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, intranasal
Drug classSerotonin 5-HT1B and 5-HT1D receptor agonist; Antimigraine agent; Triptan
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 40%
Protein binding25%
MetabolismLiver (CYP1A2-mediated, to active metabolite; also MAOTooltip monoamine oxidase)
MetabolitesN-Desmethylzolmitriptan
• Zolmitriptan N-oxide
• Indole acetic acid derivative
Elimination half-lifeZolmitriptan: 3 hours
N-Desmethylzolmitriptan: 3.5 hours
ExcretionUrine: ~65%
Feces: ~30%
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
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 Y
  • Key:ULSDMUVEXKOYBU-ZDUSSCGKSA-N Y
  (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. It is taken by mouth as a swallowed or disintegrating tablet or as a nasal spray.

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

It was patented in 1990 and was approved for medical use in 1997.