Vicriviroc Malate

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MedKoo CAT#: 565053

CAS#: 541503-81-5 (malate)

Description: Vicriviroc, also known as SCH 417690, MK-7690 and SCH-D, is a potent, orally active and selective CCR5 entry inhibitor of HIV-1 (IC50 = 0.91 nM). Vicriviroc effectively inhibits the initial stages of the virus life cycle. Vicriviroc demonstrated synergistic anti-HIV activity in combination with drugs from all other classes of approved antiretrovirals. Vicriviroc binds with higher affinity to CCR5 than SCH-C. Functional assays, including inhibition of calcium flux, guanosine 5'-[35S]triphosphate exchange, and chemotaxis, confirmed that vicriviroc acts as a receptor antagonist by inhibiting signaling of CCR5 by chemokines. Vicriviroc demonstrated diminished affinity for the human ether a-go-go related gene transcript ion channel compared to SCH-C, suggesting a reduced potential for cardiac effects. Vicriviroc represents a promising new candidate for the treatment of HIV-1 infection.

Chemical Structure

Vicriviroc Malate
CAS# 541503-81-5 (malate)

Theoretical Analysis

MedKoo Cat#: 565053
Name: Vicriviroc Malate
CAS#: 541503-81-5 (malate)
Chemical Formula: C32H44F3N5O7
Exact Mass: 0.00
Molecular Weight: 667.730
Elemental Analysis: C, 57.56; H, 6.64; F, 8.54; N, 10.49; O, 16.77

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Related CAS #: 306296-47-9 (free base)   541503-81-5 (malate)   599179-03-0 (maleate)   541503-48-4 (HCl)    

Synonym: MK 7690; MK-7690; MK7690; SCH 417690; SCH-417690; SCH417690; SCH-D; SCH-D; Vicriviroc Malate

IUPAC/Chemical Name: (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 malate


InChi Code: InChI=1S/C28H38F3N5O2.C4H6O5/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;5-2(4(8)9)1-3(6)7/h6-9,18-19,24H,10-17H2,1-5H3;2,5H,1H2,(H,6,7)(H,8,9)/t19-,24-;/m0./s1

SMILES Code: O=C(C1=C(C)N=CN=C1C)N2CCC(C)(N3C[C@H](C)N([C@H](C4=CC=C(C(F)(F)F)C=C4)COC)CC3)CC2.OC(CC(O)=O)C(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 667.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Liu AY, Zhang J, Anderson PL, Wagner T, Pan Z, Peda M, Gomez K, Beamer M, Jacobson C, Strizki J, Dezzutti CS, Piper JM; MTN-028 Protocol Team for the Microbicide Trials Network. Phase 1 Pharmacokinetic Trial of 2 Intravaginal Rings Containing Different Dose Strengths of Vicriviroc (MK-4176) and MK-2048. Clin Infect Dis. 2019 Mar 19;68(7):1129-1135. doi: 10.1093/cid/ciy652. PMID: 30289444; PMCID: PMC6424086.

2: Hoesley CJ, Chen BA, Anderson PL, Dezzutti CS, Strizki J, Sprinkle C, Heard F, Bauermeister J, Hall W, Jacobson C, Berthiaume J, Mayo A, Gundacker H, Richardson-Harman N, Piper J; Microbicide Trials Network 027 Study Team. Phase 1 Safety and Pharmacokinetics Study of MK-2048/Vicriviroc (MK-4176)/MK-2048A Intravaginal Rings. Clin Infect Dis. 2019 Mar 19;68(7):1136-1143. doi: 10.1093/cid/ciy653. PMID: 30289435; PMCID: PMC6424075.

3: Hesk D, Borges S, Hendershot S, Koharski D, McNamara P, Ren S, Saluja S, Truong V, Voronin K. Synthesis of (3) H, (2) H4 and (14) C-SCH 417690 (Vicriviroc). J Labelled Comp Radiopharm. 2016 May 15;59(5):190-6. doi: 10.1002/jlcr.3387. Epub 2016 Mar 14. PMID: 26991320.

4: Asin-Milan O, Chamberland A, Wei Y, Haidara A, Sylla M, Tremblay CL. Mutations in variable domains of the HIV-1 envelope gene can have a significant impact on maraviroc and vicriviroc resistance. AIDS Res Ther. 2013 Jun 7;10(1):15. doi: 10.1186/1742-6405-10-15. PMID: 23758814; PMCID: PMC3700831.

5: McNicholas P, Vilchez RA, Greaves W, Kumar S, Onyebuchi C, Black T, Strizki JM. Detection of HIV-1 CXCR4 tropism and resistance in treatment experienced subjects receiving CCR5 antagonist-Vicriviroc. J Clin Virol. 2012 Oct;55(2):134-9. doi: 10.1016/j.jcv.2012.06.021. Epub 2012 Jul 21. PMID: 22824230.

6: Caseiro MM, Nelson M, Diaz RS, Gathe J, de Andrade Neto JL, Slim J, Solano A, Netto EM, Mak C, Shen J, Greaves W, Dunkle LM, Vilchez RA, Zeinecker J. Vicriviroc plus optimized background therapy for treatment-experienced subjects with CCR5 HIV-1 infection: final results of two randomized phase III trials. J Infect. 2012 Oct;65(4):326-35. doi: 10.1016/j.jinf.2012.05.008. Epub 2012 May 24. PMID: 22634184.

