Vicriviroc maleate

• CAT Number: I010027
• CAS Number: 599179-03-0
• Molecular Formula: C32H42F3N5O6
• Molecular Weight: 649.71
• Purity: ≥95%
• Synonyms: SCH 417690; SCH-417690; SCH417690; SCH-D; Vicriviroc maleate;(4,6-dimethylpyrimidin-5-yl)(4-((S)-4-((R)-2-methoxy-1-(4-(trifluoromethyl)phenyl)ethyl)-3-methylpiperazin-1-yl)-4-methylpiperidin-1-yl)methanone maleate
• Target: CCR5 entry inhibitor
• Solubility: Soluble in DMSO
• Storage: 0 - 4 °C for short term, or -20 °C for long term
• Related CAS: 306296-47-9(free base)
• IUPAC Name: (Z)-but-2-enedioic acid;(4,6-dimethylpyrimidin-5-yl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methylpiperazin-1-yl]-4-methylpiperidin-1-yl]methanone
• InChI: InChI=1S/C28H38F3N5O2.C4H4O4/c1-19-16-35(14-15-36(19)24(17-38-5)22-6-8-23(9-7-22)28(29,30)31)27(4)10-12-34(13-11-27)26(37)25-20(2)32-18-33-21(25)3;5-3(6)1-2-4(7)8/h6-9,18-19,24H,10-17H2,1-5H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t19-,24-;/m0./s1
• InChIKey: GXINKQQWHLIBJA-UCIBKFKQSA-N
• SMILES: C[C@H]1CN(CCN1[C@@H](COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C.C(=C\C(=O)O)\C(=O)O

Vicriviroc Maleate（Cat No.:I010027）is a potent CCR5 receptor antagonist designed to prevent HIV-1 from entering and infecting immune cells. By blocking the CCR5 co-receptor, Vicriviroc Maleate inhibits the virus’s ability to bind and fuse with host cells, thus preventing viral replication. It has been studied as part of combination antiretroviral therapies aimed at enhancing HIV treatment outcomes. Despite its promise in clinical trials, development was discontinued due to competition from other therapies. Nonetheless, it remains important in research related to HIV, CCR5 biology, and potential treatments for CCR5-tropic viruses.

Reference

1. Expert Opin Drug Metab Toxicol. 2010 Sep;6(9):1139-50. doi:
10.1517/17425255.2010.510833.

Vicriviroc, a new CC-chemokine receptor 5 inhibitor for treatment of HIV:
properties, promises and challenges.

Lenz JC(1), Rockstroh JK.

Author information:
(1)University of Bonn, Medicine I, Sigmund-Freudstr. 25, Bonn 53105, Germany.

IMPORTANCE OF THE FIELD: Although HIV has become a treatable disease with near to
normal life expectancy, the quest for the development of better tolerated drugs
with simple dosing schedules and a high barrier to the emergence of drug
resistance remains. Vicriviroc is a small-molecule chemokine receptor antagonist
that inhibits the binding of R5-tropic HIV-1 to host cells at the CC-chemokine
receptor 5 (CCR5) co-receptor, thus, preventing viral entry. CCR5 inhibitors are
believed to possibly decrease inflammation from the immune system and thereby
offer additional properties further to their antiretroviral efficacy.
AREAS COVERED IN THIS REVIEW: This review is based on a PubMed search covering
the years 2005 – 2010 for pharmacokinetic, pharmacological and clinical data of
vicriviroc.
WHAT THE READER WILL GAIN: In this review, the pharmacokinetic, pharmacological
and clinical data of vicriviroc are presented. Moreover, the potential role of
vicriviroc in the growing HIV armamentarium is discussed.
TAKE HOME MESSAGE: Vicriviroc is being developed to be administered in
combination with a ritonavir-boosted protease inhibitor for patients with
R5-tropic virus. Early clinical trials have established the safety of vicriviroc
in both treatment-naive and -experienced R5-tropic HIV-1 infected individuals.
Recently, two Phase III clinical trials in treatment-experienced patients failed
to prove its superiority over available HIV medications. Phase III trials for
treatment-naive patients are still under planning. Clearly, more favorable study
results are needed to move vicriviroc into drug registration and approval.

2. Curr Opin Investig Drugs. 2009 Aug;10(8):845-59.

Vicriviroc, a CCR5 receptor antagonist for the potential treatment of HIV
infection.

Klibanov OM(1).

Author information:
(1)Wingate University School of Pharmacy, Wingate, NC 28174-0159, USA.


Highly active antiretroviral therapy has revolutionized the care of patients with
HIV infection, but treatment is often complicated by the development of
antiretroviral resistance. CCR5 inhibitors are a novel class of antiretroviral
agents that block the CCR5 receptor, thereby preventing HIV-1 recognition and
entry into CD4+ macrophages and T-cells. Schering-Plough Corp is developing
vicriviroc, a CCR5 inhibitor that has demonstrated good oral bioavailability, has
a long half-life that allows once daily dosing, and is primarily metabolized by
cytochrome P450 CYP3A4. In vitro and clinical data suggest that vicriviroc has
excellent antiviral potency with minimal toxicity. Phase I and II clinical trials
demonstrated promising efficacy results when vicriviroc is administered to
patients infected with CCR5-tropic HIV-1. At the time of publication, phase III
trials were ongoing or planned to investigate the efficacy and safety of
vicriviroc in antiretroviral-naïve and -experienced patients infected with HIV-1.