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SML2426

Sigma-Aldrich

BIBN4096BS

≥95% (HPLC)

Sinônimo(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

Fórmula empírica (Notação de Hill):
C38H47Br2N9O5
Número CAS:
204697-65-4
Peso molecular:
869.65
Número MDL:
MFCD07772306
Código UNSPSC:
51111800
NACRES:
NA.77

Ensaio

≥95% (HPLC)

Formulário

powder

cor

white to beige

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

−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)

chave InChI

ITIXDWVDFFXNEG-UHFFFAOYSA-N

Ações bioquímicas/fisiológicas

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Francesca Eroli et al.
Neuroscience, 351, 47-64 (2017-04-02)
Transgenic knock-in (KI) mice that express CaV2.1 channels containing an R192Q gain-of-function mutation in the α1A subunit known to cause familial hemiplegic migraine type-1 in patients, exhibit key disease characteristics and provide a useful tool to investigate pathophysiological mechanisms of
Keegan J Bohn et al.
British journal of pharmacology, 174(12), 1826-1840 (2017-03-21)
CGRP is a potent vasodilator and nociceptive neuropeptide linked to migraine. CGRP receptors are heterodimers of receptor activity modifying protein 1 (RAMP1) and either calcitonin receptor-like receptor (CLR; forms canonical CGRP receptor) or calcitonin receptor (CT receptor; forms AMY1 receptor).
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
Lars Edvinsson et al.
European journal of pharmacology, 434(1-2), 49-53 (2002-01-05)
Several lines of evidence suggest that a calcitonin-gene related peptide (CGRP) receptor antagonist may serve as a novel abortive migraine treatment. Here we present data on a human cell line and isolated human vessels for such an antagonist, BIBN4096BS. On
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+
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