Details of the Drug

General Information of Drug (ID: DMVYXR8)

Drug Name

Sumatriptan

Synonyms

Sumatran; Sumatriptanum; Sumax; GR 43175; GR 43175X; NP101; GR-43175; Imigran (TN); Imitrex (TN); KS-1116; Sumatriptanum [INN-Latin]; Sumatriptan (JAN/USP/INN); (3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide; 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide; 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide; 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide; 3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide; 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide; 3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide

Indication

Disease Entry	ICD 11	Status	REF
Cluster headache	8A81.0	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)

295.4

Logarithm of the Partition Coefficient (xlogp)

0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 9.0 mcgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 69.5 mcg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 0.17 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Bioavailability: The bioavailability of drug is 100% [3]
Clearance: The total plasma clearance of drug is 1200 mL/min [3]
Elimination: About 40% of drug is excreted in urine, with 22 +/-4% is excreted as unchanged sumatriptan and 38 +/- 7% is excreted as indole acetic acid [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.7 - 2.0 hours (subcutaneous sumatriptan), 1.4 - 1.9 hours (oral sumatriptan), 1.6 - 2.2 hours (rectal sumatriptan), and 1.7 - 2.0 hours (intrsnasal sumatriptan) [3]
Metabolism: The drug is metabolized via the monoamine oxidase A [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.67703 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.83% [7]
Vd: The volume of distribution (Vd) of drug is 50 +/- 8 L [5]
Water Solubility: The ability of drug to dissolve in water is measured as 21.4 mg/mL [4]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Cytogenetic abnormality	Not Available	HTR1F	OTALAXPA	[8]
Cytogenetic abnormality	Not Available	CALCA	OTQSXM9Z	[8]
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Chemical Identifiers

Formula: C14H21N3O2S
IUPAC Name: 1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide
Canonical SMILES: CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C
InChI: InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
InChIKey: KQKPFRSPSRPDEB-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5358
ChEBI ID: CHEBI:10650
CAS Number: 103628-46-2
DrugBank ID: DB00669
TTD ID: D0Z6UC
VARIDT ID: DR00331
ACDINA ID: D00645

