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Chemistry

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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
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 Weight 335.5 g/mol
Molecular Formula C17H25N3O2S
XLogP32
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass335.16674822 g/mol
Monoisotopic Mass335.16674822 g/mol
Topological Polar Surface Area73.6 Ų
Heavy Atom Count23
Formal Charge0
Complexity483
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameAmerge
PubMed HealthNaratriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelAMERGE 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 IngredientNaratriptan hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 2.5mg base; eq 1mg base
Market StatusPrescription
CompanyGlaxosmithkline

2 of 4  
Drug NameNaratriptan
PubMed HealthNaratriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelNaratriptan 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 IngredientNaratriptan hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 2.5mg base; eq 1mg base
Market StatusPrescription
CompanyMylan Pharms; Apotex; Sun Pharm Inds; Sandoz; Roxane; Teva Pharms; Paddock; Orchid Hlthcare; Heritage Pharms

3 of 4  
Drug NameAmerge
PubMed HealthNaratriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelAMERGE 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 IngredientNaratriptan hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 2.5mg base; eq 1mg base
Market StatusPrescription
CompanyGlaxosmithkline

4 of 4  
Drug NameNaratriptan
PubMed HealthNaratriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelNaratriptan 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 IngredientNaratriptan hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 2.5mg base; eq 1mg base
Market StatusPrescription
CompanyMylan 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-HT1A, 5-HT5A, 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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REDDY\\'S LABORATORIES","supplierCountry":"INDIA","foreign_port":"GUARULHOS","customer":"SANOFI","customerCountry":"BRAZIL","quantity":"20.00","actualQuantity":"20","unit":"KGS","unitRateFc":"13500","totalValueFC":"267901.8","currency":"USD","unitRateINR":1122525,"date":"19-Sep-2024","totalValueINR":"22450500","totalValueInUsd":"267901.8","indian_port":"Hyderabad Air","hs_no":"29359090","bill_no":"4160635","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"BRAZIL","selfForZScoreResived":"Pharma Grade","supplierPort":"Hyderabad Air","supplierAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE, HYDERABAD ANDHRA PRADESH","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1732559400,"product":"NARATRIPTAN HCL USP (FOR KOREA) (BATCH:21002970 MFG. DATE: APR-2024 RETEST DATE:MAR-2029)","address":"B.S.D.MARG, GOVANDI STATION ROAD,","city":"MUMBAI, MAHARASHTRA.","supplier":"USV PRIVATE LIMITED","supplierCountry":"INDIA","foreign_port":"SEOUL - INCHEON INT\\'","customer":"SHINPO LIMITED","customerCountry":"REPUBLIC OF KOREA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"44800","totalValueFC":"44246.8","currency":"USD","unitRateINR":3733910.3999999999,"date":"26-Nov-2024","totalValueINR":"3733910.4","totalValueInUsd":"44246.8","indian_port":"Bombay Air","hs_no":"29332990","bill_no":"5924927","productDescription":"API","marketType":"REGULATED MARKET","country":"REPUBLIC OF KOREA","selfForZScoreResived":"Pharma Grade","supplierPort":"Bombay Air","supplierAddress":"B.S.D.MARG, GOVANDI STATION ROAD,, MUMBAI, MAHARASHTRA.","customerAddress":""}]
04-Jan-2021
26-Nov-2024
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

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01

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Biotech Showcase
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Company :

Naratriptan HCl

Drug Cost (USD) : 255,088

Year : 2022

Prescribers : 66

Prescriptions : 268

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02

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Company :

Naratriptan HCl

Drug Cost (USD) : 444,944

Year : 2021

Prescribers : 96

Prescriptions : 464

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03

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Company :

Naratriptan HCl

Drug Cost (USD) : 513,604

Year : 2020

Prescribers : 108

Prescriptions : 573

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ABOUT THIS PAGE

Naratriptan Manufacturers

A Naratriptan manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Naratriptan, including repackagers and relabelers. The FDA regulates Naratriptan manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Naratriptan API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Naratriptan manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Naratriptan Suppliers

A Naratriptan supplier is an individual or a company that provides Naratriptan active pharmaceutical ingredient (API) or Naratriptan finished formulations upon request. The Naratriptan suppliers may include Naratriptan API manufacturers, exporters, distributors and traders.

click here to find a list of Naratriptan suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Naratriptan GMP

Naratriptan Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Naratriptan GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Naratriptan GMP manufacturer or Naratriptan GMP API supplier for your needs.

Naratriptan CoA

A Naratriptan CoA (Certificate of Analysis) is a formal document that attests to Naratriptan's compliance with Naratriptan specifications and serves as a tool for batch-level quality control.

Naratriptan CoA mostly includes findings from lab analyses of a specific batch. For each Naratriptan CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Naratriptan may be tested according to a variety of international standards, such as European Pharmacopoeia (Naratriptan EP), Naratriptan JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Naratriptan USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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