Ubrogepant | MK-1602 | CAS#1374248-77-7 | CGRP Antagonist

MedKoo Cat#: 319683 | Name: Ubrogepant

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Description:

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

Ubrogepant, also known as MK-1602, is a potent and selective oral calcitonin gene-related peptide (CGRP) receptor antagonist. Ubrogepant, sold under the trade name Ubrelvy, is a medication used for the acute (immediate) treatment of migraine with or without aura (a sensory phenomenon or visual disturbance) in adults. It is not indicated for the preventive treatment of migraine. It is the first drug in the class of oral calcitonin gene-related peptide receptor antagonists approved for the acute treatment of migraine. In December 2019, the U.S. Food and Drug Administration approved Ubrelvy produced by Allergan USA, Inc. for treatment of migraine after onset.

Chemical Structure

Ubrogepant

CAS#1374248-77-7

Theoretical Analysis

MedKoo Cat#: 319683

Name: Ubrogepant

CAS#: 1374248-77-7

Chemical Formula: C29H26F3N5O3

Exact Mass: 549.1988

Molecular Weight: 549.55

Elemental Analysis: C, 63.38; H, 4.77; F, 10.37; N, 12.74; O, 8.73

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 850.00	2 Weeks
25mg	USD 1,950.00	2 Weeks

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Related CAS #

No Data

Synonym

MK-1602; MK 1602; MK1602, Ubrogepant; Ubrelvy.

IUPAC/Chemical Name

(S)-N-((3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl)-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide

InChi Key

DDOOFTLHJSMHLN-ZQHRPCGSSA-N

InChi Code

InChI=1S/C29H26F3N5O3/c1-16-20(17-6-3-2-4-7-17)11-22(26(39)37(16)15-29(30,31)32)35-25(38)19-10-18-12-28(13-23(18)34-14-19)21-8-5-9-33-24(21)36-27(28)40/h2-10,14,16,20,22H,11-13,15H2,1H3,(H,35,38)(H,33,36,40)/t16-,20-,22+,28+/m1/s1

SMILES Code

O=C(C1=CN=C2C(C[C@@]3(C4=CC=CN=C4NC3=O)C2)=C1)N[C@@H]5C(N(CC(F)(F)F)[C@H](C)[C@H](C6=CC=CC=C6)C5)=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 549.55 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.

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: Ankrom W, Bondiskey P, Li CC, Palcza J, Liu W, Dockendorf MF, Matthews C, Panebianco D, Reynders T, Wagner JA, Jakate A, Mesens S, Kraft WK, Marcantonio EE. Ubrogepant Is Not Associated With Clinically Meaningful Elevations of Alanine Aminotransferase in Healthy Adult Males. Clin Transl Sci. 2020 Jan 3. doi: 10.1111/cts.12728. [Epub ahead of print] PubMed PMID: 31899602. 2: Dodick DW, Lipton RB, Ailani J, Lu K, Finnegan M, Trugman JM, Szegedi A. Ubrogepant for the Treatment of Migraine. N Engl J Med. 2019 Dec 5;381(23):2230-2241. doi: 10.1056/NEJMoa1813049. PubMed PMID: 31800988. 3: Li CC, Voss T, Kowalski K, Yang B, Jan Kleijn H, Jones CJ, Bosch R, Michelson D, DeAngelis M, Xu Y, Xie I, Kothare PA. Making Better Dose Decisions: Using Exposure-Response Modeling to Integrate Efficacy Outcome of Two Phase 2b Clinical Trials of Ubrogepant for Migraine Treatment. Clin Transl Sci. 2019 Nov 23. doi: 10.1111/cts.12730. [Epub ahead of print] PubMed PMID: 31758661. 4: Lipton RB, Dodick DW, Ailani J, Lu K, Finnegan M, Szegedi A, Trugman JM. Effect of Ubrogepant vs Placebo on Pain and the Most Bothersome Associated Symptom in the Acute Treatment of Migraine: The ACHIEVE II Randomized Clinical Trial. JAMA. 2019 Nov 19;322(19):1887-1898. doi: 10.1001/jama.2019.16711. PubMed PMID: 31742631; PubMed Central PMCID: PMC6865323. 5: Rubio-Beltran E, Chan KY, Danser AJ, MaassenVanDenBrink A, Edvinsson L. Characterisation of the calcitonin gene-related peptide receptor antagonists ubrogepant and atogepant in human isolated coronary, cerebral and middle meningeal arteries. Cephalalgia. 2019 Nov 1:333102419884943. doi: 10.1177/0333102419884943. [Epub ahead of print] PubMed PMID: 31674221. 6: Jakate A, Boinpally R, Butler M, Lu K, McGeeney D, Periclou A. Single Therapeutic and Supratherapeutic Doses of Ubrogepant Do Not Affect Cardiac Repolarization in Healthy Adults: Results From a Randomized Trial. Clin Pharmacol Ther. 2019 Oct 19. doi: 10.1002/cpt.1696. [Epub ahead of print] PubMed PMID: 31628854. 7: Chan C, Goadsby PJ. Recent Advances in Pharmacotherapy for Episodic Migraine. CNS Drugs. 2019 Nov;33(11):1053-1071. doi: 10.1007/s40263-019-00665-9. PubMed PMID: 31556018. 8: Goadsby PJ, Tepper SJ, Watkins PB, Ayele G, Miceli R, Butler M, Severt L, Finnegan M, Szegedi A, Trugman JM, Jakate A. Safety and tolerability of ubrogepant following intermittent, high-frequency dosing: Randomized, placebo-controlled trial in healthy adults. Cephalalgia. 2019 Dec;39(14):1753-1761. doi: 10.1177/0333102419869918. Epub 2019 Sep 19. PubMed PMID: 31537107; PubMed Central PMCID: PMC6900570. 9: Digre KB. What's New in the Treatment of Migraine? J Neuroophthalmol. 2019 Sep;39(3):352-359. doi: 10.1097/WNO.0000000000000837. PubMed PMID: 31393282. 10: Xu F, Sun W. Network Meta-Analysis of Calcitonin Gene-Related Peptide Receptor Antagonists for the Acute Treatment of Migraine. Front Pharmacol. 2019 Jul 12;10:795. doi: 10.3389/fphar.2019.00795. eCollection 2019. PubMed PMID: 31354502; PubMed Central PMCID: PMC6640487. 11: Goadsby PJ. Primary headache disorders: Five new things. Neurol Clin Pract. 2019 Jun;9(3):233-240. doi: 10.1212/CPJ.0000000000000654. PubMed PMID: 31341711; PubMed Central PMCID: PMC6615655. 12: Moreno-Ajona D, Chan C, Villar-Martínez MD, Goadsby PJ. Targeting CGRP and 5-HT(1F) Receptors for the Acute Therapy of Migraine: A Literature Review. Headache. 2019 Jul;59 Suppl 2:3-19. doi: 10.1111/head.13582. Review. PubMed PMID: 31291016. 13: Valade D. [New horizons for acute and prophylactic treatments of migraine]. Biol Aujourdhui. 2019;213(1-2):59-64. doi: 10.1051/jbio/2019021. Epub 2019 Jul 5. French. PubMed PMID: 31274104. 14: Negro A, Martelletti P. Gepants for the treatment of migraine. Expert Opin Investig Drugs. 2019 Jun;28(6):555-567. doi: 10.1080/13543784.2019.1618830. Epub 2019 May 17. Review. PubMed PMID: 31081399. 15: Hargreaves R, Olesen J. Calcitonin Gene-Related Peptide Modulators - The History and Renaissance of a New Migraine Drug Class. Headache. 2019 Jun;59(6):951-970. doi: 10.1111/head.13510. Epub 2019 Apr 25. PubMed PMID: 31020659. 16: Do TP, Guo S, Ashina M. Therapeutic novelties in migraine: new drugs, new hope? J Headache Pain. 2019 Apr 17;20(1):37. doi: 10.1186/s10194-019-0974-3. Review. Erratum in: J Headache Pain. 2019 May 17;20(1):55. PubMed PMID: 30995909; PubMed Central PMCID: PMC6734360. 17: Peters GL. Migraine overview and summary of current and emerging treatment options. Am J Manag Care. 2019 Jan;25(2 Suppl):S23-S34. PubMed PMID: 30681821. 18: Lambru G, Andreou AP, Guglielmetti M, Martelletti P. Emerging drugs for migraine treatment: an update. Expert Opin Emerg Drugs. 2018 Dec;23(4):301-318. doi: 10.1080/14728214.2018.1552939. Epub 2018 Nov 30. Review. PubMed PMID: 30484333. 19: Martelletti P, Giamberardino MA. Advances in orally administered pharmacotherapy for the treatment of migraine. Expert Opin Pharmacother. 2019 Feb;20(2):209-218. doi: 10.1080/14656566.2018.1549223. Epub 2018 Nov 26. Review. PubMed PMID: 30475090. 20: Tfelt-Hansen P, Loder E. The Emperor's New Gepants: Are the Effects of the New Oral CGRP Antagonists Clinically Meaningful? Headache. 2019 Jan;59(1):113-117. doi: 10.1111/head.13444. Epub 2018 Nov 19. PubMed PMID: 30451300.