Gefarnate

Names

[ CAS No. ]:
51-77-4

[ Name ]:
Gefarnate

[Synonym ]:
Gepharnate
arsanyl
(2E)-3,7-Dimethylocta-2,6-dien-1-yl (4E,8E)-5,9,13-trimethyltetradeca-4,8,12-trienoate
Gefanil
Gefarnate [INN:BAN:JAN]
(E)-Geranyl (E,E)-farnesylacetate
Gefarnyl
Osteol
EINECS 200-121-0
trans-(4,5),trans-(8,9)-Farnesylessigsaeure-geranylester
Gefarnate
(2E)-3,7-Dimethyl-2,6-octadien-1-yl (4E,8E)-5,9,13-trimethyl-4,8,12-tetradecatrienoate
(4E,8E)-5,9,13-trimethyltetradeca-4,8,12-trienoic acid [(2E)-3,7-dimethylocta-2,6-dienyl] ester
DA-688
Gefarnato [INN-Spanish]
Geranyl farnesylacetate
5,9,13-Trimethyl-4,8,12-tetradecatrienoic acid 3,7-dimethyl-2,6-octadienyl ester
(4E,8E)-Farnesylacetic acid geranyl ester
Gefarnil
Gefarnatum [INN-Latin]
4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester, (4E,8E)-

Biological Activity

[Description]:

Gefarnate is a drug used for the treatment of gastritis and gastric ulcer, and has been proposed for use in the treatment of dry eye syndrome.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vitro]

Gefarnate (0.001, 0.01, or 0.1 mg/mL) increases mucin-like glycoprotein secretion in a dose-dependent fashion, but the difference from the control is significant only at the concentration of 0.1 mg/mL. Gefarnate specifically stimulates the mucin-like glycoprotein secretion[1].

[References]

[1]. Nakamura M, et al. Gefarnate stimulates secretion of mucin-like glycoproteins by corneal epithelium in vitro and protects corneal epithelium from desiccation in vivo. Exp Eye Res. 1997 Oct;65(4):569-74.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
484.7±34.0 °C at 760 mmHg

[ Melting Point ]:
25°C

[ Molecular Formula ]:
C₂₇H₄₄O₂

[ Molecular Weight ]:
400.637

[ Flash Point ]:
93.3±24.0 °C

[ Exact Mass ]:
400.334137

[ PSA ]:
26.30000

[ LogP ]:
10.53

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.489

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XB8890000

CHEMICAL NAME :: 4,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-, 3,7-dimethyl-2,6-octadienyl ester, (E,E,E)-

CAS REGISTRY NUMBER :: 51-77-4

LAST UPDATED :: 199701

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C27-H44-O2

MOLECULAR WEIGHT :: 400.71

WISWESSER LINE NOTATION :: 1Y1&U3Y1&U3Y1&U3VO2UY1&3UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >9 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,266,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2040 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,266,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >13500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,266,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 6,457,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 6,457,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2821 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 6,457,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >13500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,266,1982

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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