Diprenorphine

Diprenorphine

Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	QV03AB92 (WHO)
Identifiers
IUPAC name (5α,7α)-17-(Cyclopropylmethyl)- 4,5-epoxy- 18,19-dihydro- 3-hydroxy- 6-methoxy- α,α-dimethyl- 6,14-ethenomorphinan- 7-methanol
CAS Number	14357-78-9 N
PubChem CID	443408
IUPHAR/BPS	1617
DrugBank	DB01548 Y
ChemSpider	391634 Y
UNII	1F0L5N25ZZ
KEGG	D07863 Y
ChEMBL	CHEMBL281786 Y
ECHA InfoCard	100.034.826
Chemical and physical data
Formula	C26H35NO4
Molar mass	425.56 g/mol
3D model (Jmol)	Interactive image
SMILES CC(C)([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
InChI InChI=1S/C26H35NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-7,15,18-19,22,28-29H,4-5,8-14H2,1-3H3/t18-,19-,22-,24-,25+,26-/m1/s1 Y Key:OIJXLIIMXHRJJH-KNLIIKEYSA-N Y
NY (what is this?)

Diprenorphine (brand name Revivon; former developmental code name M5050), also known as diprenorfin, is a non-selective, high-affinity, weak partial agonist of the μ- (MOR), κ- (KOR), and δ-opioid receptor (DOR) (with equal affinity) that is employed in veterinary medicine as an opioid antagonist. It is used to reverse the effects of super-potent opioid analgesics such as etorphine and carfentanil that are used for tranquilizing large animals. The drug is not approved for use in humans.

Diprenorphine is the strongest opioid antagonist that is commercially available (some 100 times more potent as an antagonist than nalorphine), and is used for reversing the effects of very strong opioids for which the binding affinity is so high that naloxone does not effectively or reliably reverse the narcotic effects. These super-potent opioids, with the single exception of buprenorphine (which has an improved safety-profile due to its partial agonism character), are not used in humans because the dose for a human is so small that it would be difficult to measure properly, so there is an excessive risk of overdose leading to fatal respiratory depression. However conventional opioid derivatives are not strong enough to rapidly tranquilize large animals, like elephants and rhinos, so drugs such as etorphine and carfentanil are available for this purpose.

Diprenorphine is considered to be the specific reversing agent/antagonist for etorphine and carfentanil, and is normally used to remobilise animals once veterinary procedures have been completed. Since diprenorphine also has partial agonistic properties of its own, it should not be used on humans in the event that they are accidentally exposed to etorphine or carfentanil. Naloxone or naltrexone is the preferred human opioid receptor antagonist.