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    Naloxone

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    2D Structure
    Also known as: Naloxone hcl, 357-08-4, Narcan, Narcanti, Naloxone (hydrochloride), Evzio
    Molecular Formula
    C19H22ClNO4
    Molecular Weight
    363.8  g/mol
    InChI Key
    RGPDIGOSVORSAK-STHHAXOLSA-N
    FDA UNII
    F850569PQR
    A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;hydrochloride
    2.1.2 InChI
    InChI=1S/C19H21NO4.ClH/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11;/h2-4,14,17,21,23H,1,5-10H2;1H/t14-,17+,18+,19-;/m1./s1
    2.1.3 InChI Key
    RGPDIGOSVORSAK-STHHAXOLSA-N
    2.1.4 Canonical SMILES
    C=CCN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O.Cl
    2.1.5 Isomeric SMILES
    C=CCN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    F850569PQR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Abello, Naloxone

    2. Curamed, Naloxon

    3. Dihydride, Naloxone Hydrochloride

    4. Hydrobromide, Naloxone

    5. Hydrochloride Dihydride, Naloxone

    6. Hydrochloride, Naloxone

    7. Mrz 2593

    8. Mrz 2593 Br

    9. Mrz 2593-br

    10. Mrz 2593br

    11. Mrz-2593

    12. Mrz2593

    13. Nalone

    14. Naloxon Curamed

    15. Naloxon Ratiopharm

    16. Naloxon-ratiopharm

    17. Naloxone

    18. Naloxone Abello

    19. Naloxone Hydrobromide

    20. Naloxone Hydrochloride Dihydride

    21. Naloxone Hydrochloride, (5 Beta,9 Alpha,13 Alpha,14 Alpha)-isomer

    22. Naloxone, (5 Beta,9 Alpha,13 Alpha,14 Alpha)-isomer

    23. Narcan

    24. Narcanti

    2.3.2 Depositor-Supplied Synonyms

    1. Naloxone Hcl

    2. 357-08-4

    3. Narcan

    4. Narcanti

    5. Naloxone (hydrochloride)

    6. Evzio

    7. Nih 7890

    8. En-15304

    9. Anhydrous Naloxone Hydrochloride

    10. Chebi:31892

    11. F850569pqr

    12. Nsc-757109

    13. (-)-n-allyl-14-hydroxynordihydromorphinone Hydrochloride

    14. 357-08-4 (hcl)

    15. 17-allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    16. (5alpha)-17-allyl-4,5-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    17. (4r,4as,7ar,12bs)-3-allyl-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7ah)-one Hydrochloride

    18. Nalonee

    19. Mls000069540

    20. Naloxonehydrochloride

    21. Smr000058766

    22. Unii-f850569pqr

    23. Prestwick_879

    24. Einecs 206-611-0

    25. Mfcd00069322

    26. Narcan (tn)

    27. Kloxxado

    28. Evzio (tn)

    29. Nafoxone Hydrochloride

    30. Nal-oxon Hydrochloride

    31. Naloxone Hydrochloride [usan:usp:jan]

    32. En 15304

    33. Chembl1718

    34. C19h21no4.hcl

    35. Schembl41390

    36. L-n-allyl-14-hydroxynordihydromorphinone Hydrochloride

    37. Naloxone Hydrochloride Anhydrous

    38. Dtxsid70957097

    39. Hms1568g04

    40. Naloxone Hydrochloride [mi]

    41. Act02626

    42. Naloxone Hydrochloride (jp17/usp)

    43. Naloxone Hydrochloride [jan]

    44. (5a)-17-allyl-4,5-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    45. 17-allyl-4,5-alpha-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    46. Naloxone Hydrochloride [usan]

    47. Normorphinone, N-allyl-7,8-dihydro-14-hydroxy-, Hydrochloride, (-)-

    48. S3066

    49. Naloxone Hydrochloride [vandf]

    50. Akos024418753

    51. Morphinan-6-one, 17-allyl-4,5-alpha-epoxy-3,14-dihydroxy-, Hydrochloride

    52. Naloxone Hydrochloride [mart.]

    53. Ccg-220111

    54. Cs-1335

    55. Ks-5379

    56. Naloxone Hydrochloride [who-dd]

    57. Nc00587

    58. Nsc 757109

    59. Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, Hydrochloride, (5.alpha.)-

