Gefarnate
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MedKoo CAT#: 561640

CAS#: 51-77-4

Description: Gefarnate is an antiulcer agent that stimulates in-vitro secretion of mucin-like glycoprotein in conjunctival tissue. It also ameliorates corneal epithelial damage in animal dry-eye models.


Chemical Structure

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Gefarnate
CAS# 51-77-4

Theoretical Analysis

MedKoo Cat#: 561640
Name: Gefarnate
CAS#: 51-77-4
Chemical Formula: C27H44O2
Exact Mass: 400.3341
Molecular Weight: 400.647
Elemental Analysis: C, 80.94; H, 11.07; O, 7.99

Price and Availability

Size Price Availability Quantity
250.0mg USD 450.0 2 Weeks
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Synonym: Gefarnate; Geranyl farnesylacetate; Gefarnil;

IUPAC/Chemical Name: [(2E)-3,7-Dimethylocta-2,6-dienyl] (4E,8E)-5,9,13-trimethyltetradeca-4,8,12-trienoate

InChi Key: ZPACYDRSPFRDHO-ROBAGEODSA-N

InChi Code: 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+

SMILES Code: C/C(C)=C\CC/C(C)=C/CC/C(C)=C/CCC(OC/C=C(C)/CC/C=C(C)/C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: 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.
In vitro activity: TBD
In vivo activity: Exposure to gefarnate at 0.002, 0.006, or 0.02 mg/mL for 24 hours increased the secretion of mucin-like glycoprotein from isolated rabbit conjunctival tissue in a dose-dependent manner. The secretion of mucin-like glycoprotein showed statistically significant differences at gefarnate concentrations of 0.006 and 0.02 mg/mL compared to the vehicle (0 mg/mL of gefarnate). Reference: Clin Ophthalmol. 2013;7:211-7. https://pubmed.ncbi.nlm.nih.gov/23386781/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 31.25 78.0

Preparing Stock Solutions

The following data is based on the product molecular weight 400.647 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Dota A, Takaoka-Shichijo Y, Nakamura M. Gefarnate stimulates mucin-like glycoprotein secretion in conjunctival tissue and ameliorates corneal epithelial damage in animal dry-eye models. Clin Ophthalmol. 2013;7:211-7. doi: 10.2147/OPTH.S39061. Epub 2013 Jan 29. PMID: 23386781; PMCID: PMC3563349. 2. Ohta Y, Kobayashi T, Imai Y, Inui K, Yoshino J, Nakazawa S. Effect of gefarnate on acute gastric mucosal lesion progression in rats treated with compound 48/80, a mast cell degranulator, in comparison with that of teprenone. Biol Pharm Bull. 2005 Aug;28(8):1424-30. doi: 10.1248/bpb.28.1424. PMID: 16079487.
In vitro protocol: TBD
In vivo protocol: 1. Dota A, Takaoka-Shichijo Y, Nakamura M. Gefarnate stimulates mucin-like glycoprotein secretion in conjunctival tissue and ameliorates corneal epithelial damage in animal dry-eye models. Clin Ophthalmol. 2013;7:211-7. doi: 10.2147/OPTH.S39061. Epub 2013 Jan 29. PMID: 23386781; PMCID: PMC3563349. 2. Ohta Y, Kobayashi T, Imai Y, Inui K, Yoshino J, Nakazawa S. Effect of gefarnate on acute gastric mucosal lesion progression in rats treated with compound 48/80, a mast cell degranulator, in comparison with that of teprenone. Biol Pharm Bull. 2005 Aug;28(8):1424-30. doi: 10.1248/bpb.28.1424. PMID: 16079487.

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1: Akagi M, Amagase K, Murakami T, Takeuchi K. Irsogladine: overview of the mechanisms of mucosal protective and healing- promoting actions in the gastrointestinal tract. Curr Pharm Des. 2013;19(1):106-14. Review. PubMed PMID: 22950502.

2: Peral A, Domínguez-Godínez CO, Carracedo G, Pintor J. Therapeutic targets in dry eye syndrome. Drug News Perspect. 2008 Apr;21(3):166-76. Review. PubMed PMID: 18560615.

3: Carmine AA, Brogden RN. Pirenzepine. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy in peptic ulcer disease and other allied diseases. Drugs. 1985 Aug;30(2):85-126. Review. PubMed PMID: 3928324.

4: Lux G, Rösch W. [Conservative treatment of gastric ulcer]. Med Klin. 1980 Aug 29;75(18):638-44. Review. German. PubMed PMID: 6106882.

5: Guslandi M. Review: effect of anti-ulcer drugs on gastric mucous barrier and possible cyclic AMP involvement. Int J Clin Pharmacol Ther Toxicol. 1980 Mar;18(3):140-3. Review. PubMed PMID: 6247291.

6: Vezzadini P, Ferri GL. [Medical therapy of gastric ulcer]. Clin Ter. 1979 May 15;89(3):309-17. Review. Italian. PubMed PMID: 380884.

Gefarnate

250.0mg / USD 450.0