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MedKoo Cat#: 574609 | Name: Carbovir
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Description:

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

Carbovir, also known as (-)-Carbovir, is a nucleoside/nucleotide reverse transcriptase inhibitor (NRTI) caused mitochondrial toxicity in human hepatoma carcinoma cell.

Chemical Structure

Carbovir
Carbovir
CAS#120443-30-3

Theoretical Analysis

MedKoo Cat#: 574609

Name: Carbovir

CAS#: 120443-30-3

Chemical Formula: C11H13N5O2

Exact Mass: 247.1069

Molecular Weight: 247.26

Elemental Analysis: C, 53.43; H, 5.30; N, 28.32; O, 12.94

Price and Availability

Size Price Availability Quantity
1g USD 3,650.00 2-3 months
2g USD 6,450.00 2-3 months
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Related CAS #
124915-24-8 (L-Carbovir) 120443-30-3
Synonym
(-)-Carbovir; Carbovir, (-)-; Carbovir;
IUPAC/Chemical Name
(1R-cis)-2-Amino-1,9-dihydro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-6H-Purin-6-one
InChi Key
XSSYCIGJYCVRRK-RQJHMYQMSA-N
InChi Code
InChI=1S/C11H13N5O2/c12-11-14-9-8(10(18)15-11)13-5-16(9)7-2-1-6(3-7)4-17/h1-2,5-7,17H,3-4H2,(H3,12,14,15,18)/t6-,7+/m1/s1
SMILES Code
O=C1NC(N)=NC2=C1N=CN2[C@H]3C=C[C@@H](CO)C3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 247.26 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: Huang SH, Remmel RP, Zimmerman CL. The bioavailability and nonlinear clearance of (-)-carbovir in the rat. Pharm Res. 1991 Jun;8(6):739-43. doi: 10.1023/a:1015850017201. PMID: 2062804. 2: el Dareer SM, Tillery KF, Rose LM, Struck RF, Hill DL. Disposition and metabolism of carbovir in mice dosed intravenously or orally. Drug Metab Dispos. 1990 Nov-Dec;18(6):842-5. PMID: 1981526. 3: Yeom YH, Remmel RP, Huang SH, Hua M, Vince R, Zimmerman CL. Pharmacokinetics and bioavailability of carbovir, a carbocyclic nucleoside active against human immunodeficiency virus, in rats. Antimicrob Agents Chemother. 1989 Feb;33(2):171-5. doi: 10.1128/AAC.33.2.171. PMID: 2719460; PMCID: PMC171451. 4: Miller WH, Daluge SM, Garvey EP, Hopkins S, Reardon JE, Boyd FL, Miller RL. Phosphorylation of carbovir enantiomers by cellular enzymes determines the stereoselectivity of antiviral activity. J Biol Chem. 1992 Oct 15;267(29):21220-4. PMID: 1383219. 5: Gao S, Zhu S, Huang R, Lu Y, Zheng G. Efficient synthesis of the intermediate of abacavir and carbovir using a novel (+)-γ-lactamase as a catalyst. Bioorg Med Chem Lett. 2015 Sep 15;25(18):3878-81. doi: 10.1016/j.bmcl.2015.07.054. Epub 2015 Jul 26. PMID: 26235952. 6: 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. doi: 10.1097/00002030-200205240-00021. PMID: 12004286. 7: Anderson BD, Chiang CY. Physicochemical properties of carbovir, a potential anti-HIV agent. J Pharm Sci. 1990 Sep;79(9):787-90. doi: 10.1002/jps.2600790908. PMID: 2273460. 8: Patanella JE, Walsh JS. Oxidation of carbovir, a carbocyclic nucleoside, by rat liver cytosolic enzymes. Enantioselectivity and enantiomeric inhibition. Drug Metab Dispos. 1992 Nov-Dec;20(6):912-9. PMID: 1362946. 9: Walsh JS, Patanella JE, Unger SE, Brouwer KR, Miwa GT. The metabolism and excretion of carbovir, a carbocyclic nucleoside, in the rat. Drug Metab Dispos. 1990 Nov-Dec;18(6):1084-91. PMID: 1981517. 10: Vince R, Hua M. Synthesis of carbovir and abacavir from a carbocyclic precursor. Curr Protoc Nucleic Acid Chem. 2006 Jul;Chapter 14:Unit 14.4. doi: 10.1002/0471142700.nc1404s25. PMID: 18428951. 11: 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. PMID: 22267465; PMCID: PMC3736319. 12: Brouwer KR, St Claire RL, Lagarde J, Patanella JE, Walsh JS, Miwa GT. The pharmacokinetics of (-)-carbovir in rats. Evidence for nonlinear elimination. Drug Metab Dispos. 1990 Nov-Dec;18(6):1078-83. PMID: 1981516. 13: Soria I, Zimmerman CL. Intestinal absorption of (-)-carbovir in the rat. Pharm Res. 1994 Feb;11(2):267-71. doi: 10.1023/a:1018911609410. PMID: 8165186. 14: Parker WB, White EL, Shaddix SC, Ross LJ, Buckheit RW Jr, Germany JM, Secrist JA 3rd, Vince R, Shannon WM. Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase and human DNA polymerases alpha, beta, and gamma by the 5'-triphosphates of carbovir, 3'-azido-3'-deoxythymidine, 2',3'-dideoxyguanosine and 3'-deoxythymidine. A novel RNA template for the evaluation of antiretroviral drugs. J Biol Chem. 1991 Jan 25;266(3):1754-62. PMID: 1703154. 15: Carter SG, Kessler JA, Rankin CD. Activities of (-)-carbovir and 3'-azido-3'-deoxythymidine against human immunodeficiency virus in vitro. Antimicrob Agents Chemother. 1990 Jun;34(6):1297-300. doi: 10.1128/AAC.34.6.1297. PMID: 2393292; PMCID: PMC171808. 16: Wen YD, Remmel RP, Pham PT, Vince R, Zimmerman CL. Comparative brain exposure to (-)-carbovir after (-)-carbovir or (-)-6-aminocarbovir intravenous infusion in rats. Pharm Res. 1995 Jun;12(6):911-5. doi: 10.1023/a:1016229624703. PMID: 7667200. 17: White EL, Parker WB, Macy LJ, Shaddix SC, McCaleb G, Secrist JA 3rd, Vince R, Shannon WM. Comparison of the effect of Carbovir, AZT, and dideoxynucleoside triphosphates on the activity of human immunodeficiency virus reverse transcriptase and selected human polymerases. Biochem Biophys Res Commun. 1989 Jun 15;161(2):393-8. doi: 10.1016/0006-291x(89)92611-9. PMID: 2472136. 18: Coates JA, Inggall HJ, Pearson BA, Penn CR, Storer R, Williamson C, Cameron JM. Carbovir: the (-) enantiomer is a potent and selective antiviral agent against human immunodeficiency virus in vitro. Antiviral Res. 1991 Feb;15(2):161-8. doi: 10.1016/0166-3542(91)90033-n. PMID: 1677557. 19: Mahony WB, Domin BA, Daluge SM, Miller WH, Zimmerman TP. Enantiomeric selectivity of carbovir transport. J Biol Chem. 1992 Oct 5;267(28):19792-7. PMID: 1400293. 20: Kurtzberg J, Carter SG. Differential toxicity of carbovir and AZT to human bone marrow hematopoietic progenitor cells in vitro. Exp Hematol. 1990 Nov;18(10):1094-6. PMID: 2209763.