Identification

Name
Zolmitriptan
Accession Number
DB00315  (APRD00376)
Type
Small Molecule
Groups
Approved, Investigational
Description

Zolmitriptan is a synthetic tryptamine derivative and appears as a white powder that is readily soluble in water. [Wikipedia]

Structure
Thumb
Synonyms
  • (S)-4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
  • 311C90
  • 4-[[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]methyl]oxazolidin-2-one
  • Zolmitriptan
  • Zolmitriptanum
External IDs
311 C 90 / BW 311 C 90
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ag-zolmitriptan ODTTablet, orally disintegrating2.5 mgOralAngita Pharma Inc.2015-12-10Not applicableCanada
Ccp-zolmitriptanTablet2.5 mgOralCellchem Pharmaceuticals Inc.Not applicableNot applicableCanada
Dom-zolmitriptanTablet2.5 mgOralDominion Pharmacal2013-03-12Not applicableCanada
Dom-zolmitriptan ODTTablet, orally disintegrating2.5 mgOralDominion PharmacalNot applicableNot applicableCanada
Ipg-zolmitriptanTablet2.5 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-zolmitriptanTablet2.5 mgOralJamp Pharma Corporation2014-03-13Not applicableCanada
Jamp-zolmitriptan ODTTablet, orally disintegrating2.5 mgOralJamp Pharma Corporation2014-09-14Not applicableCanada
Mar-zolmitriptanTablet2.5 mgOralMarcan Pharmaceuticals Inc2014-10-27Not applicableCanada
Mint-zolmitriptanTablet2.5 mgOralMint Pharmaceuticals Inc2014-03-18Not applicableCanada
Mint-zolmitriptan ODTTablet, orally disintegrating2.5 mgOralMint Pharmaceuticals Inc2014-03-182017-06-19Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-zolmitriptanTablet2.5 mgOralApotex Corporation2016-08-15Not applicableCanada
Apo-zolmitriptan RapidTablet, orally disintegrating2.5 mgOralApotex Corporation2016-07-22Not applicableCanada
ZolmiptriptanTablet, orally disintegrating2.5 mg/1OralGlenmark Pharmaceuticals Inc.,Usa2013-05-14Not applicableUs68462 0499 76 nlmimage10 af3cd7f6
ZolmiptriptanTablet, orally disintegrating5 mg/1OralGlenmark Pharmaceuticals Inc.,Usa2013-05-14Not applicableUs68462 0500 33 nlmimage10 ca3ce547
ZolmitriptanTablet, film coated2.5 mg/1OralCamber Pharmaceuticals2015-01-05Not applicableUs
ZolmitriptanTablet2.5 mg/1OralAjanta Pharma Limited2016-05-31Not applicableUs
ZolmitriptanTablet, film coated2.5 mg/1OralApotex Corporation2013-05-14Not applicableUs
ZolmitriptanTablet, film coated2.5 mg/1OralJubilant Cadista Pharmaceuticals Inc.2014-11-20Not applicableUs
ZolmitriptanTablet, orally disintegrating5 mg/1OralAlembic Pharmaceuticals Limited2016-12-01Not applicableUs
ZolmitriptanTablet, film coated5 mg/1OralRising Pharmaceuticals2016-01-04Not applicableUs
International/Other Brands
AscoTop (AstraZeneca) / Nomi (Square) / Zolmiles (Actavis) / Zolmit (Beximco) / Zomig / Zomigon (AstraZeneca) / Zomigoro (AstraZeneca) / Zomitan (Incepta)
Categories
UNII
2FS66TH3YW
CAS number
139264-17-8
Weight
Average: 287.3568
Monoisotopic: 287.163376931
Chemical Formula
C16H21N3O2
InChI Key
ULSDMUVEXKOYBU-ZDUSSCGKSA-N
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
IUPAC Name
(4S)-4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
SMILES
CN(C)CCC1=CNC2=CC=C(C[[email protected]]3COC(=O)N3)C=C12

Pharmacology

Indication

For the acute treatment of adult migraine with or without auras.

