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
PubChem Compound
11529527
ChemSpider
9704310
ChEBI
774351
ChEMBL
CHEMBL1200400
Wikipedia
Azathioprine
Predicted Properties
PropertyValueSource
Water Solubility2.47 mg/mLALOGPS
logP0.5ALOGPS
logP1.22Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.84Chemaxon
pKa (Strongest Basic)2.54Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area115.2 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity69.9 m3·mol-1Chemaxon
Polarizability23.87 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon