(+)-Carbovir | CAS#124915-24-8 | nucleoside analogues

MedKoo Cat#: 596952 | Name: (+)-Carbovir

Description:

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

(+)-Carbovir is a nucleoside analogues in which a methylene group has replaced the oxygen atom of the furanose ring. These analogues have the nucleobase attached at a simple alkyl carbon rather than being part of a hemiaminal ether linkage. As a result, they have increased chemical stability. They also have increased metabolic stability because they are unaffected by phosphorylases and hydrolases that cleave the glycosidic bond between the nucleobase and furanose ring of nucleosides. They retain many of the biological properties of the original nucleosides with respect to recognition by various enzymes and receptors.

Chemical Structure

(+)-Carbovir

CAS#124915-24-8 (L-Carbovir)

Theoretical Analysis

MedKoo Cat#: 596952

Name: (+)-Carbovir

CAS#: 124915-24-8 (L-Carbovir)

Chemical Formula: C11H13N5O2

Exact Mass: 247.1069

Molecular Weight: 247.25

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

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.

Bulk Inquiry

Related CAS #

124915-24-8 (L-Carbovir) 120443-30-3

Synonym

(+)-Carbovir; L-Carbovir;

IUPAC/Chemical Name

2-amino-9-((1S,4R)-4-(hydroxymethyl)cyclopent-2-en-1-yl)-1,9-dihydro-6H-purin-6-one

InChi Key

XSSYCIGJYCVRRK-NKWVEPMBSA-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+/m0/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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 247.25 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.

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: Gautam N, Lin Z, Banoub MG, Smith NA, Maayah A, McMillan J, Gendelman HE, Alnouti Y. Simultaneous quantification of intracellular lamivudine and abacavir triphosphate metabolites by LC-MS/MS. J Pharm Biomed Anal. 2018 May 10;153:248-259. doi: 10.1016/j.jpba.2018.02.036. Epub 2018 Feb 20. PubMed PMID: 29518644; PubMed Central PMCID: PMC5860827. 2: Gao S, Zhu S, Huang R, Li H, Wang H, Zheng G. Engineering the Enantioselectivity and Thermostability of a (+)-γ-Lactamase from Microbacterium hydrocarbonoxydans for Kinetic Resolution of Vince Lactam (2-Azabicyclo[2.2.1]hept-5-en-3-one). Appl Environ Microbiol. 2017 Dec 15;84(1). pii: e01780-17. doi: 10.1128/AEM.01780-17. Print 2018 Jan 1. PubMed PMID: 29054871; PubMed Central PMCID: PMC5734046. 3: Gao S, Zhou Y, Zhang W, Wang W, Yu Y, Mu Y, Wang H, Gong X, Zheng G, Feng Y. Structural insights into the γ-lactamase activity and substrate enantioselectivity of an isochorismatase-like hydrolase from Microbacterium hydrocarbonoxydans. Sci Rep. 2017 Mar 15;7:44542. doi: 10.1038/srep44542. PubMed PMID: 28295028; PubMed Central PMCID: PMC5353710. 4: 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. 5: Gao S, Huang R, Zhu S, Li H, Zheng G. Identification and characterization of a novel (+)-γ-lactamase from Microbacterium hydrocarbonoxydans. Appl Microbiol Biotechnol. 2016 Nov;100(22):9543-9553. Epub 2016 Jun 2. PubMed PMID: 27255489. 6: Diallo YL, Ollivier V, Joly V, Faille D, Catalano G, Jandrot-Perrus M, Rauch A, Yeni P, Ajzenberg N. Abacavir has no prothrombotic effect on platelets in vitro. J Antimicrob Chemother. 2016 Dec;71(12):3506-3509. Epub 2016 Aug 11. PubMed PMID: 27516475. 7: Yamamoto J, Takahata C, Kuraoka I, Hirota K, Iwai S. Chemical Incorporation of Chain-Terminating Nucleoside Analogs as 3'-Blocking DNA Damage and Their Removal by Human ERCC1-XPF Endonuclease. Molecules. 2016 Jun 11;21(6). pii: E766. doi: 10.3390/molecules21060766. PubMed PMID: 27294910. 8: 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. PubMed PMID: 26235952. 9: Ponomareva AG, Yurenko YP, Zhurakivsky RO, van Mourik T, Hovorun DM. Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation. J Biomol Struct Dyn. 2014;32(5):730-40. doi: 10.1080/07391102.2013.789401. Epub 2013 Jun 19. PubMed PMID: 23947531. 10: 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. 11: Ponomar'ova AG, Iurenko IeP, Zhurakovs'kyĭ RO, Govorun DM. [Complete conformational family of 2',3'-didehydro-2',3'-dideoxyguanosine: quantum chemical and electron density topological study]. Ukr Biokhim Zh (1999). 2012 Jan-Feb;84(1):67-78. Ukrainian. PubMed PMID: 22679760. 12: 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. 13: Forró E. [New enzymatic strategies for enantiomers of lactams and amino acids]. Acta Pharm Hung. 2011;81(3):125-33. Hungarian. PubMed PMID: 22165415. 14: 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. 15: Trost BM, Osipov M, Kaib PS, Sorum MT. Acetoxy Meldrum's acid: a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation. Org Lett. 2011 Jun 17;13(12):3222-5. doi: 10.1021/ol2011242. Epub 2011 May 26. PubMed PMID: 21615099; PubMed Central PMCID: PMC3144701. 16: Chattopadhyay A, Tripathy S. Stereodivergent route to the carbocyclic core of 2',3'-olefinic carbanucleosides: toward the synthesis of (L)-(+)- and (D)-(-)-carbovir. J Org Chem. 2011 Jul 15;76(14):5856-61. doi: 10.1021/jo200670v. Epub 2011 Jun 14. PubMed PMID: 21612257. 17: Betancor G, Puertas MC, Nevot M, Garriga C, Martínez MA, Martinez-Picado J, Menéndez-Arias L. Mechanisms involved in the selection of HIV-1 reverse transcriptase thumb subdomain polymorphisms associated with nucleoside analogue therapy failure. Antimicrob Agents Chemother. 2010 Nov;54(11):4799-811. doi: 10.1128/AAC.00716-10. Epub 2010 Aug 23. PubMed PMID: 20733040; PubMed Central PMCID: PMC2976120. 18: 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. 19: 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. 20: 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.