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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 SCH-546738

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

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

Merck
216
Curator's Comment: # Merck Research Laboratories

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
C-X-C chemokine receptor type 3
2
Target ID: P49682
Gene ID: 2833.0
Gene Symbol: CXCR3
Target Organism: Homo sapiens (Human)
Antagonist
2778
 0.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
III. Identification of novel CXCR3 chemokine receptor antagonists with a pyrazinyl-piperazinyl-piperidine scaffold.
2011 Dec 1
A selective and potent CXCR3 antagonist SCH 546738 attenuates the development of autoimmune diseases and delays graft rejection.
2012 Jan 10
Patents

Patents

US7868005
1

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 Sat Dec 16 15:10:07 GMT 2023
Edited
by admin
on Sat Dec 16 15:10:07 GMT 2023
Record UNII
RKR7RH5HBE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SCH-546738
Code 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
Code System Code Type Description
PUBCHEM
11995774
Created by admin on Sat Dec 16 15:10:07 GMT 2023 , Edited by admin on Sat Dec 16 15:10:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID40475511
Created by admin on Sat Dec 16 15:10:07 GMT 2023 , Edited by admin on Sat Dec 16 15:10:07 GMT 2023
PRIMARY
FDA UNII
RKR7RH5HBE
Created by admin on Sat Dec 16 15:10:07 GMT 2023 , Edited by admin on Sat Dec 16 15:10:07 GMT 2023
PRIMARY
CAS
906805-42-3
Created by admin on Sat Dec 16 15:10:07 GMT 2023 , Edited by admin on Sat Dec 16 15:10:07 GMT 2023
PRIMARY
NIH
NCATS
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