olcegepant   Click here for help

GtoPdb Ligand ID: 702

Synonyms: BIBN 4096 BS | BIBN4096BS
PDB Ligand
Compound class: Synthetic organic
Comment: Olcegepant is a non-peptide calcitonin gene-related peptide receptor antagonist being investigated as a potential migraine therapeutic [2,7].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 5
Rotatable bonds 16
Topological polar surface area 176.47
Molecular weight 867.21
XLogP 3.3
No. Lipinski's rules broken 2
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Canonical SMILES NCCCCC(C(=O)N1CCN(CC1)c1ccncc1)NC(=O)C(NC(=O)N1CCC(CC1)N1Cc2ccccc2NC1=O)Cc1cc(Br)c(c(c1)Br)O
Isomeric SMILES NCCCC[C@@H](C(=O)N1CCN(CC1)c1ccncc1)NC(=O)[C@H](NC(=O)N1CCC(CC1)N1Cc2ccccc2NC1=O)Cc1cc(Br)c(c(c1)Br)O
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
1. Doods H, Hallermayer G, Wu D, Entzeroth M, Rudolf K, Engel W, Eberlein W. (2000)
Pharmacological profile of BIBN4096BS, the first selective small molecule CGRP antagonist.
Br J Pharmacol, 129 (3): 420-3. [PMID:10711339]
2. Edvinsson L, Warfvinge K. (2013)
CGRP receptor antagonism and migraine therapy.
Curr Protein Pept Sci, 14 (5): 386-92. [PMID:23745702]
3. Hay DL, Christopoulos G, Christopoulos A, Sexton PM. (2006)
Determinants of 1-piperidinecarboxamide, N-[2-[[5-amino-l-[[4-(4-pyridinyl)-l-piperazinyl]carbonyl]pentyl]amino]-1-[(3,5-dibromo-4-hydroxyphenyl)methyl]-2-oxoethyl]-4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl) (BIBN4096BS) affinity for calcitonin gene-related peptide and amylin receptors--the role of receptor activity modifying protein 1.
Mol Pharmacol, 70: 1984-1991. [PMID:16959943]
4. Hay DL, Howitt SG, Conner AC, Schindler M, Smith DM, Poyner DR. (2003)
CL/RAMP2 and CL/RAMP3 produce pharmacologically distinct adrenomedullin receptors: a comparison of effects of adrenomedullin22-52, CGRP8-37 and BIBN4096BS.
Br J Pharmacol, 140 (3): 477-86. [PMID:12970090]
5. Joshi P, Anderson C, Binch H, Hadida S, Yoo S, Bergeron D, Decker C, terHaar E, Moore J, Garcia-Guzman M et al.. (2014)
Identification of potent CNS-penetrant thiazolidinones as novel CGRP receptor antagonists.
Bioorg Med Chem Lett, 24 (3): 845-9. [PMID:24405707]
6. Mallee JJ, Salvatore CA, LeBourdelles B, Oliver KR, Longmore J, Koblan KS, Kane SA. (2002)
Receptor activity-modifying protein 1 determines the species selectivity of non-peptide CGRP receptor antagonists.
J Biol Chem, 277 (16): 14294-8. [PMID:11847213]
7. Recober A, Russo AF. (2007)
Olcegepant, a non-peptide CGRP1 antagonist for migraine treatment.
IDrugs, 10 (8): 566-74. [PMID:17665333]