after inspections showed the factory where it was produced was violating good manufacturing practices.

However, following a meta-analysis in that linked the medication's use to an increased risk of heart attack , [] concerns were raised over the safety of medicines containing rosiglitazone.

In September the European Medicines Agency EMA recommended that the medication be suspended from the European market because the benefits of rosiglitazone no longer outweighed the risks. In November , the FDA lifted its earlier restrictions on rosiglitazone after reviewing the results of the RECORD clinical trial a six-year, open label randomized control trial , which failed to show elevated risk of heart attack or death associated with the medication. Dipeptidyl peptidase-4 inhibitors inhibit dipeptidyl peptidase-4 and thus reduce glucagon and blood glucose levels.

In Europe, Canada, and elsewhere metformin combined with linagliptin is marketed under the trade name Jentadueto. Sulfonylureas act by increasing insulin release from the beta cells in the pancreas.

Metformin is available combined with the sulfonylureas glipizide Metaglip and glibenclamide US: Meglitinides are similar to sulfonylureas. The combination of metformin with pioglitazone and glibenclamide [] is available in India as Triformin.

From Wikipedia, the free encyclopedia. B No risk in non-human studies. S4 Prescription only CA: Pharmacy and pharmacology portal Medicine portal. Clinical Pharmacology and Therapeutics. A review of its pharmacological properties and therapeutic use in non-insulin-dependent diabetes mellitus".

Archived from the original on 24 December Retrieved 2 January

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