Atogepant

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MedKoo CAT#: 329488

CAS#: 1374248-81-3

Description: Atogepant, also known as MK-8031 and AGN 241689, is a calcitonin gene-related peptide receptor antagonist. Atogepant belongs to the “gepants” class of drugs that work by blocking cell receptors for CGRP, a protein released at the trigeminal nerve during migraine. Gepants have been shown to reduce future attacks by about 50 percent. Atogepant was approved in Sept 2021 to prevent episodic migraines.

Chemical Structure

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Atogepant
CAS# 1374248-81-3
Instruction

Theoretical Analysis

MedKoo Cat#: 329488
Name: Atogepant
CAS#: 1374248-81-3
Chemical Formula: C29H23F6N5O3
Exact Mass: 603.17
Molecular Weight: 603.525
Elemental Analysis: C, 57.71; H, 3.84; F, 18.89; N, 11.60; O, 7.95

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: MK-8031; MK 8031; MK8031. AGN 241689; AGN-241689; AGN241689; Atogepant.

IUPAC/Chemical Name: (3'S)-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide

InChi Key: QIVUCLWGARAQIO-OLIXTKCUSA-N

InChi Code: InChI=1S/C29H23F6N5O3/c1-13-16(22-18(30)4-5-19(31)23(22)32)8-20(26(42)40(13)12-29(33,34)35)38-25(41)15-7-14-9-28(10-21(14)37-11-15)17-3-2-6-36-24(17)39-27(28)43/h2-7,11,13,16,20H,8-10,12H2,1H3,(H,38,41)(H,36,39,43)/t13-,16-,20+,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=C(F)C=CC(F)=C6F)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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 603.53 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Schwedt TJ, Lipton RB, Ailani J, Silberstein SD, Tassorelli C, Guo H, Lu K, Dabruzzo B, Miceli R, Severt L, Finnegan M, Trugman JM. Time course of efficacy of atogepant for the preventive treatment of migraine: Results from the randomized, double-blind ADVANCE trial. Cephalalgia. 2021 Sep 14:3331024211042385. doi: 10.1177/03331024211042385. Epub ahead of print. PMID: 34521260.


2: Ailani J, Lipton RB, Goadsby PJ, Guo H, Miceli R, Severt L, Finnegan M, Trugman JM; ADVANCE Study Group. Atogepant for the Preventive Treatment of Migraine. N Engl J Med. 2021 Aug 19;385(8):695-706. doi: 10.1056/NEJMoa2035908. PMID: 34407343.


3: Boinpally R, Spaventa J, Chen K, Butler M. Evaluation of the Pharmacokinetic Interaction and Safety of Atogepant Co-Administered with Acetaminophen or Naproxen in Healthy Participants: A Randomized Trial. Clin Drug Investig. 2021 Jun;41(6):557-567. doi: 10.1007/s40261-021-01034-5. Epub 2021 May 5. PMID: 33948911; PMCID: PMC8195918.


4: Boinpally R, McNamee B, Yao L, Butler M, McGeeney D, Borbridge L, Periclou A. A Single Supratherapeutic Dose of Atogepant Does Not Affect Cardiac Repolarization in Healthy Adults: Results From a Randomized, Single-Dose, Phase 1 Crossover Trial. Clin Pharmacol Drug Dev. 2021 Sep;10(9):1099-1107. doi: 10.1002/cpdd.940. Epub 2021 May 4. PMID: 33942560; PMCID: PMC8453716.


5: Boinpally R, Jakate A, Butler M, Borbridge L, Periclou A. Single-Dose Pharmacokinetics and Safety of Atogepant in Adults With Hepatic Impairment: Results From an Open-Label, Phase 1 Trial. Clin Pharmacol Drug Dev. 2021 Jul;10(7):726-733. doi: 10.1002/cpdd.916. Epub 2021 Jan 27. PMID: 33501783; PMCID: PMC8359408.


6: Negro A, Martelletti P. Novel synthetic treatment options for migraine. Expert Opin Pharmacother. 2021 May;22(7):907-922. doi: 10.1080/14656566.2020.1862793. Epub 2020 Dec 28. PMID: 33369482.


7: Melo-Carrillo A, Strassman AM, Schain AJ, Adams AM, Brin MF, Burstein R. Combined onabotulinumtoxinA/atogepant treatment blocks activation/sensitization of high-threshold and wide-dynamic range neurons. Cephalalgia. 2021 Jan;41(1):17-32. doi: 10.1177/0333102420970507. Epub 2020 Nov 17. PMID: 33200944; PMCID: PMC7786391.


8: Min KC, Kraft WK, Bondiskey P, Colón-González F, Liu W, Xu J, Panebianco D, Mixson L, Dockendorf MF, Matthews CZ, Boinpally R. Atogepant Is Not Associated With Clinically Meaningful Alanine Aminotransferase Elevations in Healthy Adults. Clin Transl Sci. 2021 Mar;14(2):599-605. doi: 10.1111/cts.12917. Epub 2020 Nov 24. PMID: 33142014; PMCID: PMC7993278.


9: Goadsby PJ, Dodick DW, Ailani J, Trugman JM, Finnegan M, Lu K, Szegedi A. Safety, tolerability, and efficacy of orally administered atogepant for the prevention of episodic migraine in adults: a double-blind, randomised phase 2b/3 trial. Lancet Neurol. 2020 Sep;19(9):727-737. doi: 10.1016/S1474-4422(20)30234-9. Erratum in: Lancet Neurol. 2020 Nov;19(11):e10. PMID: 32822633.


10: Andreou AP, Fuccaro M, Lambru G. The role of erenumab in the treatment of migraine. Ther Adv Neurol Disord. 2020 May 27;13:1756286420927119. doi: 10.1177/1756286420927119. PMID: 32523630; PMCID: PMC7257830.


11: De Matteis E, Guglielmetti M, Ornello R, Spuntarelli V, Martelletti P, Sacco S. Targeting CGRP for migraine treatment: mechanisms, antibodies, small molecules, perspectives. Expert Rev Neurother. 2020 Jun;20(6):627-641. doi: 10.1080/14737175.2020.1772758. Epub 2020 Jun 2. PMID: 32434430.


12: Tepper D. Gepants. Headache. 2020 May;60(5):1037-1039. doi: 10.1111/head.13791. PMID: 32337726.


13: Ankrom W, Xu J, Vallee MH, Dockendorf MF, Armas D, Boinpally R, Min KC. Atogepant Has No Clinically Relevant Effects on the Pharmacokinetics of an Ethinyl Estradiol/Levonorgestrel Oral Contraceptive in Healthy Female Participants. J Clin Pharmacol. 2020 Sep;60(9):1157-1165. doi: 10.1002/jcph.1610. Epub 2020 Apr 16. PMID: 32297990; PMCID: PMC7496689.


14: Moreno-Ajona D, Pérez-Rodríguez A, Goadsby PJ. Gepants, calcitonin-gene- related peptide receptor antagonists: what could be their role in migraine treatment? Curr Opin Neurol. 2020 Jun;33(3):309-315. doi: 10.1097/WCO.0000000000000806. PMID: 32251023.


15: de Vries T, Villalón CM, MaassenVanDenBrink A. Pharmacological treatment of migraine: CGRP and 5-HT beyond the triptans. Pharmacol Ther. 2020 Jul;211:107528. doi: 10.1016/j.pharmthera.2020.107528. Epub 2020 Mar 12. PMID: 32173558.


16: Dubowchik GM, Conway CM, Xin AW. Blocking the CGRP Pathway for Acute and Preventive Treatment of Migraine: The Evolution of Success. J Med Chem. 2020 Jul 9;63(13):6600-6623. doi: 10.1021/acs.jmedchem.9b01810. Epub 2020 Feb 20. PMID: 32058712.


17: 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. 2020 Apr;40(4):357-366. doi: 10.1177/0333102419884943. Epub 2019 Nov 1. PMID: 31674221.


18: 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. PMID: 31556018.


19: 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. PMID: 31081399.


20: 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. PMID: 31020659.