FASITIBANT CHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H49Cl2N6O6S.Cl
Molecular Weight	800.235
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].CC1=NC2=C(C=CC=C2OCC3=C(Cl)C=CC(=C3Cl)S(=O)(=O)NC4(CCOCC4)C(=O)N5CCN(CC5)C(=O)[C@@H](N)CCC[N+](C)(C)C)C(C)=C1

InChI

InChIKey=ZNHJDJYKDVGQSH-JMAPEOGHSA-M

InChI=1S/C36H49Cl2N6O6S.ClH/c1-24-22-25(2)40-33-26(24)8-6-10-30(33)50-23-27-28(37)11-12-31(32(27)38)51(47,48)41-36(13-20-49-21-14-36)35(46)43-17-15-42(16-18-43)34(45)29(39)9-7-19-44(3,4)5;/h6,8,10-12,22,29,41H,7,9,13-21,23,39H2,1-5H3;1H/q+1;/p-1/t29-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C36H49Cl2N6O6S
Molecular Weight	764.782
Charge	1
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17266207 | https://adisinsight.springer.com/drugs/800024707 | https://www.ncbi.nlm.nih.gov/pubmed/22638761 | https://www.ncbi.nlm.nih.gov/pubmed/19745108 | https://www.ncbi.nlm.nih.gov/pubmed/23973149 | https://clinicaltrials.gov/ct2/show/NCT02205814

Fasitibant (MEN-16132) is a non-peptide sulfonamide-containing bradykinin hB2 receptor antagonist. It inhibits pro-inflammatory response in vitro and alleviates inflammatory hyperalgesia in rodent models of osteoarthritis. Menarini Group was developing fasitibant for the treatment of osteoarthritis. Fasitibant development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
B2 bradykinin receptor 3 Target ID: P30411 Gene ID: 624.0 Gene Symbol: BDKRB2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17266207 \| https://www.ncbi.nlm.nih.gov/pubmed/16324696 \| https://www.ncbi.nlm.nih.gov/pubmed/21108627	Antagonist 2778		10.3 null [pKi]

PubMed

Title	Date	PubMed
Design and synthesis of novel sulfonamide-containing bradykinin hB2 receptor antagonists. 2. Synthesis and structure-activity relationships of alpha,alpha-cycloalkylglycine sulfonamides.	2007 Feb 8	17266207
Fasitibant prevents the bradykinin and interleukin 1β synergism on prostaglandin E₂ release and cyclooxygenase 2 expression in human fibroblast-like synoviocytes.	2012 Aug	22638761

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Other

In Vitro Use Guide

Incubation of synoviocytes with BK induced a sustained production of PGE(2) and transient COX-2 gene expression that were prevented by pretreatment with fasitibant (1 μM, 30 min preincubation).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:13:24 GMT 2023` Edited by `admin` on `Fri Dec 15 20:13:24 GMT 2023`
Record UNII	7J764K70IG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FASITIBANT CHLORIDE

Official Name

English

fasitibant chloride [INN]

Common Name

English

(4S)-4-AMINO-5-(4-(4-(2,4-DICHLORO-3-(((2,4-DIMETHYLQUINOLIN-8-YL)OXY)METHYL)BENZENESULFONAMIDO)OXANE-4-CARBONYL)PIPERAZIN-1-YL)-N,N,N-TRIMETHYL-5-OXOPENTAN-1-AMINIUM CHLORIDE

Common Name

English

1-PIPERAZINEPENTANAMINIUM, .DELTA.-AMINO-4-((4-(((2,4-DICHLORO-3-(((2,4-DIMETHYL-8-QUINOLINYL)OXY)METHYL)PHENYL)SULFONYL)AMINO)TETRAHYDRO-2H-PYRAN-4-YL)CARBONYL)-N,N,N-TRIMETHYL-.EPSILON.-OXO-, CHLORIDE (1:1), (.DELTA.S)-

Common Name

English

Fasitibant chloride [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

11535140