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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H26F3N5O3
Molecular Weight 549.5436
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UBROGEPANT

SMILES

C[C@@H]1[C@@H](C[C@H](NC(=O)C2=CN=C3C[C@]4(CC3=C2)C(=O)NC5=NC=CC=C45)C(=O)N1CC(F)(F)F)C6=CC=CC=C6

InChI

InChIKey=DDOOFTLHJSMHLN-ZQHRPCGSSA-N
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

HIDE SMILES / InChI

Description

Ubrogepant, a small molecule drug, is being developed by Merck & Co for the treatment of migraine. The calcitonin gene-related peptide receptor (CGRP) antagonist is administered orally as a film coated tablet. Ubrogepant is a competitive antagonist with high affinity, potency, and selectivity for the human CGRP receptor. In the four clinical studies (ACHIEVE I, ACHIEVE II, UBR-MD-04 and 3110-105-002) ubrogepant demonstrated efficacy, safety and tolerability in the acute treatment of migraine among a broad patient population, including those who had an insufficient response to a triptan or those patients in whom triptans were contraindicated, as well as in patients who had moderate to severe CV risk profile.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
A phase IIb randomized, double-blind, placebo-controlled trial of ubrogepant for the acute treatment of migraine.
2016 Aug
CGRP as the target of new migraine therapies - successful translation from bench to clinic.
2018 Jun
Therapeutic novelties in migraine: new drugs, new hope?
2019 Apr 17
Advances in orally administered pharmacotherapy for the treatment of migraine.
2019 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Migraine: ubrogepant 1 mg, 10 mg, 25 mg, 50 mg, 100 mg. Ubrogepant 100 mg was significantly superior to placebo for two-hour pain freedom but not for two-hour headache response.
Route of Administration: Oral
In Vitro Use Guide
The binding affinity for native (Ki=0.067 nM) and cloned human (Ki=0.070 nM) and rhesus (Ki=0.079 nM) receptors was similar for ubrogepant, with relatively lower affinities for CGRP receptors of other species (ranging from Ki=9.6 to 47 nM). Ubrogepant potently blocked human α-CGRP–stimulated cAMP response (IC50 of 0.08) and exhibited highly selective antagonist activity in relation to the CGRP receptor compared with other members of the human calcitonin receptor family.
Name Type Language
UBROGEPANT
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
UBROGEPANT [WHO-DD]
Common Name English
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)-
Systematic Name English
(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
Systematic Name English
UBROGEPANT [USAN]
Common Name English
UBROGEPANT [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Tue Oct 22 01:50:17 UTC 2019 , Edited by admin on Tue Oct 22 01:50:17 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL2364638
Created by admin on Tue Oct 22 01:50:17 UTC 2019 , Edited by admin on Tue Oct 22 01:50:17 UTC 2019
PRIMARY
INN
9803
Created by admin on Tue Oct 22 01:50:17 UTC 2019 , Edited by admin on Tue Oct 22 01:50:17 UTC 2019
PRIMARY
EPA CompTox
1374248-77-7
Created by admin on Tue Oct 22 01:50:17 UTC 2019 , Edited by admin on Tue Oct 22 01:50:17 UTC 2019
PRIMARY
PUBCHEM
68748835
Created by admin on Tue Oct 22 01:50:17 UTC 2019 , Edited by admin on Tue Oct 22 01:50:17 UTC 2019
PRIMARY
CAS
1374248-77-7
Created by admin on Tue Oct 22 01:50:17 UTC 2019 , Edited by admin on Tue Oct 22 01:50:17 UTC 2019
PRIMARY
NCI_THESAURUS
C152790
Created by admin on Tue Oct 22 01:50:17 UTC 2019 , Edited by admin on Tue Oct 22 01:50:17 UTC 2019
PRIMARY