3-Amino-6-chloro-5-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)pyrazine-2-carboxamide, (S)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H31Cl2N7O
Molecular Weight	492.445
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 3-Amino-6-chloro-5-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)pyrazine-2-carboxamide, (S)-

Structure Search

SMILES

CC[C@H]1CN(CCN1C2CCN(CC3=CC=C(Cl)C=C3)CC2)C4=NC(N)=C(N=C4Cl)C(N)=O

InChI

InChIKey=UYDYJFWSPRQEAX-KRWDZBQOSA-N

InChI=1S/C23H31Cl2N7O/c1-2-17-14-31(23-20(25)28-19(22(27)33)21(26)29-23)11-12-32(17)18-7-9-30(10-8-18)13-15-3-5-16(24)6-4-15/h3-6,17-18H,2,7-14H2,1H3,(H2,26,29)(H2,27,33)/t17-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H31Cl2N7O
Molecular Weight	492.445
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22233170

SCH 546738 is a potent and non-competitive CXCR3 antagonist. It was efficacious in multiple preclinical disease models. SCH 546738 may serve as a treatment of autoimmune diseases, including rheumatoid arthritis and multiple sclerosis, and to prevent transplant rejection.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
C-X-C chemokine receptor type 3 2 Target ID: P49682 Gene ID: 2833.0 Gene Symbol: CXCR3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22233170	Antagonist 2849		0.8 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Autoimmune diseases 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22233170	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A selective and potent CXCR3 antagonist SCH 546738 attenuates the development of autoimmune diseases and delays graft rejection.	2012-01-10	22233170
III. Identification of novel CXCR3 chemokine receptor antagonists with a pyrazinyl-piperazinyl-piperidine scaffold.	2011-12-01	22018463

Patents

Sample Use Guides

In Vivo Use Guide

SCH 546738 in 0.4% methylcellulose was administered orally twice daily at doses of 1, 3, 5, 10, 15, 30 and 40 mg/kg.

Route of Administration: Oral

In Vitro Use Guide

In a chemotaxis assay human activated T cells were treated with 1, 10 or 100 nM SCH 546738. SCH 546738 at 10 nM inhibited T cell chemotaxis induced by CXCL9, CXCL10 and CXCL11 about 90%.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 04:25:49 GMT 2025` Edited by `admin` on `Wed Apr 02 04:25:49 GMT 2025`
Record UNII	RKR7RH5HBE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCH-546738

Preferred Name

English

3-Amino-6-chloro-5-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)pyrazine-2-carboxamide, (S)-

Systematic Name

English

(S)-3-Amino-6-chloro-5-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)pyrazine-2-carboxamide

Systematic Name

English

SCH546738

Code

English

3-Amino-6-chloro-5-[(3S)-4-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-3-ethylpiperazin-1-yl]pyrazine-2-carboxamide

Systematic Name

English

2-Pyrazinecarboxamide, 3-amino-6-chloro-5-[(3S)-4-[1-[(4-chlorophenyl)methyl]-4-piperidinyl]-3-ethyl-1-piperazinyl]-

Systematic Name

English

3-Amino-6-chloro-5-[(3S)-4-[1-[(4-chlorophenyl)methyl]-4-piperidinyl]-3-ethyl-1-piperazinyl]-2-pyrazinecarboxamide

Systematic Name

English

Code System Code Type Description

PUBCHEM

11995774

Created by admin on Wed Apr 02 04:25:49 GMT 2025 , Edited by admin on Wed Apr 02 04:25:49 GMT 2025

PRIMARY

EPA CompTox

DTXSID40475511

Created by admin on Wed Apr 02 04:25:49 GMT 2025 , Edited by admin on Wed Apr 02 04:25:49 GMT 2025

PRIMARY

FDA UNII

RKR7RH5HBE

Created by admin on Wed Apr 02 04:25:49 GMT 2025 , Edited by admin on Wed Apr 02 04:25:49 GMT 2025

PRIMARY

CAS

906805-42-3

Created by admin on Wed Apr 02 04:25:49 GMT 2025 , Edited by admin on Wed Apr 02 04:25:49 GMT 2025

PRIMARY

Related Record Type Details


					5Z9PG57ZKD

3-Amino-6-chloro-5-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)pyrazine-2-carboxamide, (R)-

ENANTIOMER -> ENANTIOMER

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Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22233170

Originator

Approval Year

Targets

Conditions

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22233170