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SML3356

Sigma-Aldrich

Gefarnate

≥98% (HPLC)

Synonym(s):

(4E,​8E)​-5,​9,​13-​Trimethyl-​4,​8,​12-​tetradecatrienoic acid (2E)​-​3,​7-​dimethyl-​2,​6-​octadien-​1-​yl ester, (E,E,E)-4,8,12-Tetradecatrienoic acid, 5,9,13-trimetyl-, 3,7-dimetyl-2,6-octadienyl ester, Geranyl farnesylacetate

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About This Item

Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
51-77-4
Molecular Weight:
400.64
MDL number:
MFCD00129086
UNSPSC Code:
51111800

Quality Level

100

assay

≥98% (HPLC)

form

liquid

storage condition

desiccated

color

colorless to beige

storage temp.

−20°C

SMILES string

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

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+

InChI key

ZPACYDRSPFRDHO-ROBAGEODSA-N

Biochem/physiol Actions

Gefarnate is an anti-ulcer drug that stimulates gastric mucin secretion. Also gefarnate increase secretion of mucin-like glycoprotein in rabbit conjunctival tissue. It appears to be effective in animal dry-eye models. It is approved in Japan, where it is used to treat gastritis and gastric ulcer. Gefarnate is structurally similar to anti-ulcer drug teprenone (geranyl farnesylacetate), which induces expression of HSP70, HSPB8, and HSPB1.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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M Nakamura et al.
The British journal of ophthalmology, 82(11), 1320-1323 (1999-01-30)
The effects of three drugs for the treatment of gastritis and gastric ulcer--gefarnate, ecabet sodium, and troxipide--on periodic acid Schiff (PAS) positive cell density in rabbit conjunctiva in vivo were investigated. Eye drops containing gefarnate (0.1%, 1%), ecabet sodium (0.1%
Yoshiji Ohta et al.
Biological & pharmaceutical bulletin, 28(8), 1424-1430 (2005-08-05)
We have reported that teprenone (geranylgeranylacetone), an anti-ulcer drug, prevents acute gastric mucosal lesion progression in rats treated once with compound 48/80 (C48/80), a mast cell degranulator, possibly by suppressing mucus depletion, neutrophil infiltration, and oxidative stress in the gastric
Atsuyoshi Dota et al.
Clinical ophthalmology (Auckland, N.Z.), 7, 211-217 (2013-02-07)
The aim of this study was to evaluate the effect of gefarnate on mucin-like glycoprotein secretion in isolated rabbit conjunctival tissue, and on corneal epithelial damage in rabbit and cat dry-eye models. Conjunctival tissue isolated from rabbits was treated with

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