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MedKoo Cat#: 326931 | Name: Aplaviroc HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aplaviroc, also known as AK-602; GW-873140; GW873140A; ONO-4128, is a CCR5 entry inhibitor for the potential treatment of HIV infection. Aplaviroc (GW873140) binds specifically to human cellular CC chemokine receptor 5 (CCR5) and demonstrates potent anti-human immunodeficiency virus activity in vitro in the subnanomolar range. In vitro studies show that aplaviroc selectively inhibits the binding of a particular monoclonal antibody, 45531, to CCR5.

Chemical Structure

Aplaviroc HCl
Aplaviroc HCl
CAS#461023-63-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 326931

Name: Aplaviroc HCl

CAS#: 461023-63-2 (HCl)

Chemical Formula: C33H44ClN3O6

Exact Mass: 0.0000

Molecular Weight: 614.18

Elemental Analysis: C, 64.54; H, 7.22; Cl, 5.77; N, 6.84; O, 15.63

Price and Availability

Size Price Availability Quantity
5mg USD 650.00 2 Weeks
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Related CAS #
461443-59-4 (free base) 461023-63-2 (HCl)
Synonym
AK-602; AK602; AK 602; GW873140A; GW-873140; GW873140; GW 873140; ONO-4128; ONO 4128; ONO4128; Aplaviroc hydrochloride
IUPAC/Chemical Name
4-(4-(((3R)-1-Butyl-3-((R)-cyclohexylhydroxymethyl)-2,5-dioxo-1,4,9- triazaspiro(5.5)undec-9-yl)methyl)phenoxy)benzoic acid hydrochloride
InChi Key
QNNBMSGFNQRUEH-PQQSRXGVSA-N
InChi Code
InChI=1S/C33H43N3O6.ClH/c1-2-3-19-36-30(38)28(29(37)24-7-5-4-6-8-24)34-32(41)33(36)17-20-35(21-18-33)22-23-9-13-26(14-10-23)42-27-15-11-25(12-16-27)31(39)40;/h9-16,24,28-29,37H,2-8,17-22H2,1H3,(H,34,41)(H,39,40);1H/t28-,29-;/m1./s1
SMILES Code
O=C(O)C1=CC=C(OC2=CC=C(CN(CC3)CCC3(N(CCCC)C([C@@H]([C@@H](C4CCCCC4)O)N5)=O)C5=O)C=C2)C=C1.[H]Cl
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
>2 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
Related CAS# 461443-59-4 (Aplaviroc) 461023-63-2 (Aplaviroc hydrochloride)

Preparing Stock Solutions

The following data is based on the product molecular weight 614.18 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
1: Crabb C. GlaxoSmithKline ends aplaviroc trials. AIDS. 2006 Mar 21;20(5):641. doi: 10.1097/01.aids.0000216362.59657.96. PMID: 16514292. 2: Kitrinos KM, Amrine-Madsen H, Irlbeck DM, Word JM, Demarest JF; CCR100136 Study Team. Virologic failure in therapy-naive subjects on aplaviroc plus lopinavir-ritonavir: detection of aplaviroc resistance requires clonal analysis of envelope. Antimicrob Agents Chemother. 2009 Mar;53(3):1124-31. doi: 10.1128/AAC.01057-08. Epub 2008 Dec 15. PMID: 19075068; PMCID: PMC2650553. 3: Johnson BM, Song IH, Adkison KK, Borland J, Fang L, Lou Y, Berrey MM, Nafziger AN, Piscitelli SC, Bertino JS Jr. Evaluation of the drug interaction potential of aplaviroc, a novel human immunodeficiency virus entry inhibitor, using a modified cooperstown 5 + 1 cocktail. J Clin Pharmacol. 2006 May;46(5):577-87. doi: 10.1177/0091270006287291. PMID: 16638741. 4: Demarest JF, Sparks SS, Schell K, Shibayama S, McDanal CB, Fang L, Adkison KK, Shachoy-Clark A, Piscitelli SC. In vitro and clinical investigation of the relationship between CCR5 receptor occupancy and anti-HIV activity of Aplaviroc. J Clin Pharmacol. 2008 Oct;48(10):1179-88. doi: 10.1177/0091270008322178. Epub 2008 Aug 1. PMID: 18676693. 5: Latinovic O, Heredia A, Gallo RC, Reitz M, Le N, Redfield RR. Rapamycin enhances aplaviroc anti-HIV activity: implications for the clinical development of novel CCR5 antagonists. Antiviral Res. 2009 Jul;83(1):86-9. doi: 10.1016/j.antiviral.2009.02.199. Epub 2009 Mar 9. PMID: 19501260. 6: Nichols WG, Steel HM, Bonny T, Adkison K, Curtis L, Millard J, Kabeya K, Clumeck N. Hepatotoxicity observed in clinical trials of aplaviroc (GW873140). Antimicrob Agents Chemother. 2008 Mar;52(3):858-65. doi: 10.1128/AAC.00821-07. Epub 2007 Dec 10. PMID: 18070967; PMCID: PMC2258506. 7: Demarest JF, Amrine-Madsen H, Irlbeck DM, Kitrinos KM; CCR102881 Clinical Study Team. Virologic failure in first-line human immunodeficiency virus therapy with a CCR5 entry inhibitor, aplaviroc, plus a fixed-dose combination of lamivudine-zidovudine: nucleoside reverse transcriptase inhibitor resistance regardless of envelope tropism. Antimicrob Agents Chemother. 2009 Mar;53(3):1116-23. doi: 10.1128/AAC.01055-08. Epub 2008 Dec 15. PMID: 19075055; PMCID: PMC2650552. 8: Yeni P, Lamarca A, Berger D, Cimoch P, Lazzarin A, Salvato P, Smaill FM, Teofilo E, Madison SJ, Nichols WG, Adkison KK, Bonny T, Millard J, McCarty D; EPIC (CCR100136) study team. Antiviral activity and safety of aplaviroc, a CCR5 antagonist, in combination with lopinavir/ritonavir in HIV-infected, therapy- naïve patients: results of the EPIC study (CCR100136). HIV Med. 2009 Feb;10(2):116-24. doi: 10.1111/j.1468-1293.2008.00660.x. PMID: 19200175. 9: Adkison KK, Shachoy-Clark A, Fang L, Lou Y, Otto VR, Berrey MM, Piscitelli SC. The effects of ritonavir and lopinavir/ritonavir on the pharmacokinetics of a novel CCR5 antagonist, aplaviroc, in healthy subjects. Br J Clin Pharmacol. 2006 Sep;62(3):336-44. doi: 10.1111/j.1365-2125.2006.02661.x. PMID: 16934050; PMCID: PMC1885134. 10: Nakata H, Steinberg SM, Koh Y, Maeda K, Takaoka Y, Tamamura H, Fujii N, Mitsuya H. Potent synergistic anti-human immunodeficiency virus (HIV) effects using combinations of the CCR5 inhibitor aplaviroc with other anti-HIV drugs. Antimicrob Agents Chemother. 2008 Jun;52(6):2111-9. doi: 10.1128/AAC.01299-07. Epub 2008 Mar 31. PMID: 18378711; PMCID: PMC2415794. 11: Nolan KM, Del Prete GQ, Jordan AP, Haggarty B, Romano J, Leslie GJ, Hoxie JA. Characterization of a human immunodeficiency virus type 1 V3 deletion mutation that confers resistance to CCR5 inhibitors and the ability to use aplaviroc-bound receptor. J Virol. 2009 Apr;83(8):3798-809. doi: 10.1128/JVI.01751-08. Epub 2009 Feb 4. PMID: 19193800; PMCID: PMC2663279. 12: Gavrilyuk J, Ban H, Uehara H, Sirk SJ, Saye-Francisco K, Cuevas A, Zablowsky E, Oza A, Seaman MS, Burton DR, Barbas CF 3rd. Antibody conjugation approach enhances breadth and potency of neutralization of anti-HIV-1 antibodies and CD4-IgG. J Virol. 2013 May;87(9):4985-93. doi: 10.1128/JVI.03146-12. Epub 2013 Feb 20. PMID: 23427154; PMCID: PMC3624287. 13: Currier J, Lazzarin A, Sloan L, Clumeck N, Slims J, McCarty D, Steel H, Kleim JP, Bonny T, Millard J; ASCENT study team. Antiviral activity and safety of aplaviroc with lamivudine/zidovudine in HIV-infected, therapy-naive patients: the ASCENT (CCR102881) study. Antivir Ther. 2008;13(2):297-306. PMID: 18505181. 14: Westby M, van der Ryst E. CCR5 antagonists: host-targeted antivirals for the treatment of HIV infection. Antivir Chem Chemother. 2005;16(6):339-54. doi: 10.1177/095632020501600601. PMID: 16329283. 15: Georgopapadakou N. Discontinued drugs in 2005: anti-infectives. Expert Opin Investig Drugs. 2007 Jan;16(1):1-10. doi: 10.1517/13543784.16.1.1. PMID: 17155849. 16: Baba M. Recent advances of CCR5 antagonists. Curr Opin HIV AIDS. 2006 Sep;1(5):367-72. doi: 10.1097/01.COH.0000239848.13205.2a. PMID: 19372835. 17: Ryan CT. Trials of aplaviroc halted in treatment-naive patients. AIDS Clin Care. 2005 Nov;17(11):107-8. PMID: 16323301. 18: Donia M, McCubrey JA, Bendtzen K, Nicoletti F. Potential use of rapamycin in HIV infection. Br J Clin Pharmacol. 2010 Dec;70(6):784-93. doi: 10.1111/j.1365-2125.2010.03735.x. PMID: 21175433; PMCID: PMC3014061. 19: Reeves JD, Piefer AJ. Emerging drug targets for antiretroviral therapy. Drugs. 2005;65(13):1747-66. doi: 10.2165/00003495-200565130-00002. PMID: 16114975. 20: Arribas López JR. Efectos secundarios asociados al tratamiento con maraviroc y otros antagonistas de CCR5. Impacto potencial del bloqueo del receptor CCR5 [Secondary effects of treatment with maraviroc and other CCR5 antagonists. Potential impact of the CCR5 blocker]. Enferm Infecc Microbiol Clin. 2008 Oct;26 Suppl 11:23-7. Spanish. doi: 10.1016/s0213-005x(08)76560-1. PMID: 19133218.