Structured Indications
Pharmacodynamics

Zolmitriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonists, and has only a weak affinity for 5-HT1A, 5-HT5A, and 5-HT7 receptors and no significant affinity or pharmacological activity at 5-HT2, 5-HT3 or 5-HT4 receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic, dopamine1,; dopamine2; muscarinic, or benzodiazepine receptors. This action in humans correlates with the relief of migraine headache. In addition to causing vasoconstriction, experimental data from animal studies show that Zolmitriptan also activates 5-HT1 receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Zolmitriptan in humans.

Mechanism of action

Zolmitriptan binds with high affinity to human 5-HT1B and 5-HT1D receptors leading to cranial blood vessel constriction. Current theories proposed to explain the etiology of migraine headache suggest that symptoms are due to local cranial vasodilatation and/or to the release of sensory neuropeptides (vasoactive intestinal peptide, substance P and calcitonin gene-related peptide) through nerve endings in the trigeminal system. The therapeutic activity of zolmitriptan for the treatment of migraine headache can most likely be attributed to the agonist effects at the 5HT1B/1D receptors on intracranial blood vessels (including the arterio-venous anastomoses) and sensory nerves of the trigeminal system which result in cranial vessel constriction and inhibition of pro-inflammatory neuropeptide release.

TargetActionsOrganism
A5-hydroxytryptamine receptor 1B
agonist
Human
A5-hydroxytryptamine receptor 1D
agonist
Human
A5-hydroxytryptamine receptor 1F
agonist
Human
A5-hydroxytryptamine receptor 1A
agonist
Human
Absorption

Mean absolute oral bioavailability is approximately 40%. Food has no affect on the rate and extent of absorption.

Volume of distribution
  • 8.4±3.3 L/kg
Protein binding

25%

Metabolism

Hepatic. There have been three metabolites identified: indole acetic acid, N -oxide, and N-desmethyl metabolites. However, the N-desmethyl is the only active metabolite.

Route of elimination
Not Available
Half life

The mean elimination half-life of zolmitriptan and of the active N-desmethyl metabolite is 3 hours.

Clearance
  • 25.9 mL/min/kg
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3---(T;T) / (C;T)T AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of responding to zolmitriptan when treating (condition: cluster headache).Details

