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MedKoo Cat#: 326946 | Name: Apricitabine
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Description:

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

Apricitabine, also known as (-)-BCH-10652, is an experimental nucleoside reverse transcriptase inhibitor (NRTI) against HIV. It is structurally related to lamivudine and emtricitabine, and, like these, is an analogue of cytidine.

Chemical Structure

Apricitabine
Apricitabine
CAS#160707-69-7

Theoretical Analysis

MedKoo Cat#: 326946

Name: Apricitabine

CAS#: 160707-69-7

Chemical Formula: C8H11N3O3S

Exact Mass: 229.0521

Molecular Weight: 229.25

Elemental Analysis: C, 41.91; H, 4.84; N, 18.33; O, 20.94; S, 13.98

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
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Related CAS #
143338-12-9 ((+/-)-) 160707-68-6 (+/-)
Synonym
Apricitabine; (-)-BCH-10652; (-)-BCH10652; (-)-BCH-10652; (-)-dOTC; AVX754; AVX-754; AVX 754; BCH-10618; BCH10618; BCH 10618; SPD-754; SPD754; SPD 754
IUPAC/Chemical Name
4-amino-1-((2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl)pyrimidin-2(1H)-one
InChi Key
RYMCFYKJDVMSIR-RNFRBKRXSA-N
InChi Code
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-14-7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m1/s1
SMILES Code
O=C1N=C(N)C=CN1[C@@H]2S[C@H](CO)OC2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 229.25 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: Gaffney MM, Belliveau PP, Spooner LM. Apricitabine: a nucleoside reverse transcriptase inhibitor for HIV infection. Ann Pharmacother. 2009 Oct;43(10):1676-83. doi: 10.1345/aph.1M160. Epub 2009 Sep 8. PMID: 19737995. 2: Wainberg MA, Cahn P, Bethell RC, Sawyer J, Cox S. Apricitabine: a novel deoxycytidine analogue nucleoside reverse transcriptase inhibitor for the treatment of nucleoside-resistant HIV infection. Antivir Chem Chemother. 2007;18(2):61-70. doi: 10.1177/095632020701800201. PMID: 17542150. 3: Cahn P, Wainberg MA. Resistance profile of the new nucleoside reverse transcriptase inhibitor apricitabine. J Antimicrob Chemother. 2010 Feb;65(2):213-7. doi: 10.1093/jac/dkp422. Epub 2009 Dec 9. PMID: 20007333. 4: Cox S, Southby J. Apricitabine--a novel nucleoside reverse transcriptase inhibitor for the treatment of HIV infection that is refractory to existing drugs. Expert Opin Investig Drugs. 2009 Feb;18(2):199-209. doi: 10.1517/13543780802641337. PMID: 19236266. 5: Bethell R, De Muys J, Lippens J, Richard A, Hamelin B, Ren C, Collins P. In vitro interactions between apricitabine and other deoxycytidine analogues. Antimicrob Agents Chemother. 2007 Aug;51(8):2948-53. doi: 10.1128/AAC.01204-06. Epub 2007 May 21. PMID: 17517847; PMCID: PMC1932514. 6: Shiveley L, Struthers-Semple C, Cox S, Sawyer J. Pharmacokinetics of apricitabine, a novel nucleoside reverse transcriptase inhibitor, in healthy volunteers treated with trimethoprim-sulphamethoxazole. J Clin Pharm Ther. 2008 Feb;33(1):45-54. doi: 10.1111/j.1365-2710.2008.00889.x. PMID: 18211616. 7: Cahn P, Rolon M, Cassetti I, Shiveley L, Holdich T, Sawyer J. Multiple-dose pharmacokinetics of apricitabine, a novel nucleoside reverse transcriptase inhibitor, in patients with HIV-1 infection. Clin Drug Investig. 2008;28(2):129-38. doi: 10.2165/00044011-200828020-00007. PMID: 18211121. 