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Ubrogepant

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PMC Isochem Ubrogepant

Synopsis

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Chemistry

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Also known as: 1374248-77-7, Ubrelvy, Mk-1602, Ubrogepant anhydrous, Ad0o8x2qjr, (3'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

Molecular Formula

C₂₉H₂₆F₃N₅O₃

Molecular Weight

549.5 g/mol

InChI Key

DDOOFTLHJSMHLN-ZQHRPCGSSA-N

FDA UNII

AD0O8X2QJR

Ubrogepant is indicated for the acute treatment of migraine headaches with or without aura in adults. It was approved by the FDA on December 23, 2019, and is the first oral calcitonin gene-related peptide (CGRP) receptor antagonist approved for the acute treatment of migraine. Several oral small molecule CGRP receptor antagonists, belonging to a class of medications referred to as "gepants", have been investigated for migraines, but only ubrogepant and [rimegepant] remain in clinical development. Previous agents within this class were efficacious but limited by liver toxicity - this led to the development of ubrogepant, which was designed to be a hepatoxicity-free alternative to its predecessors. Several parenteral monoclonal antibodies acting against the CGRP pathway (e.g. [erenumab], [fremanezumab], [galcanezumab]) have also been approved in recent years. Compared to the current standard of therapy for migraine treatment, namely triptans such as [sumatriptan] and [almotriptan], CGRP antagonists present several advantages. They appear to be better tolerated, do not contribute to medication overuse headaches, and carry no apparent cardiovascular risk, making them suitable for use in patients with cardiovascular disease. The development of oral gepants, including ubrogepant, may therefore constitute a significant advance in migraine headache treatment and may become the new standard of therapy in the treatment of this debilitating condition.

Ubrogepant is a Calcitonin Gene-related Peptide Receptor Antagonist. The mechanism of action of ubrogepant is as a Calcitonin Gene-related Peptide Receptor Antagonist.

1 2D Structure

Ubrogepant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

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

2.1.3 InChI Key

DDOOFTLHJSMHLN-ZQHRPCGSSA-N

2.1.4 Canonical SMILES

CC1C(CC(C(=O)N1CC(F)(F)F)NC(=O)C2=CC3=C(CC4(C3)C5=C(NC4=O)N=CC=C5)N=C2)C6=CC=CC=C6

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H](C[C@@H](C(=O)N1CC(F)(F)F)NC(=O)C2=CC3=C(C[C@@]4(C3)C5=C(NC4=O)N=CC=C5)N=C2)C6=CC=CC=C6

2.2 Other Identifiers

2.2.1 UNII

AD0O8X2QJR

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1',2',5,7-tetrahydro-n-((3s,5s,6r)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-3-piperidinyl)-2'-oxo-, (6s)- Spiro(6h-cyclopenta(b)pyridine-6,3'-(3h)pyrrolo(2,3-b)pyridine)-3-carboxamide

2. Mk-1602

3. Ubrelvy

2.3.2 Depositor-Supplied Synonyms

1. 1374248-77-7

2. Ubrelvy

3. Mk-1602

4. Ubrogepant Anhydrous

5. Ad0o8x2qjr

6. (3'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

7. (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide

8. Spiro(6h-cyclopenta(b)pyridine-6,3'-(3h)pyrrolo(2,3-b)pyridine)-3-carboxamide, 1',2',5,7-tetrahydro-n-((3s,5s,6r)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-3-piperidinyl)-2'-oxo-, (3's)-

