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MedKoo Cat#: 318351 | Name: Naratriptan free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Naratriptan is a selective 5-HT1 receptor subtype agonist for the treatment of migraine headache. Naratriptan binds with high affinity to human cloned 5-HT1B/1D receptors. Migraines are likely due to local cranial vasodilatation and/or to the release of sensory neuropeptides (including substance P and calcitonin gene-related peptide) through nerve endings in the trigeminal system. The therapeutic activity of AMERGE for the treatment of migraine headache is thought to be due to the agonist effects at the 5-HT1B/1D receptors on intracranial blood vessels (including the arterio-venous anastomoses) and sensory nerves of the trigeminal system, which result in cranial vessel constriction and inhibition of pro-inflammatory neuropeptide release.

Chemical Structure

Naratriptan free base
Naratriptan free base
CAS#121679-13-8 (free base)

Theoretical Analysis

MedKoo Cat#: 318351

Name: Naratriptan free base

CAS#: 121679-13-8 (free base)

Chemical Formula: C17H25N3O2S

Exact Mass: 335.1667

Molecular Weight: 335.47

Elemental Analysis: C, 60.87; H, 7.51; N, 12.53; O, 9.54; S, 9.56

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Related CAS #
121679-13-8 (free base) 143388-64-1 (HCl)
Synonym
Naratriptan free base; Amerge; Colatan; GR 85548; GR-85548; GR85548;
IUPAC/Chemical Name
1H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-
InChi Key
AMKVXSZCKVJAGH-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=S(CCC1=CC2=C(NC=C2C3CCN(C)CC3)C=C1)(NC)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
1. Pauwels PJ, Colpaert FC. Selective antagonism of human 5-HT1D and 5-HT1B receptor-mediated responses in stably transfected C6-glial cells by ketanserin and GR 127,935. Eur J Pharmacol. 1996 Apr 4;300(1-2):141-5. doi: 10.1016/0014-2999(96)00011-8. PMID: 8741180. 2. Park J, Moon H, Akerman S, Holland PR, Lasalandra MP, Andreou AP, Ferrari MD, van den Maagdenberg AM, Goadsby PJ. Differential trigeminovascular nociceptive responses in the thalamus in the familial hemiplegic migraine 1 knock-in mouse: a Fos protein study. Neurobiol Dis. 2014 Apr;64:1-7. doi: 10.1016/j.nbd.2013.12.004. Epub 2013 Dec 17. PMID: 24355314. 3. Minamiyama M, Katsuno M, Adachi H, Doi H, Kondo N, Iida M, Ishigaki S, Fujioka Y, Matsumoto S, Miyazaki Y, Tanaka F, Kurihara H, Sobue G. Naratriptan mitigates CGRP1-associated motor neuron degeneration caused by an expanded polyglutamine repeat tract. Nat Med. 2012 Oct;18(10):1531-8. doi: 10.1038/nm.2932. Epub 2012 Sep 30. PMID: 23023499.
In vitro activity:
1. Pauwels PJ, Colpaert FC. Selective antagonism of human 5-HT1D and 5-HT1B receptor-mediated responses in stably transfected C6-glial cells by ketanserin and GR 127,935. Eur J Pharmacol. 1996 Apr 4;300(1-2):141-5. doi: 10.1016/0014-2999(96)00011-8. PMID: 8741180.
In vivo activity:
1. Park J, Moon H, Akerman S, Holland PR, Lasalandra MP, Andreou AP, Ferrari MD, van den Maagdenberg AM, Goadsby PJ. Differential trigeminovascular nociceptive responses in the thalamus in the familial hemiplegic migraine 1 knock-in mouse: a Fos protein study. Neurobiol Dis. 2014 Apr;64:1-7. doi: 10.1016/j.nbd.2013.12.004. Epub 2013 Dec 17. PMID: 24355314. 2. Minamiyama M, Katsuno M, Adachi H, Doi H, Kondo N, Iida M, Ishigaki S, Fujioka Y, Matsumoto S, Miyazaki Y, Tanaka F, Kurihara H, Sobue G. Naratriptan mitigates CGRP1-associated motor neuron degeneration caused by an expanded polyglutamine repeat tract. Nat Med. 2012 Oct;18(10):1531-8. doi: 10.1038/nm.2932. Epub 2012 Sep 30. PMID: 23023499.

Preparing Stock Solutions

The following data is based on the product molecular weight 335.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Tfelt-Hansen PC. Published and not fully published double-blind, randomised, controlled trials with oral naratriptan in the treatment of migraine: a review based on the GSK Trial Register. J Headache Pain. 2011 Aug;12(4):399-403. doi: 10.1007/s10194-011-0327-3. Epub 2011 Mar 25. Review. PubMed PMID: 21437713; PubMed Central PMCID: PMC3139062. 2: Lambert GA. Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. Review. PubMed PMID: 16389295. 3: Dulli DA. Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11. Review. PubMed PMID: 10410185. 4: Salonen R. Naratriptan. Int J Clin Pract. 1999 Oct-Nov;53(7):552-6. Review. PubMed PMID: 10692743. 5: Massiou H. Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. Review. PubMed PMID: 12463278. 6: Law S, Derry S, Moore RA. Naproxen with or without an antiemetic for acute migraine headaches in adults. Cochrane Database Syst Rev. 2013 Oct 20;10:CD009455. doi: 10.1002/14651858.CD009455.pub2. Review. PubMed PMID: 24142263. 7: Tfelt-Hansen P. Parenteral vs. oral sumatriptan and naratriptan: plasma levels and efficacy in migraine. a comment. J Headache Pain. 2007 Oct;8(5):273-6. Epub 2007 Oct 23. Review. PubMed PMID: 17955173; PubMed Central PMCID: PMC3476154. 8: Kunkel M. [Naratriptan. A new medical option for the pharmacist]. Med Monatsschr Pharm. 2007 May;30(5):184-6. Review. German. PubMed PMID: 17526395. 9: Becker WJ. Acute Migraine Treatment in Adults. Headache. 2015 Jun;55(6):778-93. doi: 10.1111/head.12550. Epub 2015 Apr 15. Review. PubMed PMID: 25877672. 10: Marmura MJ, Silberstein SD, Schwedt TJ. The acute treatment of migraine in adults: the american headache society evidence assessment of migraine pharmacotherapies. Headache. 2015 Jan;55(1):3-20. doi: 10.1111/head.12499. Review. PubMed PMID: 25600718. 11: Silberstein S, Patel S. Menstrual migraine: an updated review on hormonal causes, prophylaxis and treatment. Expert Opin Pharmacother. 2014 Oct;15(14):2063-70. doi: 10.1517/14656566.2014.947959. Epub 2014 Aug 6. Review. PubMed PMID: 25100506. 12: Hu Y, Guan X, Fan L, Jin L. Triptans in prevention of menstrual migraine: a systematic review with meta-analysis. J Headache Pain. 2013 Jan 30;14:7. doi: 10.1186/1129-2377-14-7. Review. PubMed PMID: 23565873; PubMed Central PMCID: PMC3620011. 13: Millson DS. Rational migraine management: optimising treatment with the triptans. Funct Neurol. 2000;15 Suppl 3:182-91. Review. PubMed PMID: 11200789. 14: Belvis R, Mas N, Aceituno A. Migraine attack treatment : a tailor-made suit, not one size fits all. Recent Pat CNS Drug Discov. 2014 Apr;9(1):26-40. Review. PubMed PMID: 24605940. 15: Nguyen TQ, Lewis JH. Sumatriptan-associated ischemic colitis: case report and review of the literature and FAERS. Drug Saf. 2014 Feb;37(2):109-21. doi: 10.1007/s40264-013-0134-7. Review. PubMed PMID: 24442762. 16: Wellington K, Jarvis B. Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. Review. PubMed PMID: 12269863. 17: Wellington K, Plosker GL. Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. Review. PubMed PMID: 12093318. 18: Becker WJ. The premonitory phase of migraine and migraine management. Cephalalgia. 2013 Oct;33(13):1117-21. doi: 10.1177/0333102412437390. Epub 2012 Feb 15. Review. PubMed PMID: 22337860. 19: Worthington I, Pringsheim T, Gawel MJ, Gladstone J, Cooper P, Dilli E, Aube M, Leroux E, Becker WJ; Canadian Headache Society Acute Migraine Treatment Guideline Development Group. Canadian Headache Society Guideline: acute drug therapy for migraine headache. Can J Neurol Sci. 2013 Sep;40(5 Suppl 3):S1-S80. Review. PubMed PMID: 23968886. 20: Reddy DS. The pathophysiological and pharmacological basis of current drug treatment of migraine headache. Expert Rev Clin Pharmacol. 2013 May;6(3):271-88. doi: 10.1586/ecp.13.14. Review. PubMed PMID: 23656340.