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MedKoo Cat#: 596954 | Name: (+)-Carbovir triphosphate

Description:

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

(+)-Carbovir triphosphate is an active metabolite of Abacavir used to study the molecular mechanism of inhibition and drug resistance for HIV-1 reverse transcriptase.

Chemical Structure

(+)-Carbovir triphosphate
(+)-Carbovir triphosphate
CAS#144606-93-9

Theoretical Analysis

MedKoo Cat#: 596954

Name: (+)-Carbovir triphosphate

CAS#: 144606-93-9

Chemical Formula: C11H16N5O11P3

Exact Mass: 487.0059

Molecular Weight: 487.19

Elemental Analysis: C, 27.12; H, 3.31; N, 14.38; O, 36.12; P, 19.07

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 #
No Data
Synonym
(+)-Carbovir triphosphate; L-CBVTP; L CBVTP; LCBVTP;
IUPAC/Chemical Name
((1R,4S)-4-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl tetrahydrogen triphosphate
InChi Key
CQCAEOCIDCCJDQ-NKWVEPMBSA-N
InChi Code
InChI=1S/C11H16N5O11P3/c12-11-14-9-8(10(17)15-11)13-5-16(9)7-2-1-6(3-7)4-25-29(21,22)27-30(23,24)26-28(18,19)20/h1-2,5-7H,3-4H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,12,14,15,17)/t6-,7+/m0/s1
SMILES Code
O=P(O)(OP(O)(OP(O)(O)=O)=O)OC[C@H]1C=C[C@@H](N2C=NC3=C2N=C(N)NC3=O)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
>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 487.19 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: Alvarez A, Rios-Navarro C, Blanch-Ruiz MA, Collado-Diaz V, Andujar I, Martinez-Cuesta MA, Orden S, Esplugues JV. Abacavir induces platelet-endothelium interactions by interfering with purinergic signalling: A step from inflammation to thrombosis. Antiviral Res. 2017 May;141:179-185. doi: 10.1016/j.antiviral.2017.03.001. Epub 2017 Mar 2. PubMed PMID: 28263802. 2: Falcinelli E, Francisci D, Belfiori B, Petito E, Guglielmini G, Malincarne L, Mezzasoma A, Sebastiano M, Conti V, Giannini S, Bonora S, Baldelli F, Gresele P. In vivo platelet activation and platelet hyperreactivity in abacavir-treated HIV-infected patients. Thromb Haemost. 2013 Aug;110(2):349-57. doi: 10.1160/TH12-07-0504. Epub 2013 May 23. PubMed PMID: 23703656. 3: Jackson A, Moyle G, Dickinson L, Back D, Khoo S, Taylor J, Gedela K, Abongomera G, Gazzard B, Boffito M. Pharmacokinetics of abacavir and its anabolite carbovir triphosphate without and with darunavir/ritonavir or raltegravir in HIV-infected subjects. Antivir Ther. 2012;17(1):19-24. doi: 10.3851/IMP1910. PubMed PMID: 22267465; PubMed Central PMCID: PMC3736319. 4: Baum PD, Sullam PM, Stoddart CA, McCune JM. Abacavir increases platelet reactivity via competitive inhibition of soluble guanylyl cyclase. AIDS. 2011 Nov 28;25(18):2243-8. doi: 10.1097/QAD.0b013e32834d3cc3. PubMed PMID: 21941165; PubMed Central PMCID: PMC3272328. 5: Goicoechea M, Jain S, Bi L, Kemper C, Daar ES, Diamond C, Ha B, Flaherty J, Sun S, Richman D, Louie S, Haubrich R; California Collaborative Treatment Group. Abacavir and tenofovir disoproxil fumarate co-administration results in a nonadditive antiviral effect in HIV-1-infected patients. AIDS. 2010 Mar 13;24(5):707-16. doi: 10.1097/QAD.0b013e32833676eb. PubMed PMID: 20087154. 6: Goicoechea M, Jain S, Bi L, Sun S, Smith G, Ha B, Richman D, Louie S, Haubrich R; California Collaborative Treatment Group. Interlaboratory measurement differences in intracellular carbovir triphosphate concentrations in HIV-infected patients: sources of variability in processing, shipping, and quantitation. J Clin Pharmacol. 2010 Aug;50(8):968-74. doi: 10.1177/0091270009352186. Epub 2009 Dec 1. PubMed PMID: 19952374. 7: Moyle G, Boffito M, Fletcher C, Higgs C, Hay PE, Song IH, Lou Y, Yuen GJ, Min SS, Guerini EM. Steady-state pharmacokinetics of abacavir in plasma and intracellular carbovir triphosphate following administration of abacavir at 600 milligrams once daily and 300 milligrams twice daily in human immunodeficiency virus-infected subjects. Antimicrob Agents Chemother. 