Zolmitriptan

Zolmitriptan
Clinical data
Trade namesZomig, others
Other namesBW-311C90; BW311C90; 311C90; BW-311-C-90; ML-004; ML004; [(4S)-2-Oxo-1,3-oxazolidin-4-yl]methyl-N,N-dimethyltryptamine
AHFS/Drugs.comMonograph
MedlinePlusa601129
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, nasal spray
Drug classSerotonin 5-HT1B and 5-HT1D receptor agonist; Antimigraine agent; Triptan
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 40%[2]
Protein binding25%[2]
MetabolismLiver (CYP1A2-mediated, to active metabolite; also MAOTooltip monoamine oxidase)[2]
Metabolites• N-Desmethylzolmitriptan[2]
• Zolmitriptan N-oxide[2]
• Indole acetic acid derivative[2]
Elimination half-lifeZolmitriptan: 3 hours[2]
N-Desmethylzolmitriptan: 3.5 hours[2]
ExcretionUrine: ~65%[2]
Feces: ~30%[2]
Identifiers
  • (S)-4-({3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.158.186 Edit this at Wikidata
Chemical and physical data
FormulaC16H21N3O2
Molar mass287.363 g·mol−1
3D model (JSmol)
  • O=C1OC[C@@H](N1)Cc2ccc3c(c2)c(c[nH]3)CCN(C)C
  • InChI=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 checkY
  • Key:ULSDMUVEXKOYBU-ZDUSSCGKSA-N checkY
  (verify)

Zolmitriptan, sold under the brand name Zomig among others, is a serotonergic medication which is used in the acute treatment of migraine attacks with or without aura and cluster headaches.[3] It is taken by mouth as a swallowed or disintegrating tablet or as a nasal spray.[3]

Side effects include neck/throat/jaw pain/tightness/pressure, dizziness, paresthesia, asthenia, somnolence, warm/cold sensations, nausea, heaviness sensation, and dry mouth.[3] The drug acts as a selective serotonin 5-HT1B and 5-HT1D receptor agonist.[3] Structurally, it is a triptan and a tryptamine derivative.[3][4]

It was patented in 1990 and was approved for medical use in 1997.[5][3]

  1. ^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
  2. ^ a b c d e f g h i j "Zolmitriptan: Uses, Interactions, Mechanism of Action". DrugBank Online. 25 November 1997. Retrieved 27 October 2024.
  3. ^ a b c d e f https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020768s023,021231s014,021450s010lbl.pdf
  4. ^ "Zolmitriptan". PubChem. Retrieved 27 October 2024.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495.