TERBOGREL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H27N5O2
Molecular Weight	405.4928
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)N\C(NC#N)=N\C1=CC(=CC=C1)C(=C/CCCC(O)=O)\C2=CC=CN=C2

InChI

InChIKey=XUTLOCQNGLJNSA-RGVLZGJSSA-N

InChI=1S/C23H27N5O2/c1-23(2,3)28-22(26-16-24)27-19-10-6-8-17(14-19)20(11-4-5-12-21(29)30)18-9-7-13-25-15-18/h6-11,13-15H,4-5,12H2,1-3H3,(H,29,30)(H2,26,27,28)/b20-11+

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9570446 | https://www.ncbi.nlm.nih.gov/pubmed/15206991 | https://www.ncbi.nlm.nih.gov/pubmed/24298905

Terbogrel, an agent having two pharmacodynamic actions, namely inhibition of thromboxane A2 synthase and antagonism of the thromboxane A2 receptor. The antithrombotic effect of terbogrel was dose-dependent and was associated with enhanced prostacyclin production. The drug was studied for the treatment of peripheral vascular disorders, pulmonary hypertension, and thrombosis. Terbogrel participated in phase II clinical trial to investigate its safety and efficacy in patients with primary pulmonary hypertension, however, this study was discontinued due to terbogrel’s induction of leg pain.

Originator

Approval Year

PubMed

Title	Date	PubMed
Effects of terbogrel on platelet function and prostaglandin endoperoxide transfer.	1998 Feb 26	9570446
Terbogrel, a dual-acting agent for thromboxane receptor antagonism and thromboxane synthase inhibition.	2000 Oct	11025320
Effects of the thromboxane synthetase inhibitor and receptor antagonist terbogrel in patients with primary pulmonary hypertension.	2002 May	12040360
Pharmacokinetics and pharmacodynamics of terbogrel, a combined thromboxane A2 receptor and synthase inhibitor, in healthy subjects.	2004 Jul	15206991

Patents

Sample Use Guides

In Vivo Use Guide

Forty-eight healthy male subjects received a single oral dose (10, 25, 50, 100, 150 or 200 mg) of terbogrel or placebo and 32 different subjects received one of the following treatments twice daily for 7 days: 50, 100 or 150 mg terbogrel, placebo, or once-a-day 330 mg acetylsalicylic acid.

Route of Administration: Oral

Name

Type

Language

TERBOGREL

Official Name

English

(5E)-6-(M-(3-TERT-BUTYL-2-CYANOGUANIDINO)PHENYL)-6-(3-PYRIDYL)-5-HEXENOIC ACID

Systematic Name

English

Terbogrel [WHO-DD]

Common Name

English

TERBOGREL [USAN]

Common Name

English

BIBV-308-SE

Code

English

BIBV 308 SE

Code

English

BIBV-308SE

Code

English

terbogrel [INN]

Common Name

English

(E)-6-(3-(((CYANOAMINO)((1,1-DIMETHYLETHYL)AMINO)METHYLENE)AMINO)PHENYL)-6-(3-PYRIDINYL)-5-HEXENOIC ACID

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471