CAS 599179-03-0|vicriviroc maleate

Introduction：Basic information about CAS 599179-03-0|vicriviroc maleate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. vicriviroc maleate BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	vicriviroc maleate
CAS Number	599179-03-0	Molecular Weight	649.701
Density	/	Boiling Point	608.1ºC at 760mmHg
Molecular Formula	C₃₂H₄₂F₃N₅O₆	Melting Point	/
MSDS	/	Flash Point	/

Names

Name	Vicriviroc Maleate
Synonym	More Synonyms

vicriviroc maleate BiologicalActivity

Description	Vicriviroc maleate is a potent, selective, oral bioavailable and CNS penetrated antagonist of CCR5, with a Ki of 2.5 nM, and also inhibits HIV-1 in PBMC cells, with IC90s of 3.3 nM (JrFL), 2.8 nM (ADA-M), 1.8 nM (301657), 4.9 nM (JV1083) and 10 nM (RU 570).
Related Catalog	Signaling Pathways >>Anti-infection >>HIVResearch Areas >>Infection
Target	CCR5:2.5 nM (Ki) HIV-1 (301657):1.8 nM (IC90, in PBMC cells) HIV-1 (ADA-M):2.8 nM (IC90, in PBMC cells) HIV-1 (JrFL):3.3 nM (IC90, in PBMC cells) HIV-1 (JV1083):4.9 nM (IC90, in PBMC cells) HIV-1 (RU 570):10 nM (IC90, in PBMC cells)
In Vitro	Vicriviroc (Sch-417690/Sch-D) is a potent, selective and oral bioavailable inhibitor of CCR5, with a Ki of 2.5 nM, and also inhibits HIV-1 in PBMC cells, with IC90s of 3.3 (JrFL), 2.8 (ADA-M), 1.8 (301657), 4.9 (JV1083) and 10 nM (RU 570). In addition, Vicriviroc shows a mean IC50 and IC90 of 0.45 nM and 4 nM for a panel of HIV isolates, and has weak activity against hERG activity (IC50, 5.8 μM)[1]. Vicriviroc inhibits chemotactic response to MIP-1α with IC50 values below 1 nM, and suppresses RANTES-induced signaling with a mean IC50 of 4.2 ± 1.3 nM. Vicriviroc potently suppresses all the viral isolates tested, with geometric mean EC50s of 0.04-2.3 nM and IC90s of 0.45-18 nM[2].
In Vivo	Vicriviroc (10 mg/kg) has good oral availablity in rats and monkeys, with no acute CNS or GI effects in rats[1].
Cell Assay	Ficoll-purified peripheral blood mononuclear cells (PBMCs) are stimulated in vitro with phytohemagglutinin (PHA) (5 μg/mL) and interleukin-2 (IL-2) (50 U/mL) for 3 to 7 days. The cells are resuspended at 4 × 106/mL in complete medium (RPMI, 10% fetal bovine serum [FBS], 50 U/mL IL-2), seeded into 96-well plates (2 × 105/well), incubated with an equal volume of culture medium containing compound (Vicriviroc) for 1 h at 37°C, and infected in triplicate with 25 to 100 50% tissue culture infectious doses (TCID50) per well of viral inoculum for 3 to 4 h. Cells are washed twice in phosphate-buffered saline (PBS) to remove residual virus and are cultured with compound for 4 to 6 days. HIV-1 replication is quantified by measurement of extracellular p24 antigen in the supernatants by enzyme-linked immunosorbent assay. The 50% effective concentrations (EC50s) and EC90s for each virus are determined using Graphpad PRISM software[2].
References	[1]. Tagat JR, et al. Piperazine-based CCR5 antagonists as HIV-1 inhibitors. IV. Discovery of 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]- 4-[4-[2-methoxy-1(R)-4-(trifluoromethyl)phenyl]ethyl-3(S)-methyl-1-piperazinyl]- 4-methylpiperidine (Sch-417690/Sch-D), a potent, highly selective, and orally bioavailable CCR5 antagonist. J Med Chem. 2004 May 6;47(10):2405-8. [2]. Strizki JM, et al. Discovery and characterization of vicriviroc (SCH 417690), a CCR5 antagonist with potent activity against human immunodeficiency virus type 1. Antimicrob Agents Chemother. 2005 Dec;49(12):4911-9.

Chemical & Physical Properties

Boiling Point	608.1ºC at 760mmHg
Molecular Formula	C₃₂H₄₂F₃N₅O₆
Molecular Weight	649.701
Exact Mass	649.308716
PSA	136.40000
LogP	4.02620
InChIKey	GXINKQQWHLIBJA-UCIBKFKQSA-N
SMILES	COCC(c1ccc(C(F)(F)F)cc1)N1CCN(C2(C)CCN(C(=O)c3c(C)ncnc3C)CC2)CC1C.O=C(O)C=CC(=O)O
Storage condition	2-8℃

Synonyms

VICRIVIROC MALEATE: SCH-D

vicriviroc Maleate salt

(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 (2Z)-but-2-enedioate (1:1)

(4,6-Dimethyl-5-pyrimidinyl){4-[(3S)-4-{(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl}-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl}methanone (2Z)-2-butenedioate (1:1)

Methanone, (4,6-dimethyl-5-pyrimidinyl)[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]-, (2Z)-2-butenedioate (1:1)

vicriviroc maleate

SCH-D

Unii-ep3qg127N9

Sch-417690

Vicriviroc (maleate)

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