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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
Molecular Formula C38H47Br2N9O5
Molecular Weight 869.645
Charge 0
Count
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
131
Curator's Comment: # Boehringer Ingelheim Pharma

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Calcitonin gene-related peptide type 1 receptor
7
Target ID: Q16602
Gene ID: 10203.0
Gene Symbol: CALCRL
Target Organism: Homo sapiens (Human)
Antagonist
2778
 14.4 pM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Sourcing

Vendor/AggregatorIDURL
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
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=
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
Molnova
M13181
https://www.molnova.com/en/serch-list.html?keywords=M13181
Molnova
M15157
https://www.molnova.com/en/serch-list.html?keywords=M15157
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
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/
PubMed

PubMed

TitleDatePubMed
CL/RAMP2 and CL/RAMP3 produce pharmacologically distinct adrenomedullin receptors: a comparison of effects of adrenomedullin22-52, CGRP8-37 and BIBN4096BS.
2003 Oct
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 Sep 22
Effects of current and prospective antimigraine drugs on the porcine isolated meningeal artery.
2006 Dec
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 Dec
Olcegepant, a non-peptide CGRP1 antagonist for migraine treatment.
2007 Aug
Treatment of migraine attacks based on the interaction with the trigemino-cerebrovascular system.
2008 Feb
Identification of potent CNS-penetrant thiazolidinones as novel CGRP receptor antagonists.
2014 Feb 1
Patents

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
Created
by admin
on Sat Dec 16 16:53:37 GMT 2023
Edited
by admin
on Sat Dec 16 16:53:37 GMT 2023
Record UNII
WOA5J8TX6M
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
SMS_ID
300000034277
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
INN
8026
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
NCI_THESAURUS
C170245
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID10174443
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL207197
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
CAS
204697-65-4
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
MESH
C492454
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
DRUG BANK
DB04869
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
WIKIPEDIA
Olcegepant
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
PUBCHEM
6918509
Created by admin on Sat Dec 16 16:53:37 GMT 2023 , Edited by admin on Sat Dec 16 16:53:37 GMT 2023
PRIMARY
Related Record Type Details
CALCITONIN GENE-RELATED PEPTIDE TYPE 1 RECEPTOR
TARGET -> INHIBITOR
Related Record Type Details
Structure of OLCEGEPANT
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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