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Substance Name: Gefarnate [INN:BAN:JAN]
RN: 51-77-4
UNII: 1ISE2Y6ULA
InChIKey: ZPACYDRSPFRDHO-ROBAGEODSA-N

Note

  • A water insoluble terpene fatty acid used in the treatment of gastrointestinal ulcers; it facilitates the healing and function of mucosal tissue.

Molecular Formula

  • C27-H44-O2

Molecular Weight

  • 400.6426
 

Classification Codes

  • Anti-Ulcer Agents
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
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Names and Synonyms

Name of Substance

  • Gefarnate
  • Gefarnate [INN:BAN:JAN]

MeSH Heading

  • Gefarnate

Synonyms

  • (E,E,E)-5,9,13-Trimethyl-4,8,12-tetradecatrienoic acid 3,7-dimethyl-2,6-octadienyl ester
  • DA 688
  • DA-688
  • EINECS 200-121-0
  • Gefarnate
  • Gefarnato
  • Gefarnato [INN-Spanish]
  • Gefarnatum
  • Gefarnatum [INN-Latin]
  • Gefarnil
  • Gefarnyl
  • Geranyl farnesylacetate
  • UNII-1ISE2Y6ULA

Systematic Names

  • 4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester, (4E,8E)-
  • 4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, (2E)-3,7-dimethyl-2,6-octadienyl ester, (4E,8E)-
  • 4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, 3,7-dimethyl-2,6-octadienyl ester, (E,E,E)-
  • Gefarnate
  • trans-3,7-Dimethyl-2,6-octadienyl 5,9,13-trimethyl-4,8,12-tetradecatrienoate

Registry Numbers

CAS Registry Number

  • 51-77-4

FDA UNII

  • 1ISE2Y6ULA

Other Registry Number

  • 30462-47-6

System Generated Number

  • 0000051774

Structure Descriptors

InChI

1S/C27H44O2/c1-22(2)12-8-14-24(5)16-10-17-25(6)18-11-19-27(28)29-21-20-26(7)15-9-13-23(3)4/h12-13,16,18,20H,8-11,14-15,17,19,21H2,1-7H3/b24-16+,25-18+,26-20+

InChIKey

ZPACYDRSPFRDHO-ROBAGEODSA-N

Smiles

CC(=CCC/C(=C/CC/C(=C/CCC(=O)OC/C=C(\C)/CCC=C(C)C)/C)/C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular > 13500mg/kg (13500mg/kg)   Drugs in Japan Vol. 6, Pg. 266, 1982.
mouse LD50 intraperitoneal > 4gm/kg (4000mg/kg)   Journal of Medicinal Chemistry. Vol. 6, Pg. 457, 1963.
mouse LD50 intravenous 2821mg/kg (2821mg/kg)   Journal of Medicinal Chemistry. Vol. 6, Pg. 457, 1963.
mouse LD50 oral > 8gm/kg (8000mg/kg)   Journal of Medicinal Chemistry. Vol. 6, Pg. 457, 1963.
mouse LD50 subcutaneous > 13500mg/kg (13500mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 373, 1969.
rat LD50 intramuscular > 13500mg/kg (13500mg/kg)   Drugs in Japan Vol. 6, Pg. 266, 1982.
rat LD50 intravenous 2040mg/kg (2040mg/kg)   Drugs in Japan Vol. 6, Pg. 266, 1982.
rat LD50 oral > 9gm/kg (9000mg/kg)   Drugs in Japan Vol. 6, Pg. 266, 1982.
rat LD50 subcutaneous > 13500mg/kg (13500mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 373, 1969.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
log P (octanol-water) 11.37 (none)   EST
Atmospheric OH Rate Constant 4.45E-10 cm3/molecule-sec 25 EST

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