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CAS 83387-25-1

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Methylnaltrexone

Description:
Methylnaltrexone is a synthetic opioid antagonist primarily used to treat opioid-induced constipation, particularly in patients with advanced illness or those receiving palliative care. It is a quaternary ammonium compound, which means it has a permanent positive charge, limiting its ability to cross the blood-brain barrier and thus reducing central nervous system side effects commonly associated with other opioids. The chemical formula for Methylnaltrexone is C21H28N2O4, and it features a structure that includes a naltrexone backbone modified with a methyl group. This modification enhances its selectivity for peripheral opioid receptors in the gastrointestinal tract. Methylnaltrexone is administered via subcutaneous injection and has a relatively rapid onset of action, typically within hours. Its efficacy is supported by clinical studies, demonstrating significant relief from constipation without precipitating withdrawal symptoms in opioid-dependent patients. As with any medication, potential side effects may include abdominal pain, diarrhea, and nausea, necessitating careful monitoring during treatment.
Formula:C21H26NO4
InChI:InChI=1S/C21H25NO4/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13/h4-5,12,16,19,25H,2-3,6-11H2,1H3/p+1/t16-,19+,20+,21-,22?/m1/s1
InChI key:InChIKey=JVLBPIPGETUEET-GAAHOAFPSA-O
SMILES:O[C@]12[C@@]34C=5C(O[C@]3(C(=O)CC1)[H])=C(O)C=CC5C[C@]2([N+](CC6CC6)(C)CC4)[H]
Synonyms:
  • (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxomorphinanium
  • Methylnaltrexonium
  • Methylnaltrexone
  • Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, (5α)-
  • N-Methylnaltrexone
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