{{위키데이터 속성 추적}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 458437709
| drug_name =
| pronounce = {{IPAc-en|ˌ|æ|z|ə|ˈ|θ|aɪ|ə|ˌ|p|r|iː|n}}{{refn|{{MerriamWebsterDictionary|Azathioprine}}}}
| IUPAC_name = 6-[(1-Methyl-4-nitro-1''H''-imidazol-5-yl)sulfanyl]-7''H''-purine
| image = Azathioprine.svg
| width = 125
| image2 = Azathioprine xtal 1984.png
| width2 = 200
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = MRK240IY2L
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1542
| 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LMEKQMALGUDUQG-UHFFFAOYSA-N
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number=446-86-6
| CAS_supplemental = <br />{{CAS|55774-33-9}} ([[나트륨]] [[염|salt]])
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2178
| ATC_prefix = L04
| ATC_suffix = AX01
| ATC_supplemental=
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2948
| PubChem = 2265
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00993
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00238
| C=9 | H=7 | N=7 | O=2 | S=1
| molecular_weight = 277.263 g/mol
| smiles = Cn1cnc(N(=O)=O)c1Sc2ncnc3nc[nH]c23
| melting_point = 238
| melting_high = 245
| bioavailability = 60±31%
| protein_bound = 20–30%
| metabolism = Activated non-enzymatically, deactivated mainly by [[:en:xanthine oxidase]]
| elimination_half-life= 26–80 minutes (azathioprine)<br />3–5 hours (drug plus metabolites)
| excretion = [[콩팥]], 98% as metabolites
<!--Clinical data-->
| tradename = Azasan, Imuran and others
| Drugs.com = {{drugs.com|monograph|Azathioprine}}
| MedlinePlus = a682167
| licence_EU = 
| licence_US = azathioprine
| pregnancy_AU = D
| pregnancy_US = D
| legal_AU = S4
| legal_CA = Rx-only
| legal_UK = POM
| legal_US = Rx-only
| routes_of_administration = Mainly by mouth (sometimes initially [[수액 (의학)|intravenous]])
}}

'''아자티오프린'''({{lang|en|azathioprine}}, '''AZA''', 상표명: '''Imuran''' 등)은 [[면역억제제]]이다.<ref name=AHFS2016/> [[류머티스 관절염]], [[다발성 맥관염 동반 육아종]], [[크론병]], [[궤양성 대장염]], 그리고 [[이식거부반응|거부반응]]을 예방하기 위한 [[장기 이식]]에 사용된다.<ref name=AHFS2016/><ref>{{저널 인용|last1=Axelrad|first1=JE|last2=Lichtiger|first2=S|last3=Yajnik|first3=V|title=Inflammatory bowel disease and cancer: The role of inflammation, immunosuppression, and cancer treatment|journal=World Journal of Gastroenterology|date=28 May 2016|volume=22|issue=20|pages=4794–801|pmid=27239106|type=Review|doi=10.3748/wjg.v22.i20.4794|pmc=4873872}}</ref><ref name=Sing2017>{{저널 인용|last1=Singer|first1=O|last2=McCune|first2=WJ|title=Update on maintenance therapy for granulomatosis with polyangiitis and microscopic polyangiitis|journal=Current Opinion in Rheumatology|date=May 2017|volume=29|issue=3|pages=248–253|doi=10.1097/BOR.0000000000000382|pmid=28306595}}</ref> 구강으로, 또는 [[수액 (의학)|정맥 주사]]를 통해 투여된다.<ref name=AHFS2016>{{웹 인용|title=Azathioprine|url=https://www.drugs.com/monograph/Azathioprine.html|publisher=The American Society of Health-System Pharmacists|accessdate=8 December 2016|url-status=live|archiveurl=https://web.archive.org/web/20160820215808/https://www.drugs.com/monograph/azathioprine.html|archivedate=20 August 2016|df=}}</ref>

