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
Migraine	8A80	Approved	[1], [2]

• Therapeutic Class: Vasoconstrictor Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 335.5
  Topological Polar Surface Area (xlogp); 2
  Rotatable Bond Count (rotbonds); 5
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 4
• 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 [5]
  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 [6]
  Metabolism: The drug is metabolized via the hepatic [7]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.21291 micromolar/kg/day [8]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.7% [6]
  Vd: The volume of distribution (Vd) of drug is 170 L [5]
  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

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	[9]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[10]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Monoamine oxidase type A (MAO-A) Main DME	DERE4TU	AOFA_HUMAN	Substrate	[11]

Molecular Expression Atlas of This Drug

• The Studied Disease: Migraine
• ICD Disease Classification: 8A80

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

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]	[33]
Oliceridine	DM6MDCF	Moderate	Additive serotonergic effects by the combination of Naratriptan and Oliceridine.	Acute pain [MG31]	[34]
Desipramine	DMT2FDC	Major	Additive serotonergic effects by the combination of Naratriptan and Desipramine.	Attention deficit hyperactivity disorder [6A05]	[35]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Naratriptan and Droxidopa.	Autonomic nervous system disorder [8D87]	[36]
Dihydrocodeine	DMB0FWL	Moderate	Additive serotonergic effects by the combination of Naratriptan and Dihydrocodeine.	Chronic pain [MG30]	[34]
Levomilnacipran	DMV26S8	Major	Additive serotonergic effects by the combination of Naratriptan and Levomilnacipran.	Chronic pain [MG30]	[35]
Sertraline	DM0FB1J	Major	Additive serotonergic effects by the combination of Naratriptan and Sertraline.	Depression [6A70-6A7Z]	[35]
Vilazodone	DM4LECQ	Major	Additive serotonergic effects by the combination of Naratriptan and Vilazodone.	Depression [6A70-6A7Z]	[35]
Nefazodone	DM4ZS8M	Major	Additive serotonergic effects by the combination of Naratriptan and Nefazodone.	Depression [6A70-6A7Z]	[35]
Vortioxetine	DM6F1PU	Major	Additive serotonergic effects by the combination of Naratriptan and Vortioxetine.	Depression [6A70-6A7Z]	[35]
Isocarboxazid	DMAF1NB	Major	Additive serotonergic effects by the combination of Naratriptan and Isocarboxazid.	Depression [6A70-6A7Z]	[33]
Milnacipran	DMBFE74	Major	Additive serotonergic effects by the combination of Naratriptan and Milnacipran.	Depression [6A70-6A7Z]	[35]
Escitalopram	DMFK9HG	Major	Additive serotonergic effects by the combination of Naratriptan and Escitalopram.	Depression [6A70-6A7Z]	[35]
Desvenlafaxine	DMHD4PE	Major	Additive serotonergic effects by the combination of Naratriptan and Desvenlafaxine.	Depression [6A70-6A7Z]	[35]
5-hydroxy-L-tryptophan	DMDWZGJ	Major	Additive serotonergic effects by the combination of Naratriptan and 5-hydroxy-L-tryptophan.	Discovery agent [N.A.]	[37]
Procarbazine	DMIK367	Major	Additive serotonergic effects by the combination of Naratriptan and Procarbazine.	Hodgkin lymphoma [2B30]	[33]
Ozanimod	DMT6AM2	Moderate	Additive serotonergic effects by the combination of Naratriptan and Ozanimod.	Multiple sclerosis [8A40]	[38]
Sibutramine	DMFJTDI	Major	Additive serotonergic effects by the combination of Naratriptan and Sibutramine.	Obesity [5B80-5B81]	[33]
Lorcaserin	DMG6OYJ	Major	Additive serotonergic effects by the combination of Naratriptan and Lorcaserin.	Obesity [5B80-5B81]	[39]
Dexfenfluramine	DMJ7YDS	Major	Additive serotonergic effects by the combination of Naratriptan and Dexfenfluramine.	Obesity [5B80-5B81]	[35]
Levomethadyl Acetate	DM06HG5	Moderate	Additive serotonergic effects by the combination of Naratriptan and Levomethadyl Acetate.	Opioid use disorder [6C43]	[34]
Oxymorphone	DM65AGJ	Moderate	Additive serotonergic effects by the combination of Naratriptan and Oxymorphone.	Pain [MG30-MG3Z]	[34]
Dezocine	DMJDB0Y	Moderate	Additive serotonergic effects by the combination of Naratriptan and Dezocine.	Pain [MG30-MG3Z]	[34]
Hydrocodone	DMQ2JO5	Moderate	Additive serotonergic effects by the combination of Naratriptan and Hydrocodone.	Pain [MG30-MG3Z]	[34]

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

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

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