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    Methylnaltrexone Bromide

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Naltrexone methobromide, 73232-52-7, Relistor, Methylnaltrexone (bromide), Methylnaltrexone, Moa-728
    Molecular Formula
    C21H26BrNO4
    Molecular Weight
    436.3  g/mol
    InChI Key
    IFGIYSGOEZJNBE-KNLJMPJLSA-N
    Methylnaltrexone Bromide is the bromide salt form of methylnaltrexone, a methyl derivative of noroxymorphone with selective, peripherally-acting mu-opioid receptor antagonistic activity. Methylnaltrexone displaces opioids from peripheral opioid receptors in the gastrointestinal tract, the bladder, and the skin, thereby reversing the opioid-related peripheral side-effects, such as constipation, urinary retention, and pruritis, respectively. Unlike naltrexone and due to the presence of a positively charged nitrogen atom in methylnaltrexone, this agent does not cross the blood-brain barrier and does not affect the centrally-mediated analgesic effect of opioids.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one;bromide
    2.1.2 InChI
    InChI=1S/C21H25NO4.BrH/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;1H/t16-,19+,20+,21-,22?;/m1./s1
    2.1.3 InChI Key
    IFGIYSGOEZJNBE-KNLJMPJLSA-N
    2.1.4 Canonical SMILES
    C[N+]1(CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O)CC6CC6.[Br-]
    2.1.5 Isomeric SMILES
    C[N+]1(CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)CC6CC6.[Br-]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. (5alpha)-17-(cyclopropylmethyl)-3,14-dihydroxy-17-methyl-4,5-epoxymorphinan-17-ium-6-one

    2. 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinanium-6-one

    3. Methyl-naltrexone Hydrobromide

    4. Methylnaltrexone

    5. Morphinan-17-ium-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-, (5alpha)-

    6. Morphinan-17-ium-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-, Bromide, (5alpha,17r)-

    7. Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, (5alpha)-

    8. Mrz 2663br

    9. Mrz-2663

    10. N-methylnaltrexone Bromide

    11. Naltrexone Mb

    12. Naltrexone Methobromide

    13. Naltrexone Methylbromide

    14. Naltrexonium Methiodide

    15. Quaternary Ammonium Naltrexone

    16. Relistor

    2.2.2 Depositor-Supplied Synonyms

    1. Naltrexone Methobromide

    2. 73232-52-7

    3. Relistor

    4. Methylnaltrexone (bromide)

    5. Methylnaltrexone

    6. Moa-728

    7. N-methylnaltrexone Bromide

    8. Mrz-2663br

    9. Mntx

    10. Moa 728

    11. Relistor (tn)

    12. N-cyclopropylmethyl-noroxymorphone Methobromide

    13. Relistormoa-728

    14. Mntx-302

    15. Moa728

    16. Schembl2798188

    17. Chembl1201770

    18. Dtxsid30868236

    19. Ono-3849

    20. Methylnaltrexone Bromide (jan/usan)

    21. Akos015896214

    22. Cs-0762

    23. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one,bromide

    24. Ac-32482

    25. Hy-75766

    26. Methylnaltrexone Bromide, >=97% (hplc)

    27. D06618

    28. Methylnaltrexone Bromide, United States Pharmacopeia (usp) Reference Standard

    29. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one;bromide

    2.3 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 436.3 g/mol
    Molecular Formula C21H26BrNO4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass435.10452 g/mol
    Monoisotopic Mass435.10452 g/mol
    Topological Polar Surface Area66.8 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity664
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameRelistor
    PubMed HealthMethylnaltrexone (Injection)
    Drug ClassesGastrointestinal Agent
    Drug LabelRELISTOR (methylnaltrexone bromide) injection, a peripherally-acting mu-opioid receptor antagonist, is a sterile, clear and colorless to pale yellow aqueous solution. The chemical name for methylnaltrexone bromide is (R)-N-(cyclopropylmethyl) noroxym...
    Active IngredientMethylnaltrexone bromide
    Dosage FormInjectable; Solution
    RouteSubcutaneous
    Strength8mg/0.4ml; 12mg/0.6ml (12mg/0.6ml)
    Market StatusPrescription
    CompanySalix Pharms

    2 of 2  
    Drug NameRelistor
    PubMed HealthMethylnaltrexone (Injection)
    Drug ClassesGastrointestinal Agent
    Drug LabelRELISTOR (methylnaltrexone bromide) injection, a peripherally-acting mu-opioid receptor antagonist, is a sterile, clear and colorless to pale yellow aqueous solution. The chemical name for methylnaltrexone bromide is (R)-N-(cyclopropylmethyl) noroxym...
    Active IngredientMethylnaltrexone bromide
    Dosage FormInjectable; Solution
    RouteSubcutaneous
    Strength8mg/0.4ml; 12mg/0.6ml (12mg/0.6ml)
    Market StatusPrescription
    CompanySalix Pharms

    4.2 Drug Indication

    Treatment of opioid-induced constipation in advanced-illness patients who are receiving palliative care when response to usual laxative therapy has not been sufficient.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Narcotic Antagonists

    Agents inhibiting the effect of narcotics on the central nervous system. (See all compounds classified as Narcotic Antagonists.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Opioid Antagonists [MoA]; Quaternary Ammonium Compounds [CS]; Opioid Antagonist [EPC]
    5.3 ATC Code

    A06AH01

    A06AH01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    A - Alimentary tract and metabolism

    A06 - Drugs for constipation

    A06A - Drugs for constipation

    A06AH - Peripheral opioid receptor antagonists

    A06AH01 - Methylnaltrexone bromide