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Biguanide - Wikipedia, the free encyclopedia

Biguanide
FromWikipedia,thefreeencyclopedia

Biguanide
biguanide
Biguanidecanrefertoamolecule,ortoa classofdrugsbaseduponthismolecule. Biguanidescanfunctionasoral antihyperglycemicdrugsusedfordiabetes mellitusorprediabetestreatment.Theyare alsousedasantimalarialdrugs.
en.wikipedia.org/wiki/Biguanide More

Identifiers

02518

HEBI:3095

(http://chemapps.stolaf.edu/jmol/jmol.php? odel=%5BnH%5D%3Ac%28%3A%5BnH2%5D%29%3A%5BnH%5D%3Ac%28%3A%5BnH%5D%29%3A%5BnH2%5D) (http://chemapps.stolaf.edu/jmol/jmol.php?model=NC%28%3DN%29NC%28N%29%3DN) SMILES InChI Properties

1.11gmol1 Relatedcompounds Dimethylamine Trimethylamine Unsymmetricaldimethylhydrazine Nitrosodimethylamine Dithiobiuret Diethylamine

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Biguanide - Wikipedia, the free encyclopedia

Triethylamine Diisopropylamine Dimethylaminopropylamine Diethylenetriamine , NDiisopropylethylamine Triisopropylamine Tris(2aminoethyl)amine Mechlorethamine HN1(nitrogenmustard) HN3(nitrogenmustard) (verify)(whatis: / ?) Exceptwherenotedotherwise,dataaregivenformaterialsintheirstandardstate(at25C,100kPa) Infoboxreferences

Biguanidecanrefertoamolecule,ortoaclassofdrugsbased uponthismolecule.Biguanidescanfunctionasoral antihyperglycemicdrugsusedfordiabetesmellitusorprediabetes treatment.Theyarealsousedasantimalarialdrugs. Thedisinfectantpolyaminopropylbiguanide(PAPB)features biguanidefunctionalgroups.

Metformin

Contents
1Examples 2History 3Pharmacotherapy 4Mechanismofaction 5Sideeffectsandtoxicity 6References

Buformin.Noteextrabutylatbottom right.

Examples
Examplesofbiguanides:
Phenformin.Noteextraphenylat right.

Metforminwidelyusedintreatmentofdiabetesmellitus type2 Phenforminwithdrawnfromthemarketinmostcountriesduetotoxiceffects Buforminwithdrawnfromthemarketduetotoxiceffects Proguanilanantimalarialdrug.

History

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Biguanide - Wikipedia, the free encyclopedia

Galegaofficinalis(Frenchlilac)wasusedfordiabetestreatmentintraditionalmedicineforcenturies.Inthe 1920s,guanidinecompoundswerediscoveredinGalegaextracts.Animalstudiesshowedthatthese compoundsloweredbloodglucoselevels.Somelesstoxicderivatives,synthalinAandsynthalinB,were usedfordiabetestreatment,butafterthediscoveryofinsulintheywereforgottenforthenextseveral decades.BiguanideswerereintroducedintoType2diabetestreatmentinthelate1950s.Initially phenforminwaswidelyused,butitspotentialforsometimesfatallacticacidosisresultedinitswithdrawal frompharmacotherapyinmostpharmacopeias(intheU.S.in1977).Metforminhasamuchbettersafety profile,anditistheprincipalbiguanidedrugusedinpharmacotherapyworldwide.

Pharmacotherapy
Biguanidesdonotaffecttheoutputofinsulin,unlikeotherhypoglycemicagentssuchassulfonylureasand meglitinides.Therefore,notonlyaretheyeffectiveinType2diabeticsbuttheycanalsobeeffectivein Type1patientsinconcertwithinsulintherapy.

Mechanismofaction
Themechanismofactionofbiguanidesisnotfullyunderstood.MainlyusedinTypeIIDiabetes, Metforminisconsideredtoincreaseinsulinsensitivityinvivo,resultinginreducedplasmaglucose concentrations,increasedglucoseuptake,anddecreasedgluconeogenesis. However,inhyperinsulinemia,biguanidescanlowerfastinglevelsofinsulininplasma.Theirtherapeutic usesderivefromtheirtendencytoreducegluconeogenesisintheliver,and,asaresult,reducethelevelof glucoseintheblood.Biguanidesalsotendtomakethecellsofthebodymorewillingtoabsorbglucose alreadypresentinthebloodstream,andthereagainreducingthelevelofglucoseintheplasma.

Sideeffectsandtoxicity
Themostcommonsideeffectisdiarrheaanddyspepsia,occurringinupto30%ofpatients.Themost importantandserioussideeffectislacticacidosis,thereforemetforminiscontraindicatedinrenal insufficiency.Renalfunctionsshouldbeassessedbeforestartingmetformin.Phenforminandbuforminare morepronetocauseacidosisthanmetforminthereforetheyhavebeenpracticallyreplacedbyit.However, whenmetforminiscombinedwithotherdrugs(combinationtherapy),hypoglycemiaandothersideeffects arepossible.

References
Rangetal.,Pharmacology,5thEdition,2003,p388 Retrievedfrom"http://en.wikipedia.org/w/index.php?title=Biguanide&oldid=544291216" Categories: Biguanides Thispagewaslastmodifiedon15March2013at05:44. TextisavailableundertheCreativeCommonsAttributionShareAlikeLicenseadditionaltermsmay apply.Byusingthissite,youagreetotheTermsofUseandPrivacyPolicy. WikipediaisaregisteredtrademarkoftheWikimediaFoundation,Inc.,anonprofitorganization.

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