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Also known as: 121679-13-8, N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethanesulfonamide, 1h-indole-5-ethanesulfonamide, n-methyl-3-(1-methyl-4-piperidinyl)-, N-methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide, Naratriptan (inn), Qx3kxl1za2

Molecular Formula

C₁₇H₂₅N₃O₂S

Molecular Weight

335.5 g/mol

InChI Key

AMKVXSZCKVJAGH-UHFFFAOYSA-N

FDA UNII

QX3KXL1ZA2

Naratriptan is a triptan drug that is selective for the 5-hydroxytryptamine1 receptor subtype. It is typically used for the treatment of migraine headaches.

Naratriptan is a Serotonin-1b and Serotonin-1d Receptor Agonist. The mechanism of action of naratriptan is as a Serotonin 1b Receptor Agonist, and Serotonin 1d Receptor Agonist.

1 2D Structure

Naratriptan

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide

2.1.2 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

2.1.3 InChI Key

AMKVXSZCKVJAGH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C

2.2 Other Identifiers

2.2.1 UNII

QX3KXL1ZA2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1h-indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, Monohydrochloride

2. Amerge

3. Colatan

4. Gr 85548a

5. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulfonamide

6. N-methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide Monohydrochloride

7. Naramig

8. Naratriptan Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 121679-13-8

2. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethanesulfonamide

3. 1h-indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-

4. N-methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide

5. Naratriptan (inn)

6. Qx3kxl1za2

7. Chembl1278

8. N-methyl-2-[3-(1-methyl-4-piperidyl)-1h-indol-5-yl]-ethanesulfonamide

9. Chebi:7478

10. Colatan

11. Naratriptan [inn]

12. Naratriptanum

13. Naramig (tn)

14. Ncgc00181786-01

15. Naratriptan [inn:ban]

16. Unii-qx3kxl1za2

17. Naratriptan [mi]

18. Gtpl45

19. Naratriptan [vandf]

20. Schembl68753

21. Naratriptan [who-dd]

22. Bidd:gt0312

23. Zinc4076

24. Dtxsid7023354

25. Naratriptan [orange Book]

26. Hy-b0197

27. Bdbm50073682

28. N-methyl-2-[3-(1-methyl-4-piperidyl)-1h-indol-5-yl]ethanesulfonamide

29. Akos015895854

30. Ac-5013

31. Bcp9000978

32. Db00952

33. Ncgc00181786-03

34. Ncgc00181786-04

35. Ncgc00181786-08

36. Ft-0656760

37. A25336

38. C07792

39. D08255

40. Ab01565792_02

41. L000432

42. Q421315

43. N-methyl-3-(1-methyl-4 -piperidinyl)-1h-indole-5-ethansulphonamide

44. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulphonamide

45. 2-[3-(1-methyl-piperidin-4-yl)-1h-indol-5-yl]-ethanesulfonic Acid Methylamide

46. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethane-1-sulfonamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₅N₃O₂S
Molecular Weight	335.5 g/mol
XLogP3	2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	335.16674822 g/mol
Monoisotopic Mass	335.16674822 g/mol
Topological Polar Surface Area	73.6 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	483
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Amerge
PubMed Health	Naratriptan (By mouth)
Drug Classes	Antimigraine
Drug Label	AMERGE contains naratriptan hydrochloride, a selective 5-HT1B/1D receptor agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide monohydrochloride, and it has the following str...
Active Ingredient	Naratriptan hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 2.5mg base; eq 1mg base
Market Status	Prescription
Company	Glaxosmithkline

2 of 4
Drug Name	Naratriptan
PubMed Health	Naratriptan (By mouth)
Drug Classes	Antimigraine
Drug Label	Naratriptan tablets, USP contain naratriptan as the hydrochloride, which is a selective 5-hydroxytryptamine1 receptor subtype agonist. Naratriptan hydrochloride, USP is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesu...
Active Ingredient	Naratriptan hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 2.5mg base; eq 1mg base
Market Status	Prescription
Company	Mylan Pharms; Apotex; Sun Pharm Inds; Sandoz; Roxane; Teva Pharms; Paddock; Orchid Hlthcare; Heritage Pharms

3 of 4
Drug Name	Amerge
PubMed Health	Naratriptan (By mouth)
Drug Classes	Antimigraine
Drug Label	AMERGE contains naratriptan hydrochloride, a selective 5-HT1B/1D receptor agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide monohydrochloride, and it has the following str...
Active Ingredient	Naratriptan hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 2.5mg base; eq 1mg base
Market Status	Prescription
Company	Glaxosmithkline

4 of 4
Drug Name	Naratriptan
PubMed Health	Naratriptan (By mouth)
Drug Classes	Antimigraine
Drug Label	Naratriptan tablets, USP contain naratriptan as the hydrochloride, which is a selective 5-hydroxytryptamine1 receptor subtype agonist. Naratriptan hydrochloride, USP is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesu...
Active Ingredient	Naratriptan hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 2.5mg base; eq 1mg base
Market Status	Prescription
Company	Mylan Pharms; Apotex; Sun Pharm Inds; Sandoz; Roxane; Teva Pharms; Paddock; Orchid Hlthcare; Heritage Pharms

4.2 Drug Indication

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

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Naratriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonist. Naratriptan has only a weak affinity for 5-HT_1A, 5-HT_5A, and 5-HT₇ receptors and no significant affinity or pharmacological activity at 5-HT₂, 5-HT₃ or 5-HT₄ receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic, dopamine1,; dopamine2; muscarinic, or benzodiazepine receptors. This action in humans correlates with the relief of migraine headache. In addition to causing vasoconstriction, experimental data from animal studies show that Naratriptan also activates 5-HT₁ receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Naratriptan in humans.

5.2 MeSH Pharmacological Classification

Serotonin 5-HT1 Receptor Agonists

Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)

Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

NARATRIPTAN

5.3.2 FDA UNII

QX3KXL1ZA2

5.3.3 Pharmacological Classes

Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]

5.4 ATC Code

N02CC02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N02 - Analgesics

N02C - Antimigraine preparations

N02CC - Selective serotonin (5ht1) agonists

N02CC02 - Naratriptan

5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed (74% oral biovaility), absorption is rapid with peak plasma concentrations after 2-5 hours. The rate of absorption is slower during a migraine attack.

Volume of Distribution

170 L

Clearance

6.6 mL/min/kg

5.6 Metabolism/Metabolites

Primarily hepatic. In vitro, naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.

5.7 Biological Half-Life

5-8 hours

5.8 Mechanism of Action

Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.

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