| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg | |||
| 100mg | |||
| Other Sizes |
Purity: ≥98%
| Targets |
CMV; DNA replication
Enocitabine targets viral DNA polymerase and cellular DNA replication machinery. As a nucleoside analog, it inhibits DNA synthesis by incorporating into the DNA chain and acting as a chain terminator. The compound also inhibits the replication of human cytomegalovirus (CMV). Its primary mechanism involves disruption of DNA polymerase function and other enzymes involved in DNA replication. |
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| 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]. In vitro, Enocitabine acts as a potent DNA replication inhibitor and DNA chain terminator. It inhibits the replication of human cytomegalovirus (CMV) in cultured Vero cells with an EC90 of 0.5 µg/ml. The compound demonstrates antileukemic activity against various leukemia cell lines. Enocitabine is resistant to deamination due to the lipophilic group at the 4-amino position of the cytosine moiety, which enhances its stability compared to cytarabine. |
| ln Vivo |
In vivo, Enocitabine is used clinically as an anticancer agent for the treatment of acute myeloid leukemia (AML). It has been shown to reduce virus yield in CMV-infected models. As a lipophilic prodrug of cytarabine, Enocitabine provides improved oral bioavailability and prolonged systemic exposure compared to the parent drug, making it effective in hematological malignancies.
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| Enzyme Assay |
The in vitro enzyme activity assay for Enocitabine typically involves measuring its inhibitory effect on viral DNA polymerase. Recombinant or purified DNA polymerase is incubated with varying concentrations of Enocitabine (or its active metabolite cytarabine triphosphate) and a DNA template with radiolabeled nucleotides. The extent of DNA synthesis inhibition is measured by scintillation counting or gel electrophoresis. The compound acts as a DNA chain terminator, and IC50 values are determined from dose-response curves.
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| Cell Assay |
In vitro cellular assays for Enocitabine involve treating cultured leukemia cell lines or CMV-infected Vero cells with varying concentrations of the compound. Cell viability and proliferation are assessed using MTT or trypan blue exclusion assays. Antiviral activity is measured by quantifying viral DNA replication via qPCR or plaque reduction assays. The EC90 for CMV inhibition (0.5 µg/ml) and IC50 for antiproliferative activity are determined from dose-response curves.
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| Animal Protocol |
In vivo animal experiments for Enocitabine typically use mouse xenograft models of acute myeloid leukemia or models of CMV infection. Tumor-bearing or virus-infected mice are administered Enocitabine via oral or intravenous routes at various doses. Tumor volume or viral load is measured at regular intervals. Survival rates and hematological parameters are monitored to assess efficacy and toxicity. The compound's antileukemic and antiviral activities are evaluated by comparing treatment groups to vehicle controls.
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| ADME/Pharmacokinetics |
Enocitabine is a lipophilic prodrug of cytarabine designed for oral administration. It is metabolized to cytarabine, which is then converted to its active triphosphate form. The compound has a molecular weight of 335.31 (C13H17N3O5S). As a lipophilic analog, Enocitabine exhibits improved oral bioavailability and resistance to deamination compared to cytarabine. Specific PK parameters including half-life and Cmax are available from clinical pharmacology studies.
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| Toxicity/Toxicokinetics |
Enocitabine is an approved anticancer drug for acute myeloid leukemia, and its safety profile has been established through clinical use. As a nucleoside analog, common adverse effects may include myelosuppression, gastrointestinal disturbances, and hepatotoxicity. The compound is contraindicated in patients with severe hepatic or renal impairment. Regular monitoring of blood counts and liver function is required during treatment. Complete toxicology data are available from the drug's clinical development program.
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| References | |
| Additional Infomation |
Enocitabine is an organic molecular entity. It is a pyrimidine antimetabolite that is converted into cytarabine in the body. (NCI)
Enocitabine (CAS#: 55726-47-1) is a lipophilic prodrug of cytarabine (Ara-C) approved for the treatment of acute myeloid leukemia (AML). It is also known as NSC-239336, BHAC, and Sunrabin. The compound exhibits both antileukemic and antiviral activities, inhibiting DNA replication and human CMV replication. Enocitabine is resistant to deamination due to its lipophilic modification at the 4-amino position. It remains a clinically used agent in certain regions for hematological malignancies. |
| Molecular Formula |
C31H55N3O6
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|---|---|
| Molecular Weight |
565.7849
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| Exact Mass |
565.409
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| Elemental Analysis |
C, 65.81; H, 9.80; N, 7.43; O, 16.97
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| CAS # |
55726-47-1
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| Related CAS # |
55726-47-1
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| PubChem CID |
71734
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Melting Point |
141-142ºC
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| Index of Refraction |
1.554
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| LogP |
9
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
23
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| Heavy Atom Count |
40
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| Complexity |
774
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| Defined Atom Stereocenter Count |
4
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| SMILES |
CCCCCCCCCCCCCCCCCCCCCC(N=C1C=CN(C(N1)=O)C2C(O)C(O)C(O2)CO)=O
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| InChi Key |
SAMRUMKYXPVKPA-VFKOLLTISA-N
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| 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
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| Chemical Name |
N-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]docosanamide
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| Synonyms |
Sunrabin; BH-AC; BHAC; BH AC;Enocitabine; Arabinoside; NSC-239336; NSC239336; NSC 239336
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~2 mg/mL (~3.5 mM)
H2O : < 0.1 mg/mL |
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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