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Casokefamide

Clinical data
Other names	L-tyrosyl-D-alanyl-L-phenylalanyl-D-alanyl-L-tyrosinamide
ATC code	None
Identifiers
IUPAC name (2S)-2-propanamido]-3-phenylpropanamido]propanamido]-3-(4-hydroxyphenyl)propanamide
CAS Number	98815-38-4
PubChem CID	5464104
ChemSpider	4576538
UNII	B453T1E8MP
ChEMBL	ChEMBL2106384
CompTox Dashboard (EPA)	DTXSID30243827
Chemical and physical data
Formula	C33H40N6O7
Molar mass	632.718 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(N(C(=O)N(C(=O)N(C(=O)N(C(=O)N)Cc1ccc(O)cc1)C)Cc2ccccc2)C)(N)Cc3ccc(O)cc3
InChI InChI=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 Key:XDRHVZLDLNGKLM-FLVVDCEDSA-N

Casokefamide (INN), also known as β-casomorphin 4027 (β-CM-4027) and -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.

See also

• Morphiceptin
• Frakefamide

References

1. ^ Brantl V, Picone D, Amodeo P, Temussi PA (March 1993). "Solution structure of casokefamide". Biochemical and Biophysical Research Communications. 191 (3): 853–9. doi:10.1006/bbrc.1993.1295. PMID 8466524.
2. ^ Schulte-Frohlinde E, Reindl W, Bierling D, et al. (March 2000). "Effects of oral casokefamide on plasma levels, tolerance, and intestinal transit in man". Peptides. 21 (3): 439–42. doi:10.1016/S0196-9781(00)00166-2. PMID 10793229. S2CID 44670226.

• Drugs not assigned an ATC code
• Antidiarrhoeals
• Opioid peptides
• Peripherally selective drugs
• Pentapeptides