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| Other Sizes |
| Targets |
2-Chloroadenine is a synthetic intermediate and purine analog rather than a direct pharmacological agent. As a building block, it does not have specific biological receptors as its primary targets. The compound is a heterocyclic building block used in the synthesis of adenosine antimetabolites with antineoplastic activity. It is also the major catabolite of 2-chloro-2'-deoxyadenosine (cladribine), a purine nucleoside analog used in the treatment of hairy cell leukemia. The compound's primary applications are as a synthetic intermediate for nucleoside analog drug discovery.
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| ln Vitro |
2-Chloroadenine is a heterocyclic building block that has been employed in the synthesis of antitumor-active adenosine antimetabolites. Additionally, it is the primary byproduct of 2-chloro-2'-deoxyadenosine breakdown.
In vitro, 2-chloroadenine is used as a biochemical reagent and organic compound for biomedical research. It is a heterocyclic building block used in the synthesis of adenosine antimetabolites with antineoplastic activity. Cellular assays are typically performed on the final nucleoside analogs synthesized from this building block. The compound's purine scaffold allows for various chemical transformations, including glycosylation, making it valuable for nucleoside analog drug discovery. The compound's role as a cladribine metabolite is relevant for studying drug metabolism. |
| ln Vivo |
In vivo, 2-chloroadenine is the major catabolite of 2-chloro-2'-deoxyadenosine (cladribine), a purine nucleoside analog used in the treatment of hairy cell leukemia. As a metabolite, it is formed through the metabolism of cladribine and may contribute to the drug's pharmacological effects or toxicity. The compound is classified for research use only and is not intended for human or veterinary therapeutic applications. Its primary value lies in its use as a synthetic intermediate and as a reference standard for drug metabolism studies.
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| Enzyme Assay |
In vitro enzyme assays for 2-chloroadenine are not typically performed, as it is primarily a synthetic intermediate. The compound is used as a building block in the synthesis of adenosine antimetabolites. A typical assay involves using the compound in chemical reactions, such as glycosylation, to prepare nucleoside analogs. The compound is dissolved in organic solvents such as DMSO or DMF. The resulting nucleoside analogs can be evaluated for biological activity. Enzyme inhibition or receptor binding assays can be performed on the final synthesized compounds. IC₅₀ or binding affinity values are calculated from dose-response curves.
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| Cell Assay |
Cellular assays for 2-chloroadenine derivatives typically evaluate antineoplastic activity. A standard protocol involves culturing cancer cell lines (e.g., leukemia cell lines) in growth medium at 37°C with 5% CO₂. Cells are treated with synthesized nucleoside analogs at varying concentrations for 24-72 hours. Cell viability is assessed using MTT or similar assays. The mechanism of action may involve incorporation into DNA or inhibition of DNA synthesis. IC₅₀ values are calculated from dose-response curves. The compound's role as a cladribine metabolite may also be studied in cellular models.
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| Animal Protocol |
In vivo animal studies for 2-chloroadenine are not standard, as it is primarily a synthetic intermediate and metabolite. The compound is classified for research use only and is not intended for human or veterinary applications. Any animal studies would typically be conducted on cladribine or other nucleoside analogs synthesized using this building block. These studies would evaluate efficacy in cancer models, pharmacokinetics, and safety. The compound's primary value lies in its use as a synthetic intermediate and as a reference standard for drug metabolism studies.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 2-chloroadenine is related to its role as a metabolite of cladribine. The compound has a molecular weight of 169.57 g/mol and a molecular formula of C₅H₄ClN₅. It is a solid at room temperature and is stored in a cool, dark place. As a purine analog, it is expected to be metabolized and excreted renally. Specific ADME data for the parent compound is limited. The compound is soluble in organic solvents.
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| Toxicity/Toxicokinetics |
2-Chloroadenine is classified for research use only and is not intended for human or veterinary applications. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound should be stored in a dry, cool place away from incompatible materials. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed. No specific LD₅₀ values or detailed toxicological profiles are available in the public domain.
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| References |
[1]. Bauta, WE, Schulmeier, BE, Bur the , BJ, et al.A new process for antineoplastic agent clofarabineOrg. Proc. Res. Dev.8(6)889-896(2004)
[2]. Bontemps, F., Delacauw, A., Cardoen, S., et al. Metabolism and cytotoxic effects of 2-chloroadenine, the major catabolite of 2-chloro-29-deoxyadenosine Biochem. Pharmacol.59(10)1237-1243(2000) |
| Additional Infomation |
2-Chloroadenine (6-Amino-2-chloropurine, CAS 1839-18-5) is a biochemical reagent with the molecular formula C₅H₄ClN₅. It is a heterocyclic building block used in the synthesis of adenosine antimetabolites with antineoplastic activity and is the major catabolite of cladribine. The compound is classified as a research-use-only compound not intended for diagnostic or therapeutic purposes. It is available from multiple commercial suppliers in various pack sizes. No clinical trials or approved drug status exist for this compound as it is not a therapeutic agent.
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| Molecular Formula |
C5H4CLN5
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| Molecular Weight |
169.57
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| Exact Mass |
169.015
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| CAS # |
1839-18-5
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| PubChem CID |
94904
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| Appearance |
Off-white to light brown solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
485.5±27.0 °C at 760 mmHg
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| Melting Point |
>300°C(dec)
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| Flash Point |
247.4±23.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.827
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| LogP |
0.35
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
154
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1=NC(=C2C(=N1)N=C([H])N2[H])N([H])[H]
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| InChi Key |
HBJGQJWNMZDFKL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H4ClN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)
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| Chemical Name |
2-chloro-7H-purin-6-amine
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 5.8973 mL | 29.4863 mL | 58.9727 mL | |
| 5 mM | 1.1795 mL | 5.8973 mL | 11.7945 mL | |
| 10 mM | 0.5897 mL | 2.9486 mL | 5.8973 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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