Casokefamide

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Chemical compound

title: "Casokefamide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antidiarrhoeals", "opioid-peptides", "peripherally-selective-drugs", "pentapeptides"] description: "Chemical compound" topic_path: "general/antidiarrhoeals" source: "https://en.wikipedia.org/wiki/Casokefamide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| IUPAC_name = (2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-3-phenylpropanamido]propanamido]-3-(4-hydroxyphenyl)propanamide | image = Casokefamide.svg | image_class = skin-invert-image | CAS_number = 98815-38-4 | CAS_supplemental = | ATC_prefix = None | ATC_suffix = | PubChem = 5464104 | ChEMBL = 2106384 | ChemSpiderID = 4576538 | UNII = B453T1E8MP | C=33 | H=40 | N=6 | O=7 | smiles = O=C(NC@@HC)C@@HCc3ccc(O)cc3 | StdInChI = 1S/C33H40N6O7/c1-19(36-32(45)26(34)16-22-8-12-24(40)13-9-22)31(44)39-28(18-21-6-4-3-5-7-21)33(46)37-20(2)30(43)38-27(29(35)42)17-23-10-14-25(41)15-11-23/h3-15,19-20,26-28,40-41H,16-18,34H2,1-2H3,(H2,35,42)(H,36,45)(H,37,46)(H,38,43)(H,39,44)/t19-,20-,26+,27+,28+/m1/s1 | StdInChIKey = XDRHVZLDLNGKLM-FLVVDCEDSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_category = | legal_status = | routes_of_administration = | synonyms = L-tyrosyl-D-alanyl-L-phenylalanyl-D-alanyl-L-tyrosinamide

Casokefamide (INN), also known as β-casomorphin 4027 (β-CM-4027) and [D-Ala2,4,Tyr5]-β-casomorphin-5-amide, is a peripherally-specific, synthetic opioid pentapeptide with the amino acid sequence Tyr-D-Ala-Phe-D-Ala-Tyr-NH2. Derived from the β-casomorphin sequence, it was designed with the intention of improving resistance to digestive enzymes so that it could be used as an antidiarrheal medicine. Unlike other casomorphins, which are generally selective μ-opioid receptor agonists, casokefamide binds to both the μ- and δ-opioid receptors. In a clinical study, casokefamide was found to be effective via the oral route for the treatment of chronic diarrhea, and did not produce any side effects. However, further clinical development was not pursued and it was never marketed.

References

References

  1. (March 1993). "Solution structure of casokefamide". Biochemical and Biophysical Research Communications.
  2. (March 2000). "Effects of oral casokefamide on plasma levels, tolerance, and intestinal transit in man". Peptides.

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antidiarrhoealsopioid-peptidesperipherally-selective-drugspentapeptides