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

Molecular Formula	C30H39NO4
Molecular Weight	477.635
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

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 20 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 2849		3.5 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1827543 https://www.ncbi.nlm.nih.gov/pubmed/2525122	Primary		Phase III 665	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 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
23.98 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
43 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
100.36 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
118.89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
125.14 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
38 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
69 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
160 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	4 mg single, intravenous dose: 4 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
237 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	8 mg single, intravenous dose: 8 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
431 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	16 mg single, intravenous dose: 16 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
81.4 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/26/1/26_1_305/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
43 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/26/1/26_1_305/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
63.73 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
124.27 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
284.39 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
299.74 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
386.71 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1944 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2781 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6478 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	4 mg single, intravenous dose: 4 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1295 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	8 mg single, intravenous dose: 8 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
22198 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	16 mg single, intravenous dose: 16 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
341.64 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/26/1/26_1_305/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
124.27 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/26/1/26_1_305/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
0.99 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1839540/	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
84 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
69 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
70 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	4 mg single, intravenous dose: 4 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
68 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	8 mg single, intravenous dose: 8 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
86 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1834144/	16 mg single, intravenous dose: 16 mg route of administration: Intravenous experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14.19 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/26/1/26_1_305/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.1 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/26/1/26_1_305/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	VAPIPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
40 mg single, oral Studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9114916/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9114916/	Sources: https://pubmed.ncbi.nlm.nih.gov/9114916/

PubMed

Title	Date	PubMed
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.	1997-09	9313928
Characteristics of the binding of [3H]-GR32191 to the thromboxane (TP-) receptor of human platelets.	1993-10	8242228
GR32191, a highly potent and specific thromboxane A2 receptor blocking drug on platelets and vascular and airways smooth muscle in vitro.	1989-07	2527074

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:19:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:19:04 GMT 2025`
Record UNII	H84XT1COAU
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VAPIPROST

Official Name

English

GR-32191

Preferred 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

GR32191

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