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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 of OLCEGEPANT

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
Molecular Formula C38H47Br2N9O5
Molecular Weight 869.645
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Boehringer Ingelheim
130

Approval Year

Unknown
149,124

Targets

Primary TargetPharmacologyConditionPotency
Calcitonin gene-related peptide type 1 receptor
9
Antagonist
2,849
 14.4 pM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Acute migraine headache
1
 Primary
Phase II
1,147
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1090 ng/mL
10 mg single, intravenous
 OLCEGEPANT plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
842 ng × h/mL
10 mg single, intravenous
 OLCEGEPANT plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.37 h
10 mg single, intravenous
 OLCEGEPANT plasma
Homo sapiens

PubMed

Patents

WO2005018603 A2
1
WO2005018603 A3
1

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).
Substance Class Chemical
Record UNII
WOA5J8TX6M
Record Status Validated (UNII)
Record Version
NIH
NCATS
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