Olcegepant, CGRP antagonist

Key facts

CAS number

204697-65-4

Form

Solid

form

Molecular weight

869.6 Da

Molecular formula

C₃₈H₄₇Br₂N₉O₅

PubChem

6918509

Nature

Synthetic

Solubility

Soluble to 50 mM in DMSO

Biochemical name

Olcegepant

Biological description

Potent (IC₅₀ = 0.03 nM (human) and 6.4 nM (rat)) and selective CGRP-1 receptor antagonist. No significant activity observed against a panel of 75 other receptors. Potently inhibits neurogenic vasodilation.

Canonical smiles

C1CN(CCC1N2CC3=CC=CC=C3NC2=O)C(=O)NC(CC4=CC(=C(C(=C4)Br)O)Br)C(=O)NC(CCCCN)C(=O)N5CCN(CC5)C6=CC=NC=C6

Isomeric smiles

C1CN(CCC1N2CC3=CC=CC=C3NC2=O)C(=O)N[C@H](CC4=CC(=C(C(=C4)Br)O)Br)C(=O)N[C@@H](CCCCN)C(=O)N5CCN(CC5)C6=CC=NC=C6

InChi

InChI=1S/C38H47Br2N9O5/c39-29-21-25(22-30(40)34(29)50)23-33(45-37(53)48-15-10-28(11-16-48)49-24-26-5-1-2-6-31(26)44-38(49)54)35(51)43-32(7-3-4-12-41)36(52)47-19-17-46(18-20-47)27-8-13-42-14-9-27/h1-2,5-6,8-9,13-14,21-22,28,32-33,50H,3-4,7,10-12,15-20,23-24,41H2,(H,43,51)(H,44,54)(H,45,53)/t32-,33+/m0/s1

InChiKey

ITIXDWVDFFXNEG-JHOUSYSJSA-N

IUPAC Name

N-[(2R)-1-[[(2S)-6-amino-1-oxo-1-(4-pyridin-4-ylpiperazin-1-yl)hexan-2-yl]amino]-3-(3,5-dibromo-4-hydroxyphenyl)-1-oxopropan-2-yl]-4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxamide