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11-SEPTEMBER-2008 12:20:15 - Metformin Metformin Systematic IUPAC name N,N-dimethylimidodicarbonimidic diamide Identifiers CAS number 657-24-9 ATC code A10BA02 A10BD02 with sulfonylureas A10BD03 with rosiglitazone A10BD05 with pioglitazone A10BD07 with sitagliptin A10BD08 with vildagliptin PubChem 4091 DrugBank APRD01099 Chemical data Formula C4H11N5 Mol. mass 129.164 g/mol 165.63 g/mol hydrochloride Synonyms 1,1-dimethylbiguanide Pharmacokinetic data Bioavailability 50 to 60% under fasting conditions Metabolism None Half life 6.2 hours Excretion Active renal tubular excretion by OCT2 Therapeutic considerations Licence data US Pregnancy cat. CAU BUS Legal status POMUK â„ž-onlyUS Routes Oral Metformin INN; trade names Glucophage, Riomet, Fortamet, Glumetza, Obimet, Dianben, Diabex, Diaformin, and others IPA: /mÉ›tˈfÉ”rmɪn/ is an oral anti-diabetic drug from the biguanide class. It is the first-line drug of choice for the treatment of type 2 diabetes, particularly in overweight and obese people and those with normal kidney function,123 and evidence suggests it may be the best choice for people with heart failure.4 Metformin is the most popular anti-diabetic drug in the United States and one of the most prescribed drugs in the country overall, with nearly 35 million prescriptions filled in 2006 for generic metformin alone.5 It is also used in the treatment of polycystic ovary syndrome. When prescribed appropriately, metformin causes few adverse effects-the most common is gastrointestinal upset-and, unlike many other anti-diabetic drugs, does not cause hypoglycemia. It also helps reduce LDL cholesterol and triglyceride levels, and may aid weight loss. As of 2008update, metformin is one of only two oral anti-diabetics in the World Health Organization Model List of Essential Medicines the other being glibenclamide.6 Contents 1 History 2 Indications 3 Contraindications 4 Adverse effects 4.1 Lactic acidosis 4.2 Gastrointestinal 4.3 Hormonal 5 Overdosage 6 Mechanism of action 7 Interactions 8 Formulations 8.1 Combinations with other drugs 9 References 10 External links History The biguanide class of anti-diabetic drugs, which also includes the withdrawn agents phenformin and buformin, originates from the French lilac Galega officinalis, a plant known for several centuries to reduce the symptoms of diabetes mellitus.7 Metformin was first described in the scientific literature in 1957.8 It was first marketed in France in 1979, but did not receive approval by the U.S. Food and Drug Administration FDA for Type 2 diabetes until 1994.9 Bristol-Myers Squibb's Glucophage was the first branded formulation of metformin to be marketed in the United States, beginning on March 3, 1995.10 Generic formulations are now available. Indications The main use for metformin is in the treatment of diabetes mellitus type 2, especially when this accompanies obesity and insulin resistance. Metformin is the only anti-diabetic drug that has been proven to reduce the cardiovascular complications of diabetes, as shown in a large study of overweight patients with diabetes.11 Unlike the other most-commonly prescribed class of oral diabetes drugs, the sulfonylureas, metformin taken alone does not induce hypoglycemia.12 Hypoglycemia during intense exercise has been documented, but is extremely rare.13 It also does not cause weight gain, and may indeed produce minor weight loss.14 Metformin also modestly reduces LDL and triglyceride levels.15 It is also being used increasingly in polycystic ovary syndrome PCOS,16 non-alcoholic fatty liver disease NAFLD17 and premature puberty,18 three other diseases that feature insulin resistance; these indications are still considered experimental. Although metformin is not licensed for use in PCOS, the United Kingdom's National Institute for Health and Clinical Excellence recommends