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe metabolism of Zolmitriptan can be decreased when combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.Experimental
AbirateroneThe serum concentration of Zolmitriptan can be increased when it is combined with Abiraterone.Approved
AcepromazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Acepromazine.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Aceprometazine.Approved
AcetophenazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Acetophenazine.Approved
AlmotriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Almotriptan.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Amitriptyline.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Amoxapine.Approved
AmperozideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Amperozide.Experimental
AmphetamineThe serum concentration of Zolmitriptan can be increased when it is combined with Amphetamine.Approved, Illicit
AripiprazoleThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Aripiprazole.Approved, Investigational
AsenapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Asenapine.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Azaperone.Investigational, Vet Approved
AzithromycinThe metabolism of Zolmitriptan can be decreased when combined with Azithromycin.Approved
BenmoxinThe metabolism of Zolmitriptan can be decreased when combined with Benmoxin.Withdrawn
BenperidolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Benperidol.Investigational
BifeprunoxThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Bifeprunox.Investigational
BortezomibThe metabolism of Zolmitriptan can be decreased when combined with Bortezomib.Approved, Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Brexpiprazole.Approved
BrofaromineThe serum concentration of Zolmitriptan can be increased when it is combined with Brofaromine.Experimental
BromocriptineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Bromocriptine.Approved, Investigational
BromperidolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Bromperidol.Investigational
BuspironeThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Buspirone.Approved, Investigational
ButaperazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Butaperazine.Experimental
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Zolmitriptan.Approved
CaffeineThe metabolism of Zolmitriptan can be decreased when combined with Caffeine.Approved
CariprazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Cariprazine.Approved
CaroxazoneThe metabolism of Zolmitriptan can be decreased when combined with Caroxazone.Withdrawn
ChlorproethazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Chlorproethazine.Experimental
ChlorpromazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Chlorpromazine.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Chlorprothixene.Approved, Investigational, Withdrawn
CimetidineThe serum concentration of Zolmitriptan can be increased when it is combined with Cimetidine.Approved
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Zolmitriptan.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Clomipramine.Approved, Vet Approved
ClopenthixolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Clopenthixol.Experimental
ClothiapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Clothiapine.Experimental
ClotrimazoleThe metabolism of Zolmitriptan can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Clozapine.Approved
CyamemazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Cyamemazine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Cyclobenzaprine.Approved
Cyproterone acetateThe serum concentration of Zolmitriptan can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DapiprazoleThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Dapiprazole.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Zolmitriptan.Investigational
DeferasiroxThe serum concentration of Zolmitriptan can be increased when it is combined with Deferasirox.Approved, Investigational
DesipramineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Desipramine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Desvenlafaxine.Approved
DextromethorphanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Dextromethorphan.Approved
DihydroergotamineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Dihydroergotamine.Approved
DixyrazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Dixyrazine.Experimental
DolasetronDolasetron may increase the serotonergic activities of Zolmitriptan.Approved
DosulepinThe metabolism of Zolmitriptan can be decreased when combined with Dosulepin.Approved
DoxepinThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Doxepin.Approved
DroperidolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Droperidol.Approved, Vet Approved
DroxidopaZolmitriptan may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Duloxetine.Approved
EcopipamThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Ecopipam.Investigational
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Zolmitriptan.Approved, Investigational
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Ergoloid mesylate.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Ergonovine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Ergotamine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Escitalopram.Approved, Investigational
FencamfamineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Fencamfamine.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FluanisoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Fluanisone.Experimental
FluoxetineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Fluphenazine.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Fluspirilene.Approved, Investigational
FluvoxamineThe metabolism of Zolmitriptan can be decreased when combined with Fluvoxamine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Frovatriptan.Approved, Investigational
FurazolidoneThe metabolism of Zolmitriptan can be decreased when combined with Furazolidone.Approved, Investigational, Vet Approved
GranisetronGranisetron may increase the serotonergic activities of Zolmitriptan.Approved, Investigational
HaloperidolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Haloperidol.Approved
HarmalineThe serum concentration of Zolmitriptan can be increased when it is combined with Harmaline.Experimental
HydracarbazineThe metabolism of Zolmitriptan can be decreased when combined with Hydracarbazine.Experimental
IloperidoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Iloperidone.Approved
ImipramineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Imipramine.Approved
IproclozideThe metabolism of Zolmitriptan can be decreased when combined with Iproclozide.Withdrawn
IproniazidThe metabolism of Zolmitriptan can be decreased when combined with Iproniazid.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Isocarboxazid.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Levomilnacipran.Approved
LidocaineThe metabolism of Zolmitriptan can be decreased when combined with Lidocaine.Approved, Vet Approved
LinezolidThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Linezolid.Approved, Investigational
LithiumThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Lithium.Approved
LobeglitazoneThe metabolism of Zolmitriptan can be decreased when combined with Lobeglitazone.Approved, Investigational
LorcaserinThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Lorcaserin.Approved
LoxapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Loxapine.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Lurasidone.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Maprotiline.Approved
MebanazineThe metabolism of Zolmitriptan can be decreased when combined with Mebanazine.Withdrawn
MelperoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Melperone.Approved, Investigational
MesoridazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Mesoridazine.Approved, Investigational
MethadoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Methadone.Approved
MethotrimeprazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Methotrimeprazine.Approved
Methylene blueThe metabolism of Zolmitriptan can be decreased when combined with Methylene blue.Approved, Investigational
MethylergometrineMethylergometrine may increase the vasoconstricting activities of Zolmitriptan.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Metoclopramide.Approved, Investigational
MexiletineThe metabolism of Zolmitriptan can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Zolmitriptan can be decreased when combined with Midostaurin.Approved
MilnacipranThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Milnacipran.Approved
MinaprineThe metabolism of Zolmitriptan can be decreased when combined with Minaprine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Mirtazapine.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Moclobemide.Approved
MolindoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Molindone.Approved
MoperoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Moperone.Experimental
MosapramineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Mosapramine.Experimental
NaratriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Naratriptan.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Nefazodone.Approved, Withdrawn
NevirapineThe metabolism of Zolmitriptan can be decreased when combined with Nevirapine.Approved
NialamideThe metabolism of Zolmitriptan can be decreased when combined with Nialamide.Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Nortriptyline.Approved
OctamoxinThe metabolism of Zolmitriptan can be decreased when combined with Octamoxin.Withdrawn
OlanzapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Olanzapine.Approved, Investigational
OndansetronOndansetron may increase the serotonergic activities of Zolmitriptan.Approved
OsanetantThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Osanetant.Investigational
OsimertinibThe serum concentration of Zolmitriptan can be decreased when it is combined with Osimertinib.Approved
OxypertineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Oxypertine.Experimental
PaliperidoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Paliperidone.Approved
PalonosetronPalonosetron may increase the serotonergic activities of Zolmitriptan.Approved, Investigational
PargylineThe metabolism of Zolmitriptan can be decreased when combined with Pargyline.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Zolmitriptan can be increased when it is combined with Peginterferon alfa-2b.Approved
PenfluridolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Penfluridol.Experimental
PerazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Perphenazine.Approved
PethidineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Pethidine.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Phenelzine.Approved
PheniprazineThe metabolism of Zolmitriptan can be decreased when combined with Pheniprazine.Withdrawn
PhenoxypropazineThe metabolism of Zolmitriptan can be decreased when combined with Phenoxypropazine.Withdrawn
PimozideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Pimozide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Pipamperone.Approved, Investigational
PipotiazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Pipotiazine.Approved, Investigational
PirlindoleThe metabolism of Zolmitriptan can be decreased when combined with Pirlindole.Approved
PivhydrazineThe metabolism of Zolmitriptan can be decreased when combined with Pivhydrazine.Withdrawn
ProcarbazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Procarbazine.Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Prochlorperazine.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Promazine.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Promethazine.Approved
PropericiazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Propericiazine.Approved
PropranololThe serum concentration of Zolmitriptan can be increased when it is combined with Propranolol.Approved, Investigational
ProthipendylThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Prothipendyl.Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Protriptyline.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Quetiapine.Approved
RacloprideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Raclopride.Investigational
RasagilineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Rasagiline.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Remoxipride.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Reserpine.Approved, Investigational
RisperidoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Risperidone.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Ritanserin.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Rizatriptan.Approved
RopiniroleThe metabolism of Zolmitriptan can be decreased when combined with Ropinirole.Approved, Investigational
SafrazineThe metabolism of Zolmitriptan can be decreased when combined with Safrazine.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Selegiline.Approved, Investigational, Vet Approved
SertindoleThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Sertindole.Approved, Investigational, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Sertraline.Approved
SimeprevirThe metabolism of Zolmitriptan can be decreased when combined with Simeprevir.Approved
SulpirideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Sulpiride.Approved, Investigational
SultoprideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Sultopride.Experimental
SumatriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Sumatriptan.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Tapentadol.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Zolmitriptan.Approved
Tenofovir disoproxilThe metabolism of Zolmitriptan can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Zolmitriptan can be decreased when it is combined with Teriflunomide.Approved
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Tetrahydropalmatine.Investigational
TheophyllineThe metabolism of Zolmitriptan can be decreased when combined with Theophylline.Approved
ThiopropazateThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Thiopropazate.Experimental
ThioproperazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Thioproperazine.Approved
ThioridazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Thioridazine.Approved, Withdrawn
ThiothixeneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Thiothixene.Approved
TiaprideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Tiapride.Approved, Investigational
TiclopidineThe metabolism of Zolmitriptan can be decreased when combined with Ticlopidine.Approved
ToloxatoneThe metabolism of Zolmitriptan can be decreased when combined with Toloxatone.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Zolmitriptan.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe metabolism of Zolmitriptan can be decreased when combined with Trans-2-Phenylcyclopropylamine.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Tranylcypromine.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Zolmitriptan.Approved, Investigational
TrifluoperazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Trifluoperazine.Approved
TrifluperidolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Trifluperidol.Experimental
TriflupromazineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Triflupromazine.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Trimipramine.Approved
TropisetronTropisetron may increase the serotonergic activities of Zolmitriptan.Approved, Investigational
VemurafenibThe serum concentration of Zolmitriptan can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Zolmitriptan.Approved
VeraliprideThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Veralipride.Experimental
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Zolmitriptan.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Zolmitriptan.Approved
ZiprasidoneThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Ziprasidone.Approved
ZotepineThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Zotepine.Approved, Investigational
ZucapsaicinThe metabolism of Zolmitriptan can be decreased when combined with Zucapsaicin.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Zuclopenthixol.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Islam Aminul, Bhar Chandan, Katam Sahadev, "Process for preparing optically pure zolmitriptan." U.S. Patent US20050245585, issued November 03, 2005.

US20050245585
General References
  1. Pascual J: [Mechanism of action of zolmitriptan]. Neurologia. 1998 Oct;13 Suppl 2:9-15. [PubMed:9859690]
  2. Martin GR: Pre-clinical pharmacology of zolmitriptan (Zomig; formerly 311C90), a centrally and peripherally acting 5HT1B/1D agonist for migraine. Cephalalgia. 1997 Oct;17 Suppl 18:4-14. [PubMed:9399012]
External Links
Human Metabolome Database
HMDB14460
KEGG Drug
D00415
KEGG Compound
C07218
PubChem Compound
60857
PubChem Substance
46506452
ChemSpider
54844
BindingDB
50033383
ChEBI
10124
ChEMBL
CHEMBL1185
Therapeutic Targets Database
DAP000077
PharmGKB
PA451975
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Zolmitriptan
ATC Codes
N02CC03 — Zolmitriptan
AHFS Codes
  • 28:32.28 — Selective Serotonin Agonists
FDA label
Download (101 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceMigraines1
1CompletedTreatmentMigraines1
3CompletedTreatmentMigraines3
4CompletedTreatmentAcute Migraine Headache1
4CompletedTreatmentMigraines1
4CompletedTreatmentMigrainous Headache1

Pharmacoeconomics

Manufacturers
  • Astrazeneca pharmaceuticals lp
  • Ipr pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Tablet, multilayer, extended releaseOral2.5 mg
TabletOral1.0 mg
Tablet, orally disintegratingOral1 mg
Tablet, film coatedOral2.5 mg/1
Tablet, film coatedOral5 mg/1
Spray, meteredNasal2.5 mg/1
Spray, meteredNasal5 mg/1
TabletOral2.5 mg/1
TabletOral5 mg/1
SprayNasal; Oral2.5 mg
SprayNasal; Oral5.0 mg
Tablet, orally disintegratingOral2.5 mg
TabletOral2.5 mg
Tablet, orally disintegratingOral2.5 mg/1
Tablet, orally disintegratingOral5 mg/1
Prices
Unit descriptionCostUnit
Zomig 6 5 mg Solution 1 Box = 6 Single Use Bottles235.62USD bottle
Zomig ZMT 6 2.5 mg Dispersible Tablet Box159.66USD box
Zomig 6 2.5 mg tablet 1 Box = 6 tablet147.23USD box
Zomig 3 5 mg tablet Box93.49USD box
Zomig ZMT 3 5 mg Dispersible Tablet Box88.21USD box
Zomig 5 mg nasal spray37.76USD each
Zomig 5 mg tablet28.82USD tablet
Zomig zmt 5 mg tablet28.27USD tablet
Zomig 2.5 mg tablet26.08USD tablet
Zomig zmt 2.5 mg tablet25.59USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5466699No1992-11-142012-11-14Us
CA2572508No2010-03-302016-08-02Canada
CA2064815No1999-11-162011-06-06Canada
US7220767Yes2001-05-282021-05-28Us
US6750237Yes2001-05-282021-05-28Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 mg/mLALOGPS
logP2.25ALOGPS
logP2.04ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.36 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.44 m3·mol-1ChemAxon
Polarizability31.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8956
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.6888
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.7674
CYP450 2C9 substrateNon-substrate0.8051
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5822
CYP450 1A2 substrateNon-inhibitor0.6189
CYP450 2C9 inhibitorNon-inhibitor0.8989
CYP450 2D6 inhibitorNon-inhibitor0.8281
CYP450 2C19 inhibitorNon-inhibitor0.831
CYP450 3A4 inhibitorNon-inhibitor0.8481
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9263
Ames testNon AMES toxic0.7651
CarcinogenicityNon-carcinogens0.9641
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.5965 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9301
hERG inhibition (predictor II)Non-inhibitor0.8949
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-1390000000-5eb2470575d7a40b35dd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0390000000-d91f1c70da42e9043a7b

