Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, (5alpha)-
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Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, (5alpha)-
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CAS No:
916055-93-1
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Formula:
C21H26NO4+
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Chemical Name:
Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, (5alpha)-
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Synonyms:
UNII-0RK7M7IABE;0RK7M7IABE;Methylnaltrexone ion;Methylnaltrexone cation;Methylnaltrexone [VANDF];Methylnaltrexone [WHO-DD];916055-93-1;SCHEMBL19236259;ZINC245204949;DB06800
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CAS No:
Description
Methylnaltrexone is a pheriphally-acting μ-opioid antagonist that acts on the gastrointestinal tract to decrease opioid-induced constipation without producing analgesic effects or withdrawal symptoms. It is also a weak CYP2D6 inhibitor. FDA approved in 2008.|Methylnaltrexone is an Opioid Antagonist. The mechanism of action of methylnaltrexone is as an Opioid Antagonist.|Methylnaltrexone is a methyl derivative of noroxymorphone with selective, opioid-receptor antagonistic activity. Methylnaltrexone displaces opioids from peripheral opioid receptors in the gastrointestinal tract, the bladder, and the skin, resulting in decreases in opioid-related constipation, urinary retention, and pruritis, respectively. Methylnaltrexone does not cross the blood-brain barrier and does not affect the centrally-mediated analgesic effect of opioids.
Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, (5alpha)- Basic Attributes
356.18618331
0RK7M7IABE
C48403
Toxicity
LD50: 50 mg/kg (primates); Orthostatic hypotension at plasma levels in excess of 1.400 ng/mL. The most common (>5%) adverse reactions reported with methylnaltrexone bromide are abdominal pain, flatulence, nausea, dizziness, diarrhea and hyperhidrosis.
11% to 15% bound to human plasma proteins.
Drug Information
Treatment of opioids induced constipation in palliative patients that are inadequately responding to laxative therapy.|FDA Label
Use of opioids induces slowing of gastrointestinal motility and transit. Following remifentanil administration, the methylnaltrexone and placebo groups showed no change in pupiliary constriction while the naloxone group showed a marked change over the time interval tested.
Agents inhibiting the effect of narcotics on the central nervous system. (See all compounds classified as Narcotic Antagonists.)
Methylnaltrexone is rapidly absorbed. Tmax (SubQ): 30 minutes (regardless of dose); Cmax, 0.15 mg/kg SubQ dose = 117 ng/mL; AUC24, 0.15 mg/kg SubQ dose = 175 ng·hr/mL;|Most of the drug is eliminated as unchanged drug (85% of administered radioactivity). Approximately half of the dose is excreted in the urine and somewhat less in feces.|Volume of distribution, steady state = 1.1 L/kg|10.5 ± 1.5 ml/min/kg (IV)
60% of the dose is metabolized. Conversion to methyl-6-naltrexol isomers (5% of total dose) and methylnaltrexone sulfate (1.3% of total dose) appear to be the primary pathways of metabolism. N‑demethylation of methylnaltrexone to produce naltrexone is not significant.
terminal: 8.89 ± 2.59 h (intravenous) terminal: 6.14- 8.83 h (subcutaneous)
Methylnaltrexone is a pheriphally-acting μ-opioid antagonists that acts on the gastrointestinal tract inhibit opioid-induced decrease in gastric motility and transit time. Because methylnaltrexone is a quaternary derivative of naltrexone, it produces its gastrointestinal effects without producing analgesic effects or withdrawal symptoms as it does not cross the blood-brain-barrier.
(5alpha)-17-(cyclopropylmethyl)-3,14-dihydroxy-17-methyl-4,5-epoxymorphinan-17-ium-6-one
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