ANCRIVIROC BESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H37BrN4O3.C6H6O3S
Molecular Weight	715.697
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC=CC=C1.CCO\N=C(\C2CCN(CC2)C3(C)CCN(CC3)C(=O)C4=C(C)C=C[N+]([O-])=C4C)C5=CC=C(Br)C=C5

InChI

InChIKey=RVIRPEALZXBUMV-REAKUJNMSA-N

InChI=1S/C28H37BrN4O3.C6H6O3S/c1-5-36-30-26(22-6-8-24(29)9-7-22)23-11-15-32(16-12-23)28(4)13-18-31(19-14-28)27(34)25-20(2)10-17-33(35)21(25)3;7-10(8,9)6-4-2-1-3-5-6/h6-10,17,23H,5,11-16,18-19H2,1-4H3;1-5H,(H,7,8,9)/b30-26+;

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11959565 | https://www.ncbi.nlm.nih.gov/pubmed/12054083 | https://adisinsight.springer.com/drugs/800014207 | https://www.ncbi.nlm.nih.gov/pubmed/11585437 | https://www.ncbi.nlm.nih.gov/pubmed/26087764

Ancriviroc (SCH 351125) is a small-molecule antagonist of the human immunodeficiency virus type 1(HIV-1) coreceptor CCR5. It has in vitro activity against R5 viruses with 50% inhibitory concentrations ranging from 1.0 to 30.9 nM. Ancriviroc is an orally bioavailable small molecule inhibitor of HIV-1 entry via CCR5 coreceptor interaction. Ancriviroc has potent activity against RANTES binding (K(i) = 2 nM), possesses subnanomolar activity in blocking viral entry and has excellent antiviral potency versus a panel of primary HIV-1 viral isolates. Ancriviroc had been in phase I clinical trials by Schering-Plough (subsidiary of Merck Sharp & Dohme) for the treatment of HIV infection. However, this research has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Structural and molecular interactions of CCR5 inhibitors with CCR5.	2006-05-05	16476734
Discovery and characterization of vicriviroc (SCH 417690), a CCR5 antagonist with potent activity against human immunodeficiency virus type 1.	2005-12	16304152
Discovery of 4-[(Z)-(4-bromophenyl)- (ethoxyimino)methyl]-1'-[(2,4-dimethyl-3- pyridinyl)carbonyl]-4'-methyl-1,4'- bipiperidine N-oxide (SCH 351125): an orally bioavailable human CCR5 antagonist for the treatment of HIV infection.	2001-10-11	11585437

Patents

Sample Use Guides

In Vivo Use Guide

Oral doses of either 50 or 100 mg b.i.d., 10 days monotherapy

Route of Administration: Oral

In Vitro Use Guide

Ancriviroc (SCH 351125) has broad and potent antiviral activity in vitro against primary HIV-1 isolates that use CCR5 as their entry coreceptor, with mean 50% inhibitory concentrations ranging between 0.4 and 9 nM.

Name

Type

Language

SCH-351125 BESYLATE

Preferred Name

English

ANCRIVIROC BESYLATE

Common Name

English

(1,4'-BIPIPERIDINE)-4-METHANIMINE, .ALPHA.-(4-BROMOPHENYL)-1'-((2,4-DIMETHYL-1-OXIDO-3-PYRIDINYL)CARBONYL)-N-ETHOXY-4'-METHYL-, (.ALPHA.Z)-, BENZENESULFONATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

9875058

Created by admin on Mon Mar 31 18:12:58 GMT 2025 , Edited by admin on Mon Mar 31 18:12:58 GMT 2025

PRIMARY

CAS

565428-86-6

Created by admin on Mon Mar 31 18:12:58 GMT 2025 , Edited by admin on Mon Mar 31 18:12:58 GMT 2025

NON-SPECIFIC STOICHIOMETRY

FDA UNII