Editing Zolmitriptan (section)

{{Short description|Medication used in treatment of migraines}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 477869605
| IUPAC_name = (''S'')-4-({3-[2-(Dimethylamino)ethyl]-1''H''-indol-5-yl}methyl)-1,3-oxazolidin-2-one
| image = Zolmitriptan.svg
| width = 220
| image2 = Zolmitriptan 3D BS.png
| width2 = 220

<!-- Clinical data -->| tradename = Zomig, others
| Drugs.com = {{drugs.com|monograph|zolmitriptan}}
| MedlinePlus = a601129
| DailyMedID = Zolmitriptan
| pregnancy_AU = B3
| routes_of_administration = [[Oral administration|By mouth]], [[nasal administration|intranasal]]
| class = [[Serotonin]] [[5-HT1B receptor|5-HT<sub>1B</sub>]] and [[5-HT1D receptor|5-HT<sub>1D</sub> receptor]] [[agonist]]; [[Antimigraine agent]]; [[Triptan]]

<!-- Legal status -->| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=[[Health Canada]] | date=6 June 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=8 June 2024}}</ref>
| legal_US = Rx-only

<!-- Pharmacokinetic data -->| bioavailability = [[Oral administration|Oral]]: 40%<ref name="DrugBank" />
| protein_bound = 25%<ref name="DrugBank" />
| metabolism = [[Liver]] ([[CYP1A2]]-mediated, to active metabolite; also {{Abbrlink|MAO|monoamine oxidase}})<ref name="DrugBank" />
| metabolites = • ''N''-Desmethylzolmitriptan<ref name="DrugBank" /><br />• Zolmitriptan ''N''-oxide<ref name="DrugBank" /><br />• Indole acetic acid derivative<ref name="DrugBank" />
| elimination_half-life = Zolmitriptan: 3{{nbsp}}hours<ref name="DrugBank">{{cite web | title=Zolmitriptan: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=25 November 1997 | url=https://go.drugbank.com/drugs/DB00315 | access-date=27 October 2024}}</ref><br />''N''-Desmethylzolmitriptan: 3.5{{nbsp}}hours<ref name="DrugBank" />
| excretion = [[Urine]]: ~65%<ref name="DrugBank" /><br />[[Feces]]: ~30%<ref name="DrugBank" />

<!-- Identifiers -->| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 139264-17-8
| ATC_prefix = N02
| ATC_suffix = CC03
| ATC_supplemental = 
| PubChem = 60857
| IUPHAR_ligand = 60
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00315
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 54844
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2FS66TH3YW
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00415
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10124
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1185
| synonyms = BW-311C90; BW311C90; 311C90; BW-311-C-90; ML-004; ML004; [(4''S'')-2-Oxo-1,3-oxazolidin-4-yl]methyl-''N'',''N''-dimethyltryptamine

<!-- Chemical data -->| C = 16
| H = 21
| N = 3
| O = 2
| SMILES = O=C1OC[C@@H](N1)Cc2ccc3c(c2)c(c[nH]3)CCN(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ULSDMUVEXKOYBU-ZDUSSCGKSA-N
}}
<!-- Definition and medical uses -->
'''Zolmitriptan''', sold under the brand name '''Zomig''' among others, is a [[serotonergic drug|serotonergic]] [[medication]] which is used in the acute treatment of [[migraine]] attacks with or without [[aura (symptom)|aura]] and [[cluster headache]]s.<ref name="Zolmig-Label">{{Cite web| title=Highlights of prescribing information | url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020768s023,021231s014,021450s010lbl.pdf | archive-url=https://web.archive.org/web/20210328172742/https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020768s023,021231s014,021450s010lbl.pdf | archive-date=2021-03-28}}</ref> It is taken [[oral administration|by mouth]] as a [[swallowing|swallowed]] or [[orally disintegrating tablet|disintegrating]] [[tablet (pharmacy)|tablet]] or as a [[nasal spray]].<ref name="Zolmig-Label" />

<!-- Side effects, mechanism of action, and chemistry -->
[[Side effect]]s include tightness in the neck or throat, [[Orofacial pain|jaw pain]], [[dizziness]], [[paresthesia]], [[asthenia]], [[somnolence]], warm/cold sensations, [[nausea]], [[chest pressure]], and [[dry mouth]].<ref name="Zolmig-Label" /> The drug acts as a [[binding selectivity|selective]] [[serotonin]] [[5-HT1B receptor|5-HT<sub>1B</sub>]] and [[5-HT1D receptor|5-HT<sub>1D</sub> receptor]] [[agonist]].<ref name="Zolmig-Label" /> [[Chemical structure|Structurally]], it is a [[triptan]] and a [[substituted tryptamine|tryptamine]] [[chemical derivative|derivative]].<ref name="Zolmig-Label" /><ref name="PubChem">{{cite web | title=Zolmitriptan | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/60857 | access-date=27 October 2024}}</ref>

<!-- History, society, and culture -->
It was [[patent]]ed in 1990 and was approved for medical use in 1997.<ref name="Fis2006">{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=531 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA531 |language=en}}</ref><ref name="Zolmig-Label" />