naratriptan 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
serotonin (5-HT1) receptor agonists, sumatriptan derivatives 1884 121679-13-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • naratriptan
  • naratriptan hydrochloride
  • naratriptan HCl
  • Molecular weight: 335.47
  • Formula: C17H25N3O2S
  • CLOGP: 1.70
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 65.20
  • ALOGS: -3.47
  • ROTB: 4
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2.50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 35 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.21 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 69 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.40 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.70 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.60 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 10, 1998 FDA GLAXOSMITHKLINE LLC

FDA Adverse Event Reporting System (Female)

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
Neovascularisation 192.57 21.72 36 3478 1109 63484399
Paradoxical drug reaction 146.36 21.72 36 3478 4116 63481392
Migraine 140.22 21.72 81 3433 103265 63382243
Anuria 107.00 21.72 36 3478 12515 63472993
Extrapyramidal disorder 104.99 21.72 36 3478 13248 63472260
Drug ineffective for unapproved indication 72.23 21.72 36 3478 34027 63451481
Cerebral vasoconstriction 55.60 21.72 13 3501 1195 63484313
Dyspepsia 42.12 21.72 39 3475 102157 63383351
Abdominal pain 33.61 21.72 59 3455 293397 63192111
Weight decreased 30.85 21.72 55 3459 276743 63208765
Dust allergy 29.38 21.72 7 3507 697 63484811
Burns third degree 29.32 21.72 6 3508 296 63485212
Spinal cord infarction 24.20 21.72 5 3509 259 63485249
Reversible cerebral vasoconstriction syndrome 24.12 21.72 8 3506 2650 63482858
Bronchial obstruction 24.10 21.72 7 3507 1500 63484008
Consciousness fluctuating 23.03 21.72 6 3508 861 63484647
Cough 22.71 21.72 50 3464 292693 63192815
Opisthotonus 22.71 21.72 5 3509 351 63485157
Nausea 21.82 21.72 99 3415 854372 62631136

FDA Adverse Event Reporting System (Male)

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
Medication overuse headache 76.47 44.86 9 162 133 34956627

FDA Adverse Event Reporting System (Geriatric)

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
Neovascularisation 200.32 24.04 36 3237 1209 79739906
Migraine 142.17 24.04 70 3203 87423 79653692
Paradoxical drug reaction 137.46 24.04 36 3237 7149 79733966
Anuria 99.47 24.04 36 3237 20927 79720188
Extrapyramidal disorder 96.71 24.04 36 3237 22643 79718472
Drug ineffective for unapproved indication 71.39 24.04 37 3236 51201 79689914
Cerebral vasoconstriction 56.93 24.04 13 3260 1457 79739658
Dyspepsia 50.20 24.04 39 3234 108648 79632467
Burns third degree 40.40 24.04 8 3265 453 79740662
Dust allergy 35.73 24.04 9 3264 1527 79739588
Abdominal pain 34.31 24.04 59 3214 389510 79351605
Treatment failure 31.76 24.04 37 3236 170449 79570666
Weight decreased 31.53 24.04 54 3219 355144 79385971
Bronchial obstruction 30.48 24.04 9 3264 2759 79738356
Nasal oedema 29.90 24.04 8 3265 1716 79739399
Medication overuse headache 29.66 24.04 7 3266 905 79740210
Tinnitus 27.44 24.04 19 3254 44314 79696801
Nasal discharge discolouration 26.90 24.04 8 3265 2513 79738602
Nausea 26.87 24.04 93 3180 957103 78784012
Reversible cerebral vasoconstriction syndrome 25.38 24.04 8 3265 3049 79738066
Cough 25.26 24.04 50 3223 366739 79374376

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N02CC02 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Selective serotonin (5HT1) agonists
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D058825 Serotonin 5-HT1 Receptor Agonists
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D014662 Vasoconstrictor Agents
CHEBI has role CHEBI:35941 serotonin 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

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Migraine indication 37796009 DOID:6364
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Acute nephropathy contraindication 58574008
Hemiplegic migraine contraindication 59292006
Hepatic failure contraindication 59927004
Cerebrovascular disease contraindication 62914000 DOID:6713
Diabetes mellitus contraindication 73211009 DOID:9351
Prinzmetal angina contraindication 87343002
Angina pectoris contraindication 194828000
Cerebrovascular accident contraindication 230690007
Transient ischemic attack contraindication 266257000 DOID:224
Cardiovascular event risk contraindication 395112001
Peripheral vascular disease contraindication 400047006
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Hypertensive urgency contraindication 443482000




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.21 acidic
pKa2 13.86 acidic
pKa3 9.38 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
5-hydroxytryptamine receptor 1B GPCR AGONIST Ki 8.48 CHEMBL CHEMBL
5-hydroxytryptamine receptor 1D GPCR AGONIST EC50 8.80 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 7.35 CHEMBL
5-hydroxytryptamine receptor 1F GPCR AGONIST Ki 8.20 IUPHAR
5-hydroxytryptamine receptor 1E GPCR AGONIST Ki 7.70 IUPHAR

External reference:

IDSource
4024101 VUID
N0000022106 NUI
D00674 KEGG_DRUG
143388-64-1 SECONDARY_CAS_RN
4021087 VANDF
4024101 VANDF
C0540623 UMLSCUI
CHEBI:7478 CHEBI
CHEMBL1200601 ChEMBL_ID
CHEMBL1278 ChEMBL_ID
DB00952 DRUGBANK_ID
C106783 MESH_SUPPLEMENTAL_RECORD_UI
4440 PUBCHEM_CID
45 IUPHAR_LIGAND_ID
7097 INN_ID
QX3KXL1ZA2 UNII
141366 RXNORM
174286 MMSL
5157 MMSL
d04285 MMSL
006605 NDDF
006606 NDDF
108408002 SNOMEDCT_US
108409005 SNOMEDCT_US
363571003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 0054-0278 TABLET 1 mg ORAL ANDA 26 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 0054-0278 TABLET 1 mg ORAL ANDA 26 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 0054-0279 TABLET 2.50 mg ORAL ANDA 26 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 0054-0279 TABLET 2.50 mg ORAL ANDA 26 sections
AMERGE HUMAN PRESCRIPTION DRUG LABEL 1 0173-0561 TABLET, FILM COATED 1 mg ORAL NDA 26 sections
AMERGE HUMAN PRESCRIPTION DRUG LABEL 1 0173-0562 TABLET, FILM COATED 2.50 mg ORAL NDA 26 sections
naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 23155-054 TABLET 1 mg ORAL ANDA 24 sections
naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 23155-054 TABLET 1 mg ORAL ANDA 24 sections
naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 23155-055 TABLET 2.50 mg ORAL ANDA 24 sections
naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 23155-055 TABLET 2.50 mg ORAL ANDA 24 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 42043-130 TABLET, FILM COATED 1 mg ORAL ANDA 26 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 42043-131 TABLET, FILM COATED 2.50 mg ORAL ANDA 26 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 50090-6162 TABLET, FILM COATED 2.50 mg ORAL ANDA 26 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 69452-340 TABLET, FILM COATED 1 mg ORAL ANDA 26 sections
Naratriptan HUMAN PRESCRIPTION DRUG LABEL 1 69452-341 TABLET, FILM COATED 2.50 mg ORAL ANDA 26 sections