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Substance Name: Metformin [USAN:INN:BAN]
RN: 657-24-9
UNII: 9100L32L2N
InChIKey: XZWYZXLIPXDOLR-UHFFFAOYSA-N

Note

  • A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289)

Molecular Formula

  • C4-H11-N5

Molecular Weight

  • 129.1659
 

Classification Codes

  • Antidiabetic
  • Drug / Therapeutic Agent
  • Hypoglycemic Agents
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Metformin
  • Metformin [USAN:INN:BAN]

MeSH Heading

  • Metformin

Synonyms

  • 1,1-Dimethylbiguanide
  • CCRIS 9321
  • Diabetosan
  • Diabex
  • Dimethylbiguanide
  • Dimethyldiguanide
  • DMGG
  • EINECS 211-517-8
  • Fluamine
  • Flumamine
  • Glifage
  • Gliguanid
  • Haurymelin
  • Imidodicarbonimidic diamide, N,N-dimethyl-
  • Islotin
  • LA-6023
  • Melbin
  • Metformin
  • Metformina
  • Metformina [DCIT]
  • Metformina [Spanish]
  • Metformine
  • Metformine [INN-French]
  • Metforminum
  • Metforminum [INN-Latin]
  • Metiguanide
  • N,N-Dimethylbiguanide
  • N,N-Dimethyldiguanide
  • N1,N1-Dimethylbiguanide
  • NNDG
  • Siofor
  • UNII-9100L32L2N

Systematic Names

  • Biguanide, 1,1-dimethyl-
  • Imidodicarbonimidic diamide-, N,N-dimethyl-
  • Metformin

Registry Numbers

CAS Registry Number

  • 657-24-9

FDA UNII

  • 9100L32L2N

System Generated Number

  • 0000657249

Structure Descriptors

InChI

1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)

InChIKey

XZWYZXLIPXDOLR-UHFFFAOYSA-N

Smiles

C(=N)(NC(=N)N)N(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LD50 parenteral 5gm/kg (5000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiwum Immunologii i Terapii Doswiadczalnej. Vol. 2, Pg. 1, 1954.
guinea pig LD50 subcutaneous 146mg/kg (146mg/kg)   Medicina Experimentalis. Vol. 8, Pg. 237, 1963.
man TDLo oral 321mg/kg/15D- (321mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"
New England Journal of Medicine. Vol. 339, Pg. 1860, 1998.
mouse LD50 intraperitoneal 247mg/kg (247mg/kg)   Journal of Medicinal Chemistry. Vol. 10, Pg. 521, 1967.
mouse LD50 oral 1450mg/kg (1450mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 subcutaneous 230mg/kg (230mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Archiwum Immunologii i Terapii Doswiadczalnej. Vol. 2, Pg. 1, 1954.
women TDLo oral 191mg/kg/9D-I (191mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Postgraduate Medical Journal. Vol. 76, Pg. 125, 2000.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.640 (none)   EST
Atmospheric OH Rate Constant 1.53E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.