9. Ubrogepant [usan]

10. Ubrogepant [usan:inn]

11. Unii-ad0o8x2qjr

12. Ubrelvy (tn)

13. Ubrogepant [mi]

14. Ubrogepant [inn]

15. Ubrogepant (usan/inn)

16. Ubrogepant [who-dd]

17. Schembl3698428

18. Chembl2364638

19. Ubrogepant [orange Book]

20. Gtpl10176

21. Dtxsid00160178

22. Ex-a3049

23. Mfcd28386182

24. Mk1602

25. Zinc95598454

26. At16059

27. Db15328

28. Ac-31965

29. Hy-12366

30. Cs-0011109

31. D10673

32. A934103

33. Q27273878

34. S-1374248-77-7

35. (6s)-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

36. (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

2.4 Create Date

2012-11-30

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₂₆F₃N₅O₃
Molecular Weight	549.5 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	549.19877419 g/mol
Monoisotopic Mass	549.19877419 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1000
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Ubrogepant is indicated for the acute treatment of migraine with or without aura in adults.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ubrogepant acutely treats migraine headache pain by blocking the activity of a key transmitter involved in migraine pathogenesis. Exposure to ubrogepant can be significantly increased in patients with severe hepatic or renal insufficiency - dose adjustments are required for these patients in order to avoid excessive exposure, and ubrogepant is not recommended in patients with end-stage renal disease.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

UBROGEPANT

5.2.2 FDA UNII

AD0O8X2QJR

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - Calcitonin Gene-related Peptide Receptor Antagonists

5.3 ATC Code

N - Nervous system

N02 - Analgesics

N02C - Antimigraine preparations

N02CD - Calcitonin gene-related peptide (cgrp) antagonists

N02CD04 - Ubrogepant

5.4 Absorption, Distribution and Excretion

Absorption

Following oral administration, T_max occurs between 0.7 and 1.5 h. When administered with a high-fat meal, T_max is delayed by approximately 2 hours and C_max was reduced by 22% with no significant changes to the AUC. Ubrogepant exhibits dose-proportional pharmacokinetics throughout the entirety of its recommended dosing range.

Route of Elimination

The main route of elimination is fecal/biliary, while renal excretion is comparatively minor - following administration of a single oral dose to healthy subjects, approximately 42% of the dose was recovered unchanged in the feces and 6% was recovered unchanged in the urine.

Volume of Distribution

The apparent central volume of distribution following oral administration is approximately 350 L.

Clearance

The apparent oral clearance of ubrogepant is approximately 87 L/h.

5.5 Metabolism/Metabolites

Ubrogepant is eliminated primarily via metabolism, the majority of which is mediated by CYP3A4. Two circulating glucuronide conjugates, along with unchanged parent drug, were found to be the most abundant circulating components in human plasma. The glucuronide metabolites reportedly carry 6000-fold less activity at CGRP receptors and are therefore considered to be pharmacologically inert.

5.6 Biological Half-Life

Ubrogepant has an elimination half-life of 5-7 hours.

5.7 Mechanism of Action

The currently accepted theory of migraine pathophysiology considers dysfunction of the central nervous system, in particular the trigeminal ganglion, to be the root cause behind the condition. Activation of the trigeminal ganglion triggers the stimulation of trigeminal afferents that project to the spinal cord and synapse on various pain-sensing intra- and extracranial structures, such as the dura mater. Pain signals are then further transmitted via second-order ascending neurons to the brainstem, hypothalamus, and thalamic nuclei, and from there to several cortical regions (e.g. auditory, visual, motor cortices). The trigeminal ganglion appears to amplify and perpetuate the migraine headache pain through the activation of perivascular fibers and the release of molecules involved in pain generation, such as calcitonin gene-related peptide (CGRP). The -isoform of CGRP, expressed in primary sensory neurons, is a potent vasodilator and has been implicated in migraine pathogenesis - CGRP levels are acutely elevated during migraine attacks, return to normal following treatment with triptan medications, and intravenous infusions of CGRP have been shown to trigger migraine-like headaches in migraine patients. In addition to its vasodilatory properties, CGRP appears to be a pronociceptive factor that modulates neuronal excitability to facilitate pain responses. Ubrogepant is a potent antagonist of the calcitonin gene-related peptide receptor - it competes with CGRP for occupancy at these receptors, preventing the actions of CGRP and its ability to amplify and perpetuate migraine headache pain, ultimately terminating the headache.

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