Taxonomy

Description
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
3-alkylindoles / Aralkylamines / Substituted pyrroles / Oxazolidinones / Benzenoids / Heteroaromatic compounds / Carbamate esters / Trialkylamines / Organic carbonic acids and derivatives / Oxacyclic compounds
show 5 more
Substituents
Tryptamine / 3-alkylindole / Indole / Aralkylamine / Oxazolidinone / Substituted pyrrole / Benzenoid / Oxazolidine / Pyrrole / Heteroaromatic compound
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamines (CHEBI:10124)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Le Grand B, Panissie A, Perez M, Pauwels PJ, John GW: Zolmitriptan stimulates a Ca(2+)-dependent K(+) current in C6 glioma cells stably expressing recombinant human 5-HT(1B) receptors. Eur J Pharmacol. 2000 Jun 2;397(2-3):297-302. [PubMed:10844127]
  2. Johnson DE, Rollema H, Schmidt AW, McHarg AD: Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain. Eur J Pharmacol. 2001 Aug 17;425(3):203-10. [PubMed:11513839]
  3. de Almeida RM, Nikulina EM, Faccidomo S, Fish EW, Miczek KA: Zolmitriptan--a 5-HT1B/D agonist, alcohol, and aggression in mice. Psychopharmacology (Berl). 2001 Sep;157(2):131-41. [PubMed:11594437]
  4. Reuter U, Salomone S, Ickenstein GW, Waeber C: Effects of chronic sumatriptan and zolmitriptan treatment on 5-HT receptor expression and function in rats. Cephalalgia. 2004 May;24(5):398-407. [PubMed:15096229]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. Whale R, Bhagwagar Z, Cowen PJ: Zolmitriptan-induced growth hormone release in humans: mediation by 5-HT1D receptors? Psychopharmacology (Berl). 1999 Jul;145(2):223-6. [PubMed:10463324]
  7. Hargreaves RJ, Shepheard SL: Pathophysiology of migraine--new insights. Can J Neurol Sci. 1999 Nov;26 Suppl 3:S12-9. [PubMed:10563228]
  8. Gowin JL, Swann AC, Moeller FG, Lane SD: Zolmitriptan and human aggression: interaction with alcohol. Psychopharmacology (Berl). 2010 Jul;210(4):521-31. doi: 10.1007/s00213-010-1851-6. Epub 2010 Apr 21. [PubMed:20407761]
  9. Pascual J: [Mechanism of action of zolmitriptan]. Neurologia. 1998 Oct;13 Suppl 2:9-15. [PubMed:9859690]
  10. Martin GR: Pre-clinical pharmacology of zolmitriptan (Zomig; formerly 311C90), a centrally and peripherally acting 5HT1B/1D agonist for migraine. Cephalalgia. 1997 Oct;17 Suppl 18:4-14. [PubMed:9399012]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  1. Whale R, Bhagwagar Z, Cowen PJ: Zolmitriptan-induced growth hormone release in humans: mediation by 5-HT1D receptors? Psychopharmacology (Berl). 1999 Jul;145(2):223-6. [PubMed:10463324]
  2. Hargreaves RJ, Shepheard SL: Pathophysiology of migraine--new insights. Can J Neurol Sci. 1999 Nov;26 Suppl 3:S12-9. [PubMed:10563228]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  4. Le Grand B, Panissie A, Perez M, Pauwels PJ, John GW: Zolmitriptan stimulates a Ca(2+)-dependent K(+) current in C6 glioma cells stably expressing recombinant human 5-HT(1B) receptors. Eur J Pharmacol. 2000 Jun 2;397(2-3):297-302. [PubMed:10844127]
