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    Chemistry

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    Also known as: 614-39-1, Procainamide hcl, Pronestyl, Procanbid, Procapan, Procan
    Molecular Formula
    C13H22ClN3O
    Molecular Weight
    271.78  g/mol
    InChI Key
    ABTXGJFUQRCPNH-UHFFFAOYSA-N
    FDA UNII
    SI4064O0LX
    Procainamide Hydrochloride
    A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.
    1 2D Structure

    Procainamide Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-amino-N-[2-(diethylamino)ethyl]benzamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C13H21N3O.ClH/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11;/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17);1H
    2.1.3 InChI Key
    ABTXGJFUQRCPNH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCN(CC)CCNC(=O)C1=CC=C(C=C1)N.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    SI4064O0LX
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Amide, Procaine

    2. Apo-procainamide

    3. Biocoryl

    4. Hydrochloride, Procainamide

    5. Novocainamide

    6. Novocamid

    7. Procainamide

    8. Procaine Amide

    9. Procamide

    10. Procan

    11. Procan Sr

    12. Procanbid

    13. Pronestyl

    14. Rhythmin

    2.3.2 Depositor-Supplied Synonyms

    1. 614-39-1

    2. Procainamide Hcl

    3. Pronestyl

    4. Procanbid

    5. Procapan

    6. Procan

    7. Procan Sr

    8. 4-amino-n-[2-(diethylamino)ethyl]benzamide Hydrochloride

    9. Procainamide (hydrochloride)

    10. Pronestyl-sr

    11. Amidoprocaine

    12. Cardiorytmin

    13. Benzamide, 4-amino-n-[2-(diethylamino)ethyl]-, Monohydrochloride

    14. 4-amino-n-[2-(diethylamino)ethyl]benzamide;hydrochloride

    15. Nsc-757279

    16. Mls000069436

    17. Chebi:8429

    18. Si4064o0lx

    19. Benzamide, 4-amino-n-(2-(diethylamino)ethyl)-, Monohydrochloride

    20. Smr000059079

    21. Procainhydrochlorid

    22. Procainii Chloridum

    23. Promide Hydrochloride

    24. Procapan Hydrochloride

    25. Novocamid Hydrochloride

    26. Procamide Hydrochloride

    27. Procardyl Hydrochloride

    28. 4-amino-n-(2-(diethylamino)ethyl)benzamide Hydrochloride

    29. Procan-sr Hydrochloride

    30. Procaine Amide Hydrochloride

    31. Supicane Amide Hydrochloride

    32. Procainamidehydrochloride

    33. Ccris 7143

    34. 4-amino-n-(2-diethylaminoethyl)benzamide Hydrochloride

    35. Sr-01000000022

    36. Cas-614-39-1

    37. Einecs 210-381-7

    38. Mfcd00012998

    39. 7699-39-0

    40. Unii-si4064o0lx

    41. Procanbid (tn)

    42. Pronestyl (tn)

    43. Procainamide Hydrochloride [usp:jan]

    44. Procan Sr (tn)

    45. 4-aminobenzoesaeure-2-diethylaminoethylester Hydrochlorid

    46. P-amino-n-(2-(diethylamino)ethyl)benzamide Hydrochloride

    47. Pronestyl Hydrochloride

    48. 4-amino-n-(2-(diethylamino)ethyl)benzamide Monohydrochloride

    49. P-amino-n-(2-(diethylamino)ethyl)benzamide Monohydrochloride

    50. Opera_id_1543

    51. Procainamidi Hydrochloridum

    52. Chembl605

    53. Epitope Id:140114

    54. Dsstox_cid_29382

    55. Dsstox_rid_83497

    56. Dsstox_gsid_49422

    57. Schembl40758

    58. Mls001148635

    59. Spectrum1500503

    60. Dtxsid2049422

    61. Benzamide, P-amino-n-(2-(diethylamino)ethyl)-, Hydrochloride

    62. Hms1569c15

    63. Hms1920l04

    64. Pharmakon1600-01500503

    65. Act08464

    66. Amy22225

    67. Bcp28404

    68. Hy-a0084

    69. Tox21_202855

    70. Tox21_500995

    71. Ccg-39233

    72. Nsc757279

    73. S4294

    74. Akos008056264

