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

Stem definition	Drug id	CAS RN
serotonin (5-HT1) receptor agonists, sumatriptan derivatives	1884	121679-13-8

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
2.50	mg	O

ADMET properties:

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

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Approvals:

Date	Agency	Company	Orphan
Feb. 10, 1998	FDA	GLAXOSMITHKLINE LLC

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Medication overuse headache	76.47	44.86	9	162	133	34956627

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N02CC02	NERVOUS SYSTEM ANALGESICS ANTIMIGRAINE PREPARATIONS Selective serotonin (5HT1) agonists
CHEBI has role	CHEBI:35941	serotonin agonists
FDA EPC	N0000175765	Serotonin-1b and Serotonin-1d Receptor Agonist
FDA MoA	N0000175763	Serotonin 1b Receptor Agonists
FDA MoA	N0000175764	Serotonin 1d Receptor 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

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

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
5-hydroxytryptamine receptor 1B	GPCR	P28222	5HT1B_HUMAN	AGONIST	Ki	8.48	CHEMBL	CHEMBL
5-hydroxytryptamine receptor 1D	GPCR	P28221	5HT1D_HUMAN	AGONIST	EC50	8.80	WOMBAT-PK	CHEMBL
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	7.35	CHEMBL
5-hydroxytryptamine receptor 1F	GPCR	P30939	5HT1F_HUMAN	AGONIST	Ki	8.20	IUPHAR
5-hydroxytryptamine receptor 1E	GPCR	P28566	5HT1E_HUMAN	AGONIST	Ki	7.70	IUPHAR

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External reference:

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ID	Source
006605	NDDF
006606	NDDF
108408002	SNOMEDCT_US
108409005	SNOMEDCT_US
141366	RXNORM
143388-64-1	SECONDARY_CAS_RN
174286	MMSL
363571003	SNOMEDCT_US
4021087	VANDF
4024101	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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	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
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

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