2009 Apr;53(4):1532-8. doi: 10.1128/AAC.01000-08. Epub 2009 Feb 2. PubMed PMID: 19188387; PubMed Central PMCID: PMC2663118. 8: Yuen GJ, Weller S, Pakes GE. A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71. Review. PubMed PMID: 18479171. 9: Pruvost A, Théodoro F, Agrofoglio L, Negredo E, Bénech H. Specificity enhancement with LC-positive ESI-MS/MS for the measurement of nucleotides: application to the quantitative determination of carbovir triphosphate, lamivudine triphosphate and tenofovir diphosphate in human peripheral blood mononuclear cells. J Mass Spectrom. 2008 Feb;43(2):224-33. PubMed PMID: 17935070. 10: Melroy J, Nair V. The antiviral activity, mechanism of action, clinical significance and resistance of abacavir in the treatment of pediatric AIDS. Curr Pharm Des. 2005;11(29):3847-52. Review. PubMed PMID: 16305515. 11: Hawkins T, Veikley W, St Claire RL 3rd, Guyer B, Clark N, Kearney BP. Intracellular pharmacokinetics of tenofovir diphosphate, carbovir triphosphate, and lamivudine triphosphate in patients receiving triple-nucleoside regimens. J Acquir Immune Defic Syndr. 2005 Aug 1;39(4):406-11. PubMed PMID: 16010161. 12: McGuigan C, Harris SA, Daluge SM, Gudmundsson KS, McLean EW, Burnette TC, Marr H, Hazen R, Condreay LD, Johnson L, De Clercq E, Balzarini J. Application of phosphoramidate pronucleotide technology to abacavir leads to a significant enhancement of antiviral potency. J Med Chem. 2005 May 19;48(10):3504-15. PubMed PMID: 15887959. 13: Balzarini J, Aquaro S, Hassan-Abdallah A, Daluge SM, Perno CF, McGuigan C. Improved antiviral activity of the aryloxymethoxyalaninyl phosphoramidate (APA) prodrug of abacavir (ABC) is due to the formation of markedly increased carbovir 5'-triphosphate metabolite levels. FEBS Lett. 2004 Aug 27;573(1-3):38-44. PubMed PMID: 15327972. 14: Cai Z, Fung EN, Sinhababu AK. Capillary electrophoresis-ion trap mass spectrometry analysis of Ziagen and its phosphorylated metabolites. Electrophoresis. 2003 Sep;24(18):3160-4. PubMed PMID: 14518039. 15: Margolis DM, Kewn S, Coull JJ, Ylisastigui L, Turner D, Wise H, Hossain MM, Lanier ER, Shaw LM, Back D. The addition of mycophenolate mofetil to antiretroviral therapy including abacavir is associated with depletion of intracellular deoxyguanosine triphosphate and a decrease in plasma HIV-1 RNA. J Acquir Immune Defic Syndr. 2002 Sep 1;31(1):45-9. PubMed PMID: 12352149. 16: Ray AS, Basavapathruni A, Anderson KS. Mechanistic studies to understand the progressive development of resistance in human immunodeficiency virus type 1 reverse transcriptase to abacavir. J Biol Chem. 2002 Oct 25;277(43):40479-90. Epub 2002 Aug 9. PubMed PMID: 12176989. 17: Harris M, Back D, Kewn S, Jutha S, Marina R, Montaner JS. Intracellular carbovir triphosphate levels in patients taking abacavir once a day. AIDS. 2002 May 24;16(8):1196-7. PubMed PMID: 12004286. 18: Ray AS, Yang Z, Shi J, Hobbs A, Schinazi RF, Chu CK, Anderson KS. Insights into the molecular mechanism of inhibition and drug resistance for HIV-1 RT with carbovir triphosphate. Biochemistry. 2002 Apr 23;41(16):5150-62. PubMed PMID: 11955063. 19: Kewn S, Hoggard PG, Sales SD, Jones K, Maher B, Khoo SH, Back DJ. Development of enzymatic assays for quantification of intracellular lamivudine and carbovir triphosphate levels in peripheral blood mononuclear cells from human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 2002 Jan;46(1):135-43. PubMed PMID: 11751124; PubMed Central PMCID: PMC126990. 20: Ray AS, Anderson KS. Mechanistic studies to understand the inhibition of wild type and mutant HIV-1 reverse transcriptase by Carbovir-triphosphate. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):1247-50. PubMed PMID: 11562995.