zolmitriptan indications/contra

Stem definitionDrug idCAS RN
serotonin (5-HT1) receptor agonists, sumatriptan derivatives 2869 139264-17-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zolmitriptan
  • zipton
  • zominat
  • zomigoro
  • 311C90
Zolmitriptan binds with high affinity to human recombinant 5-HT1D and 5-HT1B receptors, and moderate affinity for 5-HT1A receptors. The N-desmethyl metabolite also has high affinity for 5-HT1B/1D and moderate affinity for 5-HT1A receptors. Migraines are likely 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 tablets for the treatment of migraine headache is thought to be due to the agonist effects at the 5-HT1B/1D receptors on intracranial blood vessels (including the arteriovenous anastomoses) and sensory nerves of the trigeminal system which result in cranial vessel constriction and inhibition of pro-inflammatory neuropeptide release.
  • Molecular weight: 287.36
  • Formula: C16H21N3O2
  • CLOGP: 1.29
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 57.36
  • ALOGS: -3.18
  • ROTB: 5

Drug dosage:

DoseUnitRoute
2.50 mg N
2.50 mg O

Approvals:

DateAgencyCompanyOrphan
Nov. 25, 1997 FDA IPR

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Migraine 121.68 36.17 31 499 9985 3375344
Headache 83.58 36.17 41 489 91939 3293390
Drug interaction 64.63 36.17 28 502 46784 3338545
Exposure during pregnancy 60.40 36.17 23 507 27540 3357789
Medication overuse headache 55.17 36.17 7 523 35 3385294
Drug hypersensitivity 54.65 36.17 23 507 35657 3349672
Dyspnoea 48.90 36.17 30 500 102904 3282425
Ischaemic stroke 47.88 36.17 13 517 5257 3380072
Cerebrovascular accident 41.78 36.17 19 511 35269 3350060
Chest discomfort 39.85 36.17 15 515 17270 3368059
Drug abuse 39.00 36.17 15 515 18315 3367014
Abortion induced 37.73 36.17 10 520 3681 3381648

Pharmacologic Action:

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SourceCodeDescription
ATC N02CC03 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Selective serotonin (5HT1) agonists
FDA MoA N0000175763 Serotonin 1b Receptor Agonists
FDA MoA N0000175764 Serotonin 1d Receptor Agonists
FDA EPC N0000175765 Serotonin-1b and Serotonin-1d Receptor Agonist
CHEBI has role CHEBI:35941 serotonergic agonist
CHEBI has role CHEBI:50514 vasoconstrictor agent
CHEBI has role CHEBI:35472 anti-inflammatory drug
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D058825 Serotonin 5-HT1 Receptor Agonists
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Migraine indication 37796009 DOID:6364
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Hemiplegic migraine contraindication 59292006
Cerebral arteriosclerosis contraindication 65312002
Wolff-Parkinson-White pattern contraindication 74390002 DOID:384
Vascular insufficiency of intestine contraindication 82196007
Prinzmetal angina contraindication 87343002
Kidney disease contraindication 90708001 DOID:2527
Angina pectoris contraindication 194828000
Cerebrovascular accident contraindication 230690007 DOID:6713
Disease of liver contraindication 235856003 DOID:409
Transient ischemic attack contraindication 266257000 DOID:224
Raynaud's phenomenon contraindication 266261006
Cerebral ischemia contraindication 287731003
Cardiovascular event risk contraindication 395112001
Peripheral vascular disease contraindication 400047006
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Hypertensive urgency contraindication 443482000

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.47 acidic
pKa2 8.28 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
2.5MG/SPRAY ZOMIG ASTRAZENECA N021450 Sept. 16, 2013 RX SPRAY NASAL June 12, 2018 NEW PATIENT POPULATION
5MG/SPRAY ZOMIG ASTRAZENECA N021450 Sept. 30, 2003 RX SPRAY NASAL June 12, 2018 NEW PATIENT POPULATION