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 1D receptor (HTR1D)	TT6MSOK	5HT1D_HUMAN	Agonist	[9]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[10]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[11]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
5-hydroxytryptamine receptor 1F (HTR1F)	OTALAXPA	5HT1F_HUMAN	Drug Response	[8]
Calcitonin gene-related peptide 1 (CALCA)	OTQSXM9Z	CALCA_HUMAN	Drug Response	[8]
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3 (GNB3)	OTA6HYBA	GBB3_HUMAN	Drug Response	[12]
Nuclear receptor subfamily 0 group B member 2 (NR0B2)	OT7UVICX	NR0B2_HUMAN	Gene/Protein Processing	[13]
Pro-opiomelanocortin (POMC)	OTV41F7T	COLI_HUMAN	Gene/Protein Processing	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Major	Decreased metabolism of Sumatriptan caused by Methylene blue mediated inhibition of non-CYP450 enzyme.	Acquired methaemoglobinaemia [3A93]	[15]
Oliceridine	DM6MDCF	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Oliceridine.	Acute pain [MG31]	[16]
Desipramine	DMT2FDC	Major	Additive serotonergic effects by the combination of Sumatriptan and Desipramine.	Attention deficit hyperactivity disorder [6A05]	[17]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Sumatriptan and Droxidopa.	Autonomic nervous system disorder [8D87]	[18]
Dihydrocodeine	DMB0FWL	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Dihydrocodeine.	Chronic pain [MG30]	[16]
Levomilnacipran	DMV26S8	Major	Additive serotonergic effects by the combination of Sumatriptan and Levomilnacipran.	Chronic pain [MG30]	[17]
Sertraline	DM0FB1J	Major	Additive serotonergic effects by the combination of Sumatriptan and Sertraline.	Depression [6A70-6A7Z]	[17]
Vilazodone	DM4LECQ	Major	Additive serotonergic effects by the combination of Sumatriptan and Vilazodone.	Depression [6A70-6A7Z]	[17]
Nefazodone	DM4ZS8M	Major	Additive serotonergic effects by the combination of Sumatriptan and Nefazodone.	Depression [6A70-6A7Z]	[17]
Paroxetine	DM5PVQE	Major	Additive serotonergic effects by the combination of Sumatriptan and Paroxetine.	Depression [6A70-6A7Z]	[17]
Vortioxetine	DM6F1PU	Major	Additive serotonergic effects by the combination of Sumatriptan and Vortioxetine.	Depression [6A70-6A7Z]	[17]
Isocarboxazid	DMAF1NB	Major	Decreased metabolism of Sumatriptan caused by Isocarboxazid mediated inhibition of non-CYP450 enzyme.	Depression [6A70-6A7Z]	[15]
Milnacipran	DMBFE74	Major	Additive serotonergic effects by the combination of Sumatriptan and Milnacipran.	Depression [6A70-6A7Z]	[17]
Escitalopram	DMFK9HG	Major	Additive serotonergic effects by the combination of Sumatriptan and Escitalopram.	Depression [6A70-6A7Z]	[17]
Tranylcypromine	DMGB5RE	Major	Decreased metabolism of Sumatriptan caused by Tranylcypromine mediated inhibition of non-CYP450 enzyme.	Depression [6A70-6A7Z]	[15]
Desvenlafaxine	DMHD4PE	Major	Additive serotonergic effects by the combination of Sumatriptan and Desvenlafaxine.	Depression [6A70-6A7Z]	[17]
Phenelzine	DMHIDUE	Major	Decreased metabolism of Sumatriptan caused by Phenelzine mediated inhibition of non-CYP450 enzyme.	Depression [6A70-6A7Z]	[15]
5-hydroxy-L-tryptophan	DMDWZGJ	Major	Additive serotonergic effects by the combination of Sumatriptan and 5-hydroxy-L-tryptophan.	Discovery agent [N.A.]	[19]
Procarbazine	DMIK367	Major	Decreased metabolism of Sumatriptan caused by Procarbazine mediated inhibition of non-CYP450 enzyme.	Hodgkin lymphoma [2B30]	[15]
Ozanimod	DMT6AM2	Major	Decreased metabolism of Sumatriptan caused by Ozanimod mediated inhibition of non-CYP450 enzyme.	Multiple sclerosis [8A40]	[20]
Granisetron	DMIUW25	Major	Additive serotonergic effects by the combination of Sumatriptan and Granisetron.	Nausea/vomiting [MD90]	[21]
Dolasetron	DMMG26Z	Major	Additive serotonergic effects by the combination of Sumatriptan and Dolasetron.	Nausea/vomiting [MD90]	[21]
Ondansetron	DMOTQ1I	Major	Additive serotonergic effects by the combination of Sumatriptan and Ondansetron.	Nausea/vomiting [MD90]	[21]
Sibutramine	DMFJTDI	Major	Additive serotonergic effects by the combination of Sumatriptan and Sibutramine.	Obesity [5B80-5B81]	[15]
Lorcaserin	DMG6OYJ	Major	Additive serotonergic effects by the combination of Sumatriptan and Lorcaserin.	Obesity [5B80-5B81]	[22]
Dexfenfluramine	DMJ7YDS	Major	Additive serotonergic effects by the combination of Sumatriptan and Dexfenfluramine.	Obesity [5B80-5B81]	[17]
Levomethadyl Acetate	DM06HG5	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Levomethadyl Acetate.	Opioid use disorder [6C43]	[23]
Oxymorphone	DM65AGJ	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Oxymorphone.	Pain [MG30-MG3Z]	[16]
Levorphanol	DMGS80V	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Levorphanol.	Pain [MG30-MG3Z]	[16]
Dezocine	DMJDB0Y	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Dezocine.	Pain [MG30-MG3Z]	[16]
Nalbuphine	DMOSQGU	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Nalbuphine.	Pain [MG30-MG3Z]	[16]
Buprenorphine	DMPRI8G	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Buprenorphine.	Pain [MG30-MG3Z]	[16]
Hydrocodone	DMQ2JO5	Moderate	Additive serotonergic effects by the combination of Sumatriptan and Hydrocodone.	Pain [MG30-MG3Z]	[16]
Fentanyl	DM8WAHT	Major	Additive serotonergic effects by the combination of Sumatriptan and Fentanyl.	Sensation disturbance [MB40]	[17]
Tizanidine	DMR2IQ4	Moderate	Additive CNS depression effects by the combination of Sumatriptan and Tizanidine.	Tonus and reflex abnormality [MB47]	[24]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
D&C red no. 27	E00381	83511	Colorant
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite	E00392	104805	Diluent
Calcium hydrogenphosphate	E00294	24441	Diluent
Carmellose sodium	E00625	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Hypromellose	E00634	Not Available	Coating agent
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
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium bicarbonate	E00424	516892	Alkalizing agent; Diluent
Sodium chloride	E00077	5234	Diluent; Tonicity 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
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water	E00035	962	Solvent
Haematite red	E00236	14833	Colorant
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
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⏷ Show the Full List of 30 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Sumatriptan 100 mg tablet	100 mg	Oral Tablet	Oral
Sumatriptan 25 mg tablet	25 mg	Oral Tablet	Oral
Sumatriptan 50 mg tablet	50 mg	Oral Tablet	Oral
Sumatriptan Succinate eq 25mg base tablet	eq 25mg base	Tablet	Oral
Sumatriptan Succinate eq 100mg base tablet	eq 100mg base	Tablet	Oral
Sumatriptan Succinate 3mg injectable	3mg	Injectable	Subcutaneous

