Editing Cisplatin (section)

{{Short description|Chemical compound and pharmaceutical drug}}
{{redirect|Cisplatine|the Brazilian province that existed from 1821 to 1828|Cisplatina|the conflict in that province|Cisplatine War}}
{{cs1 config|name-list-style=vanc}}
{{Use dmy dates|date=June 2023}}
{{Infobox drug
| Verifiedfields     = changed
| Watchedfields      = changed
| verifiedrevid      = 457790642
| drug_name          = 
| type               = 
| IUPAC_name         = [[Polyhedral symbol|(''SP''-4-2)]]-diamminedichloridoplatinum(II)
| image              = CisplatinTR.svg
| image_class        = skin-invert-image
| alt                = 
| caption            = 
| imageL             = Cisplatin-3D-balls.png
| image_classL       = bg-transparent
| widthL             = 140
| imageR             = Cisplatin-3D-vdW.png
| image_classR       = bg-transparent

<!--Clinical data-->| tradename          = Platinol, others
| synonyms           = Cisplatinum, platamin, neoplatin, cismaplat, ''cis''-diamminedichloroplatinum(II) (CDDP)
| Drugs.com          = {{drugs.com|monograph|cisplatin}}
| MedlinePlus        = a684036
| licence_EU         = 
| licence_US         = 
| DailyMedID         = Cisplatin
| pregnancy_AU       = D
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Cisplatin Use During Pregnancy | website=Drugs.com | date=12 September 2019 | url=https://www.drugs.com/pregnancy/cisplatin.html | access-date=25 February 2020}}</ref>
| pregnancy_US       = N
| pregnancy_US_comment = <ref name="Drugs.com pregnancy" />
| pregnancy_category = Contraindicated<ref name="Drugs.com pregnancy" />
| legal_AU           = S4
| legal_CA           = Rx-only
| legal_UK           = POM
| legal_US           = Rx-only
| legal_status       = 
| routes_of_administration = [[Intravenous therapy|Intravenous]]
| ATC_prefix         = L01
| ATC_suffix         = XA01

<!--Pharmacokinetic data-->| bioavailability    = 100% (IV)
| protein_bound      = > 95%
| metabolism         = 
| elimination_half-life = 30–100 hours
| excretion          = Renal

<!--Identifiers-->| CAS_number_Ref     = {{cascite|correct|??}}
| CAS_number         = 15663-27-1 <!-- verified against list from Chemical Abstracts Service -->
| PubChem            = 2767
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = DB00515
| ChemSpiderID_Ref   = {{chemspidercite|changed|chemspider}}
| ChemSpiderID       = 76401
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = Q20Q21Q62J
| KEGG_Ref           = {{keggcite|correct|kegg}}
| KEGG               = D00275
| ChEBI_Ref          = {{ebicite|correct|EBI}}
| ChEBI              = 27899
| ChEMBL_Ref         = {{ebicite|changed|EBI}}
| ChEMBL             = 2068237
| PDB_ligand         = CPT

<!--Chemical data-->| chemical_formula   = [Pt(NH<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>]
| N                  = 2
| H                  = 6
| Cl                 = 2
| Pt                 = 1
| smiles             = [NH3+][Pt+2](Cl)(Cl)[NH3+]
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = LXZZYRPGZAFOLE-UHFFFAOYSA-L
}}

<!-- Definition and medical uses -->
'''Cisplatin''' is a chemical compound with [[chemical formula|formula]] ''cis''-{{chem2|[Pt(NH3)2Cl2]}}. It is a [[coordination complex]] of [[platinum]] that is used as a [[chemotherapy medication]] used to treat a number of [[cancers]].<ref name=AHFS2016/> These include [[testicular cancer]], [[ovarian cancer]], [[cervical cancer]], [[bladder cancer]], [[head and neck cancer]], [[esophageal cancer]], [[lung cancer]], [[mesothelioma]], [[brain tumors]] and [[neuroblastoma]].<ref name=AHFS2016/> It is given by [[intravenous|injection into a vein]].<ref name=AHFS2016/>

<!-- Side effects and mechanisms -->
Common side effects include [[bone marrow suppression]], [[hearing problems]] including severe hearing loss, [[nephrotoxicity|kidney damage]], and [[vomiting]].<ref name=AHFS2016/><ref>{{cite journal | vauthors = Oun R, Moussa YE, Wheate NJ | title = The side effects of platinum-based chemotherapy drugs: a review for chemists | journal = Dalton Transactions | volume = 47 | issue = 19 | pages = 6645–6653 | date = May 2018 | pmid = 29632935 | doi = 10.1039/c8dt00838h }}</ref><ref name="pmid29051464">{{cite journal |vauthors=Callejo A, Sedó-Cabezón L, Juan ID, Llorens J |title=Cisplatin-Induced Ototoxicity: Effects, Mechanisms and Protection Strategies |journal=Toxics |volume=3 |issue=3 |pages=268–293 |date=July 2015 |pmid=29051464 |pmc=5606684 |doi=10.3390/toxics3030268|doi-access=free |bibcode=2015Toxic...3..268C }}</ref> Other serious side effects include numbness, trouble walking, [[allergic reactions]], [[electrolyte problems]], and [[heart disease]].<ref name=AHFS2016/> Use during pregnancy can cause harm to the developing fetus.<ref name="Drugs.com pregnancy" /><ref name=AHFS2016/> Cisplatin is in the [[platinum-based antineoplastic]] family of medications.<ref name=AHFS2016/> It works in part by binding to DNA and inhibiting [[DNA replication|its replication]].<ref name=AHFS2016/>

<!-- History and culture -->
Cisplatin was first reported in 1845 and licensed for medical use in 1978 and 1979.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495|page=513|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA513 |language=en|url-status=live|archive-url=https://web.archive.org/web/20161220163817/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA513 |archive-date=20 December 2016}}</ref><ref name=AHFS2016>{{cite web |title=Cisplatin |url= https://www.drugs.com/monograph/cisplatin.html |publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221012444/https://www.drugs.com/monograph/cisplatin.html|archive-date=21 December 2016}}</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><ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref>