Details of the Drug

General Information of Drug (ID: DMO50U2)

Drug Name

Naratriptan

Synonyms

Colatan; Naramig; Naratriptanum; Amerge (TN); Naramig (TN); Naratriptan (INN); Amerge, Naramig,Naratriptan; N-methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide; N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide; N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide

Indication

Disease Entry	ICD 11	Status	REF
Headache	8A80-8A84	Approved	[1]
Migraine	8A80	Approved	[2]
Migraine disorder	N.A.	Approved	[1]
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Therapeutic Class

Vasoconstrictor Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

335.5

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: 69% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The clearance of drug is 6.6 mL/min/kg []
Elimination: 50% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 - 8 hours [5]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.21291 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.7% [5]
Vd: The volume of distribution (Vd) of drug is 170 L []
Water Solubility: The ability of drug to dissolve in water is measured as 35 mg/mL [3]

Chemical Identifiers

Formula: C17H25N3O2S
IUPAC Name: N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Canonical SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C
InChI: InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
InChIKey: AMKVXSZCKVJAGH-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4440
ChEBI ID: CHEBI:7478
CAS Number: 121679-13-8
DrugBank ID: DB00952
TTD ID: D0T3KI
VARIDT ID: DR01282
INTEDE ID: DR1131
ACDINA ID: D00457

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 1B receptor (HTR1B)	TTK8CXU	5HT1B_HUMAN	Agonist	[7]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[8]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Monoamine oxidase type A (MAO-A)_{Main DME}	DERE4TU	AOFA_HUMAN	Substrate	[9]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3 (GNB3)	OTA6HYBA	GBB3_HUMAN	Drug Response	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Headache

ICD Disease Classification

8A80-8A84

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
5-HT 1B receptor (HTR1B)	DTT	HTR1B	3.68E-03	0.16	0.92
Organic cation transporter 1 (SLC22A1)	DTP	SLC22A1	5.15E-01	1.61E-02	7.93E-02
Monoamine oxidase type A (MAO-A)	DME	MAOA	4.12E-01	-2.32E-02	-8.23E-02

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Naratriptan (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Major	Additive serotonergic effects by the combination of Naratriptan and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[11]
Oliceridine	DM6MDCF	Moderate	Additive serotonergic effects by the combination of Naratriptan and Oliceridine.	Acute pain [MG31]	[12]
Desipramine	DMT2FDC	Major	Additive serotonergic effects by the combination of Naratriptan and Desipramine.	Attention deficit hyperactivity disorder [6A05]	[13]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Naratriptan and Droxidopa.	Autonomic nervous system disorder [8D87]	[14]
Dihydrocodeine	DMB0FWL	Moderate	Additive serotonergic effects by the combination of Naratriptan and Dihydrocodeine.	Chronic pain [MG30]	[12]
Levomilnacipran	DMV26S8	Major	Additive serotonergic effects by the combination of Naratriptan and Levomilnacipran.	Chronic pain [MG30]	[13]
Sertraline	DM0FB1J	Major	Additive serotonergic effects by the combination of Naratriptan and Sertraline.	Depression [6A70-6A7Z]	[13]
Vilazodone	DM4LECQ	Major	Additive serotonergic effects by the combination of Naratriptan and Vilazodone.	Depression [6A70-6A7Z]	[13]
Nefazodone	DM4ZS8M	Major	Additive serotonergic effects by the combination of Naratriptan and Nefazodone.	Depression [6A70-6A7Z]	[13]
Vortioxetine	DM6F1PU	Major	Additive serotonergic effects by the combination of Naratriptan and Vortioxetine.	Depression [6A70-6A7Z]	[13]
Isocarboxazid	DMAF1NB	Major	Additive serotonergic effects by the combination of Naratriptan and Isocarboxazid.	Depression [6A70-6A7Z]	[11]
Milnacipran	DMBFE74	Major	Additive serotonergic effects by the combination of Naratriptan and Milnacipran.	Depression [6A70-6A7Z]	[13]
Escitalopram	DMFK9HG	Major	Additive serotonergic effects by the combination of Naratriptan and Escitalopram.	Depression [6A70-6A7Z]	[13]
Desvenlafaxine	DMHD4PE	Major	Additive serotonergic effects by the combination of Naratriptan and Desvenlafaxine.	Depression [6A70-6A7Z]	[13]
5-hydroxy-L-tryptophan	DMDWZGJ	Major	Additive serotonergic effects by the combination of Naratriptan and 5-hydroxy-L-tryptophan.	Discovery agent [N.A.]	[15]
Procarbazine	DMIK367	Major	Additive serotonergic effects by the combination of Naratriptan and Procarbazine.	Hodgkin lymphoma [2B30]	[11]
Ozanimod	DMT6AM2	Moderate	Additive serotonergic effects by the combination of Naratriptan and Ozanimod.	Multiple sclerosis [8A40]	[16]
Sibutramine	DMFJTDI	Major	Additive serotonergic effects by the combination of Naratriptan and Sibutramine.	Obesity [5B80-5B81]	[11]
Lorcaserin	DMG6OYJ	Major	Additive serotonergic effects by the combination of Naratriptan and Lorcaserin.	Obesity [5B80-5B81]	[17]
Dexfenfluramine	DMJ7YDS	Major	Additive serotonergic effects by the combination of Naratriptan and Dexfenfluramine.	Obesity [5B80-5B81]	[13]
Levomethadyl Acetate	DM06HG5	Moderate	Additive serotonergic effects by the combination of Naratriptan and Levomethadyl Acetate.	Opioid use disorder [6C43]	[12]
Oxymorphone	DM65AGJ	Moderate	Additive serotonergic effects by the combination of Naratriptan and Oxymorphone.	Pain [MG30-MG3Z]	[12]
Dezocine	DMJDB0Y	Moderate	Additive serotonergic effects by the combination of Naratriptan and Dezocine.	Pain [MG30-MG3Z]	[12]
Hydrocodone	DMQ2JO5	Moderate	Additive serotonergic effects by the combination of Naratriptan and Hydrocodone.	Pain [MG30-MG3Z]	[12]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium	E00625	Not Available	Disintegrant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 4000	E00654	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Naratriptan 1 mg tablet	1 mg	Oral Tablet	Oral
Naratriptan 2.5 mg tablet	2.5 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Naratriptan FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 45).
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Triptans in pregnancy. Ther Drug Monit. 2008 Feb;30(1):5-9.
8	OCT1 mediates hepatic uptake of sumatriptan and loss-of-function OCT1 polymorphisms affect sumatriptan pharmacokinetics. Clin Pharmacol Ther. 2016 Jun;99(6):633-41.
9	Migraine pharmacotherapy with oral triptans: a rational approach to clinical management. Expert Opin Pharmacother. 2000 Mar;1(3):391-404.
10	G protein beta3 polymorphism and triptan response in cluster headache. Clin Pharmacol Ther. 2007 Oct;82(4):396-401. doi: 10.1038/sj.clpt.6100159. Epub 2007 Mar 14.
11	Chan BSH, Graudins A, Whyte IM, Dawson AH, Braitberg G, Duggin GG "Serotonin syndrome resulting from drug interactions." Med J Aust 169 (1998): 523-5. [PMID: 9861909]
12	Vizcaychipi MP, Walker S, Palazzo M "Serotonin syndrome triggered by tramadol." Br J Anaesth 99 (2007): 919. [PMID: 18006535]
13	Achamallah NS "Visual hallucinations after combining fluoxetine and dextromethorphan ." Am J Psychiatry 149 (1992): 1406. [PMID: 1530079]
14	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
15	Ciraulo DA, Shader RI "Fluoxetine drug-drug interactions: I. Antidepressants and antipsychotics." J Clin Psychopharmacol 10 (1990): 48-50. [PMID: 1968472]
16	Alvine G, Black DW, Tsuang D "Case of delirium secondary to phenelzine/L-tryptophan combination." J Clin Psychiatry 51 (1990): 311. [PMID: 2365671]
17	Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ.