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CTAP (peptide)

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Opioid antagonist peptide selective for the mu receptor

CTAP
Names

IUPAC name (4R,7S,10S,13R,16S,19R)-N-[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-10-[3-(diaminomethylideneamino)propyl]-7-[(1R)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-3,3-dimethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
Identifiers
CAS Number	103429-32-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1795717
ChemSpider	8594132
IUPHAR/BPS	1635
PubChem CID	10418702
InChI InChI=1S/C51H69N13O11S2/c1-26(65)39(42(53)68)62-49(75)41-51(3,4)77-76-25-38(61-43(69)33(52)21-28-11-6-5-7-12-28)47(73)59-36(22-29-16-18-31(67)19-17-29)45(71)60-37(23-30-24-57-34-14-9-8-13-32(30)34)46(72)58-35(15-10-20-56-50(54)55)44(70)63-40(27(2)66)48(74)64-41/h5-9,11-14,16-19,24,26-27,33,35-41,57,65-67H,10,15,20-23,25,52H2,1-4H3,(H2,53,68)(H,58,72)(H,59,73)(H,60,71)(H,61,69)(H,62,75)(H,63,70)(H,64,74)(H4,54,55,56)/t26-,27-,33-,35+,36+,37-,38+,39+,40+,41-/m1/s1 Key: OFMQLVRLOGHAJI-FGHAYEPSSA-N
SMILES C[C@H]([C@H]1C(=O)N[C@@H](C(SSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCN=C(N)N)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)[C@@H](CC5=CC=CC=C5)N)(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N)O
Properties
Chemical formula	C₅₁H₆₉N₁₃O₁₁S₂
Molar mass	1104.31 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

CTAP is an opioid antagonistpeptide, which is an analogue ofsomatostatin.^[1] It displays high selectivity for the mu-opioid receptor.

Pharmacology

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CTAP is described as being amu-selective opioid antagonist.^[2]^[3] In other words, when blocking opioid receptors, it is much more selective for the mu-opioid receptors than the other receptors. For example, inNorway rats, it has anIC₅₀ value of 0.0021 μM at mu opioid 1 receptors,^[4] but has a value of 5.31 μM at delta opioid 1 receptors,^[5] which shows that it is much more selective for mu receptors, as can be seen by the smaller value. Additionally, it is able to cross theblood–brain barrier (BBB).^[6]

References

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^Chieng, B.; Connor, M.; Christie, M. J. (September 1996). "The mu-opioid receptor antagonist D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2 (CTOP) [but not D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 (CTAP)] produces a nonopioid receptor-mediated increase in K+ conductance of rat locus ceruleus neurons".Molecular Pharmacology.50 (3):650–655.doi:10.1016/S0026-895X(25)09334-4.ISSN 0026-895X.PMID 8794906.
^Abbruscato, T. J.; Thomas, S. A.; Hruby, V. J.; Davis, T. P. (January 1997). "Blood-brain barrier permeability and bioavailability of a highly potent and mu-selective opioid receptor antagonist, CTAP: comparison with morphine".The Journal of Pharmacology and Experimental Therapeutics.280 (1):402–409.doi:10.1016/S0022-3565(24)36405-5.ISSN 0022-3565.PMID 8996221.
^Steinmiller, Caren L.; Young, Alice M. (January 2008)."Pharmacological selectivity of CTAP in a warm water tail-withdrawal antinociception assay in rats".Psychopharmacology.195 (4):497–507.doi:10.1007/s00213-007-0898-5.ISSN 0033-3158.PMC 2565866.PMID 17882404.
^"AID 151435 - Binding affinity for rat brain Opioid receptor mu 1 - PubChem".pubchem.ncbi.nlm.nih.gov. Retrieved2025-07-31.
^"AID 149515 - Binding affinity for rat brain Opioid receptor delta 1 - PubChem".pubchem.ncbi.nlm.nih.gov. Retrieved2025-07-31.
^Egleton, Richard D.; Abbruscato, Thomas J.; Thomas, Sarah A.; Davis, Thomas P. (1998-11-01)."Transport of Opioid Peptides into the Central Nervous System".Journal of Pharmaceutical Sciences.87 (11):1433–1439.Bibcode:1998JPhmS..87.1433E.doi:10.1021/js980062b.ISSN 0022-3549.PMID 9811502.