Methylnaltrexone Bromide

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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

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

Methylnaltrexone Bromide

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 Formula	C₂₁H₂₆BrNO₄
Molecular Weight	436.3 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	435.10452 g/mol
Monoisotopic Mass	435.10452 g/mol
Topological Polar Surface Area	66.8 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	664
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Relistor
PubMed Health	Methylnaltrexone (Injection)
Drug Classes	Gastrointestinal Agent
Drug Label	RELISTOR (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 Ingredient	Methylnaltrexone bromide
Dosage Form	Injectable; Solution
Route	Subcutaneous
Strength	8mg/0.4ml; 12mg/0.6ml (12mg/0.6ml)
Market Status	Prescription
Company	Salix Pharms

2 of 2
Drug Name	Relistor
PubMed Health	Methylnaltrexone (Injection)
Drug Classes	Gastrointestinal Agent
Drug Label	RELISTOR (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 Ingredient	Methylnaltrexone bromide
Dosage Form	Injectable; Solution
Route	Subcutaneous
Strength	8mg/0.4ml; 12mg/0.6ml (12mg/0.6ml)
Market Status	Prescription
Company	Salix 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

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