ANCRIVIROC

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H37BrN4O3
Molecular Weight	557.522
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCO\N=C(\C1CCN(CC1)C2(C)CCN(CC2)C(=O)C3=C(C)[N+]([O-])=CC=C3C)C4=CC=C(Br)C=C4

InChI

InChIKey=ZGDKVKUWTCGYOA-URGPHPNLSA-N

InChI=1S/C28H37BrN4O3/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/h6-10,17,23H,5,11-16,18-19H2,1-4H3/b30-26+

HIDE SMILES / InChI

Molecular Formula	C28H37BrN4O3
Molecular Weight	557.522
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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
Discovery and characterization of vicriviroc (SCH 417690), a CCR5 antagonist with potent activity against human immunodeficiency virus type 1.	2005 Dec	16304152
Structural and molecular interactions of CCR5 inhibitors with CCR5.	2006 May 5	16476734

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:40:15 UTC 2023` Edited by `admin` on `Fri Dec 15 15:40:15 UTC 2023`
Record UNII	322WXU4AU2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANCRIVIROC

Official 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)-

Common Name

English

4-((Z)-(4-BROMOPHENYL)(ETHOXYIMINO)METHYL)-1'-((2,4-DIMETHYL-1-OXIDOPYRIDIN-3-YL)CARBONYL)-4'-METHYL(1,4'-BIPIPERIDINYL)

Systematic Name

English

SCH351125

Code

English

ANCRIVIROC [USAN]

Common Name

English

SCH-351125

Code

English

ancriviroc [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1660