DOMITROBAN, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H27NO4S
Molecular Weight	377.498
Optical Activity	( + / - )
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCC\C=C/C[C@H]1[C@@H]2CC[C@@H](C2)[C@@H]1NS(=O)(=O)C3=CC=CC=C3

InChI

InChIKey=PWTCIBWRMQFJBC-ZEMKZVSASA-N

InChI=1S/C20H27NO4S/c22-19(23)11-7-2-1-6-10-18-15-12-13-16(14-15)20(18)21-26(24,25)17-8-4-3-5-9-17/h1,3-6,8-9,15-16,18,20-21H,2,7,10-14H2,(H,22,23)/b6-1-/t15-,16+,18+,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H27NO4S
Molecular Weight	377.498
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800001843 | https://www.ncbi.nlm.nih.gov/pubmed/9874175 | Morton, I.K., Hall, J.M. (2012) Concise Dictionary of Pharmacological Agents, page 103, retrieved from: https://books.google.ru/books?id=tsjrCAAAQBAJ | Robertson.D. et al. (1998) Annual Reports in Medicinal Chemistry, v.3, page 229, retrieved from: https://books.google.ru/books?id=tbUvRs_qr2IC

Domitroban is a phenylsulfony;aminobicycloheptenoic acid derivative. It is a thromboxane A2 receptor antagonist. It is a potential antiasthmatic and an experimental cerebroprotective drug. It inhibits proteinuria in animal models of renal injury. Calcium salt of R-domitroban had been in phase II clinical trial for the treatment of allergic rhinitis. Also, it was in preregistration stage for the treatment of asthma in Japan. However, these studies were discontinued.

Approval Year

PubMed

Title	Date	PubMed
Kinetic studies on stereospecific recognition by the thromboxane A2/prostaglandin H2 receptor of the antagonist, S-145.	1991 Aug	1833018
Cloning and expression of cDNA for a human thromboxane A2 receptor.	1991 Feb 14	1825698
Binding of a novel radioiodinated thromboxane A2/prostaglandin H2 antagonist to guinea pig lung membranes.	1992	1419073
Mouse thromboxane A2 receptor: cDNA cloning, expression and northern blot analysis.	1992 May 15	1375456
Antiproteinuric effect of a thromboxane receptor antagonist, S-1452, on rat diabetic nephropathy and murine lupus nephritis.	1995 Jan	7899476
Effect of beraprost sodium, a stable prostacyclin analogue, on pulmonary thromboembolism in mice.	1995 Jan 15	7740511
Role of thromboxane A2, endothelin-1 and endothelin-3 in rat nephrotoxic serum nephritis.	1996 Apr	8804153
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.	1997 Sep	9313928
Binding of YM158, a new dual antagonist for leukotriene D4 and thromboxane A2 receptors, to guinea pig lung membranes.	1998 Dec 4	9874175

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:05:13 UTC 2023` Edited by `admin` on `Sat Dec 16 11:05:13 UTC 2023`
Record UNII	6C4W5D1SE7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOMITROBAN, (±)-

Common Name

English

7-(3-((PHENYLSULFONYL)AMINO)BICYCLO(2.2.1)HEPT-2-YL)-5-HEPTENOIC ACID, (±)-(5Z)-

Systematic Name

English

S-145 (THROMBOXANE ANTAGONIST)

Code

English

(±)-S-145

Code

English

S-145

Code

English

DOMITROBAN (±)-FORM [MI]

Common Name

English

5-HEPTENOIC ACID, 7-((1R,2S,3S,4S)-3-((PHENYLSULFONYL)AMINO)BICYCLO(2.2.1)HEPT-2-YL)-, (5Z)-REL-

Systematic Name

English

Code System Code Type Description

CAS

115266-92-7

Created by admin on Sat Dec 16 11:05:13 UTC 2023 , Edited by admin on Sat Dec 16 11:05:13 UTC 2023

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FDA UNII

6C4W5D1SE7

Created by admin on Sat Dec 16 11:05:13 UTC 2023 , Edited by admin on Sat Dec 16 11:05:13 UTC 2023

PRIMARY

PUBCHEM

5312138

Created by admin on Sat Dec 16 11:05:13 UTC 2023 , Edited by admin on Sat Dec 16 11:05:13 UTC 2023

PRIMARY

MERCK INDEX

m4735

Created by admin on Sat Dec 16 11:05:13 UTC 2023 , Edited by admin on Sat Dec 16 11:05:13 UTC 2023

PRIMARY

Merck Index

Related Record Type Details


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DOMITROBAN

ENANTIOMER -> RACEMATE