OLCEGEPANT

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H47Br2N9O5
Molecular Weight	869.645
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCCC[C@H](NC(=O)[C@@H](CC1=CC(Br)=C(O)C(Br)=C1)NC(=O)N2CCC(CC2)N3CC4=C(NC3=O)C=CC=C4)C(=O)N5CCN(CC5)C6=CC=NC=C6

InChI

InChIKey=ITIXDWVDFFXNEG-JHOUSYSJSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10711339 | https://www.ncbi.nlm.nih.gov/pubmed/17665333

Olcegepant is a potent and selective CGRP (Calcitonin gene-related peptide) antagonist. The drug was tested in phase II clinical trial, in patients with a migraine, however, the development was terminated.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcitonin gene-related peptide type 1 receptor 9 Target ID: Q16602 Gene ID: 10203.0 Gene Symbol: CALCRL Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17665333	Antagonist 2849		14.4 pM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute migraine headache 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17665333	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1090 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15265053	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:		OLCEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
842 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15265053	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:		OLCEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.37 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15265053	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:		OLCEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BFKX	https://www.1pchem.com/search?query=1P00BFKX
1PlusChem LLC	1P01EORF	https://www.1pchem.com/search?query=1P01EORF
AK Scientific	3947AH	https://aksci.com/item_detail.php?cat=3947AH
BLD Pharm	BD630527	http://www.bldpharm.com/search/Search.html?keyword=BD630527
BOC Sciences	204697-65-4	http://www.bocsci.com/description.asp?cas=204697-65-4
Chem Scene	CS-0360	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0360
Chem Scene	CS-6321	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6321
eMolecules	189882834	https://orderbb.emolecules.com/search/#?query=189882834
eMolecules	275102703	https://orderbb.emolecules.com/search/#?query=275102703
eMolecules	275148762	https://orderbb.emolecules.com/search/#?query=275148762
eMolecules	300734873	https://orderbb.emolecules.com/search/#?query=300734873
eMolecules	44466379	https://orderbb.emolecules.com/search/#?query=44466379
mcule	MCULE-1480295529	https://mcule.com/MCULE-1480295529/
mcule	MCULE-5381903141	https://mcule.com/MCULE-5381903141/
MedChem Express	HY-10095	https://www.medchemexpress.com/search.html?q=HY-10095A&ft=&fa=&fp=
MedChem Express	HY-10095A	https://www.medchemexpress.com/search.html?q=HY-10095A&ft=&fa=&fp=
Molnova	M13181	https://www.molnova.com/en/serch-list.html?keywords=M13181
Molnova	M15157	https://www.molnova.com/en/serch-list.html?keywords=M15157
MolPort	MolPort-023-277-207	https://www.molport.com/shop/molecule-link/MolPort-023-277-207
MolPort	MolPort-046-417-620	https://www.molport.com/shop/molecule-link/MolPort-046-417-620
MuseChem	I002580	https://www.musechem.com/product/I002580.html
MuseChem	I013727	https://www.musechem.com/product/I013727.html
ShangHai Biochempartner	BCP29403	http://www.biochempartner.com/search_BCP29403
Tocris	4561	https://www.tocris.com/search.php?Type=QuickSearch&Value=4561
Toronto Research Chemicals	B694920	https://www.trc-canada.com/product-detail/?CatNum=B694920
Toronto Research Chemicals	O516000	https://www.trc-canada.com/product-detail/?CatNum=O516000

PubMed

Title	Date	PubMed
Identification of potent CNS-penetrant thiazolidinones as novel CGRP receptor antagonists.	2014-02-01	24405707
CGRP receptor antagonism and migraine therapy.	2013-08	23745702
A flexible and high throughput liquid chromatography-tandem mass spectrometric assay for the quantitation of telcagepant in human plasma.	2009-05-15	19346171
Treatment of migraine attacks based on the interaction with the trigemino-cerebrovascular system.	2008-02	18217201
Olcegepant, a non-peptide CGRP1 antagonist for migraine treatment.	2007-08	17665333
Effects of current and prospective antimigraine drugs on the porcine isolated meningeal artery.	2006-12	17103145
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.	2006-12	16959943
Development of human calcitonin gene-related peptide (CGRP) receptor antagonists. 1. Potent and selective small molecule CGRP antagonists. 1-[N2-[3,5-dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1-piperidinyl]carbonyl]-D-tyrosyl]-l-lysyl]-4-(4-pyridinyl)piperazine: the first CGRP antagonist for clinical trials in acute migraine.	2005-09-22	16161996
CL/RAMP2 and CL/RAMP3 produce pharmacologically distinct adrenomedullin receptors: a comparison of effects of adrenomedullin22-52, CGRP8-37 and BIBN4096BS.	2003-10	12970090
Effects of the CGRP receptor antagonist BIBN4096BS on capsaicin-induced carotid haemodynamic changes in anaesthetised pigs.	2003-09	12970078
Receptor activity-modifying protein 1 determines the species selectivity of non-peptide CGRP receptor antagonists.	2002-04-19	11847213
Pharmacological profile of BIBN4096BS, the first selective small molecule CGRP antagonist.	2000-02	10711339

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical trial, patients received intravenous 10 min infusion of olcegepant at doses ranging from 0.1 to 10.0 mg.

Route of Administration: Intravenous

In Vitro Use Guide

SK-N-MC (neuroblastoma cell line of human origin) cell membranes were treated with olcegepant at concentrations from 10(-13) to 10(-9) in a binding assay and at 10 nM in a functional assay (stimulation of cyclic AMP formation).

Name

Type

Language

OLCEGEPANT

Official Name

English

BIBN 4096 BS

Preferred Name

English

Olcegepant [WHO-DD]

Common Name

English

BIBN-4096 BS

Code

English

N-((1R)-2-(((1S)-5-AMINO-1-((4-(PYRIDIN-4-YL)PIPERAZIN-1-YL)CARBONYL)PENTYL)AMINO)-1-(3,5-DIBROMO-4-HYDROXYBENZYL)-2-OXOETHYL)-4-(2-OXO-1,4-DIHYDROQUINAZOLIN-3(2H)-YL)PIPERIDINE-1-CARBOXAMIDE

Common Name

English

BIBN-4096BS

Code

English

olcegepant [INN]

Common Name

English

Code System Code Type Description

FDA UNII

WOA5J8TX6M