CIPROSTENE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H36O4
Molecular Weight	364.5188
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@]2(C)C\C(C[C@H]12)=C/CCCC(O)=O

InChI

InChIKey=VKPYUUBEDXIQIB-QBPWRKFFSA-N

InChI=1S/C22H36O4/c1-3-4-5-9-17(23)11-12-18-19-13-16(8-6-7-10-21(25)26)14-22(19,2)15-20(18)24/h8,11-12,17-20,23-24H,3-7,9-10,13-15H2,1-2H3,(H,25,26)/b12-11+,16-8-/t17-,18+,19+,20+,22-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3068680 | https://www.ncbi.nlm.nih.gov/pubmed/3896365 | https://www.ncbi.nlm.nih.gov/pubmed/1632305

Ciprostene is a synthetic, chemically stable analog of prostacyclin (PGI2). In animal models, administration of ciprostene resulted in dose-dependent hypotension, tachycardia, and inhibition of ex vivo ADP-induced platelet aggregation. Ciprostene was evaluated in clinical trials in patients with peripheral vascular disease. It was found to reduce restenosis in patients with coronary artery disease undergoing therapeutic percutaneous transluminal coronary angioplasty.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid IP receptor 19 Target ID: CHEMBL1995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21129424 \| https://www.ncbi.nlm.nih.gov/pubmed/3005377	Agonist 2752

Patents

Name

Type

Language

(Z)-(3AS,5R,6R,6AR)-HEXAHYDRO-5-HYDROXY-6-((E)-(3S)-3-HYDROXY-1-OCTENYL)-3A-METHYL-.DELTA.(SUP 2)(1H),.DELTA.-PENTALENEVALERATE

Preferred Name

English

CIPROSTENE

Official Name

English

ciprostene [INN]

Common Name

English

PENTANOIC ACID, 5-(HEXAHYDRO-5-HYDROXY-6-(3-HYDROXY-1-OCTENYL)-3A-METHYL-2(1H)-PENTALENYLIDENE,(3AS-(2Z,3A.ALPHA.,5.BETA.,6.ALPHA.(1E,3R*),6A.ALPHA.))-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568