Drug/Small Molecule:

sumatriptan

Overview

Generic Names:	NP101; Sumatriptan Succinate; Sumatriptanum [INN-Latin]; estradiol; sumatriptan; triptan
IUPAC Name:	1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide
Trade Names:	Imigran; Imitrex; Sumatran; Sumax
PharmGKB Accession Id:	PA451566

Description

A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraine disorders. A transdermal patch version of sumatriptan is currently in phase I trials in the U.S. under the code name NP101 (NuPathe).

Indication

For the treatment of migraine attacks with or without aura in adults

ATC Therapeutic Category

• N02CC:Selective serotonin (5HT1) agonists

Pharmacology and Interactions

Mechanism Of Action

Sumatriptan stimulates 5-HT receptors of the 1D subtype, most likely presynaptic receptors, resulting in selective vasoconstriction of inflamed and dilated cranial blood vessels in the carotid circulation. Sumatriptan also blocks the release of vasoactive neuropeptides from perivascular trigeminal axons in the dura mater during migraine and may inhibit the release of inflammatory mediators from the trigeminal nerve.

Pharmacology

Sumatriptan, an antimigraine drug, is structurally similar to serotonin. It is thought that the cerebral blood vessel constriction induced by activation of 5-HT1 receptors on those vessels may contribute to the antimigrainous effect of sumatriptan in humans.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme.

Protein Binding

14%-21%

Absorption

Approximately 15%

Half Life

2.5 hours

Toxicity

Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.

Chemical Properties

Chemical Formula:

C₁₄H₂₁N₃O₂S

SMILES Code:

CNS(=O)(=O)Cc1ccc2c(c1)c(c[nH]2)CCN(C)C

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

295.4 / 295.1354

Curated Annotations ()

1. rs5443 at chr12:6825136 in GNB3, USP5
   A study on a total of 180 migraine and cluster headache patients found that pain relief by triptans is significantly modulated by this common genetic GNB3 variant.

   Variant Name:

   GNB3:825C>T; GNB3:Ser275Ser

   Related Drugs:

   almotriptan, eletriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan

   Related Diseases:

   Migraine without Aura

   Evidence:

   PMID:17361120
   

Curated Information

The following genes are in curated knowledge about this drug.

	Gene	Relationship	Evidence
	GNB3		Variants
	USP5		Variants

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

• MAOA

Drug Targets

• HTR1D
• HTR1B
• HTR1F
• HTR2B

PharmGKB Curated Pathways

• Anti-estrogen Pathway (Aromatase Inhibitor)

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Curated Information

The following diseases are in curated knowledge about this drug.

	Disease	Relationship	Evidence
	Atrial Fibrillation		Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

1. Physicochemical determinants of human renal clearance

LinkOuts

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.