Azathioprine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Azathioprine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Azathioprine?

The molecule Azathioprine presents a molecular formula of C17H21NO4 and its IUPAC name is 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine.

Azathioprine is an immunosuppressive medication used to prevent the body from rejecting transplanted organs. It is also used to treat a number of autoimmune diseases, including rheumatoid arthritis, Crohn's disease, and ulcerative colitis. Azathioprine works by suppressing the immune system..

Azathioprine was first synthesized in the early 1950s. It is a prodrug, meaning that it is inactive until it is metabolized by the body. Once it is metabolized, it becomes the active drug, 6-mercaptopurine. Azathioprine is typically taken in pill form, although it can also be given as an injection..

The exact mechanism of action of azathioprine is not fully understood. It is thought to work by inhibiting the production of certain immune cells, such as T-lymphocytes and B-lymphocytes. Azathioprine can take several weeks or months to take effect..

Common side effects of azathioprine include nausea, vomiting, diarrhea, and hair loss. More serious side effects include liver damage, bone marrow suppression, and an increased risk of developing certain types of cancer. Azathioprine should not be used by pregnant women or women who are breastfeeding..

Azathioprine is a powerful immunosuppressive drug that can have serious side effects. It should be used only under the supervision of a healthcare provider..

3D structure

Cartesian coordinates

Geometry of Azathioprine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Azathioprine LOALFJPXZIHKNH-KRWDZBQOSA-N chemical compound 2D structure molecule svg
Azathioprine

 

Molecule descriptors

 
IUPAC name6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine
InChI codeInChI=1S/C17H21NO4/c1-3-10-13(19)6-5-11-12-7-8-22-17(4-2,9-14(20)21)16(12)18-15(10)11/h5-6,18-19H,3-4,7-9H2,1-2H3,(H,20,21)/t17-/m0/s1
InChI KeyLOALFJPXZIHKNH-KRWDZBQOSA-N
SMILESCCc1c(O)ccc2c3c([nH]c12)[C@](CC)(CC(=O)O)OCC3

