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    Chemistry

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    Also known as: 366-70-1, Procarbazine hcl, Matulane, Nathulane, Natunalar, Natulan
    Molecular Formula
    C12H20ClN3O
    Molecular Weight
    257.76  g/mol
    InChI Key
    DERJYEZSLHIUKF-UHFFFAOYSA-N
    FDA UNII
    XH0NPH5ZX8
    Procarbazine Hydrochloride
    An antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease.
    1 2D Structure

    Procarbazine Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(2-methylhydrazinyl)methyl]-N-propan-2-ylbenzamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C12H19N3O.ClH/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3;/h4-7,9,13-14H,8H2,1-3H3,(H,15,16);1H
    2.1.3 InChI Key
    DERJYEZSLHIUKF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)NC(=O)C1=CC=C(C=C1)CNNC.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    XH0NPH5ZX8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Hydrochloride, Procarbazine

    2. Matulane

    3. Monohydrobromide, Procarbazine

    4. Monohydrochloride, Procarbazine

    5. Natulan

    6. Procarbazine

    7. Procarbazine Monohydrobromide

    8. Procarbazine Monohydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 366-70-1

    2. Procarbazine Hcl

    3. Matulane

    4. Nathulane

    5. Natunalar

    6. Natulan

    7. Ibenzmethyzine Hydrochloride

    8. Procarbazine.hcl

    9. Mih Hydrochloride

    10. Pcb Hydrochloride

    11. Procarbazine (hydrochloride)

    12. Nsc-77213

    13. Nci-c01810

    14. N-isopropyl-4-((2-methylhydrazinyl)methyl)benzamide Hydrochloride

    15. Ro 4-6467/1

    16. Chebi:71428

    17. Xh0nph5zx8

    18. P-(n'-methylhydrazinomethyl)-n-isopropylbenzamide Hydrochloride

    19. 366-70-1 (hcl)

