Diprenorphine

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Diprenorphine
Clinical data
Trade namesRevivon
Other namesDiprenorfin; M5050
AHFS/Drugs.comInternational Drug Names
ATCvet code
Identifiers
  • (5α,7α)-17-(Cyclopropylmethyl)- 4,5-epoxy- 18,19-dihydro- 3-hydroxy- 6-methoxy- α,α-dimethyl- 6,14-ethenomorphinan- 7-methanol
JSmol)
  • 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=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 checkY
  • Key:OIJXLIIMXHRJJH-KNLIIKEYSA-N checkY
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Diprenorphine (brand name Revivon; former developmental code name M5050),

tranquilizing large animals. The drug is not approved for use in humans.[5]

Diprenorphine is the strongest opioid antagonist that is commercially available (some 100 times more potent as an antagonist than

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,[9] and is normally used to remobilise animals once veterinary procedures have been completed.[10] Since diprenorphine also has partial agonistic properties of its own, it should not be used on humans if they are accidentally exposed to etorphine or carfentanil. Naloxone or naltrexone is the preferred human opioid receptor antagonist.[11]

In theory, diprenorphine could also be used as an antidote for treating overdose of certain opioid derivatives which are used in humans, particularly buprenorphine for which the binding affinity is so high that naloxone does not reliably reverse the narcotic effects. However, diprenorphine is not generally available in hospitals; instead a vial of diprenorphine is supplied with etorphine or carfentanil specifically for reversing the effects of the drug, so the use of diprenorphine for treating a buprenorphine overdose is not usually carried out in practice.

Because diprenorphine is a weak partial agonist of the

silent antagonist, it can produce some opioid effects in the absence of other opioids at sufficient doses.[12] Moreover, due to partial agonism of the KOR, where it appears to possess significantly greater intrinsic activity relative to the MOR, diprenorphine can produce sedation as well as, in humans, hallucinations.[3][5][13][14][15]

References

  1. ^ US 3433791, "Endoethano Nor Oripavines & Nor Thebaines" 
  2. PMID 15032698
    .
  3. ^
    ISBN 978-0-8493-7653-5
    .
  4. ISBN 978-0-470-75245-6
    .
  5. ^
    ISBN 978-0-7020-5423-5
    .
  6. S2CID 99996951
    .
  7. PMID 4637947
    .
  8. ^ "Medication Assisted Treatment". SAMHSA.gov. September 2015. p. 1.
  9. PMID 4077657
    .
  10. PMID 4817959
    .
  11. ^ Caulkett NA, Arnemo JM (2007). "Chemical Immobilization of Free-Ranging Terrestrial Mammals.". In Tranquilli WJ, Thurmon JC, Grimm KA (eds.). Lumb and Jones' Veterinary Anesthesia and Analgesia (4th ed.). Philadelphia: Lippincott, Williams and Wilkins. p. 815.
  12. ISBN 978-1-4051-4777-4
    .
  13. ISBN 978-1-4377-1985-7
    .
  14. ISBN 978-0-7881-8130-6
    .
  15. PMID 3038579
    .
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