Editing Azathioprine (section)

{{Short description|Immunosuppressive medication}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 458437709
| drug_name =
| image = Azathioprine.svg
| image_class = skin-invert-image
| width = 125
| alt = 
| image2 = Azathioprine xtal 1984.png
| width2 = 200
| alt2 = 
| caption =

<!-- Clinical data -->
| pronounce = {{IPAc-en|ˌ|æ|z|ə|ˈ|θ|aɪ|ə|ˌ|p|r|iː|n}}{{refn|{{MerriamWebsterDictionary|Azathioprine}}}}
| tradename = Azasan, Imuran, Jayempi, others
| Drugs.com = {{drugs.com|monograph|azathioprine}}
| MedlinePlus = a682167
| licence_EU = 
| DailyMedID = Azathioprine
| licence_US = 
| pregnancy_AU = D
| pregnancy_AU_comment = 
| pregnancy_category = 
| routes_of_administration = [[By mouth]], [[Intravenous therapy|intravenous]]
| class = 
| ATCvet = 
| ATC_prefix = L04
| ATC_suffix = AX01
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = 
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment = 
| legal_CA = Rx-only
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = 
| legal_US = Rx-only
| legal_US_comment = 
| legal_EU = Rx-only
| legal_EU_comment = <ref name="Jayempi EPAR">{{cite web | title=Jayempi EPAR | website=European Medicines Agency | date=20 April 2021 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/jayempi | access-date=4 March 2023}}</ref><ref>{{cite web | title=Jayempi Product information | website=Union Register of medicinal products | url=https://ec.europa.eu/health/documents/community-register/html/h1557.htm | access-date=3 March 2023}}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 60±31%
| protein_bound = 20–30%
| metabolism = Activated non-enzymatically, deactivated mainly by [[xanthine oxidase]]
| metabolites = 
| onset = 
| elimination_half-life= 26–80 minutes (azathioprine)<br />3–5 hours (drug plus metabolites)
| duration_of_action = 
| excretion = [[Kidney]], 98% as metabolites

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number=446-86-6
| CAS_supplemental = <br />{{CAS|55774-33-9}} ([[sodium]] [[salt (chemistry)|salt]])
| PubChem = 2265
| IUPHAR_ligand = 
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00993
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2178
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = MRK240IY2L
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00238
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2948
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1542
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = AZA

<!-- Chemical and physical data -->
| IUPAC_name = 6-[(1-Methyl-4-nitro-1''H''-imidazol-5-yl)sulfanyl]-7''H''-purine
| C=9 | H=7 | N=7 | O=2 | S=1
| SMILES = Cn1cnc(N(=O)=O)c1Sc2ncnc3nc[nH]c23
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LMEKQMALGUDUQG-UHFFFAOYSA-N
| density = 
| density_notes = 
| melting_point = 238
| melting_high = 245
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}

<!-- Definition and medical uses -->
'''Azathioprine''', sold under the brand name '''Imuran''', among others, is an [[immunosuppressive medication]].<ref name=AHFS2016/> It is used for the treatment of [[rheumatoid arthritis]], [[granulomatosis with polyangiitis]], [[Crohn's disease]], [[ulcerative colitis]], and [[systemic lupus erythematosus]], and in [[kidney transplant]]s to prevent [[transplant rejection|rejection]]. It is listed by the International Agency for Research on Cancer as a [[group 1 carcinogen|group 1 human carcinogen]].<ref name=AHFS2016/><ref>{{cite journal | vauthors = Axelrad JE, Lichtiger S, Yajnik V | title = Inflammatory bowel disease and cancer: The role of inflammation, immunosuppression, and cancer treatment | journal = World Journal of Gastroenterology | volume = 22 | issue = 20 | pages = 4794–4801 | date = May 2016 | pmid = 27239106 | pmc = 4873872 | doi = 10.3748/wjg.v22.i20.4794 | type = Review | doi-access = free }}</ref><ref name=Sing2017>{{cite journal | vauthors = Singer O, McCune WJ | title = Update on maintenance therapy for granulomatosis with polyangiitis and microscopic polyangiitis | journal = Current Opinion in Rheumatology | volume = 29 | issue = 3 | pages = 248–253 | date = May 2017 | pmid = 28306595 | doi = 10.1097/BOR.0000000000000382 | s2cid = 35805200 }}</ref><ref>{{cite journal | vauthors = Jordan N, D'Cruz D | title = Current and emerging treatment options in the management of lupus | journal = ImmunoTargets and Therapy | volume = 5 | pages = 9–20 | date = 2016 | pmid = 27529058 | pmc = 4970629 | doi = 10.2147/ITT.S40675 | doi-access = free }}</ref> It is taken by mouth or [[intravenous|injected into a vein]].<ref name=AHFS2016>{{cite web|title=Azathioprine|url=https://www.drugs.com/monograph/Azathioprine.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20160820215808/https://www.drugs.com/monograph/azathioprine.html|archive-date=20 August 2016}}</ref>

<!-- Side effects and mechanism -->
Common side effects include [[bone marrow suppression|bone-marrow suppression]] and [[vomiting]].<ref name=AHFS2016/> Bone-marrow suppression is especially common in people with a [[genetics|genetic]] deficiency of the enzyme [[thiopurine S-methyltransferase]].<ref name=AHFS2016/> Other serious risk factors include an increased risk of certain [[cancer]]s.<ref name=AHFS2016/> Use during [[pregnancy]] may result in harm to the baby.<ref name=AHFS2016/> Azathioprine belongs to the [[purine analogue]]s subclass of [[antimetabolite]]s family of medications.<ref name=AHFS2016/><ref name=Sam2016/> It works via [[6-thioguanine]] to disrupt the making of [[RNA]] and [[DNA]] by cells.<ref name=AHFS2016/><ref name=Sam2016/>

<!-- History and culture -->
Azathioprine was first made in 1957.<ref name=Sam2016>{{cite book| vauthors = Sami N |title=Autoimmune Bullous Diseases: Approach and Management|date=2016|publisher=Springer|isbn=9783319267289|page=83|url=https://books.google.com/books?id=eMSbCwAAQBAJ&pg=PA83|url-status=live|archive-url=https://web.archive.org/web/20161221162220/https://books.google.ca/books?id=eMSbCwAAQBAJ&pg=PA83|archive-date=2016-12-21}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> In 2018, it was the 358th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.<ref>{{cite web | title = Azathioprine - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Azathioprine | access-date = 7 October 2022}}</ref>
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