Casokefamide

Casokefamide

Systematic (IUPAC) name
L-tyrosyl-D-alanyl-L-phenylalanyl-D-alanyl-L-tyrosinamide
Identifiers
CAS Number	98815-38-4
ATC code	None
PubChem	CID: 5464104
ChemSpider	4576538
ChEMBL	CHEMBL2106384
Chemical data
Formula	C33H40N6O7
Molecular mass	632.707 g/mol
SMILES O=C(N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N)Cc1ccc(O)cc1)C)Cc2ccccc2)C)[C@@H](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 [D-Ala^2,4,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 potentially 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