A CGRP receptor antagonist
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Olcegepant

Item No. 46436

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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
CAS Number
204697-65-4
Synonyms
  • BIBN 4096
  • BIBN 4096BS
Molecular Formula
C38H47Br2N9O5
Formula Weight
869.7
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
O=C1N(C2CCN(CC2)C(N[C@@H](C(N[C@@H](CCCCN)C(N3CCN(C4=CC=NC=C4)CC3)=O)=O)CC5=CC(Br)=C(C(Br)=C5)O)=O)CC6=CC=CC=C6N1
InChi Code
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
InChi Key
ITIXDWVDFFXNEG-JHOUSYSJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Olcegepant is a nonpeptide calcitonin gene-related peptide (CGRP) receptor antagonist (Ki = 14.4 pM).1 It inhibits α-CGRP- or β-CGRP-induced decreases in mean arterial blood pressure (MABP) and increases in middle meningeal artery (MMA) diameter in a closed cranial window rat model of migraine.2 Olcegepant also inhibits vasodilation induced by electrical trigeminal ganglion stimulation in marmoset facial skin (ID50 = ~3 µg/kg).1 It reduces mechanical hypersensitivity in a rat model of inflammatory pain at 3 and 10 mg/kg.3 Olcegepant decreases muscularis externa leukocyte infiltration and improves gastrointestinal motility in a mouse model of postoperative ileus.4 It also decreases IL-6 bronchoalveolar lavage fluid (BALF) levels and recovery time to baseline weight in a mouse model of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) infection.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Doods, H., Hallermayer, G., Wu, D., et al. Pharmacological profile of BIBN4096BS, the first selective small molecule CGRP antagonist. Br. J. Pharmacol. 129(3), 420-423 (2000).

    2. Petersen, K.A., Birk, S., Doods, H., et al. Inhibitory effect of BIBN4096BS on cephalic vasodilatation induced by CGRP or transcranial electrical stimulation in the rat. Br. J. Pharmacol. 143(6), 697-704 (2004).

    3. Hirsch, S., Corradini, L., Just, S., et al. The CGRP receptor antagonist BIBN4096BS peripherally alleviates inflammatory pain in rats. Pain 154(5), 700-707 (2013).

    4. Glowka, T.R., Steinebach, A., Stein, K., et al. The novel CGRP receptor antagonist BIBN4096BS alleviates a postoperative intestinal inflammation and prevents postoperative ileus. Neurogastroenterol. Motil. 27(7), 1038-1049 (2015).

    5. Rahman, S.M., Buchholz, D.W., Imbiakha, B., et al. Migraine inhibitor olcegepant reduces weight loss and IL-6 release in SARS-CoV-2-infected older mice with neurological signs. J. Virol. 98(7), e0006624 (2024).