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Details

Stereochemistry RACEMIC
Molecular Formula C22H23ClO5
Molecular Weight 402.868
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ICI-192605

SMILES

OC(=O)CC\C=C/C[C@H]1CO[C@H](O[C@H]1C2=CC=CC=C2O)C3=CC=CC=C3Cl

InChI

InChIKey=WHUIENZXNGAHQI-YGPRPMEGSA-N
InChI=1S/C22H23ClO5/c23-18-11-6-4-9-16(18)22-27-14-15(8-2-1-3-13-20(25)26)21(28-22)17-10-5-7-12-19(17)24/h1-2,4-7,9-12,15,21-22,24H,3,8,13-14H2,(H,25,26)/b2-1-/t15-,21+,22+/m0/s1

HIDE SMILES / InChI
Molecular Formula C22H23ClO5
Molecular Weight 402.868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

ICI 192605 is an antagonist of thromboxane receptor. The drug reached human studies as a potent and orally-active inhibitor of U-46619 induced platelet aggregation. It was tested in clinical trial in asthma patients in Japan, however its development was terminated.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Thromboxane A2 receptor
20
Target ID: P21731
Gene ID: 6915.0
Gene Symbol: TBXA2R
Target Organism: Homo sapiens (Human)
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
438
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8148229/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8148229/
Sources:
https://pubmed.ncbi.nlm.nih.gov/8148229/
PubMed

PubMed

TitleDatePubMed
Improved synthetic routes to the novel thromboxane receptor antagonist ICI 192605: activity of synthetic 1,3-dioxane intermediates.
1990-01
The synthesis of a novel thromboxane receptor antagonist 4(Z)-6-(2-o-chlorophenyl-4-o-hydroxyphenyl-1,3-dioxan-cis-5-yl) hexenoic acid ICI 192605.
1988-08
Patents

Patents

US2003050305
1
US2013267561
1
US2015158838
1

Sample Use Guides

In Vitro Use Guide
Human radial arterial segments were treated with ICI 192605 at concentration of 1 uM. Responsiveness to the most potent isoprostane, 15-E2t-IsoP, was abolished by ICI 192605. Likewise in pressurized arteries, both 15-E2t-IsoP and 15-F1t-IsoP caused concentration-dependent decreases in diameter, with 15-E2tIsoP showing greater potency than 15-F2t-IsoP, which were blocked by ICI 192605.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:11:41 GMT 2025
Edited
by admin
on Mon Mar 31 18:11:41 GMT 2025
Record UNII
FQ9418XA31
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ICI-192,605
Preferred Name English
ICI-192605
Code English
4-HEXENOIC ACID, 6-((2R,4R,5S)-2-(2-CHLOROPHENYL)-4-(2-HYDROXYPHENYL)-1,3-DIOXAN-5-YL)-, (4Z)-REL-
Systematic Name English
Code System Code Type Description
FDA UNII
FQ9418XA31
Created by admin on Mon Mar 31 18:11:41 GMT 2025 , Edited by admin on Mon Mar 31 18:11:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID801026087
Created by admin on Mon Mar 31 18:11:41 GMT 2025 , Edited by admin on Mon Mar 31 18:11:41 GMT 2025
PRIMARY
CAS
117621-64-4
Created by admin on Mon Mar 31 18:11:41 GMT 2025 , Edited by admin on Mon Mar 31 18:11:41 GMT 2025
PRIMARY
PUBCHEM
6438399
Created by admin on Mon Mar 31 18:11:41 GMT 2025 , Edited by admin on Mon Mar 31 18:11:41 GMT 2025
PRIMARY
NIH
NCATS
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