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Substance Name: Terbinafine [USAN:INN:BAN]
RN: 91161-71-6
UNII: G7RIW8S0XP
InChIKey: DOMXUEMWDBAQBQ-WEVVVXLNSA-N

Note

  • A naphthalene derivative that inhibits fungal SQUALENE EPOXIDASE and is used to treat DERMATOMYCOSES of the skin and nails.

Molecular Formula

  • C21-H25-N

Molecular Weight

  • 291.4355
 

Classification Codes

  • Anti-Infective Agents
  • Antifungal
  • Antifungal Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data

Names and Synonyms

Name of Substance

  • Terbinafine
  • Terbinafine [USAN:INN:BAN]

MeSH Heading

  • Terbinafine

Synonyms

  • (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine
  • (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine
  • BRN 4256376
  • EC 618-706-8
  • Lamasil
  • Lamisil
  • Lamisil AT
  • Lamisil Tablet
  • SF 86-327
  • SF-86-327
  • Terbinafine
  • UNII-G7RIW8S0XP

Systematic Names

  • (2E)-N,6,6-Trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine
  • 1-Naphthalenemethanamine, N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-, (E)-

Registry Numbers

CAS Registry Number

  • 91161-71-6

FDA UNII

  • G7RIW8S0XP

System Generated Number

  • 0091161716

Structure Descriptors

InChI

InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+

InChIKey

DOMXUEMWDBAQBQ-WEVVVXLNSA-N

Smiles

CN(C\C=C\C#CC(C)(C)C)Cc1cccc2ccccc12

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 3918ug/kg (3.918mg/kg) GASTROINTESTINAL: OTHER CHANGES Kiso to Rinsho. Clinical Report. Vol. 27, Pg. 6087, 1993.
man TDLo oral 89mg/kg/25D-I (89mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 American Journal of Gastroenterology. Vol. 93, Pg. 459, 1998.
mouse LD50 intravenous 393mg/kg (393mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 "Proceedings of the International Congress of Chemotherapy, 13th, Vienna, 1983," Spitzy, K.H. and K. Karrer, eds., 18 vols., Vienna, Austria, Verlag H. Egermann, 1983Vol. 6, Pg. 116/52, 1983.
mouse LD50 oral 4gm/kg (4000mg/kg)   Drugs of the Future. Vol. 9, Pg. 427, 1984.
rat LD50 intravenous 213mg/kg (213mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 "Proceedings of the International Congress of Chemotherapy, 13th, Vienna, 1983," Spitzy, K.H. and K. Karrer, eds., 18 vols., Vienna, Austria, Verlag H. Egermann, 1983Vol. 6, Pg. 116/52, 1983.
rat LD50 oral 4gm/kg (4000mg/kg)   Drugs of the Future. Vol. 9, Pg. 427, 1984.
women TDLo oral 200mg/kg/40D- (200mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: ANOREXIA (HUMAN

LIVER: "JAUNDICE, CHOLESTATIC"		 Journal of Hepathology. Vol. 24, Pg. 753, 1996.
women TDLo oral 210mg/kg/6W-I (210mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE Lancet. Vol. 340, Pg. 728, 1992.