일반적인 부작용으로는 [[골수억제]], [[구토]]가 포함된다.<ref name=AHFS2016/> 골수억제는 특히 [[TMPT]](thiopurine S-methyltransferase) [[유전학|유전]]적 결함이 있는 사람들에게서 흔히 관찰된다.<ref name=AHFS2016/> 다른 심각한 위험 요인으로는 [[림프종]]의 위험 증가가 포함된다.<ref name=AHFS2016/> [[임신]] 중 투여하면 태아에 위험을 초래할 수 있다.<ref name=AHFS2016/> 아자티오프린은 [[퓨린 유사물]]이자 [[대사길항물질]] 계열의 약물이다.<ref name=AHFS2016/><ref name=Sam2016/> 세포의 [[RNA]]와 [[DNA]] 생성에 지장을 주기 위해 [[6-티오구아닌]]을 통해 동작한다.<ref name=AHFS2016/><ref name=Sam2016/>

아자티오프린은 1957년 처음 개발되었다.<ref name=Sam2016>{{서적 인용|last1=Sami|first1=Naveed|title=Autoimmune Bullous Diseases: Approach and Management|date=2016|publisher=Springer|isbn=9783319267289|page=83|url=https://books.google.ca/books?id=eMSbCwAAQBAJ&pg=PA83|language=en|url-status=live|archiveurl=https://web.archive.org/web/20161221162220/https://books.google.ca/books?id=eMSbCwAAQBAJ&pg=PA83|archivedate=2016-12-21|df=}}</ref> [[의료제도]]에 필수적인 가장 효과적이고 안전한 의약품 목록인 [[WHO 필수 의약품 목록]]에 등재되어 있다.<ref name=WHO19th>{{웹 인용|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|website=World Health Organization|accessdate=8 December 2016|date=April 2015|url-status=live|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}}</ref> [[개발도상국]]의 도매가는 1개월 기준 대략 US$7.63–17.19이다.<ref name=ERC2014>{{웹 인용|title=Azathioprine|url=http://mshpriceguide.org/en/single-drug-information/?DMFId=82&searchYear=2014|website=International Drug Price Indicator Guide|accessdate=8 December 2016|보존url=https://web.archive.org/web/20181006154909/http://mshpriceguide.org/en/single-drug-information/?DMFId=82&searchYear=2014|보존날짜=2018-10-06|url-status=dead}}</ref> 미국 내 도매가는 1개월 당 대략 US$35.34이다.<ref>{{웹 인용|title=NADAC as of 2016-12-07 {{!}} Data.Medicaid.gov|url=https://data.medicaid.gov/Drug-Prices/NADAC-as-of-2016-12-07/ry9m-tx78|website=Centers for Medicare and Medicaid Services|accessdate=20 December 2016|url-status=live|archiveurl=https://web.archive.org/web/20161221003023/https://data.medicaid.gov/Drug-Prices/NADAC-as-of-2016-12-07/ry9m-tx78|archivedate=21 December 2016|df=}}</ref> 2016년, 200만 건 이상의 처방과 더불어 미국에서 219번째로 많이 처방을 받은 약물이었다.<ref>{{웹 인용|title=The Top 300 of 2019 |url=https://clincalc.com/DrugStats/Top300Drugs.aspx |website=clincalc.com |accessdate=22 December 2018}}</ref>

== 합성 ==
[[파일:Azathioprine synthesis.svg|770px|아자티오프린 합성의 전반적인 과정]]

== 각주 ==
{{각주}}

== 외부 링크 ==
* [https://web.archive.org/web/20190312073255/https://www.aspenpharma.com.au/products/details/index/id/714/product/Imuran Imuran]
* [https://web.archive.org/web/20060411012544/http://www.salix.com/products/products_azasan.asp Azasan] (manufacturer's website)
* U.S. National Center for Biotechnology Information: Medical Genetics Summaries - [https://www.ncbi.nlm.nih.gov/books/NBK100661/ Azathioprine Therapy and ''TPMT'' Genotype]
* [http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Azathioprine U.S. National Library of Medicine: Drug Information Portal - Azathioprine]

[[분류:화학요법]]
[[분류:IARC 1군 발암 물질]]
[[분류:퓨린]]
[[분류:세계 보건 기구 필수 의약품]]
[[분류:전구약물]]
[[분류:간독소]]
[[분류:면역 억제제]]
[[분류:항류머티즘제]]
[[분류:항암제]]
[[분류:퓨린 대항제]]