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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=CC=CC=C4NC3=O)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
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

Curator's Comment: # Boehringer Ingelheim Pharma

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1090 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
842 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.37 h
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

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
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
INN   WHO-DD  
INN  
Official Name English
Olcegepant [WHO-DD]
Common Name English
BIBN 4096 BS
Code 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
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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SMS_ID
300000034277
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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INN
8026
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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NCI_THESAURUS
C170245
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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EPA CompTox
DTXSID10174443
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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ChEMBL
CHEMBL207197
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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CAS
204697-65-4
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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MESH
C492454
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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DRUG BANK
DB04869
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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WIKIPEDIA
Olcegepant
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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PUBCHEM
6918509
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
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