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SML2426

Sigma-Aldrich

BIBN4096BS

≥95% (HPLC)

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
MDL number:
MFCD07772306
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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+
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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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