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Chemistry

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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

Naltrexone Methobromide
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

Naltrexone Methobromide

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


API Reference Price

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14-Feb-2022
19-Mar-2022
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