Olcegepant
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MedKoo CAT#: 326787

CAS#: 204697-65-4

Description: Olcegepant, also known as BIBN-4096 or BIBN-4096BS is is the first potent and selective non-peptide antagonist of the calcitonin gene-related peptide 1 (CGRP1) receptor, a key modulator in neurogenic inflammatory pain. In preclinical studies, olcegepant attenuated arterial dilation induced by CGRP or electrical stimulation. In a phase II clinical trial, olcegepant reduced the severity of headache in 60% of migraine sufferers and met secondary endpoints including headache-free rate and rate of sustained response. The compound appears to be an effective anti-migraine medication that is well tolerated and does not display the vasoconstrictive effect that precludes the use of triptans and dihydroergotamine in certain patients.


Price and Availability

Size
Price

10mg
USD 600
Size
Price

Size
Price

Olcegepant, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326787
Name: Olcegepant
CAS#: 204697-65-4
Chemical Formula: C38H47Br2N9O5
Exact Mass: 867.2067
Molecular Weight: 869.66
Elemental Analysis: C, 52.48; H, 5.45; Br, 18.38; N, 14.50; O, 9.20


Synonym: BIBN-4096; BIBN4096; BIBN 4096; BIBN-4096BS; BIBN4096BS; BIBN 4096BS; Olcegepant.

IUPAC/Chemical Name: 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

InChi Key: ITIXDWVDFFXNEG-JHOUSYSJSA-N

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

SMILES Code: O=C(N1CCC(N2C(NC3=C(C=CC=C3)C2)=O)CC1)N[C@H](CC4=CC(Br)=C(O)C(Br)=C4)C(N[C@H](C(N5CCN(C6=CC=NC=C6)CC5)=O)CCCCN)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Yao G, Yu T, Han X, Mao X, Li B. Therapeutic effects and safety of olcegepant and telcagepant for migraine: A meta-analysis. Neural Regen Res. 2013 Apr 5;8(10):938-47. doi: 10.3969/j.issn.1673-5374.2013.10.009. PubMed PMID: 25206386; PubMed Central PMCID: PMC4145922.

2: Michot B, Bourgoin S, Viguier F, Hamon M, Kayser V. Differential effects of calcitonin gene-related peptide receptor blockade by olcegepant on mechanical allodynia induced by ligation of the infraorbital nerve vs the sciatic nerve in the rat. Pain. 2012 Sep;153(9):1939-48. doi: 10.1016/j.pain.2012.06.009. Epub 2012 Jul 15. PubMed PMID: 22795918.

3: Tvedskov JF, Tfelt-Hansen P, Petersen KA, Jensen LT, Olesen J. CGRP receptor antagonist olcegepant (BIBN4096BS) does not prevent glyceryl trinitrate-induced migraine. Cephalalgia. 2010 Nov;30(11):1346-53. doi: 10.1177/0333102410363491. Epub 2010 Apr 7. PubMed PMID: 20959429.

4: Sixt ML, Messlinger K, Fischer MJ. Calcitonin gene-related peptide receptor antagonist olcegepant acts in the spinal trigeminal nucleus. Brain. 2009 Nov;132(Pt 11):3134-41. doi: 10.1093/brain/awp168. Epub 2009 Sep 8. PubMed PMID: 19737844.

5: Recober A, Russo AF. Olcegepant, a non-peptide CGRP1 antagonist for migraine treatment. IDrugs. 2007 Aug;10(8):566-74. PubMed PMID: 17665333.