Structure via PubChem · Public domain (PubChem)
azathioprine
Sign in to saveAlso known as Azasan®, BW-57-322, Imuran®, 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine, 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine, Imuran (TN), Imuran (tn)
Azathioprine, sold under the brand name Imuran, among others, is an immunosuppressive medication. It is used for the treatment of rheumatoid arthritis, granulomatosis with polyangiitis, Crohn's disease, ulcerative colitis, and systemic lupus erythematosus, and in kidney transplants to prevent rejection. It is listed by the International Agency for Research on Cancer as a group 1 human carcinogen. It is taken by mouth or injected into a vein.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 458437709
- Drug.image
- Azathioprine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 125
- Drug.image2
- Azathioprine xtal 1984.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200
- Drug.tradename
- Azasan, Imuran, Jayempi, others
- Drug.MedlinePlus
- a682167
- Drug.DailyMedID
- Azathioprine
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth, intravenous
- Drug.ATC_prefix
- L04
- Drug.ATC_suffix
- AX01
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
via Wikipedia infobox
Chemical data
- Formula
- C9H7N7O2S
- Molecular weight
- 277.27 g/mol
- IUPAC name
- 6-(3-methyl-5-nitroimidazol-4-yl)sulfanyl-7H-purine
- SMILES
- CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
- InChIKey
- LMEKQMALGUDUQG-UHFFFAOYSA-N
- XLogP
- 0.1
- Polar surface area
- 143 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
26,406 papers- Azathioprine in dermatology.Journal of the American Academy of Dermatology · 1991
- Azathioprine in dermatology.Acta dermatovenerologica Croatica : ADC · 2007
- Is weekly azathioprine pulse effective and safe in dermatological conditions?Dermatologic therapy · 2021
- Azathioprine.Clinics in rheumatic diseases · 1984
- Azathioprine in dermatology: the past, the present, and the future.Journal of the American Academy of Dermatology · 2006
via PubMed
Wikidata facts
- Subclass of
- thiopurine
- Has part
- carbon
- Mass
- 277.038193
- Has use
- medication
Show 11 more facts
- subject has role
- essential medicine
- chemical formula
- C₉H₇N₇O₂S
- medical condition treated
- Crohn's disease
- Commons category
- Azathioprine
- canonical SMILES
- CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
- legal status (medicine)
- boxed warning
- MCN code
- 2933.59.34
- has characteristic
- bitterness
- stylized name
- azaTHIOprine
- physically interacts with
- Phosphoribosyl pyrophosphate amidotransferase
- significant drug interaction
- rac-warfarin
Sources (10)
via Wikidata · CC0
~19 min read
Encyclopedic overview
19 sectionsContents
- Medical uses
- Transplantation
- Rheumatoid arthritis
- Inflammatory bowel disease
- Others
- Adverse effects
- Pharmacogenetics
- Cancers
- Skin cancers
- Overdose
- Interactions
- Pregnancy and breastfeeding
- Pharmacology
- Pharmacokinetics
- Mechanism of action
- Chemistry
- History
- References
- Further reading
Azathioprine, sold under the brand name Imuran, among others, is an immunosuppressive medication. It is used for the treatment of rheumatoid arthritis, granulomatosis with polyangiitis, Crohn's disease, ulcerative colitis, and systemic lupus erythematosus, and in kidney transplants to prevent rejection. It is listed by the International Agency for Research on Cancer as a group 1 human carcinogen. It is taken by mouth or injected into a vein.
Common side effects include bone-marrow suppression and vomiting. Bone-marrow suppression is especially common in people with a genetic deficiency of the enzyme thiopurine S-methyltransferase. Other serious risk factors include an increased risk of certain cancers. Use during pregnancy may result in harm to the baby. Azathioprine belongs to the purine analogues subclass of antimetabolites family of medications. It works via 6-thioguanine to disrupt the making of RNA and DNA by cells.
Excerpted from Wikipedia’s “azathioprine” article, available under the CC BY-SA 4.0 licence.