Drug Information

General Information
Drug ID
DR00113
Drug Name
Azathioprine
Synonyms
6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine; 6-((1-Methyl-4-nitroimidazol-5-yl)thio)purine; 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine; 6-(1'-Methyl-4'-nitro-5'-imidazolyl)mercaptopurine; 6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin [Czech]; 6-(1-Methyl-p-nitro-5-imidazolyl)-thiopurine; 6-(1-Methyl-p-nitro-5-imidazolyl)thiopurine; 6-(3-Methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-7H-purine; 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine; 6-(Methyl-p-nitro-5-imidazolyl)-thiopurine; 6-(Methyl-p-nitro-5-imidazolyl)thiopurine; 6-({4-nitro-1-methyl-1H-imidazol-5-yl}sulfanyl)-7H-purine; 6-1'-Methyl,4'-nitro,5'-imidazolyl mercaptopurine; 6-[(1-Methyl-4-nitroimidazol-5-yl)-thio] purine; 6-[(1-Methyl-4-nitroimidazol-5-yl)thio]purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-1H-Purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-7H-purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-9H-purine; A 4638; AI-981/34845012; Azamun; Azamun (TN); Azamun [Czech]; Azanin; Azasan; Azasan (TN); Azasan, Imuran, Azamun, BW-57-322, NSC-39084, Azathioprine; Azathioprin; Azathioprine (JP15/USP/INN); Azathioprine [USAN:INN:BAN:JAN]; Azathioprine sodium; Azathioprinum; Azathioprinum [INN-Latin]; Azathiopurine; Azatiopr in; Azatioprin; Azatioprina; Azatioprina [INN-Spanish]; Azothioprine; B. W. 57-322; BW 57-322; BW 57322; BW-57-322; Ccucol; Cytostatics; Immuran; Imuran; Imuran (TN); Imurek; Imurel; Imurel (TN); Methylnitroimidazolylmercaptopurine; Muran; Thiopurine 6-(1-methyl-4-nitroimidazol-5-yl); [Methyl(nitroimidazolyl)mercaptopurine]
Drug Type
Small molecular drug
Indication Organ transplant rejection [ICD11:NE84] Approved [1]
Therapeutic Class
Immunosuppressive Agents
Structure
3D MOL 2D MOL
Formula
C9H7N7O2S
Canonical SMILES
CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
InChI
InChI=1S/C9H7N7O2S/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,(H,10,11,12,13)
InChIKey
LMEKQMALGUDUQG-UHFFFAOYSA-N
CAS Number
CAS 446-86-6
Pharmaceutical Properties Molecular Weight 277.27 Topological Polar Surface Area 143
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
XLogP
0.1
PubChem CID
2265
PubChem SID
10321142 ,10560483 ,10584680 ,11110740 ,11110741 ,11142069 ,11335761 ,11361000 ,11362878 ,11364839 ,11365440 ,11367401 ,11368002 ,11369963 ,11371476 ,11373003 ,11373785 ,11375563 ,11376164 ,11378131 ,11461972 ,11466122 ,11467242 ,11483991 ,11485723 ,11487884 ,11490124 ,11492058 ,11493878 ,11524329 ,11533962 ,11536345 ,12294767 ,14775167 ,14824335 ,15222101 ,17390031 ,17404591 ,24278074 ,4476272 ,4486208 ,4503338 ,545491 ,7592075 ,7695226 ,7847305 ,7978746 ,8149210 ,8151523 ,9055
ChEBI ID
ChEBI:2948
TTD Drug ID
D07QCE
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
References
1 Azathioprine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22.

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