that women with PCOS and a body mass index above 25 be given metformin when other therapy has failed to produce results.19 The benefit of metformin in NAFLD has not been extensively studied and may be only temporary.20 It may reduce weight gain in patients taking atypical antipsychotics.21 Contraindications Metformin is contraindicated in people with any condition that could increase the risk of lactic acidosis, including kidney disorders creatinine levels over 150 μmol/l,22 although this is an arbitrary limit, lung disease and liver disease. Heart failure has long been considered a contraindication for metformin use, although a 2007 systematic review showed metformin to be the only anti-diabetic drug not associated with harm in people with heart failure.4 It is recommended that metformin be temporarily discontinued before any radiographic study involving iodinated contrast such as a contrast-enhanced CT scan or angiogram, as contrast dye may temporarily impair kidney function, indirectly leading to lactic acidosis by causing retention of metformin in the body.2324 It is recommended that metformin be resumed after two days, assuming kidney function is normal.2324 Adverse effects Lactic acidosis The most serious potential side effect of metformin is lactic acidosis; this complication is very rare, and seems limited to those with impaired liver or kidney function. Phenformin, another biguanide, was withdrawn because of an increased risk of lactic acidosis up to 60 cases per million patient-years. However, metformin is safer than phenformin, and the risk of developing lactic acidosis is not increased by the medication so long as it is not prescribed to known high-risk groups.25 Gastrointestinal The most common adverse effect of metformin is gastrointestinal upset, including diarrhea, cramps, nausea and vomiting; metformin is more commonly associated with gastrointestinal side effects than most other anti-diabetic drugs.15 In a clinical trial of 286 subjects, 53.2% of the 141 who were given immediate-release metformin as opposed to placebo reported diarrhea, versus 11.7% for placebo, and 25.5% reported nausea/vomiting, versus 8.3% for those on placebo.26 Gastrointestinal upset can cause severe discomfort for patients; it is most common when metformin is first administered, or when the dose is increased. The discomfort can often be avoided by beginning at a low dose 1 to 1.7 grams per day and increasing the dose gradually. Gastrointestinal upset after prolonged, steady use is less common. Long-term use of metformin has been associated with increased homocysteine levels27 and malabsorption of vitamin B12.2829 Higher doses and prolonged use are associated with increased incidence of B12 deficiency, and some researchers recommend screening or prevention strategies.30 Hormonal There is an initial report, involving four patients with impaired thyroid function, that metformin can suppress the TSH level with no accompanying symptoms of hyperthyroidism or changes in measured thyroid hormone levels. The mechanism is currently unknown.31 Overdosage A review of intentional and accidental metformin overdoses reported to Poison control centers over a 5-year period found that serious adverse events were rare, though elderly patients appeared to be at greater risk.32 Intentional overdoses with up to 63 g of metformin have been reported in the medical literature.33 The major potentially life-threatening complication of metformin overdose is lactic acidosis. Treatment of metformin overdose is generally supportive, but may include sodium bicarbonate to address acidosis and standard hemodialysis or continuous veno-venous hemofiltration to rapidly remove metformin and correct acidosis.3435 Mechanism of action Metformin improves hyperglycemia primarily through its suppression of hepatic glucose production, especially hepatic gluconeogenesis.36 The average person with type 2 diabetes has three times the normal rate of gluconeogenesis; metformin treatment reduces this by over one third.37 Metformin activates AMP-activated protein kinase AMPK, a liver enzyme that plays an important role in insulin signaling, whole body energy balance, and the metabolism of glucose and fats;38 activation of AMPK is required for metformin's inhibitory effect on the production of glucose by liver cells.39 Research published in 2008 further elucidated metformin's mechanism of action, showing that activation of AMPK is required for an increase in the expression of SHP, which in turn inhibits the expression of the hepatic gluconeogenic genes PEPCK and Glc-6-Pase.40 Metformin is frequently used in research along with AICAR as an AMPK agonist. The mechanism by which biguanides increase the activity of AMPK remains uncertain; however, research suggests that metformin increases the amount of cytosolic AMP as opposed to a change in total AMP or total AMP/ATP.41 In addition to suppressing hepatic glucose production, metformin increases insulin sensitivity, enhances peripheral glucose uptake, decreases fatty acid oxidation, and decreases absorption of glucose from the gastrointestinal tract.42 Increased peripheral utilization of glucose may be due to improved insulin binding to insulin receptors.43 AMPK probably also plays a role, as metformin administration increases AMPK activity in skeletal muscle.44 AMPK is known to cause GLUT4 translocation, resulting in insulin-independent glucose uptake. Some metabolic actions of metformin do appear to occur by AMPK-independent mechanisms; a recent study found that the metabolic actions of metformin in the heart muscle can occur independent of changes in AMPK activity and may be mediated by p38 MAPK- and PKC-dependent mechanisms.45 Metformin is not metabolized, rather it is primarily excreted in the urine with an elimination half-life of 6.2 hours.46 Interactions The H2-receptor antagonist cimetidine causes an increase in the plasma concentration of metformin, by reducing clearance of metformin by the kidneys;47 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.48 A small double-blind, randomized study found the antibiotic cefalexin to also increase metformin concentrations by a similar mechanism;49 theoretically, other cationic medications may produce the same effect.48 Formulations Metformin 500 mg tablets Metformin 500 mg tablets Metformin IR immediate release is available in 500 mg, 850 mg, and 1000 mg tablets, all now generic in the US. Metformin SR slow release or XR extended release was introduced in 2004, in 500 mg and 750 mg strengths, mainly to counteract the most common gastrointestinal side effects, as well as to increase patient compliance by reducing pill burden. No difference in effectiveness exists between the two preparations. Combinations with other drugs Metformin is often prescribed to type 2 diabetes patients in combination with rosiglitazone. This drug actively reduces insulin resistance, complementing the action of the metformin. In 2002, the two drugs were combined into a single product, Avandamet, marketed by GlaxoSmithKline.50 In 2005, all current stock of Avandamet was seized by the FDA and removed from the market, after inspections showed the factory where it was produced was violating Good Manufacturing Practices.51 The drug pair continued to be prescribed separately in the absence of Avandamet, which was available again by the end of that year. In the United States, metformin is also available in combination with pioglitazone trade name Actoplus Met, the sulfonylureas glipizide trade name Metaglip and glibenclamide trade name Glucovance, the dipeptidyl peptidase-4 inhibitor sitagliptin trade name Janumet, and the meglitinide repaglinide PrandiMet. Generic formulations of metformin/glipizide, metformin/glibenclamide, and metformin/rosiglitazone are available. References ^ Clinical Guidelines Task Force, International Diabetes Federation 2005. Glucose control: oral therapyPDF 100 KiB. In: Global Guideline for Type 2 Diabetes. Brussels: International Diabetes Federation, 35-8. Retrieved on November 6, 2007. ^ National Institute for Health and Clinical Excellence. Clinical guideline 66: Diabetes - type 2 update. London, 2008. ^ American Diabetes Association 2007. Standards of medical care in diabetes-2007. Diabetes Care 30 Suppl 1: S4-S41. doi:10.2337/dc07-S004. PMID 17192377. ^ a b Eurich DT, McAlister FA, Blackburn DF, et al. 2007. Benefits and harms of antidiabetic agents in patients with diabetes and heart failure: systematic review. BMJ 335 7618: 497. doi:10.1136/bmj.39314.620174.80. PMID 17761999. ^ Top 200 Generic Drugs by Units in 2006PDF 19.4 KiB. Drug Topics March 5, 2007. Retrieved on April 8, 2007. ^ March 2007 WHO Model List of Essential MedicinesPDF 612 KiB, 15th ion, World Health Organization, p. 21. Retrieved on 2007-11-19. ^ Witters L 2001. The blooming of the French lilac. J Clin Invest 108 8: 1105-7. doi:10.1172/JCI14178. PMID 11602616. Full text at PMC: 209536 ^ Ungar G, Freedman L, Shapiro S 1957. Pharmacological studies of a new oral hypoglycemic drug. Proc Soc Exp Biol Med 95 1: 190-2. PMID 13432032. ^ U.S. Food and Drug Administration December 30, 1994. FDA Approves New Diabetes Drug. Press release. Retrieved on 2007-01-06. ^ GLUCOPHAGE Label and Approval History. U.S. Food and Drug Administration. Retrieved on 2007-01-08. Data available for download on FDA website. ^ Effect of intensive blood-glucose control with metformin on complications in overweight patients with type 2 diabetes UKPDS 34. UK Prospective Diabetes Study UKPDS Group 1998. Lancet 352 9131: 854-65. doi:10.1016/S0140-67369807037-8. PMID 9742977. ^ Kilo C, Mezitis N, Jain R, Mersey J, McGill J, Raskin P 2003. Starting patients with type 2 diabetes on insulin therapy using once-daily injections of biphasic insulin aspart 70/30, biphasic human insulin 70/30, or NPH insulin in combination with metformin. J Diabetes Complications 17 6: 307-13. doi:10.1016/S1056-87270300076-X. PMID 14583174. ^ DiPiro, Joseph T.; Talbert, Robert L.; Yee, Gary C.; Matzke, Gary R.; Wells, Barbara G.; Posey, L. Michael 2005. Pharmacotherapy: a pathophysiologic approach. New York: McGraw-Hill. ISBN 0071416137. ^ Stumvoll M, Nurjhan N, Perriello G, Dailey G, Gerich JE 1995. Metabolic effects of metformin in non-insulin-dependent diabetes mellitus. N Engl J Med 333 9: 550-4. doi:10.1056/NEJM199508313330903. PMID 7623903. ^ a b Bolen S, Feldman L, Vassy J, et al 2007. Systematic review: comparative effectiveness and safety of oral medications for type 2 diabetes mellitus. Ann Intern Med 147 6: 386-99. PMID 17638715. ^ Lord JM, Flight IHK, Norman RJ 2003. Metformin in polycystic ovary syndrome: systematic review and meta-analysis. BMJ 327 7421: 951-3. doi:10.1136/bmj.327.7421.951. PMID 14576245. ^ Marchesini G, Brizi M, Bianchi G, Tomassetti S, Zoli M, Melchionda N 2001. Metformin in non-alcoholic steatohepatitis. Lancet 358 9285: 893-4. doi:10.1016/S0140-67360106042-1. PMID 11567710. ^ Ibáñez L, Ong K, Valls C, Marcos MV, Dunger DB, de Zegher F 2006. Metformin treatment to prevent early puberty in girls with precocious pubarche. J. Clin. Endocrinol. Metab. 91 8: 2888-91. doi:10.1210/jc.2006-0336. PMID 16684823. ^ National Institute for Health and Clinical Excellence. 11 Clinical guideline 11 : Fertility: assessment and treatment for people with fertility problems . London, 2004. ^ Nair S, Diehl AM, Wiseman M, Farr GH Jr, Perrillo RP 2004. Metformin in the treatment of non-alcoholic steatohepatitis: a pilot open label trial. Aliment Pharmacol Ther 20 1: 23-28. doi:10.1111/j.1365-2036.2004.02025.x. PMID 15225167. ^ Wu RR, Zhao JP, Jin H, et al 2008. Lifestyle intervention and metformin for treatment of antipsychotic-induced weight gain: a randomized controlled trial. JAMA 299 2: 185-93. doi:10.1001/jama.2007.56-b. PMID 18182600. ^ Jones G, Macklin J, Alexander W 2003. Contraindications to the use of metformin. BMJ 326 7379: 4-5. doi:10.1136/bmj.326.7379.4. PMID 12511434. ^ a b Weir J March 19, 1999. Guidelines with Regard to Metformin-Induced Lactic Acidosis and X-ray Contrast Medium Agents. Royal College of Radiologists. Retrieved on 2007-10-26 through the Internet Archive. ^ a b Thomsen HS, Morcos SK 2003. Contrast media and the kidney: European Society of Urogenital Radiology ESUR guidelines. Br J Radiol 76 908: 513-8. doi:10.1259/bjr/26964464. PMID 12893691. ^ Salpeter S, Greyber E, Pasternak G, Salpeter E 2003. Risk of fatal and nonfatal lactic acidosis with metformin use in type 2 diabetes mellitus: systematic review and meta-analysis. Arch Intern Med 163 21: 2594-602. doi:10.1001/archinte.163.21.2594. PMID 14638559. ^ October 2004 Drug Facts and Comparisons 2005, 59th ion, Lippincott Williams Wilkins. ISBN 1-57439-193-3. ^ Wulffele MG, Kooy A, Lehert P, Bets D, Ogterop JC, Borger van der Burg B, Donker AJ, Stehouwer CD. Nov 2003. Effects of short-term treatment with metformin on serum concentrations of homocysteine, folate and vitamin B12 in type 2 diabetes mellitus: a randomized, placebo-controlled trial. J Intern Med 254 5: 455-63. doi:10.1046/j.1365-2796.2003.01213.x. PMID 14535967. ^ Andrès E, Noel E, Goichot B 2002. Metformin-associated vitamin B12 deficiency. Arch Intern Med 162 19: 2251-2. doi:10.1001/archinte.162.19.2251-a. PMID 12390080. ^ Gilligan M 2002. Metformin and vitamin B12 deficiency. Arch Intern Med 162 4: 484-5. doi:10.1001/archinte.162.4.484. PMID 11863489. ^ Ting R, Szeto C, Chan M, Ma K, Chow K 2006. Risk factors of vitamin B12 deficiency in patients receiving metformin. Arch Intern Med 166 18: 1975-9. doi:10.1001/archinte.166.18.1975. PMID 17030830. ^ Vigersky RA, Filmore-Nassar A, Glass AR 2006. Thyrotropin suppression by metformin. J Clin Endocrinol Metab 91 1: 225-7. doi:10.1210/jc.2005-1210. PMID 16219720. ^ Spiller HA, Quadrani DA 2004. Toxic effects from metformin exposure. The Annals of pharmacotherapy 38 5: 776-80. doi:10.1345/aph.1D468. PMID 15031415. ^ Gjedde S, Christiansen A, Pedersen SB, Rungby J 2003. Survival following a metformin overdose of 63 g: a case report. Pharmacol. Toxicol. 93 2: 98-9. doi:10.1034/j.1600-0773.2003.930207.x. PMID 12899672. ^ Harvey B, Hickman C, Hinson G, Ralph T, Mayer A 2005. Severe lactic acidosis complicating metformin overdose successfully treated with high-volume venovenous hemofiltration and aggressive alkalinization. Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies 6 5: 598-601. PMID 16148825. ^ Guo PY, Storsley LJ, Finkle SN 2006. Severe lactic acidosis treated with prolonged hemodialysis: recovery after massive overdoses of metformin. Seminars in dialysis 19 1: 80-3. doi:10.1111/j.1525-139X.2006.00123.x. PMID 16423187. ^ Kirpichnikov D, McFarlane SI, Sowers JR 2002. Metformin: an update. Ann Intern Med 137 1: 25-33. PMID 12093242. ^ Hundal R, Krssak M, Dufour S, Laurent D, Lebon V, Chandramouli V, Inzucchi S, Schumann W, Petersen K, Landau B, Shulman G 2000. Mechanism by which metformin reduces glucose production in type 2 diabetes PDF. Diabetes 49 12: 2063-9. doi:10.2337/diabetes.49.12.2063. PMID 11118008. ^ Towler MC, Hardie DG 2007. AMP-activated protein kinase in metabolic control and insulin signaling. Circ Res 100 3: 328-41. doi:10.1161/01.RES.0000256090.42690.05. PMID 17307971. ^ Zhou G, Myers R, Li Y, Chen Y, Shen X, Fenyk-Melody J, Wu M, Ventre J, Doebber T, Fujii N, Musi N, Hirshman M, Goodyear L, Moller D 2001. Role of AMP-activated protein kinase in mechanism of metformin action. J Clin Invest 108 8: 1167-74. doi:10.1172/JCI13505. PMID 11602624. ^ Kim YD, Park KG, Lee YS, et al. 2008. Metformin inhibits hepatic gluconeogenesis through AMP-activated protein kinase-dependent regulation of the orphan nuclear receptor SHP. Diabetes 57 2: 306-14. doi:10.2337/db07-0381. PMID 17909097. ^ Zhang L, He H, Balschi JA 2007. Metformin and phenformin activate AMP-activated protein kinase in the heart by increasing cytosolic AMP concentration. Am J Physiol Heart Circ Physiol 293 1: H457-66. doi:10.1152/ajpheart.00002.2007. PMID 17369473. ^ Royal Pharmaceutical Society of Great Britain and the British Medical Association. Chapter 6:Endocrine system-6.1.2.2 Biguanides, British National Formulary, 54. ^ Bailey CJ, Turner RC 1996. Metformin. N Engl J Med 334 9: 574-9. doi:10.1056/NEJM199602293340906. PMID 8569826. ^ Musi N, Hirshman MF, Nygren J, et al. 2002. Metformin increases AMP-activated protein kinase activity in skeletal muscle of subjects with type 2 diabetes. Diabetes 51 7: 2074-81. PMID 12086935. ^ Saeedi R, Parsons HL, Wambolt RB, et al. 2008. Metabolic actions of metformin in the heart can occur by AMPK-independent mechanisms. Am J Physiol Heart Circ Physiol 294 6: H2497-506. doi:10.1152/ajpheart.00873.2007. PMID 18375721. ^ Heller, Jacqueline B. 2007. Metformin overdose in dogs and cats. Veterinary Medicine April: 231-233. ^ Somogyi A, Stockley C, Keal J, Rolan P, Bochner F 1987. Reduction of metformin renal tubular secretion by cimetidine in man. Br J Clin Pharmacol 23 5: 545-51. PMID 3593625. ^ a b Glucophage Side Effects Drug Interactions. RxList.com 2007. Retrieved on 2007-11-19. ^ Jayasagar G, Krishna Kumar M, Chandrasekhar K, Madhusudan Rao C, Madhusudan Rao Y 2002. Effect of cephalexin on the pharmacokinetics of metformin in healthy human volunteers. Drug Metabol Drug Interact 19 1: 41-8. PMID 12222753. ^ GlaxoSmithKline October 12, 2002. FDA Approves GlaxoSmithKline's Avandamet rosiglitazone maleate and metformin HCl, The Latest Advancement in the Treatment of Type 2 Diabetes. Press release. Retrieved on 2006-12-27. ^ U.S. Food and Drug Administration March 4, 2005. Questions and Answers about the Seizure of Paxil CR and Avandamet. Press release. Retrieved on 2006-12-27. External links Pharmacy and Pharmacology portal Metformin at the Open Directory Project Metformin drug information from Lexi-Comp. Includes dosage information and a comprehensive list of international brand names v d e Oral antidiabetic drugs and Insulin analogs A10 Insulin sensitizers Biguanides Metformin, Buformin‡, Phenformin‡ TZDs PPAR Pioglitazone, Rivoglitazone†, Rosiglitazone, Troglitazone‡ Secretagogues Sulfonylureas 1st generation: Carbutamide, Chlorpropamide, Gliclazide, Tolbutamide, Tolazamide 2nd generation: Glipizide, Glibenclamide Glyburide, Gliquidone, Glyclopyramide 3rd generation: Glimepiride Meglitinides Nateglinide, Repaglinide, Mitiglinide Glucagon-like peptide-1 analog Exenatide, Liraglutide†, Albiglutide†, Taspoglutide†DPP-4 inhibitors Alogliptin†, Linagliptin†, Saxagliptin†, Sitagliptin, Vildagliptin Alpha-glucosidase inhibitors Acarbose, Miglitol, Voglibose Amylin analog Pramlintide Experimental Dual PPAR agonists Aleglitazar†, Muraglitazar§, Tesaglitazar§ SGLT2 inhibitor Dapagliflozin†, Remogliflozin†, Sergliflozin†Insulin analogs fast acting Insulin lispro, Insulin aspart, Insulin glulisine, long acting Insulin glargine, Insulin detemir, Inhalable insulin Exubera †Undergoing clinical trials. ‡ Withdrawn from market. §Development halted. Retrieved from http://en..org/wiki/Metformin Categories: Anti-diabetic drugs | Guanidines | World Health Organization essential medicinesHidden categories: Articles containing potentially dated statements from 2008 | All articles containing potentially dated statements Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français Italiano Magyar Nederlands Polski Português РуÑ?Ñ?кий Shqip Suomi This page was last modified on 9 September 2008, at 01:04
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