    20. Nsc-77213 Hcl

    21. Mbh

    22. 1-(p-isopropylcarbamoylbenzyl)-2-methylhydrazine Hydrochloride

    23. 1-methyl-2-(p-isopropylcarbamoylbenzyl)hydrazine Hydrochloride

    24. 1-methyl-2-p-(isopropylcarbamoyl)benzohydrazine Hydrochloride

    25. N-isopropyl-p-(2-methylhydrazinomethyl)benzamide Hydrochloride

    26. Nsc 77213

    27. 2-(p-(isopropylcarbamoyl)benzyl)-1-methylhydrazine Hydrochloride

    28. N-isopropyl-alpha-(2-methylhydrazino)-p-toluamide Hydrochloride

    29. Ro-4-6467 Hydrochloride

    30. Nsc77213

    31. Nci-c 01810

    32. Nci-c-01810

    33. Benzamide, N-(1-methylethyl)-4-((2-methylhydrazino)methyl)-, Monohydrochloride

    34. Procarbazine Hydrochloride (matulane)

    35. Ro-46467/1

    36. Ro 4 6467/1

    37. 4-[(2-methylhydrazinyl)methyl]-n-propan-2-ylbenzamide;hydrochloride

    38. Dsstox_cid_1190

    39. N-(1-methylethyl)-4-[(2-methylhydrazino)methyl]benzamide Hydrochloride

    40. Dsstox_rid_76000

    41. Dsstox_gsid_21190

    42. Natulan Hydrochloride

    43. Procarbazine Chloridrate

    44. Ibenzmethyzin Hydrochloride

    45. 4-[(2-methylhydrazin-1-yl)methyl]-n-(propan-2-yl)benzamide Hydrochloride

    46. Ccris 531

    47. Ncgc00016438-01

    48. Ro-4646711

    49. Cas-366-70-1

    50. Ibz

    51. Ro-4-6467/1

    52. Einecs 206-678-6

    53. Unii-xh0nph5zx8

    54. Ai3-50844

    55. Sr-01000763375

    56. Matulane (tn)

    57. Mfcd00072082

    58. N-isopropyl-4-[(2-methylhydrazino)methyl]benzamide Hydrochloride

    59. Procarbazine Hydrochloride [usan:usp:jan]

    60. N-isopropyl-alpha-(2-methylhydrazino)-p-toluamide Monohydrochloride

    61. P-toluamide, N-isopropyl-alpha-(2-methylhydrazino)-, Hydrochloride

    62. Procarbazini Hydrochloridum

    63. Chlorhydrate De 1-methyl 2 P (isopropylcarbamoyl)benzyl-hydrazine [french]

    64. Schembl4012

    65. Methyl)benzamide Hydrochloride

    66. Procarbazine Monohydrochloride

    67. Mls001401414

    68. P-toluamide, Monohydrochloride

    69. Chembl1200410

    70. Dtxsid3021190

    71. Amy8865

    72. Hms1571o06

    73. Bcp02880

    74. Chlorhydrate De 1-methyl 2 P (isopropylcarbamoyl)benzyl-hydrazine

    75. Procarbazine Hydrochloride (natulan)

    76. Tox21_110439

    77. Tox21_302318

    78. Bdbm50247906

    79. P-toluamide, N-isopropyl-alpha-(2-methylhydrazino)-, Monohydrochloride

    80. S1995

    81. Wln: 1y1&mvr D1mm1 &gh

    82. N-isopropyl-4-((2-methylhydrazinyl)

    83. Akos015895395

    84. Tox21_110439_1

    85. Ccg-100985

    86. Nc00235

    87. Procarbazine Hydrochloride (jp17/usp)

    88. Procarbazine Hydrochloride [mi]

    89. Procarbazine Hydrochloride [jan]

    90. Ncgc00016438-04

    91. Ncgc00255389-01

    92. Procarbazine Hydrochloride [iarc]

    93. Procarbazine Hydrochloride [usan]

    94. Ac-12163

    95. As-13285

    96. Bp164298

    97. Hy-13733

    98. Procarbazine Hydrochloride [mart.]

    99. Procarbazine Hydrochloride [vandf]

    100. Ro 4-646711

    101. Smr000469151

    102. Bcp0726000264

    103. Procarbazine Hydrochloride [usp-rs]

    104. Procarbazine Hydrochloride [who-dd]

    105. Procarbazine Hydrochloride [who-ip]

    106. Db-048987

    107. Procarbazine Hydrochloride, >=98% (hplc)

    108. Ft-0603386

    109. P2550

    110. C07376

    111. D00478

    112. Procarbazine Hydrochloride [orange Book]

    113. 366p701

    114. A823326

    115. Procarbazine Hydrochloride [usp Monograph]

    116. Procarbazini Hydrochloridum [who-ip Latin]

    117. Sr-01000763375-4

    118. Q26840941

    119. Z1550675463

    120. 4-[(methylhydrazo)methyl]-n-propan-2-ylbenzamide Hydrochloride

    121. Methyl-[[4-(propan-2-ylcarbamoyl)phenyl]methylamino]azanium;chloride

    122. N-isopropyl-4-((2-methylhydrazinyl)methyl)benzamidehydrochloride

    123. 4-[(2-methyl-hydrazino)-methyl]-benzoic Acid Isopropylamide Hydrochloride

    124. 4-[(2-methylhydrazinyl)methyl]-n-propan-2-yl-benzamide Hydrochloride

    125. N-isopropyl-.alpha.-(2-methylhydrazino)-p-toluamide Monohydrochloride

    126. Procarbazine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 257.76 g/mol
    Molecular Formula C12H20ClN3O
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass257.1294900 g/mol
    Monoisotopic Mass257.1294900 g/mol
    Topological Polar Surface Area53.2 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity210
    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 NameMatulane
    PubMed HealthProcarbazine (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelMatulane (procarbazine hydrochloride), a hydrazine derivative antineoplastic agent, is available as capsules containing the equivalent of 50 mg procarbazine as the hydrochloride. Each capsule also contains cornstarch, mannitol and talc. Gelatin capsu...
    Active IngredientProcarbazine hydrochloride
    Dosage FormCapsule
    RouteOral
    Strengtheq 50mg base
    Market StatusPrescription
    CompanySigma Tau

    2 of 2  
    Drug NameMatulane
    PubMed HealthProcarbazine (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelMatulane (procarbazine hydrochloride), a hydrazine derivative antineoplastic agent, is available as capsules containing the equivalent of 50 mg procarbazine as the hydrochloride. Each capsule also contains cornstarch, mannitol and talc. Gelatin capsu...
    Active IngredientProcarbazine hydrochloride
    Dosage FormCapsule
    RouteOral
    Strengtheq 50mg base
    Market StatusPrescription
    CompanySigma Tau

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Alkylating Drug [EPC]; Alkylating Activity [MoA]

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