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MedKoo Cat#: 319860 | Name: Telcagepant

Description:

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

Telcagepant, also known as MK0974, is a calcitonin gene-related peptide receptor antagonist under development for the acute treatment and prevention of migraine.

Chemical Structure

Telcagepant
Telcagepant
CAS#781649-09-0 (free base)

Theoretical Analysis

MedKoo Cat#: 319860

Name: Telcagepant

CAS#: 781649-09-0 (free base)

Chemical Formula: C26H27F5N6O3

Exact Mass: 566.2065

Molecular Weight: 566.53

Elemental Analysis: C, 55.12; H, 4.80; F, 16.77; N, 14.83; O, 8.47

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
781649-09-0 (free base) 953077-35-5 (potassium)
Synonym
MK0974; MK-0974; MK 0974; Telcagepant
IUPAC/Chemical Name
N-((3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl)-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide
InChi Key
CGDZXLJGHVKVIE-DNVCBOLYSA-N
InChi Code
InChI=1S/C26H27F5N6O3/c27-18-4-1-3-17(21(18)28)15-6-7-19(23(38)36(13-15)14-26(29,30)31)33-24(39)35-11-8-16(9-12-35)37-20-5-2-10-32-22(20)34-25(37)40/h1-5,10,15-16,19H,6-9,11-14H2,(H,33,39)(H,32,34,40)/t15-,19-/m1/s1
SMILES Code
O=C(N1CCC(N(C2=CC=CN=C2N3)C3=O)CC1)N[C@H]4C(N(CC(F)(F)F)C[C@H](C5=CC=CC(F)=C5F)CC4)=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
Telcagepant was developed by Merck & Co. In the acute treatment of migraine, it was found to have equal potency to rizatriptan and zolmitriptan in two Phase III clinical trials. The company has now terminated development of the drug. The calcitonin gene-related peptide (CGRP) is a strong vasodilator primarily found in nervous tissue. Since vasodilation in the brain is thought to be involved in the development of migraine and CGRP levels are increased during migraine attacks, this peptide may be an important target for potential new antimigraine drugs. Telcagepant acts as a calcitonin gene-related peptide receptor (CRLR) antagonist and blocks this peptide. It is believed to constrict dilated blood vessels within the brain.

