Olcegepant
Olcegepant (CAS 204697-65-4) is a non-peptide antagonist targeting the calcitonin gene-related peptide type 1 (CGRP1) receptor, which mediates neurogenic inflammatory pain pathways implicated in migraine pathophysiology. In functional assays using SK-N-MC cells, olcegepant blocks CGRP-induced cAMP generation (pA2 11.2) and demonstrates potent receptor inhibition (IC50: 0.1 nM in human cerebral arteries). Animal studies indicate olcegepant reduces capsaicin-induced Fos expression in the spinal trigeminal nucleus, suggesting it acts centrally rather than peripherally. Clinical trials indicate olcegepant ameliorates migraine severity without vasoconstrictive effects, highlighting its relevance as a research tool for migraine therapeutics.
| Storage | Store at -20°C |
| M.Wt | 869.66 |
| Cas No. | 204697-65-4 |
| Formula | C38H47Br2N9O5 |
| Synonyms | BIBN-4096; BIBN-4096BS;BIBN4096BS; BIBN 4096BS |
| Solubility | ≥87 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O |
| Chemical Name | N-[(2R)-1-[[(2S)-6-amino-1-oxo-1-(4-pyridin-4-ylpiperazin-1-yl)hexan-2-yl]amino]-3-(3,5-dibromo-4-hydroxyphenyl)-1-oxopropan-2-yl]-4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxamide |
| SDF | Download SDF |
| Canonical SMILES | C1CN(CCC1N2CC3=CC=CC=C3NC2=O)C(=O)NC(CC4=CC(=C(C(=C4)Br)O)Br)C(=O)NC(CCCCN)C(=O)N5CCN(CC5)C6=CC=NC=C6 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Kinase experiment [1]: | |
|
Binding studies |
SK-N-MC cell membranes (25 μg) were incubated in 1 mL of binding buffer [10 mM HEPES, pH 7.4, 5 mM MgCl2 and 0.2% bovine serum albumin (BSA)] containing 10 pM 125I-CGRP and inhibitor. After incubation at room temperature for 3 hrs, the assay was terminated by filtration through GFB glass fibre filter plates that had been blocked with 0.5% polyethyleneimine for 3 hrs. The filters were washed three times with ice-cold assay buffer, and then the plates were air dried. Scintillation fluid (50 mL) was added and the radioactivity was counted on a Topcount. Non-specific binding was determined by using a final concentration of 500 pM Olcegepant. Data analysis was carried out by using Prism and the Ki was determined by using the Cheng–Prusoff equation. |
| Cell experiment [1]: | |
|
Cell lines |
SK-N-MC cells |
|
Preparation method |
The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
|
Reacting condition |
10 mins |
|
Applications |
In SK-N-MC cells, CGRP-induced cAMP production was antagonised by both CGRP-(8-37) and Olcegepant with pA2 values of 7.8 and 11.2, respectively. |
| Animal experiment [2]: | |
|
Animal models |
Rats |
|
Dosage form |
900 μg/kg; i.v.; 10 mins |
|
Applications |
Pre-treatment with Olcegepant (900 μg/kg) inhibited the capsaicin-induced expression of Fos (57%) throughout the spinal trigeminal nucleus, but did not change the expression of phosphorylated extracellular signal-regulated kinase in the trigeminal ganglion. |
|
Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
|
References: [1]. Edvinsson L, Alm R, Shaw D, Rutledge RZ, Koblan KS, Longmore J, Kane SA. Effect of the CGRP receptor antagonist BIBN4096BS in human cerebral, coronary and omental arteries and in SK-N-MC cells. Eur J Pharmacol. 2002;434(1-2):49-53. [2]. Sixt ML, Messlinger K, Fischer MJ. Calcitonin gene-related peptide receptor antagonist olcegepant acts in the spinal trigeminal nucleus. Brain. 2009;132(Pt 11):3134-41. |
|
| Description | Olcegepant is a non-peptide antagonist of the calcitonin gene-related peptide 1 (CGRP1) with an IC50 value of 0.03nM. | |||||
| Targets | CGRP1 | |||||
| IC50 | 0.03 nM | |||||
Quality Control & MSDS
- View current batch:
Chemical structure
Related Biological Data
