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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H39NO4.ClH
Molecular Weight 514.096
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VAPIPROST HYDROCHLORIDE

SMILES

Cl.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=ZYOBZRTZRQKKNC-UGNABIHOSA-N
InChI=1S/C30H39NO4.ClH/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);1H/b2-1-;/t26-,27-,28-,30+;/m0./s1

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
GR32191, a highly potent and specific thromboxane A2 receptor blocking drug on platelets and vascular and airways smooth muscle in vitro.
1989 Jul
Characteristics of the binding of [3H]-GR32191 to the thromboxane (TP-) receptor of human platelets.
1993 Oct
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
1997 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: intravenous route is possible https://www.ncbi.nlm.nih.gov/pubmed/1834144
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 HYDROCHLORIDE
JAN   USAN  
USAN  
Official Name English
VAPIPROST HCL
Common Name English
GR 32191B
Code English
VAPIPROST HYDROCHLORIDE [USAN]
Common Name English
VAPIPROST HYDROCHLORIDE [JAN]
Common Name English
GR-32191B
Code English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID9045689
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
FDA UNII
292V8Q1MXQ
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
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NCI_THESAURUS
C76905
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
PRIMARY
PUBCHEM
6918029
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
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USAN
BB-7
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
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ChEMBL
CHEMBL65030
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
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CAS
87248-13-3
Created by admin on Fri Dec 15 15:43:03 GMT 2023 , Edited by admin on Fri Dec 15 15:43:03 GMT 2023
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