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Sumatriptan 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: 54).
3	Comparative clinical pharmacokinetics of single doses of sumatriptan following subcutaneous, oral, rectal and intranasal administration. Eur J Pharm Sci. 1998 Apr;6(2):99-104.
4	BDDCS applied to over 900 drugs
5	FDA Approved Drug Products: Sumatriptan Nasal Spray
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	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
9	Irritable bowel syndrome: new agents targeting serotonin receptor subtypes. Drugs. 2001;61(3):317-32.
10	Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
11	HT29-MTX and Caco-2/TC7 monolayers as predictive models for human intestinal absorption: role of the mucus layer. J Pharm Sci. 2001 Oct;90(10):1608-19. Comparative Study
12	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.
13	A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. Toxicol Sci. 2005 Feb;83(2):282-92.
14	The effects of oral sumatriptan, a 5-HT1 receptor agonist, on circulating ACTH and cortisol concentrations in man. Br J Clin Pharmacol. 1995 Apr;39(4):389-95. doi: 10.1111/j.1365-2125.1995.tb04467.x.
15	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]
16	Vizcaychipi MP, Walker S, Palazzo M "Serotonin syndrome triggered by tramadol." Br J Anaesth 99 (2007): 919. [PMID: 18006535]
17	Achamallah NS "Visual hallucinations after combining fluoxetine and dextromethorphan ." Am J Psychiatry 149 (1992): 1406. [PMID: 1530079]
18	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
19	Ciraulo DA, Shader RI "Fluoxetine drug-drug interactions: I. Antidepressants and antipsychotics." J Clin Psychopharmacol 10 (1990): 48-50. [PMID: 1968472]
20	Alvine G, Black DW, Tsuang D "Case of delirium secondary to phenelzine/L-tryptophan combination." J Clin Psychiatry 51 (1990): 311. [PMID: 2365671]
21	Canadian Pharmacists Association.
22	Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ.
23	Das PK, Warkentin DI, Hewko R, Forrest DL "Serotonin syndrome after concomitant treatment with linezolid and meperidine." Clin Infect Dis 46 (2008): 264-5. [PMID: 18171260]
24	Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.