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Methoclocinnamox
Chemical compound From Wikipedia, the free encyclopedia
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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]
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Pharmacology
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Pharmacodynamics
MCCAM acts as a selective pseudo-irreversible partial agonist of the μ-opioid receptor (MOR).[1] It shows both opioid agonist- and antagonist-like effects in animals.[1] More specifically, it has analgesic effects, mixed reinforcing effects, appears to lack significant respiratory depression, alleviates opioid withdrawal symptoms, and provides long-lasting blockade and protection against the effects of MOR full agonists (including their reinforcing effects as well as their toxic and lethal effects, for instance in overdose).[1] Due to its pseudo-irreversible nature, MCCAM is insurmountable by conventional reversible MOR ligands, for instance morphine, alfentanil, and naltrexone.[1] MCCAM is buprenorphine-like in many regards, but differs from buprenorphine in its pseudo-irreversibility.[1]
Pharmacokinetics
MCCAM is known to be partially metabolically converted into clocinnamox (CCAM), a MOR pseudo-irreversible antagonist.[1] In monkeys, with oral administration of MCCAM, 70 to 80% of the drug is eliminated as conjugated CCAM, whereas with subcutaneous injection, up to 70% of the drug is excreted unchanged.[1] As such, the metabolism of MCCAM, and by extension its effects, differ by route of administration.[1] The metabolism of MCCAM also shows species differences between rodents and monkeys.[1]
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Chemistry
MCCAM, also known as O-methylclocinnamox, is structurally related to the MOR irreversible antagonists clocinnamox (CCAM) and methocinnamox (MCAM).[1][4][5] CCAM and its analogues were derived by structural modification of buprenorphine.[8]
History
Clocinnamox (CCAM) was first described in the scientific literature by 1992.[9] MCCAM was first described by 1995.[1] It was developed by researchers at the National Institute on Drug Abuse (NIDA) of the United States National Institutes of Health (NIH).[1] The drug was of interest in the possible treatment of opioid dependence.[1] However, it was never marketed.[2][3] Methocinnamox (MCAM), a close analogue of MCCAM, was first described in 2000.[4][5] MCAM was under development for the treatment of opioid dependence and opioid overdose by 2020.[10][4][6][7]
References
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