Drug Information

Drug (ID: DG00614) and It's Reported Resistant Information

• Name: Azathioprine
• Synonyms: Azathioprine; 446-86-6; Imuran; Azothioprine; Azathioprin; Azatioprin; Azamun; Azanin; Azathiopurine; Imurel; Azasan; Ccucol; Imurek; Muran; Rorasul; BW 57-322; NSC-39084; BW-57-322; NCI-C03474; 6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine; Imuran (TN); NSC 39084; 6-(1-Methyl-p-nitro-5-imidazolyl)-thiopurine; 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine; UNII-MRK240IY2L; 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine; 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-9H-purine; 6-((1-Methyl-4-nitroimidazol-5-yl)thio)purine; Azathioprine (Azasan, Imuran); 1H-Purine, 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-; 1H-Purine, 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-; Purine, 6-(1-methyl-4-nitro-5-imidazolylthio)-; 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine; 6-(Methyl-p-nitro-5-imidazolyl)-thiopurine; MFCD00069203; MRK240IY2L; BW 57322; Azamun [Czech]; 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-7H-purine; CHEBI:2948; B. W. 57-322; NSC39084; 6-(1'-Methyl-4'-nitro-5'-imidazolyl)mercaptopurine; Purine, 6-((1-methyl-4-nitroimidazol-5-yl)thio)-; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-7H-purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-9H-purine; NCGC00015060-06; NCGC00015060-14; Azatioprina; CAS-446-86-6; DSSTox_CID_119; 6-[(1-Methyl-4-nitroimidazol-5-yl)thio]purine; DSSTox_RID_75381; DSSTox_GSID_20119; Azathioprinum [INN-Latin]; Azatioprina [INN-Spanish]; Azamune; Methylnitroimidazolylmercaptopurine; CCRIS 62; Azasan (TN); HSDB 7084; SR-01000075537; Purine, 6-[(1-methyl-4-nitroimidazol-5-yl)thio]-; EINECS 207-175-4; 6-(1-methyl-4-nitro-1H-imidazol-5-ylthio)-9H-purine; 6-1'-Methyl,4'-nitro,5'-imidazolyl mercaptopurine; azanine; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin [Czech]; Azothioprin; Jayempi; Azoran; AI3-50290; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin; Prestwick_41; Azathiopurine,(S); [Methyl(nitroimidazolyl)mercaptopurine]; Azathioprine [USAN:USP:INN:BAN:JAN]; Spectrum_000064; Azathioprine, >=98%; 6-(Methyl-p-nitro-5-imidazolyl)thiopurine; Prestwick0_000094; Prestwick1_000094; Prestwick2_000094; Prestwick3_000094; Spectrum2_000068; Spectrum3_000308; Spectrum4_000243; Spectrum5_000848; Lopac-A-4638; ChemDiv1_002659; 6-(1-Methyl-p-nitro-5-imidazolyl)thiopurine; A 4638; Thiopurine 6-(1-methyl-4-nitroimidazol-5-yl); SCHEMBL4278; CHEMBL1542; Lopac0_000027; Oprea1_375441; Oprea1_533384; Oprea1_633462; BSPBio_000048; BSPBio_001876; CBDivE_013132; KBioGR_000646; KBioGR_002427; KBioSS_000464; KBioSS_002433; AI-981/34845012; MLS001049307; DivK1c_000586; SPECTRUM1500133; SPBio_000255; SPBio_001987; BPBio1_000054; GTPL7120; DTXSID4020119; Azathioprine (JP17/USP/INN); HMS501N08; HMS594I19; KBio1_000586; KBio2_000464; KBio2_002427; KBio2_003032; KBio2_004995; KBio2_005600; KBio2_007563; KBio3_001376; KBio3_002906; cMAP_000046; NINDS_000586; 6-({4-nitro-1-methyl-1H-imidazol-5-yl}sulfanyl)-7H-purine; 6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-1H-purine; HMS1568C10; HMS1920E17; HMS2091K19; HMS2095C10; HMS2802J03; HMS3259P03; HMS3260E15; HMS3655M04; HMS3712C10; Pharmakon1600-01500133; ACT02232; BCP09492; HY-B0256; ZINC4258316; Tox21_110074; Tox21_400024; Tox21_500027; BDBM50373919; CCG-16168; CCG-39877; NSC755900; s1721; STK831906; AKOS005609209; AKOS028108935; Tox21_110074_1; AC-4230; CCG-220094; DB00993; KS-1146; LP00027; MCULE-8637589610; NC00614; NSC-755900; SDCCGMLS-0065415.P001; SDCCGSBI-0050016.P005; IDI1_000586; NCGC00015060-01; NCGC00015060-02; NCGC00015060-03; NCGC00015060-04; NCGC00015060-05; NCGC00015060-07; NCGC00015060-08; NCGC00015060-09; NCGC00015060-10; NCGC00015060-11; NCGC00015060-12; NCGC00015060-13; NCGC00015060-15; NCGC00015060-16; NCGC00015060-18; NCGC00015060-19; NCGC00015060-29; NCGC00090836-01; NCGC00090836-02; NCGC00090836-03; NCGC00090836-04; NCGC00090836-05; NCGC00090836-06; NCGC00094593-01; NCGC00094593-02; NCGC00094593-03; NCGC00260712-01; BA166065; L996; SMR000427366; 6-1'-Methyl,5'-imidazolyl mercaptopurine; SBI-0050016.P003; Azathioprine 100 microg/mL in Acetonitrile; 6-(1-Methyl-4-nitromidazol-5-ylthio)purine; AB00443544; EU-0100027; FT-0602904; FT-0662375; SW198560-2; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purine; Azathioprine, meets USP testing specifications; C06837; D00238; D70170; Q18939; AB00443544-03; AB00443544-11; AB00443544_12; AB00443544_13; 055A974; 446A866; A826664; SR-01000762955; 6-(1-Methyl-4-nitro-5-imidazolythio)-9H-pur-ine; SR-01000075537-1; SR-01000075537-4; SR-01000762955-2; BRD-K32821942-001-05-6; BRD-K32821942-001-10-6; BRD-K60324116-001-01-5; WLN: T56 BM DN FN HNJ IS- ET5N CNJ A1 DNW; Z57063156; 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purin; 6-(3-methyl-5-nitro-imidazol-4-yl)sulfanyl-9H-purine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-9H-purine; 9H-Purine, 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-; Azathioprine, European Pharmacopoeia (EP) Reference Standard; 6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-1H-purine #; Azathioprine, United States Pharmacopeia (USP) Reference Standard; Azathioprine, Pharmaceutical Secondary Standard; Certified Reference Material
• Indication:
  In total 1 Indication(s)
  Organ transplant rejection [ICD-11: NE84]; Approved; [1]
• Drug Resistance Disease(s):
  Disease(s) with Clinically Reported Resistance for This Drug (2 diseases)
  Inflammatory bowel diseases [ICD-11: DD72]; [2]
  Rheumatoid arthritis [ICD-11: FA20]; [1]
• Target: Amidophosphoribosyltransferase (PPAT); PUR1_HUMAN; [1]
• Formula: C9H7N7O2S
• IsoSMILES: CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
• 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
• PubChem CID: 2265
• ChEBI ID: CHEBI:2948
• TTD Drug ID: D07QCE
• VARIDT ID: DR00113
• INTEDE ID: DR0164
• DrugBank ID: DB00993

