Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H22ClNO4S |
Molecular Weight | 407.911 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(CCC(O)=O)C2=C(C[C@@H](CC2)NS(=O)(=O)C3=CC=C(Cl)C=C3)C=C1
InChI
InChIKey=HWEOXFSBSQIWSY-MRXNPFEDSA-N
InChI=1S/C20H22ClNO4S/c1-13-2-3-14-12-16(6-9-19(14)18(13)10-11-20(23)24)22-27(25,26)17-7-4-15(21)5-8-17/h2-5,7-8,16,22H,6,9-12H2,1H3,(H,23,24)/t16-/m1/s1
Molecular Formula | C20H22ClNO4S |
Molecular Weight | 407.911 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Terutroban (S18886), a specific thromboxane A2 receptor antagonist, which improves endothelial function and has an antiatherosclerotic effect. The compound is under development by Servier for the potential treatment of cardiovascular diseases and coronary artery disease. In addition, it participated in phase III clinical trials PERFORM (Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack), but this study was stopped, and the result was not achieved.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P21731 Gene ID: 6915.0 Gene Symbol: TBXA2R Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12498008 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Unknown Approved UseUnknown |
|||
Preventing | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
236 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
42 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
496 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
124 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1480 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1023 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
283 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3029 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
495 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5852 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15978101 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERUTROBAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.1442 |
unhealthy, ADULT n = 6 Health Status: unhealthy Condition: peripheral artery disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: Page: p.1442 |
PubMed
Title | Date | PubMed |
---|---|---|
[Terutroban and endothelial TP receptors in atherogenesis]. | 2006 Apr |
|
Increased spontaneous tone in renal arteries of spontaneously hypertensive rats. | 2007 Sep |
|
Two isoforms of cyclooxygenase contribute to augmented endothelium-dependent contractions in femoral arteries of 1-year-old rats. | 2008 Feb |
|
Effect of the thromboxane prostaglandin receptor antagonist terutroban on arterial thrombogenesis after repeated administration in patients treated for the prevention of ischemic stroke. | 2009 |
|
Rationale and design of a randomized, double-blind, parallel-group study of terutroban 30 mg/day versus aspirin 100 mg/day in stroke patients: the prevention of cerebrovascular and cardiovascular events of ischemic origin with terutroban in patients with a history of ischemic stroke or transient ischemic attack (PERFORM) study. | 2009 |
|
New antiplatelet agents: why they are needed. | 2009 Dec |
|
New antiplatelet agents. | 2009 Sep |
|
Pharmacokinetic, pharmacodynamic and clinical profile of novel antiplatelet drugs targeting vascular diseases. | 2010 Feb 1 |
|
[Update on new antithrombotic treatments]. | 2010 Jan 20 |
|
Antiplatelet drugs--do we need new options? With a reappraisal of direct thromboxane inhibitors. | 2010 May 7 |
|
Controversies and future perspectives of antiplatelet therapy in secondary stroke prevention. | 2010 Oct |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:33:20 UTC 2023
by
admin
on
Fri Dec 15 16:33:20 UTC 2023
|
Record UNII |
A6WX9391D8
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C1327
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB23570
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
100000089023
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
8452
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
DTXSID30870091
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
C501362
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
A6WX9391D8
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
CHEMBL2107786
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
9938840
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
TERUTROBAN
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
C90753
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY | |||
|
165538-40-9
Created by
admin on Fri Dec 15 16:33:20 UTC 2023 , Edited by admin on Fri Dec 15 16:33:20 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> INHIBITOR |
|
||
|
SALT/SOLVATE -> PARENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|