    60. Hy-17417

    61. Naloxone Hydrochloride [green Book]

    62. Naloxone Hydrochloride [orange Book]

    63. Sw197001-3

    64. Naloxone Hydrochloride [usp Monograph]

    65. D01340

    66. Suboxone Component Naloxone Hydrochloride

    67. Targiniq Component Naloxone Hydrochloride

    68. Naloxone Hydrochloride Anhydrous [who-ip]

    69. Talwin Nx Component Naloxone Hydrochloride

    70. 357n084

    71. Naloxone Hydrochloride Component Of Suboxone

    72. Naloxone Hydrochloride Component Of Targiniq

    73. Sr-01000597918

    74. Sr-01000737374

    75. Naloxone Hydrochloride Component Of Talwin Nx

    76. Sr-01000597918-1

    77. Sr-01000737374-3

    78. W-106655

    79. Q27114711

    80. Naloxoni Hydrochloridum Anhydrous [who-ip Latin]

    81. (5alpha)-17-allyl-3,14-dihydroxy-4,5-epoxymorphinan-6-one Hydrochloride

    82. 17-allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one Hydrochloride

    83. (17r)-17-allyl-3,14-dihydroxy-6-oxo-4,5alpha-epoxymorphinan-17-ium Chloride

    84. (5?)-4,5-epoxy-3,14-dihydro-17-(2-propenyl)morphinan-6-one Hydrochloride

    85. (5a)-4,5-epoxy-3,14-dihydroxy-17-(2-propen-1-yl)-morphinan-6-one Hydrochloride

    86. (5alpha)-4,5-epoxy-3,14-dihydroxy-17-(2-propen-1-yl)morphinan-6-one Hydrochloride (1:1)

    87. (5alpha,17r)-17-allyl-3,14-dihydroxy-6-oxo-4,5-epoxymorphinan-17-ium Chloride

    88. 17-allyl-4,5.alpha.-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride

    89. Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, Hydrochloride, (5alpha)-

    90. (4r,4as,12bs)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;hydrochloride

    91. (4r,4as,7ar,12bs)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;hydrochloride

    92. (5alpha)-4,5-epoxy-3,14-dihydro-17-(2-pr Openyl)morphinan-6-one Hydrochloride

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 363.8 g/mol
    Molecular Formula C19H22ClNO4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass363.1237359 g/mol
    Monoisotopic Mass363.1237359 g/mol
    Topological Polar Surface Area70 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity594
    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 4  
    Drug NameEvzio
    PubMed HealthNaloxone (Injection)
    Drug ClassesToxicology-Antidote Agent
    Drug LabelEVZIO (naloxone hydrochloride injection, USP) is a pre-filled, single-use auto-injector. EVZIO is not made with natural rubber latex. Chemically, naloxone hydrochloride is the hydrochloride salt of 17-Allyl-4,5-epoxy-3,14-dihydroxymorphinan-6-one h...
    Active IngredientNaloxone hydrochloride
    Dosage FormSolution
    RouteIntramuscular, subcutaneous
    Strength0.4mg/0.4ml
    Market StatusPrescription
    CompanyKaleo

    2 of 4  
    Drug NameNaloxone hydrochloride
    Drug LabelAmpul, Fliptop Vial, Opioid AntagonistProtect from light.RxNaloxone Hydrochloride Injection, USP is a sterile, nonpyrogenic solution of naloxone hydrochloride in water for injection. Each milliliter (mL) contains 0.4 mg naloxone hydrochloride and sod...
    Active IngredientNaloxone hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength1mg/ml; 0.4mg/ml
    Market StatusPrescription
    CompanyHospira; Intl Medication; Mylan Institutional

    3 of 4  
    Drug NameEvzio
    PubMed HealthNaloxone (Injection)
    Drug ClassesToxicology-Antidote Agent
    Drug LabelEVZIO (naloxone hydrochloride injection, USP) is a pre-filled, single-use auto-injector. EVZIO is not made with natural rubber latex. Chemically, naloxone hydrochloride is the hydrochloride salt of 17-Allyl-4,5-epoxy-3,14-dihydroxymorphinan-6-one h...
    Active IngredientNaloxone hydrochloride
    Dosage FormSolution
    RouteIntramuscular, subcutaneous
    Strength0.4mg/0.4ml
    Market StatusPrescription
    CompanyKaleo

    4 of 4  
    Drug NameNaloxone hydrochloride
    Drug LabelAmpul, Fliptop Vial, Opioid AntagonistProtect from light.RxNaloxone Hydrochloride Injection, USP is a sterile, nonpyrogenic solution of naloxone hydrochloride in water for injection. Each milliliter (mL) contains 0.4 mg naloxone hydrochloride and sod...
    Active IngredientNaloxone hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength1mg/ml; 0.4mg/ml
    Market StatusPrescription
    CompanyHospira; Intl Medication; Mylan Institutional

    4.2 Drug Indication

    Treatment of opioid-induced constipation

    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]; Opioid Antagonist [EPC]