Type(s) of Resistant Mechanism of This Drug

  IDUE: Irregularity in Drug Uptake and Drug Efflux

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-15: Musculoskeletal/connective-tissue diseases

Rheumatoid arthritis [ICD-11: FA20]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Irregularity in Drug Uptake and Drug Efflux (IDUE)

Key Molecule: ATP-binding cassette sub-family C5 (ABCC5) [1]

• Molecule Alteration: Expression; Up-regulation
• Resistant Disease: Rheumatoid arthritis [ICD-11: FA20.0]
• Experimental Note: Identified from the Human Clinical Data
• Mechanism Description: MTX is a substrate for eight ABC transporters. In vitro studies demonstrated that RAFLS treated with MTX had higher ABCB1 expression levels than controls, with a positive correlation between ABCB1 expression levels and RA treatment duration. In addition to MTX, other DMARDs (e.g. sulfasalazine, leflunomide, bucillamine, azathioprine), glucocorticoids (e.g. betamethasone, dexamethasone), and NSAIDs (e.g. celecoxib and indomethacin) are also substrates of ABC transporters.

References

• Ref 1: Drug-resistance in rheumatoid arthritis: the role of p53 gene mutations, ABC family transporters and personal factors .Curr Opin Pharmacol. 2020 Oct;54:59-71. doi: 10.1016/j.coph.2020.08.002. Epub 2020 Sep 14. 10.1016/j.coph.2020.08.002
• Ref 2: Drug resistance in inflammatory bowel diseases .Curr Opin Pharmacol. 2015 Dec;25:56-61. doi: 10.1016/j.coph.2015.11.003. Epub 2015 Nov 29. 10.1016/j.coph.2015.11.003