Synonym
Carbathymidine; Carbocyclic thymidine
IUPAC/Chemical Name
2,4(1H,3H)-Pyrimidinedione, 1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methyl-, (1R-(1alpha,3beta,4alpha))-
InChi Key
ZOZRLTAJWLEGLG-XHNCKOQMSA-N
InChi Code
InChI=1S/C11H16N2O4/c1-6-4-13(11(17)12-10(6)16)8-2-7(5-14)9(15)3-8/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)/t7-,8-,9+/m0/s1
SMILES Code
O=C1NC(C(C)=CN1[C@@H]2C[C@@H](O)[C@H](CO)C2)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
240.26
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.
| 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: Schelling P, Claus MT, Johner R, Marquez VE, Schulz GE, Scapozza L. Biochemical and structural characterization of (South)-methanocarbathymidine that specifically inhibits growth of herpes simplex virus type 1 thymidine kinase-transduced osteosarcoma cells. J Biol Chem. 2004 Jul 30;279(31):32832-8. doi: 10.1074/jbc.M313343200. Epub 2004 May 25. PMID: 15163659.
2: Béres J, Sági G, Tömösközi I, Gruber L, Baitz-Gács E, Otvös L, De Clercq E. Stereospecific synthesis and antiviral properties of different enantiomerically pure carbocyclic 2'-deoxyribonucleoside analogues derived from common chiral pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one. J Med Chem. 1990 May;33(5):1353-60. doi: 10.1021/jm00167a011. PMID: 2158560.
3: Kato A, Yasuda Y, Kitamura Y, Kandeel M, Kitade Y. Carbocyclic thymidine derivatives efficiently inhibit Plasmodium falciparum thymidylate kinase (PfTMK). Parasitol Int. 2012 Sep;61(3):501-3. doi: 10.1016/j.parint.2012.03.001. Epub 2012 Mar 9. PMID: 22425904.
4: Aviñó A, Mazzini S, Ferreira R, Gargallo R, Marquez VE, Eritja R. The effect on quadruplex stability of North-nucleoside derivatives in the loops of the thrombin-binding aptamer. Bioorg Med Chem. 2012 Jul 15;20(14):4186-93. doi: 10.1016/j.bmc.2012.06.005. Epub 2012 Jun 9. PMID: 22727781; PMCID: PMC3534854.
5: Boyer PL, Vu BC, Ambrose Z, Julias JG, Warnecke S, Liao C, Meier C, Marquez VE, Hughes SH. The nucleoside analogue D-carba T blocks HIV-1 reverse transcription. J Med Chem. 2009 Sep 10;52(17):5356-64. doi: 10.1021/jm801176e. PMID: 19678643; PMCID: PMC2756836.
