Kelatorphan

Kelatorphan
Clinical data
ATC code	None;
Legal status
Legal status	In general: non-regulated;
Identifiers
	IUPAC name N-[(2R)-2-benzyl-4-(hydroxyamino)-4-oxobutanoyl]-L-alanine;
CAS Number	92175-57-0;
PubChem CID	123982;
DrugBank	DB08040;
ChemSpider	110501;
UNII	46BBW2U5D6;
CompTox Dashboard (EPA)	DTXSID90238911 ;
Chemical and physical data
Formula	C14H18N2O5
Molar mass	294.307 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H](NC(=O)[C@H](Cc1ccccc1)CC(=O)NO)C;
	InChI InChI=1S/C14H18N2O5/c1-9(14(19)20)15-13(18)11(8-12(17)16-21)7-10-5-3-2-4-6-10/h2-6,9,11,21H,7-8H2,1H3,(H,15,18)(H,16,17)(H,19,20)/t9-,11+/m0/s1; Key:OJCFZTVYDSKXNM-GXSJLCMTSA-N;

Kelatorphan is a drug which acts as a powerful and complete inhibitor of nearly all of the enzymes responsible for catabolism of the endogenous enkephalins, including neutral endopeptidase (NEP), dipeptidyl peptidase III (DPP3), aminopeptidase N (APN), and angiotensin-converting enzyme (ACE).^[1]^[2]^[3] In mice, with the intracerebroventricular co-administration of a 50 μg dose of kelatorphan (this route is necessary because kelatorphan is incapable of crossing the blood-brain-barrier)^[4] hence alongside exogenous [Met]enkephalin (ED₅₀ approximately 10 ng), it potentiated the analgesic effects of the latter by 50,000 times.^[1] Kelatorphan also displays potent antinociceptive effects alone,^[5] and does not depress respiration, although at high doses it actually increases it.^[4]