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 055A974
  • 1H-PURINE, 6-((1-METHYL-4-NITRO-1H-IMIDAZOL-5-YL)THIO)
  • 1H-Purine, 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-
  • 1H-Purine, 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-
  • 446-86-6
  • 446A866
  • 6-((1-METHYL-4-NITROIMIDAZOL-5-YL)THIO)PURINE6-((1-METHYL-4-NITRO-1H-IMIDAZOL-5-YL)THIO)-1H-PURINE
  • 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine
  • 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-9H-purine
  • 6-((1-Methyl-4-nitroimidazol-5-yl)thio)purine
  • 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-7H-purine
  • 6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purin
  • 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine
  • 6-(1'-Methyl-4'-nitro-5'-imidazolyl)mercaptopurine
  • 6-(1-Methyl-4-nitro-5-imidazolythio)-9H-pur-ine
  • 6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine
  • 6-(1-Methyl-4-nitroimidazol-5-ylthio)purin
  • 6-(1-Methyl-4-nitroimidazol-5-ylthio)purine
  • 6-(1-Methyl-4-nitromidazol-5-ylthio)purine
  • 6-(1-Methyl-p-nitro-5-imidazolyl)-thiopurine
  • 6-(1-Methyl-p-nitro-5-imidazolyl)thiopurine
  • 6-(1-methyl-4-nitro-1H-imidazol-5-ylthio)-9H-purine
  • 6-(3-methyl-5-nitro-imidazol-4-yl)sulfanyl-9H-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,5'-imidazolyl mercaptopurine
  • 6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-1H-purine
  • 6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-1H-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)sulfanyl]-9H-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
  • 9H-Purine, 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-
  • A 4638
  • A826664
  • AB00443544
  • AB00443544-03
  • AB00443544-11
  • AB00443544_12
  • AB00443544_13
  • AC-4230
  • ACT02232
  • AI-981/34845012
  • AI3-50290
  • Azamun
  • Azamune
  • Azanin
  • Azasan
  • Azathioprin
  • Azathioprine
  • Azathioprine (Azasan, Imuran)
  • Azathioprine (JP17/USP/INN)
  • Azathioprine, meets USP testing specifications
  • Azathioprinum
  • Azathiopurine
  • Azathiopurine,(S)
  • Azatioprin
  • Azatioprina
  • Azoran
  • Azothioprin
  • Azothioprine
  • B. W. 57-322
  • BA166065
  • BCP09492
  • BDBM50373919
  • BPBio1_000054
  • BSPBio_000048
  • BSPBio_001876
  • BW 57-322
  • BW 57322
  • BW-57-322
  • C06837
  • CBDivE_013132
  • CCG-16168
  • CCG-220094
  • CCG-39877
  • CCRIS 62
  • Ccucol
  • ChemDiv1_002659
  • D00238
  • D70170
  • DB00993
  • DSSTox_CID_119
  • DSSTox_GSID_20119
  • DSSTox_RID_75381
  • DivK1c_000586
  • EU-0100027
  • FT-0602904
  • FT-0662375
  • GTPL7120
  • HMS1568C10
  • HMS1920E17
  • HMS2091K19
  • HMS2095C10
  • HMS2802J03
  • HMS3259P03
  • HMS3260E15
  • HMS3655M04
  • HMS3712C10
  • HMS501N08
  • HMS594I19
  • HSDB 7084
  • HY-B0256
  • IDI1_000586
  • Imuran
  • Imurek
  • Imurel
  • Jayempi
  • KBio1_000586
  • KBio2_000464
  • KBio2_002427
  • KBio2_003032
  • KBio2_004995
  • KBio2_005600
  • KBio2_007563
  • KBio3_001376
  • KBio3_002906
  • KBioGR_000646
  • KBioGR_002427
  • KBioSS_000464
  • KBioSS_002433
  • KS-1146
  • LP00027
  • Lopac-A-4638
  • Lopac0_000027
  • MFCD00069203
  • MLS001049307
  • MRK240IY2L
  • Methylnitroimidazolylmercaptopurine
  • Muran
  • NC00614
  • NCGC00015060-01
  • NCGC00015060-02
  • NCGC00015060-03
  • NCGC00015060-04
  • NCGC00015060-05
  • NCGC00015060-06
  • NCGC00015060-07
  • NCGC00015060-08
  • NCGC00015060-09
  • NCGC00015060-10
  • NCGC00015060-11
  • NCGC00015060-12
  • NCGC00015060-13
  • NCGC00015060-14
  • 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
  • NCI-C03474
  • NINDS_000586
  • NSC 39084
  • NSC-39084
  • NSC-755900
  • NSC39084
  • NSC755900
  • Oprea1_375441
  • Oprea1_533384
  • Oprea1_633462
  • Pharmakon1600-01500133
  • Prestwick0_000094
  • Prestwick1_000094
  • Prestwick2_000094
  • Prestwick3_000094
  • Prestwick_41
  • Purine, 6-((1-methyl-4-nitroimidazol-5-yl)thio)-
  • Purine, 6-(1-methyl-4-nitro-5-imidazolylthio)-
  • Purine, 6-[(1-methyl-4-nitroimidazol-5-yl)thio]-
  • Q18939
  • Rorasul
  • SBI-0050016.P003
  • SDCCGMLS-0065415.P001
  • SDCCGSBI-0050016.P005
  • SMR000427366
  • SPECTRUM1500133
  • SR-01000075537
  • SR-01000075537-1
  • SR-01000075537-4
  • SR-01000762955
  • SR-01000762955-2
  • STK831906
  • SW198560-2
  • Thiopurine 6-(1-methyl-4-nitroimidazol-5-yl)
  • WLN: T56 BM DN FN HNJ IS- ET5N CNJ A1 DNW
  • Z57063156
  • azanine
  • azathioprine
  • cMAP_000046
  • s1721

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4258316
  • CAS-446-86-6
  • UNII-MRK240IY2L
  • AKOS005609209
  • AKOS028108935
  • BRD-K32821942-001-05-6
  • BRD-K32821942-001-10-6
  • BRD-K60324116-001-01-5
  • DTXSID4020119
  • CHEMBL1542
  • CHEBI:2948
  • Tox21_110074
  • Tox21_400024
  • Tox21_500027
  • Tox21_110074_1
  • EINECS 207-175-4
  • SPBio_000255
  • SPBio_001987
  • SCHEMBL4278
  • Spectrum_000064
  • Spectrum2_000068
  • Spectrum3_000308
  • Spectrum4_000243
  • Spectrum5_000848

Physico-Chemical properties

IUPAC name6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine
Molecular formulaC17H21NO4
Molecular weight303.353
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity84.69
LogP3.1
Topological polar surface area82.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.