Preparing Stock Solutions

The following data is based on the product molecular weight 566.53 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: Gottschalk PC. Telcagepant-almost gone, but not to be forgotten (invited editorial related to Ho et al., 2015). Cephalalgia. 2016 Feb;36(2):103-5. doi: 10.1177/0333102415584311. Epub 2015 May 5. PubMed PMID: 25944815. 2: Ho TW, Ho AP, Ge YJ, Assaid C, Gottwald R, MacGregor EA, Mannix LK, van Oosterhout WP, Koppenhaver J, Lines C, Ferrari MD, Michelson D. Randomized controlled trial of the CGRP receptor antagonist telcagepant for prevention of headache in women with perimenstrual migraine. Cephalalgia. 2016 Feb;36(2):148-61. doi: 10.1177/0333102415584308. Epub 2015 Apr 29. PubMed PMID: 25926620. 3: Ho TW, Connor KM, Zhang Y, Pearlman E, Koppenhaver J, Fan X, Lines C, Edvinsson L, Goadsby PJ, Michelson D. Randomized controlled trial of the CGRP receptor antagonist telcagepant for migraine prevention. Neurology. 2014 Sep 9;83(11):958-66. doi: 10.1212/WNL.0000000000000771. Epub 2014 Aug 8. PubMed PMID: 25107879. 4: Cui XP, Ye JX, Lin H, Mu JS, Lin M. Efficacy, safety, and tolerability of telcagepant in the treatment of acute migraine: a meta-analysis. Pain Pract. 2015 Feb;15(2):124-31. doi: 10.1111/papr.12158. Epub 2013 Dec 30. PubMed PMID: 24382126. 5: Hostetler ED, Joshi AD, Sanabria-Bohórquez S, Fan H, Zeng Z, Purcell M, Gantert L, Riffel K, Williams M, O'Malley S, Miller P, Selnick HG, Gallicchio SN, Bell IM, Salvatore CA, Kane SA, Li CC, Hargreaves RJ, de Groot T, Bormans G, Van Hecken A, Derdelinckx I, de Hoon J, Reynders T, Declercq R, De Lepeleire I, Kennedy WP, Blanchard R, Marcantonio EE, Sur C, Cook JJ, Van Laere K, Evelhoch JL. In vivo quantification of calcitonin gene-related peptide receptor occupancy by telcagepant in rhesus monkey and human brain using the positron emission tomography tracer [11C]MK-4232. J Pharmacol Exp Ther. 2013 Nov;347(2):478-86. doi: 10.1124/jpet.113.206458. Epub 2013 Aug 23. PubMed PMID: 23975906. 6: Depré M, Macleod C, Palcza J, Behm M, de Lepeleire I, Han T, Panebianco D, Smith W, Blanchard R, Chodakewitz J, Murphy M, de Hoon J. Lack of hemodynamic interaction between CGRP-receptor antagonist telcagepant (MK-0974) and sumatriptan: results from a randomized study in patients with migraine. Cephalalgia. 2013 Dec;33(16):1292-301. doi: 10.1177/0333102413494272. Epub 2013 Jun 24. PubMed PMID: 23798725. 7: Yao G, Yu T, Han X, Mao X, Li B. Therapeutic effects and safety of olcegepant and telcagepant for migraine: A meta-analysis. Neural Regen Res. 2013 Apr 5;8(10):938-47. doi: 10.3969/j.issn.1673-5374.2013.10.009. PubMed PMID: 25206386; PubMed Central PMCID: PMC4145922. 8: Hopkins CR. ACS chemical neuroscience molecule spotlight on Telcagepant (MK-0974). ACS Chem Neurosci. 2011 Jul 20;2(7):334-5. doi: 10.1021/cn200059f. Review. PubMed PMID: 22816019; PubMed Central PMCID: PMC3369750. 9: Chaitman BR, Ho AP, Behm MO, Rowe JF, Palcza JS, Laethem T, Heirman I, Panebianco DL, Kobalava Z, Martsevich SY, Free AL, Bittar N, Chrysant SG, Ho TW, Chodakewitz JA, Murphy MG, Blanchard RL. A randomized, placebo-controlled study of the effects of telcagepant on exercise time in patients with stable angina. Clin Pharmacol Ther. 2012 Mar;91(3):459-66. doi: 10.1038/clpt.2011.246. Epub 2012 Jan 25. PubMed PMID: 22278333. 10: Ho TW, Ho AP, Chaitman BR, Johnson C, Mathew NT, Kost J, Fan X, Aurora SK, Brandes JL, Fei K, Beebe L, Lines C, Krucoff MW. Randomized, controlled study of telcagepant in patients with migraine and coronary artery disease. Headache. 2012 Feb;52(2):224-35. doi: 10.1111/j.1526-4610.2011.02052.x. Epub 2012 Jan 6. PubMed PMID: 22221076. 11: Behm MO, Blanchard RL, Murphy MG, Palcza JS, Harris DE, Butterfield KL, Smith WB, Preston RA, Chodakewitz JA, Krucoff MW. Effect of telcagepant on spontaneous ischemia in cardiovascular patients in a randomized study. Headache. 2011 Jun;51(6):954-60. doi: 10.1111/j.1526-4610.2011.01901.x. PubMed PMID: 21631478. 12: Van der Schueren BJ, Blanchard R, Murphy MG, Palcza J, De Lepeleire I, Van Hecken A, Depré M, de Hoon JN. The potent calcitonin gene-related peptide receptor antagonist, telcagepant, does not affect nitroglycerin-induced vasodilation in healthy men. Br J Clin Pharmacol. 2011 May;71(5):708-17. doi: 10.1111/j.1365-2125.2010.03869.x. PubMed PMID: 21480950; PubMed Central PMCID: PMC3093076. 13: Ho TW, Bigal M. Excellent tolerability but relatively low initial clinical efficacy of telcagepant in migraine: a response. Headache. 2011 Apr;51(4):617-8. doi: 10.1111/j.1526-4610.2011.01870.x. PubMed PMID: 21457247. 14: Hewitt DJ, Martin V, Lipton RB, Brandes J, Ceesay P, Gottwald R, Schaefer E, Lines C, Ho TW. Randomized controlled study of telcagepant plus ibuprofen or acetaminophen in migraine. Headache. 2011 Apr;51(4):533-43. doi: 10.1111/j.1526-4610.2011.01860.x. PubMed PMID: 21457238. 15: Tfelt-Hansen P. Optimal balance of efficacy and tolerability of oral triptans and telcagepant: a review and a clinical comment. J Headache Pain. 2011 Jun;12(3):275-80. doi: 10.1007/s10194-011-0309-5. Epub 2011 Feb 25. Review. PubMed PMID: 21350792; PubMed Central PMCID: PMC3094671. 16: Tfelt-Hansen P. Pain freedom at 2 hours in migraine after telcagepant 300 mg. CNS Drugs. 2011 Mar;25(3):269-70. doi: 10.2165/11587770-000000000-00000. PubMed PMID: 21323397. 17: Han TH, Blanchard RL, Palcza J, Martucci A, Miller-Stein CM, Gutierrez M, Panebianco D, Rippley RK, Lines C, Murphy MG. The Dose Proportionality of Telcagepant after Administration of Single Oral and Intravenous Doses in Healthy Adult Subjects. Arch Drug Inf. 2010 Dec;3(4):55-62. PubMed PMID: 21221171; PubMed Central PMCID: PMC3015066. 18: Connor KM, Aurora SK, Loeys T, Ashina M, Jones C, Giezek H, Massaad R, Williams-Diaz A, Lines C, Ho TW. Long-term tolerability of telcagepant for acute treatment of migraine in a randomized trial. Headache. 2011 Jan;51(1):73-84. doi: 10.1111/j.1526-4610.2010.01799.x. Epub 2010 Nov 10. PubMed PMID: 21070230. 19: Tfelt-Hansen P. Excellent tolerability but relatively low initial clinical efficacy of telcagepant in migraine. Headache. 2011 Jan;51(1):118-23. doi: 10.1111/j.1526-4610.2010.01797.x. Epub 2010 Nov 10. Review. PubMed PMID: 21070229. 20: Ho TW, Olesen J, Dodick DW, Kost J, Lines C, Ferrari MD. Antimigraine efficacy of telcagepant based on patient's historical triptan response. Headache. 2011 Jan;51(1):64-72. doi: 10.1111/j.1526-4610.2010.01790.x. Epub 2010 Nov 4. PubMed PMID: 21054362.