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 1D GPCR AGONIST Ki 8.90 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 1B GPCR AGONIST Ki 7.70 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 1F GPCR Ki 7.45 WOMBAT-PK
5-hydroxytryptamine receptor 1E GPCR Ki 7.70 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.60 WOMBAT-PK
Adrenergic receptor alpha-2 GPCR Kd 8.15 CHEMBL
D(2) dopamine receptor GPCR Kd 10.40 CHEMBL
D(1A) dopamine receptor GPCR Kd 9.52 CHEMBL

External reference:

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IDSource
DB00315 DRUGBANK_ID
60 IUPHAR_LIGAND_ID
4021094 VUID
N0000148550 NUI
C0528166 UMLSCUI
D00415 KEGG_DRUG
2FS66TH3YW UNII
7408 INN_ID
60857 PUBCHEM_CID
4021094 VANDF
N0000006502 NDFRT
N0000148550 NDFRT
006460 NDDF
135775 RXNORM
d04253 MMSL
52759 MMSL
108406003 SNOMEDCT_US
5712 MMSL
363582006 SNOMEDCT_US
CHEMBL1185 ChEMBL_ID
CHEBI:10124 CHEBI
C089750 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 0115-0671 TABLET 2.50 mg ORAL NDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 0115-0672 TABLET 5 mg ORAL NDA 18 sections
Zolmitriptan Orally Disintegrating HUMAN PRESCRIPTION DRUG LABEL 1 0115-0691 TABLET, ORALLY DISINTEGRATING 2.50 mg ORAL NDA 18 sections
Zolmitriptan Orally Disintegrating HUMAN PRESCRIPTION DRUG LABEL 1 0115-0692 TABLET, ORALLY DISINTEGRATING 5 mg ORAL NDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 0378-4260 TABLET, FILM COATED 2.50 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 0378-4261 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
ZOMIG HUMAN PRESCRIPTION DRUG LABEL 1 21695-955 SPRAY, METERED 5 mg NASAL NDA 19 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 27241-021 TABLET 2.50 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 27241-022 TABLET 5 mg ORAL ANDA 18 sections
ZOLMITRIPTAN HUMAN PRESCRIPTION DRUG LABEL 1 31722-458 TABLET, FILM COATED 2.50 mg ORAL ANDA 18 sections
ZOLMITRIPTAN HUMAN PRESCRIPTION DRUG LABEL 1 31722-459 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 33342-112 TABLET, FILM COATED 2.50 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 33342-113 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 33342-139 TABLET, ORALLY DISINTEGRATING 2.50 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 33342-140 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 46708-181 TABLET, ORALLY DISINTEGRATING 2.50 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 46708-182 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 46708-462 TABLET, FILM COATED 2.50 mg ORAL ANDA 17 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 46708-463 TABLET, FILM COATED 5 mg ORAL ANDA 17 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 55801-322 TABLET, FILM COATED 2.50 mg ORAL ANDA 16 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 55801-323 TABLET, FILM COATED 5 mg ORAL ANDA 16 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 59746-432 TABLET, FILM COATED 2.50 mg ORAL ANDA 17 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 59746-433 TABLET, FILM COATED 5 mg ORAL ANDA 17 sections
Zolmitriptan OD HUMAN PRESCRIPTION DRUG LABEL 1 59746-461 TABLET, ORALLY DISINTEGRATING 2.50 mg ORAL ANDA 18 sections
Zolmitriptan OD HUMAN PRESCRIPTION DRUG LABEL 1 59746-462 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 60505-3693 TABLET, FILM COATED 2.50 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 60505-3694 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 60505-3718 TABLET, ORALLY DISINTEGRATING 2.50 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 60505-3719 TABLET, ORALLY DISINTEGRATING 5 mg ORAL ANDA 18 sections
Zolmitriptan HUMAN PRESCRIPTION DRUG LABEL 1 63548-0101 TABLET, FILM COATED 2.50 mg ORAL ANDA 18 sections