Methoclocinnamox

Not to be confused with Methocinnamox.
Methoclocinnamox
Clinical data
Other namesMCCAM; MC-CAM; NIH-10420; O-Methylclocinnamox
Identifiers
  • (E)-N-[(4R,4aS,7aR,12bR)-3-(cyclopropylmethyl)-9-methoxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(4-chlorophenyl)prop-2-enamide
    or
    (2E)-3-(4-chlorophenyl)-N-[(5α)-17-(cyclopropylmethyl)-3-methoxy-6-oxo-4,5-epoxymorphinan-14-yl]acrylamide
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC30H31ClN2O4
Molar mass519.04 g·mol−1
3D model (JSmol)
  • COC1=C2C3=C(C[C@@H]4[C@]5([C@]3(CCN4CC6CC6)[C@@H](O2)C(=O)CC5)NC(=O)/C=C/C7=CC=C(C=C7)Cl)C=C1
  • InChI=1S/C30H31ClN2O4/c1-36-23-10-7-20-16-24-30(32-25(35)11-6-18-4-8-21(31)9-5-18)13-12-22(34)28-29(30,26(20)27(23)37-28)14-15-33(24)17-19-2-3-19/h4-11,19,24,28H,2-3,12-17H2,1H3,(H,32,35)/b11-6+/t24-,28+,29+,30-/m1/s1
  • Key:LZSMGMMAKBCSRL-WDJVXPEUSA-N

Methoclocinnamox (MCCAM; developmental code name NIH-10420) is a selective pseudo-irreversible partial agonist of the μ-opioid receptor (MOR).[1] It shows a mixture of opioid agonist- and antagonist-like effects.[1] The drug has long-lasting effects and is insurmountable by other MOR ligands.[1]

MCCAM was derived from clocinnamox (CCAM), was first described by 1995, and was of interest in the potential treatment of opioid dependence.[1] However, it was not further developed and was never marketed.[2][3] A close analogue of MCCAM, methocinnamox (MCAM), which in contrast to MCCAM acts as a MOR pseudo-irreversible antagonist, was first described in 2000[4][5] and is under development for the treatment of opioid use disorder and opioid overdose as of 2023.[4][6][7]

  1. ^ a b c d Woods JH, Lewis JW, Winger G, Butelman E, Broadbear J, Zernig G (1995). "Methoclocinnamox: A μ Partial Agonist With Pharmacotherapeutic Potential for Heroin Abuse". In National Institute on Drug Abuse (ed.). NIDA Research Monograph. DHEW publication. National Institute on Drug Abuse. pp. 195–219. Retrieved 9 August 2024.
  2. ^ "Compound: CHEMBL386272". EMBL-EBI. Retrieved 13 September 2024.
  3. ^ "D0F1EB (MC-CAM) - Therapeutic Target Database". TTD. Retrieved 13 September 2024.
  4. ^ a b Cite error: The named reference JordanKennalleyRoberts2022 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference BroadbearSumpterBurke2000 was invoked but never defined (see the help page).
  6. ^ Maguire DR, France CP (March 2023). "Behavioral pharmacology of methocinnamox: A potential new treatment for opioid overdose and opioid use disorder". Journal of the Experimental Analysis of Behavior. 119 (2): 392–406. doi:10.1002/jeab.831. PMC 10281830. PMID 36759567.
  7. ^ Alvarez-Hernandez J (7 March 2023). "UT Health San Antonio Professor France leads novel drug discovery research". UT Health San Antonio. Retrieved 9 August 2024. Charles P. France, PhD, the Robert A. Welch Distinguished University Chair in Chemistry, professor of pharmacology and professor of psychiatry in the Joe R. and Teresa Lozano Long School of Medicine at The University of Texas Health Science Center at San Antonio (UT Health San Antonio), recently received a $4.12 million award from the U.S. National Institutes of Health (NIH) to investigate innovative drug development research of the compound methocinnamox (MCAM) to help combat the opioid epidemic. [...] This NIH funding mechanism, specifically UG3/UH3, has one precise objective to advance the discovery into the clinical setting. "We want to get this into the clinic," France said. [...] "Under the best of conditions, we hope to have this compound into a phase one clinical trial sometime in 2024."