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

Drug dosage:

Dose	Unit	Route
2.50	mg	O

ADMET properties:

Property	Value	Reference
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:

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

FDA Adverse Event Reporting System (Female)

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	169.65	22.98	32	2920	981	50601191
Paradoxical drug reaction	128.81	22.98	32	2920	3615	50598557
Migraine	126.16	22.98	69	2883	75211	50526961
Anuria	93.22	22.98	32	2920	11212	50590960
Extrapyramidal disorder	91.79	22.98	32	2920	11738	50590434
Drug ineffective for unapproved indication	70.14	22.98	31	2921	21250	50580922
Cerebral vasoconstriction	52.10	22.98	12	2940	980	50601192
Dyspepsia	42.69	22.98	35	2917	74062	50528110
Abdominal pain	32.44	22.98	53	2899	236175	50365997
Weight decreased	24.29	22.98	45	2907	221200	50380972
Spinal cord infarction	24.23	22.98	5	2947	244	50601928

FDA Adverse Event Reporting System (Male)

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	48.90	43.67	6	149	118	29574254

FDA Adverse Event Reporting System (Geriatric)

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	175.51	25.78	32	2845	1071	64494784
Migraine	130.44	25.78	61	2816	62616	64433239
Paradoxical drug reaction	120.90	25.78	32	2845	6088	64489767
Anuria	85.27	25.78	32	2845	18932	64476923
Extrapyramidal disorder	84.32	25.78	32	2845	19520	64476335
Drug ineffective for unapproved indication	69.95	25.78	32	2845	31101	64464754
Cerebral vasoconstriction	52.81	25.78	12	2865	1210	64494645
Dyspepsia	48.53	25.78	35	2842	80277	64415578
Burns third degree	34.68	25.78	7	2870	402	64495453
Abdominal pain	33.37	25.78	54	2823	312321	64183534
Treatment failure	33.26	25.78	33	2844	116783	64379072
Nasal oedema	28.39	25.78	7	2870	1001	64494854
Dust allergy	28.09	25.78	7	2870	1046	64494809
Tinnitus	28.03	25.78	18	2859	34115	64461740
Weight decreased	27.29	25.78	47	2830	285692	64210163
Bronchial obstruction	26.72	25.78	8	2869	2366	64493489
Nausea	26.70	25.78	86	2791	785714	63710141

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
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|

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
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 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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	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

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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
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	23 sections
naratriptan	HUMAN PRESCRIPTION DRUG LABEL	1	23155-055	TABLET	2.50 mg	ORAL	ANDA	23 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	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