  5. Johnson DE, Rollema H, Schmidt AW, McHarg AD: Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain. Eur J Pharmacol. 2001 Aug 17;425(3):203-10. [PubMed:11513839]
  6. de Almeida RM, Nikulina EM, Faccidomo S, Fish EW, Miczek KA: Zolmitriptan--a 5-HT1B/D agonist, alcohol, and aggression in mice. Psychopharmacology (Berl). 2001 Sep;157(2):131-41. [PubMed:11594437]
  7. Reuter U, Salomone S, Ickenstein GW, Waeber C: Effects of chronic sumatriptan and zolmitriptan treatment on 5-HT receptor expression and function in rats. Cephalalgia. 2004 May;24(5):398-407. [PubMed:15096229]
  8. Gowin JL, Swann AC, Moeller FG, Lane SD: Zolmitriptan and human aggression: interaction with alcohol. Psychopharmacology (Berl). 2010 Jul;210(4):521-31. doi: 10.1007/s00213-010-1851-6. Epub 2010 Apr 21. [PubMed:20407761]
  9. Pascual J: [Mechanism of action of zolmitriptan]. Neurologia. 1998 Oct;13 Suppl 2:9-15. [PubMed:9859690]
  10. Martin GR: Pre-clinical pharmacology of zolmitriptan (Zomig; formerly 311C90), a centrally and peripherally acting 5HT1B/1D agonist for migraine. Cephalalgia. 1997 Oct;17 Suppl 18:4-14. [PubMed:9399012]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that trig...
Gene Name
HTR1F
Uniprot ID
P30939
Uniprot Name
5-hydroxytryptamine receptor 1F
Molecular Weight
41708.505 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Reuter U, Salomone S, Ickenstein GW, Waeber C: Effects of chronic sumatriptan and zolmitriptan treatment on 5-HT receptor expression and function in rats. Cephalalgia. 2004 May;24(5):398-407. [PubMed:15096229]
  3. Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [PubMed:15320857]
  4. Villalon CM, Centurion D, Valdivia LF, De Vries P, Saxena PR: An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210. [PubMed:12434581]
  5. Bhalla P, Sharma HS, Wurch T, Pauwels PJ, Saxena PR: Molecular cloning and expression of the porcine trigeminal ganglion cDNA encoding a 5-ht(1F) receptor. Eur J Pharmacol. 2002 Feb 1;436(1-2):23-33. [PubMed:11834243]
  6. Wainscott DB, Johnson KW, Phebus LA, Schaus JM, Nelson DL: Human 5-HT1F receptor-stimulated [35S]GTPgammaS binding: correlation with inhibition of guinea pig dural plasma protein extravasation. Eur J Pharmacol. 1998 Jul 3;352(1):117-24. [PubMed:9718276]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Johnson DE, Rollema H, Schmidt AW, McHarg AD: Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain. Eur J Pharmacol. 2001 Aug 17;425(3):203-10. [PubMed:11513839]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Rolan P: Potential drug interactions with the novel antimigraine compound zolmitriptan (Zomig, 311C90). Cephalalgia. 1997 Oct;17 Suppl 18:21-7. [PubMed:9399014]
  2. Wild MJ, McKillop D, Butters CJ: Determination of the human cytochrome P450 isoforms involved in the metabolism of zolmitriptan. Xenobiotica. 1999 Aug;29(8):847-57. [PubMed:10553725]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34