CTAP (peptide)

Last updated
CTAP
CTAP (drug).svg
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
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • 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
  • 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
C51H69N13O11S2
Molar mass 1104.31 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

CTAP is an opioid antagonist peptide, which is an analogue of somatostatin. [1] It displays high selectivity for the mu-opioid receptor.

Pharmacology

CTAP is described as being a mu-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, in Norway rats, it has an IC50 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 the blood–brain barrier (BBB). [6]

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ "AID 151435 - Binding affinity for rat brain Opioid receptor mu 1 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-07-31.
  5. ↑ "AID 149515 - Binding affinity for rat brain Opioid receptor delta 1 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-07-31.
  6. ↑ 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.
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