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SML2426

BIBN4096BS

Name: BIBN4096BS
Brand: SIGMA

≥95% (HPLC), CGRP receptor antagonist, powder

Synonym(s):

1-[3,5-Dibromo-N-[[4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl)-1-piperidinyl]carbonyl]-D-tyrosyl-L-lysyl]-4-(4-pyridinyl)-piperazine, 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, BIBN 4096, BIBN 4096 BS, Olcegepant, [R-(R*,S*)]-N-[2-[ [5-Amino-1-[[4-(4-pyridinyl)-1-piperazinyl]carbonyl]pentyl]amino]-1-[ (3,5-dibromo-4-hydroxyphenyl)methyl]-2-oxoethyl]-4-(1,4-dihydro-2-oxo-3(2H)-quinazolinyl)-1-piperidinecarboxamide

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About This Item

Empirical Formula (Hill Notation):

C₃₈H₄₇Br₂N₉O₅

CAS Number:

204697-65-4

Molecular Weight:

869.65

UNSPSC Code:

51111800

NACRES:

NA.77

MDL number:

MFCD07772306

Assay:

≥95% (HPLC)

Form:

powder

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Properties

Product Name

BIBN4096BS, ≥95% (HPLC)

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

Brc1c(c(cc(c1)CC(NC(=O)N4CCC(CC4)N5Cc6c(cccc6)NC5=O)C(=O)NC(CCCCN)C(=O)N2CCN(CC2)c3ccncc3)Br)O

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)

InChI key

ITIXDWVDFFXNEG-UHFFFAOYSA-N

Description

Biochem/physiol Actions

BIBN4096BS (Olcegepant) is a potent calcitonin gene-related peptide (CGRP) receptor antagonist with higher affinity/potency toward human over rat & mouse receptor (human/rat Ki = 14.4 pM/3.4 nM by binding assay; human/mouse Kb = 8 pM//7.711 nM by cellular cAMP assay). BIBN4096BS inhibits facial blood flow by electrical stimulation of marmoset monkey trigeminal ganglion (IC50 = 3 μg/kg i.v.) without any intrinsic cardiovascular effects. Studies using anaesthetized rats reveals that BIBN4096BS antagonism against trigeminal nociceptive stimulation by capsaicin is limited to the spinal trigeminal nucleus, but not trigeminal ganglion. Also widely employed for in vivo studies in mice.

Potent calcitonin gene-related peptide (CGRP) receptor antagonist with therapeutic efficacy against migraine in vivo.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000524376

0000477842

0000465110

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The CGRP receptor antagonist BIBN4096 inhibits prolonged meningeal afferent activation evoked by brief local K+ stimulation but not cortical spreading depression-induced afferent sensitization.

Jun Zhao et al.

Pain reports, 3(1), e632-e632 (2018-02-13)

Cortical spreading depression (CSD) is believed to promote migraine headache by enhancing the activity and mechanosensitivity of trigeminal intracranial meningeal afferents. One putative mechanism underlying this afferent response involves an acute excitation of meningeal afferents by cortical efflux of K+

Mucosal glucagon-like peptide 1 (GLP-1) responses are mediated by calcitonin gene-related peptide (CGRP) in the mouse colon and both peptide responses are area-specific.

I R Tough et al.

Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 30(1) (2017-07-12)

Glucagon-like peptide (GLP)-1 is an incretin hormone and its mimetics are proven antidiabetic and antiobesity drugs. GLP-1 exerts antimotility and mucosal proliferative activities but its epithelial ion transport effects are uncharacterized and these may contribute to the gastrointestinal (GI) disturbance

Calcitonin gene-related peptide receptor antagonist olcegepant acts in the spinal trigeminal nucleus.

Marie-Luise Sixt et al.

Brain : a journal of neurology, 132(Pt 11), 3134-3141 (2009-09-10)

Several lines of evidence suggest a major role of calcitonin gene-related peptide (CGRP) in the pathogenesis of migraine and other primary headaches. Inhibition of CGRP receptors by olcegepant and telcagepant has been successfully used to treat acute migraine and to

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