VAPIPROST

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H39NO4
Molecular Weight	477.635
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1C[C@H](OCC2=CC=C(C=C2)C3=CC=CC=C3)[C@H](CC\C=C/CCC(O)=O)[C@H]1N4CCCCC4

InChI

InChIKey=GQGRDYWMOPRROR-XUSMOFMBSA-N

InChI=1S/C30H39NO4/c32-27-21-28(35-22-23-15-17-25(18-16-23)24-11-5-3-6-12-24)26(13-7-1-2-8-14-29(33)34)30(27)31-19-9-4-10-20-31/h1-3,5-6,11-12,15-18,26-28,30,32H,4,7-10,13-14,19-22H2,(H,33,34)/b2-1-/t26-,27-,28-,30+/m0/s1

HIDE SMILES / InChI

Description
Sources: http://adisinsight.springer.com/drugs/800000070 | https://www.ncbi.nlm.nih.gov/pubmed/1793065 | https://www.ncbi.nlm.nih.gov/pubmed/1834144

Vapiprost is a potent dicyclopentadiene thromboxane receptor antagonist that was being developed by Glaxo Wellcome in Japan. Vapiprost has been shown to be a potent and specific thromboxane (Tx)A2 receptor blocking drug in vitro using platelets and both vascular and airways smooth muscle preparations from different species. The drug is active in various experimental models of thrombosis. The potential clinical applications for a thromboxane receptor blocking drug include the treatment of thrombotic events and occlusive vascular disease. Phase III trials were underway in Japan for the treatment of deep vein thrombosis, which later were discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thromboxane A2 receptor 19 Target ID: CHEMBL2069 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2527074 \| https://www.ncbi.nlm.nih.gov/pubmed/8242228 \| https://www.ncbi.nlm.nih.gov/pubmed/2527074	Antagonist 2778		3.5 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1827543 https://www.ncbi.nlm.nih.gov/pubmed/2525122	Primary		Phase III 656	Unknown Approved Use Unknown
Deep vein thrombosis 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10455258 https://www.ncbi.nlm.nih.gov/pubmed/7495079	Primary		Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.	1997 Sep	9313928

Patents

Sample Use Guides

In Vivo Use Guide

Vapiprost (GR32191) (80mg p.o.) caused a marked inhibition of PGD2 but not methacholine-induced bronchospasm in asthmatic subjects, and also caused a modest reduction in allergen-induced bronchospasm.

Route of Administration: Oral

In Vitro Use Guide

In in vitro experiments with human platelet, vapiprost inhibited the aggregation and ATP release stimulated with U-46619, collagen or arachidonic acid (AA) at an IC50 of less than 2.1 x 10(-8) M.

Name

Type

Language

VAPIPROST

Official Name

English

4-HEPTENOIC ACID, 7-(5-((1,1'-BIPHENYL)-4-YLMETHOXY)-3-HYDROXY-2-(1-PIPERIDINYL)CYCLOPENTYL)-, (1R-(1.ALPHA.(Z),2.BETA.,3.BETA.,5.ALPHA.))-

Common Name

English

vapiprost [INN]

Common Name

English

GR 32191

Code

English

GR-32191

Code

English

(+)-(4Z)-7-((1R,2R,3S,5S)-5-(4-BIPHENYLMETHOXY)-3-HYDROXY-2-PIPERIDINOCYCLOPENTYL)-4-HEPTENOIC ACID

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1327