WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 412307
CAS#: 13089-44-6
Description: Carbocyclic arabinosyladenine is an adenosine deaminase resistant antiviral agent
MedKoo Cat#: 412307
Name: Carbocyclic arabinosyladenine
CAS#: 13089-44-6
Chemical Formula: C10H11N5O4
Exact Mass: 265.0811
Molecular Weight: 265.23
Elemental Analysis: C, 45.29; H, 4.18; N, 26.41; O, 24.13
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Synonym: Carbocyclic arabinosyladenine; C-Ara-A; Carbocyclic arabinofuranosyladenine; Cyclaradine; Cyclic arabinosyladenine
IUPAC/Chemical Name: Furo(2',3':4,5)oxazolo(3,2-e)purine-8-methanol, 4-amino-6a,7,8,9a-tetrahydro-7-hydroxy-, (6aS-(6aalpha,7alpha,8beta,9aalpha))-
InChi Key: MQMVTEZRMYGLFD-FJFJXFQQSA-N
InChi Code: InChI=1S/C10H11N5O4/c11-7-4-8(13-2-12-7)15-9-6(19-10(15)14-4)5(17)3(1-16)18-9/h2-3,5-6,9,16-17H,1H2,(H2,11,12,13)/t3-,5-,6+,9-/m1/s1
SMILES Code: OC[C@@H]1[C@@H](O)[C@@](O2)([H])[C@@](N3C2=NC4=C(N)N=CN=C34)([H])O1
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
The following data is based on the product molecular weight 265.23 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: Israëls T, van de Wetering MD, Hesseling P, van Geloven N, Caron HN, Molyneux EM. Malnutrition and neutropenia in children treated for Burkitt lymphoma in Malawi. Pediatr Blood Cancer. 2009 Jul;53(1):47-52. doi: 10.1002/pbc.22032. PMID: 19338050.
2: Katagiri N, Kokufuda H, Makino M, Vince R, Kaneko C. Deamination of cyclaradine by adenosine deaminase under high pressure. Nucleosides Nucleotides. 1998 Jan-Mar;17(1-3):81-9. doi: 10.1080/07328319808005159. PMID: 9708342.
3: Katagiri N, Kokufuda H, Makino M, Matsuhashi Y, Kaneko C, Vince R. A highly efficient synthesis of cyclaradine and its behaviour towards adenosine deaminase. Nucleic Acids Symp Ser. 1997;(37):3-4. PMID: 9585970.
4: Lim J, Schwartz J, Loebenberg D, Miller GH, Symchowicz S, Lin C. Evaluation of (+)-cyclaradine-5'-esters as prodrugs for (+)-cyclaradine in animals. Antimicrob Agents Chemother. 1987 Jul;31(7):998-1001. doi: 10.1128/aac.31.7.998. PMID: 3662479; PMCID: PMC174859.
5: Schwartz J, Ostrander M, Butkiewicz NJ, Lieberman M, Lin C, Lim J, Miller GH. Activity of (+)-cyclaradine (Sch 31172) against herpes simplex virus in vitro and in vivo. Antimicrob Agents Chemother. 1987 Jan;31(1):21-6. doi: 10.1128/aac.31.1.21. PMID: 3032089; PMCID: PMC174644.
6: Lim JM, Lin CC. Column-switching high-performance liquid chromatographic method for determination of a new antiviral agent, cyclaradine, in serum. Antimicrob Agents Chemother. 1986 Jun;29(6):977-9. doi: 10.1128/aac.29.6.977. PMID: 3729365; PMCID: PMC180487.
7: Shannon WM, Westbrook L, Arnett G, Daluge S, Lee H, Vince R. Comparison of the efficacy of vidarabine, its carbocyclic analog (cyclaradine), and cyclaradine-5'-methoxyacetate in the treatment of herpes simplex virus type 1 encephalitis in mice. Antimicrob Agents Chemother. 1983 Oct;24(4):538-43. doi: 10.1128/aac.24.4.538. PMID: 6651280; PMCID: PMC185370.
8: Vince R, Daluge S, Lee H, Shannon WM, Arnett G, Schafer TW, Nagabhushan TL, Reichert P, Tsai H. Carbocyclic arabinofuranosyladenine (cyclaradine): efficacy against genital herpes in guinea pigs. Science. 1983 Sep 30;221(4618):1405-6. doi: 10.1126/science.6684328. PMID: 6684328.
9: Vince R, Daluge S. Carbocyclic arabinosyladenine, an adenosine deaminase resistant antiviral agent. J Med Chem. 1977 Apr;20(4):612-3. doi: 10.1021/jm00214a040. PMID: 191615.
