Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00054)
Name
Azathioprine
Synonyms    Click to Show/Hide the Synonyms of This API
azathioprine; 446-86-6; Imuran; Azothioprine; Azathioprin; Azatioprin; Azamun; Azanin; Imurel; Azathiopurine; Azasan; Ccucol; Imurek; 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; Azoran; AI3-50290; 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin; Prestwick_41; Azathiopurine,(S); [Methyl(nitroimidazolyl)mercaptopurine]; PubChem9256; 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; 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-[(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; 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; AK-98682; SMR000427366; 6-1'-Methyl,5'-imidazolyl mercaptopurine; SBI-0050016.P003; AB0014998; 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; 1767-EP0930075A1; 1767-EP2272822A1; 1767-EP2272825A2; 1767-EP2272827A1; 1767-EP2272832A1; 1767-EP2275420A1; 1767-EP2277865A1; 1767-EP2277876A1; 1767-EP2281815A1; 1767-EP2292227A2; 1767-EP2292614A1; 1767-EP2295409A1; 1767-EP2295412A1; 1767-EP2295413A1; 1767-EP2295426A1; 1767-EP2295427A1; 1767-EP2298743A1; 1767-EP2301933A1; 1767-EP2311827A1; 1767-EP2311837A1; 1767-EP2314590A1; 1767-EP2316834A1; 1767-EP2371811A2; C06837; D00238; Q18939; AB00443544-03; AB00443544-11; AB00443544_12; AB00443544_13; 055A974; 446A866; 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-(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
Clinical Status
Approved
Disease Indication Rheumatoid arthritis ICD-11: FA20 [1]
PubChem CID
2265
Formula
C9H7N7O2S
Canonical SMILES
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=2265"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 277.27 Topological Polar Surface Area 143
XlogP 0.1 Complexity 354
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Azathioprine 100 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose monohydrate; Magnesium stearate; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Salix Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Cadila Healthcare; Zydus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
          Azathioprine 50 mg tablet Click to Show/Hide the Full List of Formulation(s):          9 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Anhydrous lactose; Magnesium stearate; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Amneal Pharmaceuticals; Cardinal Health; NCS HealthCare of KY, Inc dba Vangard Labs
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose monohydrate; Magnesium stearate; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Glenmark Pharmaceutials
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose; Magnesium stearate; Povidone; Starch, potato
                   Dosage Form Oral Tablet
                   Company Sebela Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Anhydrous lactose; Magnesium stearate; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company Amneal Pharmaceuticals; Aphena Pharma Solutions-Tennessee; Cardinal Health; Roxane Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose monohydrate; Magnesium stearate; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company Aphena Pharma Solutions-Tennessee; Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital; Cadila Healthcare; Physicians Total Care; Rebel Distributors; Zydus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             Drug Formulation 7 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Bryant Ranch Prepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             Drug Formulation 8 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company Aidarex Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             Drug Formulation 9 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
          Azathioprine 75 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose monohydrate; Magnesium stearate; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Salix Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Cadila Healthcare; Zydus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
          Azathioprine 25 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Povidone; Starch, corn
                   Dosage Form Oral Tablet
                   Company Cadila Healthcare; Zydus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
References
1 FDA label for approved azathioprine from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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