Vicriviroc maleate

Category	Human immunodeficiency Virus (HIV)
CAS	599179-03-0
Description	Vicriviroc maleate is a CCR5 antagonist.

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Product Information

Synonyms	1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-piperidine (2Z)-2-butenedioate (1:1)
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
Molecular Weight	649.7
Molecular Formula	C32H42F3N5O6
Canonical SMILES	CC1CN(CCN1C(COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C.C(=CC(=O)O)C(=O)O
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
Boiling Point	608.1°C at 760mmHg
Melting Point	>177°C (dec.)
Purity	≥98% (HPLC)
Solubility	10 mM in DMSO
Appearance	White to Off-White Solid
Storage	Please store the product under the recommended conditions in the Certificate of Analysis.
Complexity	892
Exact Mass	649.30871856
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). 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.
In Vivo	Vicriviroc (10 mg/kg) has good oral availablity in rats and monkeys, with no acute CNS or GI effects in rats.
PSA	136.40000
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)