7: Tsibris AM, Hu Z, Paredes R, Leopold KE, Putcharoen O, Schure AL, Mazur N, Coakley E, Su Z, Gulick RM, Kuritzkes DR. Vicriviroc resistance decay and relative replicative fitness in HIV-1 clinical isolates under sequential drug selection pressures. J Virol. 2012 Jun;86(12):6416-26. doi: 10.1128/JVI.00286-12. Epub 2012 Apr 4. PMID: 22491471; PMCID: PMC3393533.

8: Berro R, Klasse PJ, Jakobsen MR, Gorry PR, Moore JP, Sanders RW. V3 determinants of HIV-1 escape from the CCR5 inhibitors Maraviroc and Vicriviroc. Virology. 2012 Jun 5;427(2):158-65. doi: 10.1016/j.virol.2012.02.006. Epub 2012 Mar 16. Erratum in: Virology. 2012 Jun 20;428(1):76. Jakobsen, Martin R [added]; Gorry, Paul R [added]. PMID: 22424737; PMCID: PMC3320651.

9: Kasserra C, Li J, March B, O'Mara E. Effect of vicriviroc with or without ritonavir on oral contraceptive pharmacokinetics: a randomized, open-label, parallel-group, fixed-sequence crossover trial in healthy women. Clin Ther. 2011 Oct;33(10):1503-14. doi: 10.1016/j.clinthera.2011.08.012. Epub 2011 Oct 19. PMID: 22015327.

10: Kasserra C, O'Mara E. Pharmacokinetic interaction of vicriviroc with other antiretroviral agents: results from a series of fixed-sequence and parallel- group clinical trials. Clin Pharmacokinet. 2011 Apr;50(4):267-80. doi: 10.2165/11584560-000000000-00000. PMID: 21348539.

11: McNicholas PM, Mann PA, Wojcik L, Qiu P, Lee E, McCarthy M, Shen J, Black TA, Strizki JM. Mapping and characterization of vicriviroc resistance mutations from HIV-1 isolated from treatment-experienced subjects enrolled in a phase II study (VICTOR-E1). J Acquir Immune Defic Syndr. 2011 Mar 1;56(3):222-9. doi: 10.1097/QAI.0b013e3181ff63ee. PMID: 21209592.

12: Lenz JC, Rockstroh JK. Vicriviroc, a new CC-chemokine receptor 5 inhibitor for treatment of HIV: properties, promises and challenges. Expert Opin Drug Metab Toxicol. 2010 Sep;6(9):1139-50. doi: 10.1517/17425255.2010.510833. PMID: 20712521.

13: Wilkin TJ, Su Z, Krambrink A, Long J, Greaves W, Gross R, Hughes MD, Flexner C, Skolnik PR, Coakley E, Godfrey C, Hirsch M, Kuritzkes DR, Gulick RM. Three- year safety and efficacy of vicriviroc, a CCR5 antagonist, in HIV-1-infected treatment-experienced patients. J Acquir Immune Defic Syndr. 2010 Aug;54(5):470-6. doi: 10.1097/qai.0b013e3181e2cba0. PMID: 20672447; PMCID: PMC2917795.

14: Kasserra C, Sansone-Parsons A, Keung A, Tetteh E, Assaf M, O'Mara E, Marbury T. Renal insufficiency has no effect on the pharmacokinetics of vicriviroc in a ritonavir-containing regimen. Clin Pharmacokinet. 2010 Jun;49(6):397-406. doi: 10.2165/11319470-000000000-00000. PMID: 20481650.

15: Yeh TM, Evans SR, Gulick RM, Clifford DB. Vicriviroc and peripheral neuropathy: results from AIDS Clinical Trials Group 5211. HIV Clin Trials. 2010 Jan-Feb;11(1):51-8. doi: 10.1310/hct1101-51. PMID: 20400411; PMCID: PMC2958041.

16: McNicholas P, Wei Y, Whitcomb J, Greaves W, Black TA, Tremblay CL, Strizki JM. Characterization of emergent HIV resistance in treatment-naive subjects enrolled in a vicriviroc phase 2 trial. J Infect Dis. 2010 May 15;201(10):1470-80. doi: 10.1086/652189. PMID: 20373959.

17: O'Mara E, Kasserra C, Huddlestone JR, Wan Y, Soni P, Caceres M, Medlock M, Morrison R, Devinsky O. Effect of vicriviroc on the QT/corrected QT interval and central nervous system in healthy subjects. Antimicrob Agents Chemother. 2010 Jun;54(6):2448-54. doi: 10.1128/AAC.01447-09. Epub 2010 Mar 29. PMID: 20350942; PMCID: PMC2876383.

18: Disappointing results for vicriviroc. AIDS Patient Care STDS. 2010 Mar;24(3):197-8. PMID: 20238442.

19: Ogert RA, Hou Y, Ba L, Wojcik L, Qiu P, Murgolo N, Duca J, Dunkle LM, Ralston R, Howe JA. Clinical resistance to vicriviroc through adaptive V3 loop mutations in HIV-1 subtype D gp120 that alter interactions with the N-terminus and ECL2 of CCR5. Virology. 2010 Apr 25;400(1):145-55. doi: 10.1016/j.virol.2010.01.037. Epub 2010 Feb 21. PMID: 20172579.

20: Crawford KW, Li C, Keung A, Su Z, Hughes MD, Greaves W, Kuritzkes D, Gulick R, Flexner C; ACTG A5211 Study Team. Pharmacokinetic/pharmacodynamic modeling of the antiretroviral activity of the CCR5 antagonist Vicriviroc in treatment experienced HIV-infected subjects (ACTG protocol 5211). J Acquir Immune Defic Syndr. 2010 Apr;53(5):598-605. doi: 10.1097/QAI.0b013e3181c9caac. PMID: 20071999; PMCID: PMC2862681.