    75. Ac-7552

    76. Ks-5258

    77. Lp00995

    78. Nc00535

    79. Nsc 757279

    80. Procainamide Hydrochloride (jp17/usp)

    81. Procainamide Hydrochloride [mi]

    82. Procainamide Hydrochloride [jan]

    83. Ncgc00094291-01

    84. Ncgc00094291-02

    85. Ncgc00094291-03

    86. Ncgc00094291-04

    87. Ncgc00094291-05

    88. Ncgc00260401-01

    89. Ncgc00261680-01

    90. Procainamide Hydrochloride [mart.]

    91. Procainamide Hydrochloride [vandf]

    92. Procainamide Hydrochloride [usp-rs]

    93. Procainamide Hydrochloride [who-dd]

    94. Procainamide Hydrochloride [who-ip]

    95. Db-053889

    96. Procainamide Hydrochloride, >=98% (hplc)

    97. Eu-0100995

    98. Ft-0603493

    99. Sw196878-3

    100. Vu0239777-5

    101. A14240

    102. Bim-0050968.0001

    103. D00477

    104. D97622

    105. P 9391

    106. Procainamide Hydrochloride [orange Book]

    107. 4-amino-n-(2-diethylamino-ethyl)-benzamide Hcl

    108. Procainamide Hydrochloride [ep Monograph]

    109. Procainamide Hydrochloride [usp Monograph]

    110. Procainamidi Hydrochloridum [who-ip Latin]

    111. Procainamide Hydrochloride, Purum, >=98.0% (at)

    112. Sr-01000000022-2

    113. Sr-01000000022-6

    114. W-105155

    115. Procainamide Hydrochloride 100 Microg/ml In Methanol

    116. Q27108080

    117. F0850-6742

    118. 4-amino-n-[2'-(diethylamino)ethyl]benzamide Hydrochloride

    119. 4-amino-n-[2-(diethylamino)ethyl]-benzamide Hydrochloride

    120. P-amino-n-(2-(diethylamino)ethy)benzamide Monohydrochloride

    121. Benzamide, 4-amino-n-(2-(diethylamino)ethyl)-, Hydrochloride (1:1)

    122. Procainamide Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    123. 4-amino-n-(2-(diethylamino)ethyl)benzamide Monohydrochloride [who-ip]

    124. Procainamide Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

    125. Procainamide Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 271.78 g/mol
    Molecular Formula C13H22ClN3O
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count6
    Exact Mass271.1451400 g/mol
    Monoisotopic Mass271.1451400 g/mol
    Topological Polar Surface Area58.4 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity221
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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 2  
    Drug NameProcainamide hydrochloride
    Drug LabelProcainamide Hydrochloride Injection, USP is a sterile, nonpyrogenic solution of procainamide hydrochloride in water for injection. Each milliliter of the 2 mL vial contains procainamide hydrochloride 500 mg; methylparaben 1 mg and sodium metabisulfi...
    Active IngredientProcainamide hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength500mg/ml; 100mg/ml
    Market StatusPrescription
    CompanyHospira

    2 of 2  
    Drug NameProcainamide hydrochloride
    Drug LabelProcainamide Hydrochloride Injection, USP is a sterile, nonpyrogenic solution of procainamide hydrochloride in water for injection. Each milliliter of the 2 mL vial contains procainamide hydrochloride 500 mg; methylparaben 1 mg and sodium metabisulfi...
    Active IngredientProcainamide hydrochloride
    Dosage FormInjectable
    RouteInjection
    Strength500mg/ml; 100mg/ml
    Market StatusPrescription
    CompanyHospira

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Arrhythmia Agents

    Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

    Voltage-Gated Sodium Channel Blockers

    A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Antiarrhythmic [EPC]

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