Zolmitriptan

Zolmitriptan
Clinical data
Trade names	Zomig, others
Other names	BW-311C90; BW311C90; 311C90; BW-311-C-90; ML-004; ML004; [(4S)-2-Oxo-1,3-oxazolidin-4-yl]methyl-N,N-dimethyltryptamine; [(4S)-2-Oxo-1,3-oxazolidin-4-yl]methyl-DMT
AHFS/Drugs.com	Monograph
MedlinePlus	a601129
License data	US DailyMed: Zolmitriptan;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth, intranasal
Drug class	Serotonin 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F receptor agonist; Antimigraine agent; Triptan
ATC code	N02CC03 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: ℞-only;
Pharmacokinetic data
Bioavailability	Oral: 40%
Protein binding	25%
Metabolism	Liver (CYP1A2-mediated, to active metabolite; also MAO-ATooltip monoamine oxidase A)
Metabolites	• N-Desmethylzolmitriptan; • Zolmitriptan N-oxide; • Indole acetic acid derivative
Elimination half-life	Zolmitriptan: 3 hours; N-Desmethylzolmitriptan: 3.5 hours
Excretion	Urine: ~65%; Feces: ~30%
Identifiers
	IUPAC name (S)-4-({3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one;
CAS Number	139264-17-8 ;
PubChem CID	60857;
IUPHAR/BPS	60;
DrugBank	DB00315 ;
ChemSpider	54844 ;
UNII	2FS66TH3YW;
KEGG	D00415 ;
ChEBI	CHEBI:10124 ;
ChEMBL	ChEMBL1185 ;
CompTox Dashboard (EPA)	DTXSID8045933 ;
ECHA InfoCard	100.158.186
Chemical and physical data
Formula	C16H21N3O2
Molar mass	287.363 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1OC[C@@H](N1)Cc2ccc3c(c2)c(c[nH]3)CCN(C)C;
	InChI 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 ; Key:ULSDMUVEXKOYBU-ZDUSSCGKSA-N ;
	(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.^[4] It is taken by mouth as a swallowed or disintegrating tablet or as a nasal spray.^[4]

Side effects include tightness in the neck or throat, jaw pain, dizziness, paresthesia, asthenia, somnolence, warm/cold sensations, nausea, chest pressure, and dry mouth.^[4] The drug acts as a selective serotonin 5-HT_1B and 5-HT_1D receptor agonist.^[4] Structurally, it is a triptan and a tryptamine derivative.^[4]^[5]

It was patented in 1990 and was approved for medical use in 1997.^[6]^[4]

^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
^ ^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.
^ ^a ^b Cite error: The named reference Yu2008 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f "Highlights of prescribing information" (PDF). Archived from the original (PDF) on 2021-03-28.
^ "Zolmitriptan". PubChem. Retrieved 27 October 2024.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495.

[1] "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.

[DrugBank-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.

[Yu2008-3] Cite error: The named reference Yu2008 was invoked but never defined (see the help page).

[Zolmig-Label-4] ^ ^a ^b ^c ^d ^e ^f "Highlights of prescribing information" (PDF). Archived from the original (PDF) on 2021-03-28.

[PubChem-5] "Zolmitriptan". PubChem. Retrieved 27 October 2024.

[Fis2006-6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 9783527607495.

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