Synonym
SN-1212; KP-1212; SN1212; KP1212; SN 1212; KP 1212
IUPAC/Chemical Name
2'-Deoxy-5,6-dihydro-5-azacytidine
InChi Key
LAOLDMMWVYDDID-KVQBGUIXSA-N
InChi Code
InChI=1S/C8H14N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h4-6,13-14H,1-3H2,(H3,9,10,11,15)/t4-,5+,6+/m0/s1
SMILES Code
OC[C@@H]1[C@H](C[C@H](N2C(N=C(NC2)N)=O)O1)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
>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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
230.22
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: Rawson JM, Heineman RH, Beach LB, Martin JL, Schnettler EK, Dapp MJ, Patterson SE, Mansky LM. 5,6-Dihydro-5-aza-2'-deoxycytidine potentiates the anti-HIV-1 activity of ribonucleotide reductase inhibitors. Bioorg Med Chem. 2013 Nov 15;21(22):7222-8. doi: 10.1016/j.bmc.2013.08.023. PubMed PMID: 24120088; PubMed Central PMCID: PMC3930610.
2: Harris KS, Brabant W, Styrchak S, Gall A, Daifuku R. KP-1212/1461, a nucleoside designed for the treatment of HIV by viral mutagenesis. Antiviral Res. 2005 Jul;67(1):1-9. PubMed PMID: 15890415.
3: Clay PG, McRae M, Laurent JP. Safety, Tolerability, and Pharmacokinetics of KP-1461 in Phase I Clinical Studies: A Single Oral Dose Study in Non-HIV-Infected Adults, and a 14-Day Dose-Escalating Study in Highly Antiretroviral-Experienced HIV-Infected Adults. J Int Assoc Physicians AIDS Care (Chic). 2011 Jul-Aug;10(4):232-8. doi: 10.1177/1545109711406442. PubMed PMID: 21593403.
4: Peng CS, Fedeles BI, Singh V, Li D, Amariuta T, Essigmann JM, Tokmakoff A. Two-dimensional IR spectroscopy of the anti-HIV agent KP1212 reveals protonated and neutral tautomers that influence pH-dependent mutagenicity. Proc Natl Acad Sci U S A. 2015 Mar 17;112(11):3229-34. doi: 10.1073/pnas.1415974112. PubMed PMID: 25733867; PubMed Central PMCID: PMC4371980.
5: Murakami E, Basavapathruni A, Bradley WD, Anderson KS. Mechanism of action of a novel viral mutagenic covert nucleotide: molecular interactions with HIV-1 reverse transcriptase and host cell DNA polymerases. Antiviral Res. 2005 Jul;67(1):10-7. PubMed PMID: 15950748.
6: Li D, Fedeles BI, Singh V, Peng CS, Silvestre KJ, Simi AK, Simpson JH, Tokmakoff A, Essigmann JM. Tautomerism provides a molecular explanation for the mutagenic properties of the anti-HIV nucleoside 5-aza-5,6-dihydro-2'-deoxycytidine. Proc Natl Acad Sci U S A. 2014 Aug 12;111(32):E3252-9. doi: 10.1073/pnas.1405635111. PubMed PMID: 25071207; PubMed Central PMCID: PMC4136561.
7: Matoušová M, Votruba I, Otmar M, Tloušťová E, Günterová J, Mertlíková-Kaiserová H. 2´-deoxy-5,6-dihydro-5-azacytidine - a less toxic alternative of 2´-deoxy-5-azacytidine: a comparative study of hypomethylating potential. Epigenetics. 2011 Jun;6(6):769-76. PubMed PMID: 21566456; PubMed Central PMCID: PMC3142367.
