Olcegepant | BIBN-4096 | BIBN-4096BS | CAS#204697-65-4 | CGRP receptor antagonist

Olcegepant
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WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Olcegepant

CAS# 204697-65-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326787
Name: Olcegepant
CAS#: 204697-65-4
Chemical Formula: C38H47Br2N9O5
Exact Mass: 867.21
Molecular Weight: 869.660
Elemental Analysis: C, 52.48; H, 5.45; Br, 18.38; N, 14.50; O, 9.20

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 625	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Olcegepant (BIBN-4096) is a potent and selective non-peptide antagonist of the calcitonin gene-related peptide 1 (CGRP1) receptor with IC50 of 0.03 nM and Ki of 14.4 pM.
In vitro activity:	IBN4096BS completely inhibited the specific binding of 125I-CGRP to SK-N-MC cells and displayed an affinity (Ki) of 14.4±6.3 pM (n=4) for the human CGRP receptor (Figure 2A). The endogenous ligand CGRP itself and the peptidic antagonist CGRP(8-37) displayed affinities (Ki) of 31.7±1.6 pM (n=15) and 3.6±0.7 nm (n=4), respectively. Employing the same cell line it was shown that BIBN4096BS is a pure antagonist. Reference: Br J Pharmacol. 2000 Feb;129(3):420-3. https://pubmed.ncbi.nlm.nih.gov/10711339/
In vivo activity:	Like naratriptan (0.1 to 0.3mg/kg, subcutaneously), olcegepant (0.3 to 0.9mg/kg, intravenously) markedly reduced mechanical allodynia in CCI-ION rats. In contrast, in CCI-SN rats, mechanical allodynia was completely unaffected and hyperalgesia was only marginally reduced by these drugs. A supra-additive antiallodynic effect was observed in CCI-ION rats treated with olcegepant (0.3mg/kg intravenously) plus naratriptan (0.1mg/kg subcutaneously), whereas this drug combination remained inactive in CCI-SN rats. Olcegepant (0.6mg/kg, intravenously) significantly reduced the number of c-Fos immunolabeled cells in spinal nucleus of the trigeminal nerve and upregulation of ATF3 transcript (a marker of neuron injury) but not that of interleukin-6 in trigeminal ganglion of CCI-ION rats. Reference: Pain. 2012 Sep;153(9):1939-1948. https://pubmed.ncbi.nlm.nih.gov/22795918/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	50.0	57.49
	1M HCl	50.0	57.49

Preparing Stock Solutions

The following data is based on the product molecular weight 869.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Wang Y, Li Y, Wang M. Involvement of CGRP receptors in retinal spreading depression. Pharmacol Rep. 2016 Oct;68(5):935-8. doi: 10.1016/j.pharep.2016.05.001. Epub 2016 Jun 27. PMID: 27362770. 2. Doods H, Hallermayer G, Wu D, Entzeroth M, Rudolf K, Engel W, Eberlein W. Pharmacological profile of BIBN4096BS, the first selective small molecule CGRP antagonist. Br J Pharmacol. 2000 Feb;129(3):420-3. doi: 10.1038/sj.bjp.0703110. PMID: 10711339; PMCID: PMC1571877. 3. Kitagawa S, Tang C, Unekawa M, Kayama Y, Nakahara J, Shibata M. Sustained Effects of CGRP Blockade on Cortical Spreading Depolarization-Induced Alterations in Facial Heat Pain Threshold, Light Aversiveness, and Locomotive Activity in the Light Environment. Int J Mol Sci. 2022 Nov 9;23(22):13807. doi: 10.3390/ijms232213807. PMID: 36430285; PMCID: PMC9698572. 4. 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):1939-1948. doi: 10.1016/j.pain.2012.06.009. Epub 2012 Jul 15. PMID: 22795918.
In vitro protocol:	1. Wang Y, Li Y, Wang M. Involvement of CGRP receptors in retinal spreading depression. Pharmacol Rep. 2016 Oct;68(5):935-8. doi: 10.1016/j.pharep.2016.05.001. Epub 2016 Jun 27. PMID: 27362770. 2. Doods H, Hallermayer G, Wu D, Entzeroth M, Rudolf K, Engel W, Eberlein W. Pharmacological profile of BIBN4096BS, the first selective small molecule CGRP antagonist. Br J Pharmacol. 2000 Feb;129(3):420-3. doi: 10.1038/sj.bjp.0703110. PMID: 10711339; PMCID: PMC1571877.
In vivo protocol:	1. Kitagawa S, Tang C, Unekawa M, Kayama Y, Nakahara J, Shibata M. Sustained Effects of CGRP Blockade on Cortical Spreading Depolarization-Induced Alterations in Facial Heat Pain Threshold, Light Aversiveness, and Locomotive Activity in the Light Environment. Int J Mol Sci. 2022 Nov 9;23(22):13807. doi: 10.3390/ijms232213807. PMID: 36430285; PMCID: PMC9698572. 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):1939-1948. doi: 10.1016/j.pain.2012.06.009. Epub 2012 Jul 15. PMID: 22795918.

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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.

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