Olcegepant
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Olcegepant
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CAS No:
204697-65-4
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Formula:
C38H47Br2N9O5
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Chemical Name:
Olcegepant
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Synonyms:
Piperazine,1-[3,5-dibromo-N-[[4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl)-1-piperidinyl]carbonyl]-D-tyrosyl-L-lysyl]-4-(4-pyridinyl)-;1-Piperidinecarboxamide,N-[2-[[5-amino-1-[[4-(4-pyridinyl)-1-piperazinyl]carbonyl]pentyl]amino]-1-[(3,5-dibromo-4-hydroxyphenyl)methyl]-2-oxoethyl]-4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl)-,[R-(R*,S*)]-;1-Piperidinecarboxamide,N-[(1R)-2-[[(1S)-5-amino-1-[[4-(4-pyridinyl)-1-piperazinyl]carbonyl]pentyl]amino]-1-[(3,5-dibromo-4-hydroxyphenyl)methyl]-2-oxoethyl]-4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl)-;1-[3,5-Dibromo-N-[[4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl)-1-piperidinyl]carbonyl]-D-tyrosyl-L-lysyl]-4-(4-pyridinyl)piperazine;BIBN 4096BS;Olcegepant;BIBN 4096;502641-03-4
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CAS No:
Description
Olcegepant is a potent and selective non-peptide antagonist of the calcitonin gene-related peptide 1 (CGRP1) receptor with IC50 of 0.03 nM and Ki of 14.4 pM for human CGRP.
Boehringer Ingelheim Pharmaceuticals’ olcegepant (BIBN 4096) is a selective Calcitonin Gene-Related Peptide (CGRP) antagonist, a new class of drugs in development for the treatment of acute migraine attacks. Olcegepant is undergoing phase II trials in Europe and the US, with preliminary results suggesting that CGRP antagonists may represent a potential new approach to the treatment of migraine.
Drug Information
For the treatment of migraine headaches.
Olcegepant is a calcitonin gene-related peptide (CGRP) antagonist. In preclinical studies, olcegepant attenuated arterial dilation induced by CGRP or electrical stimulation. In a phase II clinical trial, olcegepant reduced the severity of headache in 60% of migraine sufferers and met secondary endpoints including headache-free rate and rate of sustained response. Only mild-to-moderate transient adverse events were observed, with no adverse cardiovascular symptoms reported. The compound appears to be an effective anti-migraine medication that is well tolerated and does not display the vasoconstrictive effect that precludes the use of triptans and dihydroergotamine in certain patients.
Migraine involves dysfunction of brainstem pathways that normally modulate sensory input. The involvement of calcitonin gene-related peptide (CGRP) in migraine pathology is supported by both clinical and experimental evidence. The release of CGRP and other neuropeptides from trigeminal nerves is thought to mediate neurogeate inflammation within the meninges which contributes to the generation of severe cerebral pain experienced during migraine attack. CGRP antagonists such as olcegepant bind at CGRP receptors, blocking the effect CGRP and thus reducing inflammation.
(R-(R*,S*))-N-(2-((5-amino-1-((4-(4-pyridinyl)-1-piperazinyl)carbonyl)pentyl)amino)-1-((3,5-dibromo-4-hydroxyphenyl)methyl)-2-oxoethyl)-4-(1,4-dihydro-2-oxo-3(2H)quinazolinyl)-1-piperidinecarboxamide
Olcegepant Use and Manufacturing
Olcegepant is a potent and selective calcitonin gene-related peptide (CGRP) receptor antagonist. Olcegepant displays high affinity for human CGRP receptors and exhibits no significant affinity for 75 other receptors. Olcegepant may a be viable option for the treatment of acute migraines.
Computed Properties
Molecular Weight:869.6
XLogP3:3.1
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:12
Exact Mass:869.20464
Monoisotopic Mass:867.20669
Topological Polar Surface Area:177
Heavy Atom Count:54
Complexity:1250
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes