PREDNISOLONE FARNESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H50O6
Molecular Weight	578.7786
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](O)(C(=O)COC(=O)\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

InChI

InChIKey=SBQAKZYUNWNIRL-WIPKXTQKSA-N

InChI=1S/C36H50O6/c1-23(2)9-7-10-24(3)11-8-12-25(4)19-32(40)42-22-31(39)36(41)18-16-29-28-14-13-26-20-27(37)15-17-34(26,5)33(28)30(38)21-35(29,36)6/h9,11,15,17,19-20,28-30,33,38,41H,7-8,10,12-14,16,18,21-22H2,1-6H3/b24-11+,25-19+/t28-,29-,30-,33+,34-,35-,36-/m0/s1

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Description
Sources: https://www.google.com/patents/US5015746
Curator's Comment: http://www.thepharmaletter.com/article/prednisolone-farnesylate-launch-in-japan; http://adisinsight.springer.com/drugs/800002180

Prednisolone farnesylate, a synthetic glucocorticoid, is a terpene-modified compound of prednisolone with an antiinflammatory and antirheumatic action. Glucocorticoid receptor agonists. Farnerate Gel (trade name from Dainippon Pharmaceuticals) and Farnezone Gel (Taiho Pharmaceuticalshave) were launched in Japan in 1998 as topical rheumatoid arthritis (RA) product to treat symptoms associated with RA such as finger, hand and elbow swelling and pain.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid and meneralocorticoid receptor agonists/antagonists 22 Target ID: map07225 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D01998	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: http://adisinsight.springer.com/drugs/800002180	Primary		Approved 8429	Farnezone Approved Use Symptoms of rheumatoid arthritis (swelling and pain in the fingers, hands and elbows). Launch Date 1999

PubMed

Title	Date	PubMed
[A 13-week dermal toxicity study of prednisolone farnesylate (PNF) gel in rats with a recovery period of 5 weeks].	1992 Nov	1293330
[Reproductive and developmental toxicity study of prednisolone farnesylate (PNF)--teratogenicity study in rabbits by subcutaneous administration].	1992 Nov	1293325
[A 13-week percutaneous toxicity study of prednisolone farnesylate (PNF) gel in beagle dogs with a recovery period of 5 weeks].	1992 Nov	1293321
Treatment of the chronic inflammation in peripheral target tissue improves the crushed nerve recovery in the rat: histopathological assessment of the nerve recovery.	2002 Oct 15	12220695

Patents

Sample Use Guides

In Vivo Use Guide

Gel 14 mg/g (1.4%) is applied to treat symptoms of rheumatoid arthritis such as swelling and pain in the fingers, hands and elbows

Route of Administration: Topical

In Vitro Use Guide

Prednisolone farnesylate (PNF) was tested for mutagenicity by Ames test using Salmonella typhimurium (TA100, TA1535, TA98, TA1537) and Escherichia coli (WP2 uvrA), for clastogenic activity in vitro by the chromosomal aberration test in a Chinese hamster fibroblast cell line (CHL). In Ames test, PNF with and without metabolic activation showed no mutagenicity in any strains at any dose levels 312-5,000 micrograms/plate. n the chromosomal aberration test, PNF with metabolic activation produced a slight increase in the incidence of structural chromosomal aberrations in CHL cells at 1,500 micrograms/ml.

Name

Type

Language

PREDNISOLONE FARNESYLATE

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 11,17-DIHYDROXY-21-((3,7,11-TRIMETHYL-1-OXO-2,6,10-DODECATRIENYL)OXY)-, (11.BETA.,21(2E,6E))-

Systematic Name

English

PREDNISOLONE FARNESIL

Common Name

English

Prednisolone farnesylate [WHO-DD]

Common Name

English

PNF 21

Common Name

English

PREDNISOLONE 21-ALL-TRANS-FARNESYLATE

Common Name

English

PREDNISOLONE FARNESYLATE [JAN]

Common Name

English

Code System Code Type Description

PUBCHEM

5282229