8: Cahn P, Cassetti I, Wood R, Phanuphak P, Shiveley L, Bethell RC, Sawyer J. Efficacy and tolerability of 10-day monotherapy with apricitabine in antiretroviral-naive, HIV-infected patients. AIDS. 2006 Jun 12;20(9):1261-8. doi: 10.1097/01.aids.0000232233.41877.63. PMID: 16816554. 9: Frankel FA, Coutsinos D, Xu H, Wainberg MA. Kinetics of inhibition of HIV type 1 reverse transcriptase-bearing NRTI-associated mutations by apricitabine triphosphate. Antivir Chem Chemother. 2007;18(2):93-101. doi: 10.1177/095632020701800205. PMID: 17542154. 10: Cox S, Southby J, Linet O, Tackwell K, Borin M, Perry K. Comparison of the pharmacokinetics of apricitabine in the presence and absence of ritonavir- boosted tipranavir: a phase I, open-label, controlled, single-centre study. Clin Drug Investig. 2009;29(11):721-8. doi: 10.2165/11319890-000000000-00000. PMID: 19813775. 11: Holdich T, Sawyer J. Influence of food on the pharmacokinetics of apricitabine, a novel deoxycytidine analogue reverse transcriptase inhibitor. Expert Opin Pharmacother. 2008 Aug;9(12):2021-5. doi: 10.1517/14656566.9.12.2021. PMID: 18671458. 12: Babayeva M, Cox S, White MP, Taft DR. Renal excretion of apricitabine in rats: ex vivo and in vivo studies. Eur J Drug Metab Pharmacokinet. 2011 Sep;36(3):141-50. doi: 10.1007/s13318-011-0038-9. Epub 2011 Apr 6. PMID: 21744041. 13: Cahn P, Altclas J, Martins M, Losso M, Cassetti I, Cooper DA, Cox S. Antiviral activity of apricitabine in treatment-experienced HIV-1-infected patients with M184V who are failing combination therapy. HIV Med. 2011 Jul;12(6):334-42. doi: 10.1111/j.1468-1293.2010.00887.x. Epub 2010 Nov 3. PMID: 21054750. 14: Holdich T, Shiveley LA, Sawyer J. Effect of Lamivudine on the plasma and intracellular pharmacokinetics of apricitabine, a novel nucleoside reverse transcriptase inhibitor, in healthy volunteers. Antimicrob Agents Chemother. 2007 Aug;51(8):2943-7. doi: 10.1128/AAC.01013-06. Epub 2007 Jan 22. PMID: 17242147; PMCID: PMC1932547. 15: de Baar MP, de Rooij ER, Smolders KG, van Schijndel HB, Timmermans EC, Bethell R. Effects of apricitabine and other nucleoside reverse transcriptase inhibitors on replication of mitochondrial DNA in HepG2 cells. Antiviral Res. 2007 Oct;76(1):68-74. doi: 10.1016/j.antiviral.2007.05.004. Epub 2007 Jun 21. PMID: 17628710. 16: Waters L, Nelson MR. New drugs. HIV Med. 2005 Jul;6(4):225-31. doi: 10.1111/j.1468-1293.2005.00310.x. PMID: 16011526. 17: De Clercq E. Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416. doi: 10.1517/14728214.13.3.393. PMID: 18764719. 18: Holdich T, Shiveley L, Sawyer J. Pharmacokinetics of single oral doses of apricitabine, a novel deoxycytidine analogue reverse transcriptase inhibitor, in healthy volunteers. Clin Drug Investig. 2006;26(5):279-86. doi: 10.2165/00044011-200626050-00005. PMID: 17163261. 19: Oliveira M, Moisi D, Spira B, Cox S, Brenner BG, Wainberg MA. Apricitabine does not select additional drug resistance mutations in tissue culture in human immunodeficiency virus type 1 variants containing K65R, M184V, or M184V plus thymidine analogue mutations. Antimicrob Agents Chemother. 2009 Apr;53(4):1683-5. doi: 10.1128/AAC.01168-08. Epub 2009 Feb 17. PMID: 19223637; PMCID: PMC2663123. 20: Nakatani-Freshwater T, Babayeva M, Dontabhaktuni A, Taft DR. Effects of trimethoprim on the clearance of apricitabine, a deoxycytidine analog reverse transcriptase inhibitor, and Lamivudine in the isolated perfused rat kidney. J Pharmacol Exp Ther. 2006 Nov;319(2):941-7. doi: 10.1124/jpet.106.108522. Epub 2006 Aug 22. PMID: 16926264.

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