Enocitabine (NSC-239336; BHAC; Sunrabin; Arabinoside) is a cytarabine analogue, cytosine analogue and DNA chain terminator approved as an anticancer drug for the treatment of acute myeloid leukemia. It also functions as a DNA replication inhibitor, which prevents the cytomegalovirus from proliferating and replicating.
Physicochemical Properties
| Molecular Formula | C31H55N3O6 |
| Molecular Weight | 565.7849 |
| Exact Mass | 565.409 |
| Elemental Analysis | C, 65.81; H, 9.80; N, 7.43; O, 16.97 |
| CAS # | 55726-47-1 |
| Related CAS # | 55726-47-1 |
| PubChem CID | 71734 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Melting Point | 141-142ºC |
| Index of Refraction | 1.554 |
| LogP | 9 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 23 |
| Heavy Atom Count | 40 |
| Complexity | 774 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | CCCCCCCCCCCCCCCCCCCCCC(N=C1C=CN(C(N1)=O)C2C(O)C(O)C(O2)CO)=O |
| InChi Key | SAMRUMKYXPVKPA-VFKOLLTISA-N |
| InChi Code | InChI=1S/C31H55N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(36)32-26-22-23-34(31(39)33-26)30-29(38)28(37)25(24-35)40-30/h22-23,25,28-30,35,37-38H,2-21,24H2,1H3,(H,32,33,36,39)/t25-,28-,29+,30-/m1/s1 |
| Chemical Name | N-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]docosanamide |
| Synonyms | Sunrabin; BH-AC; BHAC; BH AC;Enocitabine; Arabinoside; NSC-239336; NSC239336; NSC 239336 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | CMV; DNA replication |
| ln Vitro |
Enocitabine is resistant to deamination due to the presence of a highly lipophilic group in enocitabine at the cytosine moiety of cytarabine's 4-amino position[1]. Enocitabine and pirarubicin work together to increase the cytotoxic activities of HeLa S3 human uterine cervix carcinoma and K562 human myelocytic leukemia cells. When it comes to HeLa S3 and K562 cells, etoposide and enocitabine work in concert[2]. Enocitabine significantly suppresses the synthesis of HCMV DNA and causes the human cytomegalovirus (HCMV)-infected cells to produce triphosphate forms of the nucleoside analogs[3]. |
| References |
[1]. Clinical pharmacokinetics of cytarabine formulations.Clin Pharmacokinet. 2002;41(10):705-18. [2]. In vitro combined effects of pirarubicin (THP) and various antitumor drugs on human tumor cell lines. Gan To Kagaku Ryoho. 1990 Apr;17(4 Pt 1):633-8. [3]. Antiviral effect of antileukemic drugs N4-behenoyl-1-beta-D-arabinofuranosylcytosine (BH-AC) and 2,2'-anhydro-1-beta-D-arabinofuranosylcytosine (cyclo-C) against human cytomegalovirus. J Med Virol. 1990 Jun;31(2):141-7. |
| Additional Infomation |
Enocitabine is an organic molecular entity. Enocitabine is a pyrimidine antimetabolite converted to Cytarabine in the body. (NCI) |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~2 mg/mL (~3.5 mM) H2O : < 0.1 mg/mL |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7675 mL | 8.8374 mL | 17.6747 mL | |
| 5 mM | 0.3535 mL | 1.7675 mL | 3.5349 mL | |
| 10 mM | 0.1767 mL | 0.8837 mL | 1.7675 mL |