6099. Methylnaltrexone Bromide

Nomenclature

CAS number: 73232-52-7; 83387-25-1 (methylnaltrexonium)
(5α)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxomorphinanium bromide; N-cyclopropylmethyl-noroxymorphone methobromide; naltrexone methobromide; Relistor (Progenics).
C21H26BrNO4; mol wt 436.34.
C 57.80%, H 6.01%, Br 18.31%, N 3.21%, O 14.67%.

Description and references

Peripheral opioid receptor antagonist; quaternary derivative of naltrexone, q.v., that does not readily cross the blood brain barrier. Prepn: L. I. Goldberg et al., US 4176186 (1979 to Boehringer Ing.). Determn by HPLC and solid phase extraction in plasma and urine: J. Osinski et al., J. Chromatogr. B 780, 251 (2002) DOI PubMed. Clinical evaluation in methadone-induced constipation: C.-S. Yuan et al., J. Am. Med. Assoc. 283, 367 (2000) DOI PubMed. Clinical pharmacokinetics: idem et al., J. Clin. Pharmacol. 45, 538 (2005) DOI PubMed. Review of therapeutic potential in opioid-induced bowel dysfunction: J. F. Foss, Am. J. Surg. 182, Suppl. 5A, 19S-26S (2001) DOI PubMed; of preclinical and clinical experience: C.-S. Yuan, J. Support. Oncol. 2, 111-117 (2004) PubMed.

Chemical structure

Properties

Crystals from methanol/ether, mp 253°.

Therapeutic Category

Narcotic antagonist. In treatment of opioid bowel dysfunction.

Keywords

Narcotic Antagonist