SSR-182289A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H33F2N5O4S.ClH
Molecular Weight	634.137
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(=O)NC1=C(C=CC=C1C2=CC=CC=C2)S(=O)(=O)N[C@@H](CCCC3=NC=C(N)C=C3)C(=O)N4CCC(CC4)=C(F)F

InChI

InChIKey=JOWCHVSUAJPEIA-SNYZSRNZSA-N

InChI=1S/C30H33F2N5O4S.ClH/c1-20(38)35-28-25(21-7-3-2-4-8-21)10-6-12-27(28)42(40,41)36-26(11-5-9-24-14-13-23(33)19-34-24)30(39)37-17-15-22(16-18-37)29(31)32;/h2-4,6-8,10,12-14,19,26,36H,5,9,11,15-18,33H2,1H3,(H,35,38);1H/t26-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C30H33F2N5O4S
Molecular Weight	597.676
Charge	0
Count

Stereochemistry	ABSOLUTE
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

Approval Year

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:59:49 GMT 2023` Edited by `admin` on `Sat Dec 16 02:59:49 GMT 2023`
Record UNII	TJU7LB4AF2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SSR-182289A

Code

English

N-(2-(((1S)-4-(5-AMINO-2-PYRIDYL)-1-(4-(DIFLUOROMETHYLENE)PIPERIDINE-1-CARBONYL)BUTYL)SULFAMOYL)-6-PHENYL-PHENYL)ACETAMIDE HYDROCHLORIDE

Systematic Name

English

ACETAMIDE, N-(3-((((1S)-4-(5-AMINO-2-PYRIDINYL)-1-((4-(DIFLUOROMETHYLENE)-1-PIPERIDINYL)CARBONYL)BUTYL)AMINO)SULFONYL)(1,1'-BIPHENYL)-2-YL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

ACETAMIDE, N-(3-((((1S)-4-(5-AMINO-2-PYRIDINYL)-1-((4-(DIFLUOROMETHYLENE)-1-PIPERIDINYL)CARBONYL)BUTYL)AMINO)SULFONYL)(1,1'-BIPHENYL)-2-YL)-, MONOHYDROCHLORIDE

Systematic Name

English

SSR182289A

Code

English

Code System Code Type Description

FDA UNII

TJU7LB4AF2

Created by admin on Sat Dec 16 02:59:49 GMT 2023 , Edited by admin on Sat Dec 16 02:59:49 GMT 2023

PRIMARY

PUBCHEM

69820681

Created by admin on Sat Dec 16 02:59:49 GMT 2023 , Edited by admin on Sat Dec 16 02:59:49 GMT 2023

PRIMARY

CAS

362615-85-8

Created by admin on Sat Dec 16 02:59:49 GMT 2023 , Edited by admin on Sat Dec 16 02:59:49 GMT 2023

PRIMARY

Related Record Type Details


					H6SN9DF6JS

SSR-182289

ACTIVE MOIETY

Comments:

Class: Antithrombotic; Mechanism of Action: Thrombin inhibitor; Highest Development Phase: Discontinued for Thrombosis; Most Recent Event: 23 Mar 2009 Discontinued - Phase-II for Thrombosis in Europe (PO)


					H6SN9DF6JS

SSR-182289

ACTIVE MOIETY

Comments:

The compound is a potent inhibitor of thrombin's activities in vitro and demonstrates potent oral anti-thrombotic potencies in three rat models of thrombosis. The observed in vitro potency could be rationalized through the examination of the interactions within the SSR182289A 1 - thrombin crystal structure. SSR182289A 1, has been therefore selected for further development.


					H6SN9DF6JS

SSR-182289

ACTIVE MOIETY

Comments:

SSR182289A competitively inhibits human thrombin (K(i) = 0.031 +/- 0.002 microM) and shows good selectivity with respect to other human proteases, e.g., trypsin (K(i) = 54 +/- 2 microM), factor Xa (K(i) = 167 +/- 9 microM), and factor VIIa, factor IXa, plasmin, urokinase, tPA, kallikrein, and activated protein C (all K(i) values >250 microM). In human plasma, SSR182289A demonstrated anticoagulant activity in vitro as measured by standard clotting parameters (EC100 thrombin time 96 +/- 7 nM) and inhibited tissue factor-induced thrombin generation (IC50 of 0.15 +/- 0.02 microM). Hence, SSR182289A is a potent, selective, and orally active thrombin inhibitor.