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    Naltrexone Hydrochloride

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    2D Structure
    Also known as: Naltrexone hcl, 16676-29-2, Trexan, Depade, Antaxone, Revia
    Molecular Formula
    C20H24ClNO4
    Molecular Weight
    377.9  g/mol
    InChI Key
    RHBRMCOKKKZVRY-ITLPAZOVSA-N
    FDA UNII
    Z6375YW9SF
    Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.
    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-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;hydrochloride
    2.1.2 InChI
    InChI=1S/C20H23NO4.ClH/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11;/h3-4,11,15,18,22,24H,1-2,5-10H2;1H/t15-,18+,19+,20-;/m1./s1
    2.1.3 InChI Key
    RHBRMCOKKKZVRY-ITLPAZOVSA-N
    2.1.4 Canonical SMILES
    C1CC1CN2CCC34C5C(=O)CCC3(C2CC6=C4C(=C(C=C6)O)O5)O.Cl
    2.1.5 Isomeric SMILES
    C1CC1CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    Z6375YW9SF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Antaxone

    2. Celupan

    3. En 1639a

    4. En-1639a

    5. En1639a

    6. Nalorex

    7. Naltrexone

    8. Nemexin

    9. Revia

    10. Trexan

    2.3.2 Depositor-Supplied Synonyms

    1. Naltrexone Hcl

    2. 16676-29-2

    3. Trexan

    4. Depade

    5. Antaxone

    6. Revia

    7. Naltrexone (hydrochloride)

    8. En-1639a

    9. Nih 8503

    10. Celupan

    11. Nemexin

    12. N-cyclopropylmethyl-noroxymorphone Hydrochloride

    13. Mls000069607

    14. Naltrexone Hydrochloride [usp]

    15. Z6375yw9sf

    16. Vivitrex

    17. 17-(cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy-morphinan-6-one Hydrochloride

    18. Nalorex

    19. Smr000058767

    20. En-1639a (as Hydrochloride)

    21. En 1639a

    22. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;hydrochloride

    23. Naltrexone Hydrochloride (usp)

    24. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7ah)-one Hydrochloride

    25. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, Hydrochloride (1:1), (5alpha)-

    26. Ccris 1168

    27. Einecs 240-723-0

    28. Unii-z6375yw9sf

    29. Naltrel

    30. Naltrexone.hcl

    31. Naltrexone Depot

    32. Prestwick_348

    33. Mfcd00069324

    34. (5alpha)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    35. Revia (tn)

    36. Xr-ntx

    37. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride

    38. Opera_id_1828

    39. Naltrexone Monohydrochloride

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

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

    42. Schembl37713

    43. Mls001076516

    44. Mls002153483

    45. Mls002695940

    46. Cyto-205

    47. Chembl1201149

    48. Dtxsid50937236

    49. Pti-901

    50. Chebi:134687

    51. Bcp08343

    52. Naltrexone Hydrochloride [mi]

    53. S2103

    54. Vp-004

    55. Akos015994597

    56. Ccg-268383

    57. Cs-0763

    58. Hs-0003

    59. Nc00693

    60. 17-cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    61. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-alpha-oxy-3,14-dihydoxy-, Hydrochloride

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

    63. Naltrexone Hydrochloride [mart.]

    64. Naltrexone Hydrochloride [vandf]

    65. Naltrexone Hydrochloride [who-dd]

    66. Bn164635

    67. Hy-76710

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

    69. N1176

    70. Naltrexone Hydrochloride [green Book]

    71. Sw196619-3

    72. Naltrexone Hydrochloride [orange Book]

    73. D02095

    74. Embeda Component Naltrexone Hydrochloride

    75. H10489

    76. Naltrexone Hydrochloride [ep Monograph]

    77. Naltrexone Hydrochloride [usp Monograph]

    78. Troxyca Component Naltrexone Hydrochloride

    79. 676n292

    80. Contrave Component Naltrexone Hydrochloride

    81. Naltrexone Hydrochloride Component Of Embeda

    82. Naltrexone Hydrochloride Component Of Troxyca

    83. Naltrexone Hydrochloride Component Of Contrave

    84. Q27096434

    85. Z1558290144

    86. Naltrexone Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

    87. Naltrexone Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    88. (5a)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-morphinan-6-one Hydrochloride

    89. 17-(cyclopropylmethyl)-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one Hydrochloride

    90. 17-cyclopropylmethyl)-4,5.alpha.-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    91. (1s,5r,13r,17s)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one Hydrochloride

    92. (4r,4as,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;hydron;chloride

    93. (5alpha,17r)-17-(cyclopropylmethyl)-3,14-dihydroxy-6-oxo-4,5-epoxymorphinan-17-ium Chloride

    94. Morphinan-6-one, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-, (5.alpha.)-, Hydrochloride (1:1)

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 377.9 g/mol
    Molecular Formula C20H24ClNO4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass377.1393859 g/mol
    Monoisotopic Mass377.1393859 g/mol
    Topological Polar Surface Area70 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity621
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameNaltrexone hydrochloride
    PubMed HealthNaltrexone
    Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
    Drug LabelNaltrexone hydrochloride, an opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone differs in structure from oxymorphone in that the methyl group on the nitrogen atom is replaced by a cyclopropylmethy...
    Active IngredientNaltrexone hydrochloride
    Dosage FormTablet
    RouteOral
    Strength25mg; 100mg; 50mg
    Market StatusPrescription
    CompanyAccord Hlthcare; Mallinckrodt; Sun Pharma Global; Elite Labs; Barr

    2 of 6  
    Drug NameRevia
    PubMed HealthNaltrexone
    Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
    Drug LabelREVIA (naltrexone hydrochloride tablets USP), an opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone differs in structure from oxymorphone in that the methyl group on the nitrogen atom is replaced...
    Active IngredientNaltrexone hydrochloride
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyTeva Womens

    3 of 6  
    Drug NameVivitrol
    Active IngredientNaltrexone
    Dosage FormFor suspension, extended release
    RouteIntramuscular
    Strength380mg/vial
    Market StatusPrescription
    CompanyAlkermes

    4 of 6  
    Drug NameNaltrexone hydrochloride
    PubMed HealthNaltrexone
    Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
    Drug LabelNaltrexone hydrochloride, an opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone differs in structure from oxymorphone in that the methyl group on the nitrogen atom is replaced by a cyclopropylmethy...
    Active IngredientNaltrexone hydrochloride
    Dosage FormTablet
    RouteOral
    Strength25mg; 100mg; 50mg
    Market StatusPrescription
    CompanyAccord Hlthcare; Mallinckrodt; Sun Pharma Global; Elite Labs; Barr

    5 of 6  
    Drug NameRevia
    PubMed HealthNaltrexone
    Drug ClassesEthanol Dependency, Opioid Dependency, Toxicology-Antidote Agent
    Drug LabelREVIA (naltrexone hydrochloride tablets USP), an opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone differs in structure from oxymorphone in that the methyl group on the nitrogen atom is replaced...
    Active IngredientNaltrexone hydrochloride
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyTeva Womens

    6 of 6  
    Drug NameVivitrol
    Active IngredientNaltrexone
    Dosage FormFor suspension, extended release
    RouteIntramuscular
    Strength380mg/vial
    Market StatusPrescription
    CompanyAlkermes

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Alcohol Deterrents

    Substances interfering with the metabolism of ethyl alcohol, causing unpleasant side effects thought to discourage the drinking of alcoholic beverages. Alcohol deterrents are used in the treatment of alcoholism. (See all compounds classified as Alcohol Deterrents.)

    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]; Opioid Antagonist [EPC]