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MedKoo Cat#: 592345 | Name: Aplaviroc

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
Aplaviroc
CAS#461443-59-4 (free base)

Theoretical Analysis

MedKoo Cat#: 592345

Name: Aplaviroc

CAS#: 461443-59-4 (free base)

Chemical Formula: C33H43N3O6

Exact Mass: 577.3152

Molecular Weight: 577.72

Elemental Analysis: C, 68.61; H, 7.50; N, 7.27; O, 16.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
461443-59-4 (free base) 461023-63-2 (HCl)
Synonym
Aplaviroc;; AK-602; AK602; AK 602; GW873140A; GW-873140; GW873140; GW 873140; ONO-4128; ONO 4128; ONO4128;
IUPAC/Chemical Name
Benzoic acid, 4-(4-(((3R)-1-butyl-3-((R)-cyclohexylhydroxymethyl)-2,5-dioxo-1,4,9-triazaspiro(55)undec-9-yl)methyl)phenoxy)-
InChi Key
GWNOTCOIYUNTQP-FQLXRVMXSA-N
InChi Code
InChI=1S/C33H43N3O6/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)/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
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 577.72 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
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PubMed PMID: 24628038; PubMed Central PMCID: PMC4105926. 4: Steen A, Sparre-Ulrich AH, Thiele S, Guo D, Frimurer TM, Rosenkilde MM. Gating function of isoleucine-116 in TM-3 (position III:16/3.40) for the activity state of the CC-chemokine receptor 5 (CCR5). Br J Pharmacol. 2014 Mar;171(6):1566-79. doi: 10.1111/bph.12553. PubMed PMID: 24328926; PubMed Central PMCID: PMC3954493. 5: Ban H, Nagano M, Gavrilyuk J, Hakamata W, Inokuma T, Barbas CF 3rd. Facile and stabile linkages through tyrosine: bioconjugation strategies with the tyrosine-click reaction. Bioconjug Chem. 2013 Apr 17;24(4):520-32. doi: 10.1021/bc300665t. Epub 2013 Mar 27. PubMed PMID: 23534985; PubMed Central PMCID: PMC3658467. 6: Steen A, Thiele S, Guo D, Hansen LS, Frimurer TM, Rosenkilde MM. Biased and constitutive signaling in the CC-chemokine receptor CCR5 by manipulating the interface between transmembrane helices 6 and 7. J Biol Chem. 2013 May 3;288(18):12511-21. doi: 10.1074/jbc.M112.449587. Epub 2013 Mar 14. PubMed PMID: 23493400; PubMed Central PMCID: PMC3642299. 7: 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. PubMed PMID: 23427154; PubMed Central PMCID: PMC3624287. 8: Thiele S, Steen A, Jensen PC, Mokrosinski J, Frimurer TM, Rosenkilde MM. Allosteric and orthosteric sites in CC chemokine receptor (CCR5), a chimeric receptor approach. J Biol Chem. 2011 Oct 28;286(43):37543-54. doi: 10.1074/jbc.M111.243808. Epub 2011 Aug 30. PubMed PMID: 21878623; PubMed Central PMCID: PMC3199500. 9: Shin N, Solomon K, Zhou N, Wang KH, Garlapati V, Thomas B, Li Y, Covington M, Baribaud F, Erickson-Viitanen S, Czerniak P, Contel N, Liu P, Burn T, Hollis G, Yeleswaram S, Vaddi K, Xue CB, Metcalf B, Friedman S, Scherle P, Newton R. Identification and characterization of INCB9471, an allosteric noncompetitive small-molecule antagonist of C-C chemokine receptor 5 with potent inhibitory activity against monocyte migration and HIV-1 infection. J Pharmacol Exp Ther. 2011 Jul;338(1):228-39. doi: 10.1124/jpet.111.179531. Epub 2011 Apr 1. PubMed PMID: 21459966. 10: Labrecque J, Metz M, Lau G, Darkes MC, Wong RS, Bogucki D, Carpenter B, Chen G, Li T, Nan S, Schols D, Bridger GJ, Fricker SP, Skerlj RT. HIV-1 entry inhibition by small-molecule CCR5 antagonists: a combined molecular modeling and mutant study using a high-throughput assay. Virology. 2011 May 10;413(2):231-43. doi: 10.1016/j.virol.2011.02.016. Epub 2011 Mar 9. PubMed PMID: 21388649. 11: Da LT, Wu YD. Theoretical studies on the interactions and interferences of HIV-1 glycoprotein gp120 and its coreceptor CCR5. J Chem Inf Model. 2011 Feb 28;51(2):359-69. doi: 10.1021/ci1003448. Epub 2011 Feb 2. PubMed PMID: 21284403. 12: 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. Review. PubMed PMID: 21175433; PubMed Central PMCID: PMC3014061. 13: Gavrilyuk J, Uehara H, Otsubo N, Hessell A, Burton DR, Barbas CF 3rd. Potent inhibition of HIV-1 entry with a chemically programmed antibody aided by an efficient organocatalytic synthesis. Chembiochem. 2010 Oct 18;11(15):2113-8. doi: 10.1002/cbic.201000432. PubMed PMID: 20845359. 14: Tilton JC, Wilen CB, Didigu CA, Sinha R, Harrison JE, Agrawal-Gamse C, Henning EA, Bushman FD, Martin JN, Deeks SG, Doms RW. A maraviroc-resistant HIV-1 with narrow cross-resistance to other CCR5 antagonists depends on both N-terminal and extracellular loop domains of drug-bound CCR5. J Virol. 2010 Oct;84(20):10863-76. doi: 10.1128/JVI.01109-10. Epub 2010 Aug 11. PubMed PMID: 20702642; PubMed Central PMCID: PMC2950574. 15: Nakata H, Kruhlak M, Kamata W, Ogata-Aoki H, Li J, Maeda K, Ghosh AK, Mitsuya H. Effects of CC chemokine receptor 5 (CCR5) inhibitors on the dynamics of CCR5 and CC-chemokine-CCR5 interactions. Antivir Ther. 2010;15(3):321-31. doi: 10.3851/IMP1529. PubMed PMID: 20516552. 16: Pfaff JM, Wilen CB, Harrison JE, Demarest JF, Lee B, Doms RW, Tilton JC. HIV-1 resistance to CCR5 antagonists associated with highly efficient use of CCR5 and altered tropism on primary CD4+ T cells. J Virol. 2010 Jul;84(13):6505-14. doi: 10.1128/JVI.00374-10. Epub 2010 Apr 21. PubMed PMID: 20410277; PubMed Central PMCID: PMC2903254. 17: Tilton JC, Amrine-Madsen H, Miamidian JL, Kitrinos KM, Pfaff J, Demarest JF, Ray N, Jeffrey JL, Labranche CC, Doms RW. HIV type 1 from a patient with baseline resistance to CCR5 antagonists uses drug-bound receptor for entry. AIDS Res Hum Retroviruses. 2010 Jan;26(1):13-24. doi: 10.1089/aid.2009.0132. PubMed PMID: 20055594; PubMed Central PMCID: PMC2858898. 18: 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. PubMed PMID: 19501260. 19: Arribas López JR. [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. Review. Spanish. PubMed PMID: 19133218. 20: Arenzana-Seisdedos F. [Viral entry as therapeutic target. Current situation of entry inhibitors]. Enferm Infecc Microbiol Clin. 2008 Oct;26 Suppl 11:5-11. Review. Spanish. PubMed PMID: 19133215.