Azathioprine sodiumProduct ingredient for Azathioprine
- Name
- Azathioprine sodium
- Drug Entry
- Azathioprine
Azathioprine is a prodrug of 6-mercaptopurine, first synthesized in 1956 by Gertrude Elion, William Lange, and George Hitchings in an attempt to produce a derivative of 6-mercaptopurine with a better therapeutic index.9,10,11 Azathioprine is used to treat inflammatory conditions like rheumatoid arthritis and as an immunosuppressant in the prevention of renal transplant rejection.12
Azathiprine was granted FDA approval on 20 March 1968.12
- Accession Number
- DBSALT000012
- Structure
- Synonyms
- Not Available
- UNII
- AM94R510MS
- CAS Number
- 55774-33-9
- Weight
- Average: 299.244
Monoisotopic: 299.020137836 - Chemical Formula
- C9H6N7NaO2S
- InChI Key
- WISNYKIQFMKSDQ-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H6N7O2S.Na/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8;/h2-4H,1H3;/q-1;+1
- IUPAC Name
- sodium 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-9H-purin-9-ide
- SMILES
- [Na+].CN1C=NC(=C1SC1=NC=NC2=C1N=C[N-]2)N(=O)=O
- External Links
- PubChem Compound
- 11529527
- ChemSpider
- 9704310
- ChEBI
- 774351
- ChEMBL
- CHEMBL1200400
- Wikipedia
- Azathioprine
- Predicted Properties
Property Value Source Water Solubility 2.47 mg/mL ALOGPS logP 0.5 ALOGPS logP 1.22 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 9.84 Chemaxon pKa (Strongest Basic) 2.54 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 115.2 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 69.9 m3·mol-1 Chemaxon Polarizability 23.87 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon