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Methocinnamox

From Wikipedia, the free encyclopedia

Methocinnamox
Names
IUPAC name
(E)-N-[(4R,4aS,7aR,12bR)-3-(cyclopropylmethyl)-9-hydroxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(4-methylphenyl)prop-2-enamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C30H32N2O4/c1-18-2-4-19(5-3-18)8-11-25(35)31-30-13-12-23(34)28-29(30)14-15-32(17-20-6-7-20)24(30)16-21-9-10-22(33)27(36-28)26(21)29/h2-5,8-11,20,24,28,33H,6-7,12-17H2,1H3,(H,31,35)/b11-8+/t24-,28+,29+,30-/m1/s1
    Key: PJOHVEQSYPOERL-SHEAVXILSA-N
  • CC1=CC=C(C=C1)C=CC(=O)NC23CCC(=O)C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7
Properties
C30H32N2O4
Molar mass 484.596 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methocinnamox is an opioid antagonist.

Mechanism of action

Methocinnamox is an opioid antagonist, it works at the µ-opioid receptor.[1] By being an antagonist, it binds to the receptor but does not activate it, thus blocking the action of agonists such as Fentanyl.

Therapeutic potential

Opioid overdose

In rats, methocinnamox is able to reverse the respiratory depressant effects of fentanyl. However, unlike naloxone, another opioid antagonist, its action lasts around 2 weeks if administered subcutaneously and up to 5 days if administered intravenously.[2] This could make it a better antidote than naloxone in opioid overdoses, because naloxone usually lasts around 30 minutes, there is a need for repeated administration and a danger of renarcotization.[3] By acting longer, methocinnamox prevents these dangers.

Other tests have also shown this result, methocinnamox was able to reverse the respiratory depressant effect of heroin.

References

  1. ^ Gerak, Lisa R.; Minervini, Vanessa; Latham, Elizabeth; Ghodrati, Saba; Lillis, Katherine V.; Wooden, Jessica; Disney, Alex; Husbands, Stephen M.; France, Charles P. (November 2019). "Methocinnamox Produces Long-Lasting Antagonism of the Behavioral Effects of µ-Opioid Receptor Agonists but Not Prolonged Precipitated Withdrawal in Rats". The Journal of Pharmacology and Experimental Therapeutics. 371 (2): 507–516. doi:10.1124/jpet.119.260331. ISSN 1521-0103. PMC 6863459. PMID 31439807.
  2. ^ Jimenez, Victor M.; Castaneda, Gabriel; France, Charles P. (April 2021). "Methocinnamox Reverses and Prevents Fentanyl-Induced Ventilatory Depression in Rats". The Journal of Pharmacology and Experimental Therapeutics. 377 (1): 29–38. doi:10.1124/jpet.120.000387. ISSN 1521-0103. PMC 7985616. PMID 33431611.
  3. ^ "Opioid Overdose Limitations in Naloxone Reversal". pubs.asahq.org. Retrieved 2024-02-11.
This page was last edited on 12 February 2024, at 21:39
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