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    Technical details about Uracil Mustard, learn more about the structure, uses, toxicity, action, side effects and more

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    Uracil Mustard

    APIs // Active Pharmaceutical Ingredients

    DOSSIERs // Finished Dosage Forms

    DIGITAL CONTENT

    PharmaCompass

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    2D Structure
    Also known as: Uramustine, 66-75-1, Desmethyldopan, Aminouracil mustard, Demethyldopan, Uramustin
    Molecular Formula
    C8H11Cl2N3O2
    Molecular Weight
    252.09  g/mol
    InChI Key
    IDPUKCWIGUEADI-UHFFFAOYSA-N
    FDA UNII
    W7KQ46GJ8U
    Nitrogen mustard derivative of URACIL. It is a alkylating antineoplastic agent that is used in lymphatic malignancies, and causes mainly gastrointestinal and bone marrow damage.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[bis(2-chloroethyl)amino]-1H-pyrimidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)
    2.1.3 InChI Key
    IDPUKCWIGUEADI-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=C(C(=O)NC(=O)N1)N(CCCl)CCCl
    2.2 Other Identifiers
    2.2.1 UNII
    W7KQ46GJ8U
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-(bis(2-chloroethyl)amino)-2,4-(1h,3h)pyrimidinedione

    2. Mustard, Uracil

    3. Uramustine

    2.3.2 Depositor-Supplied Synonyms

    1. Uramustine

    2. 66-75-1

    3. Desmethyldopan

    4. Aminouracil Mustard

    5. Demethyldopan

    6. Uramustin

    7. Chlorethaminacil

    8. Uracil Nitrogen Mustard

    9. Uracilmostaza

    10. Nordopan

    11. Uracillost

    12. 5-aminouracil Mustard

    13. 5-bis(2-chloroethyl)aminouracil

    14. 5-n,n-bis(2-chloroethyl)aminouracil

    15. U-8344

    16. Nsc-34462

    17. 5-(di-2-chloroethyl)aminouracil

    18. 5-[bis(2-chloroethyl)amino]uracil

    19. Uracil Mustard [usan]

    20. Ent 50439

    21. Cb-4835

    22. Rcra Waste Number U237

    23. Nci-c04820

    24. Sk-19849

    25. 5-(bis(2-chloroethyl)amino)uracil

    26. 2,6-dihydroxy-5-bis[2-chloroethyl]aminopyrimidine

    27. 5-[di(beta-chloroethyl)amino]uracil

    28. Uramustine (inn)

    29. Uramustine [inn]

    30. U 8344

    31. 5-[bis(2-chloroethyl)amino]-1h-pyrimidine-2,4-dione

    32. 5-(bis(2-chlorethyl)amino)-2,4(1h,3h)pyrimidinedione

    33. Uracil Mustard (usan)

    34. 5-(bis(2-chloroethyl)amino)-2,4(1h,3h)pyrimidinedione

    35. 2,4(1h,3h)-pyrimidinedione, 5-(bis(2-chloroethyl)amino)-

    36. 2,6-dihydroxy-5-bis(2-chloroethyl)aminopyrimidine

    37. Uracil, 5-(bis(2-chloroethyl)amino)-

    38. W7kq46gj8u

    39. Chebi:9884

    40. 5-[di(2-chloroethyl)amino]uracil

    41. 5-[di(.beta.-chloroethyl)amino]uracil

    42. Uracil, 5-[bis(2-chloroethyl)amino]-

    43. 5-[bis(2-chloroethyl)amino]-2,4(1h,3h)-pyrimidinedione

    44. Ncgc00160575-01

    45. Uramustinum

    46. 2,4(1h,3h)-pyrimidinedione, 5-[bis(2-chloroethyl)amino]-

    47. Uramustina

    48. Uracil Lost

    49. Uracil Lost [german]

    50. Uramustinum [inn-latin]

    51. Uramustina [inn-spanish]

    52. 5-(bis(2-chloroethyl)amino)pyrimidine-2,4(1h,3h)-dione

    53. 5-[bis(2-chloroethyl)amino]pyrimidine-2,4(1h,3h)-dione

    54. 5-(di(2-chloroethyl)amino)uracil

    55. 5-(di-(beta-chloroethyl)amino)uracil

    56. Ccris 618

    57. Uracil Mustard (tn)

    58. Hsdb 3261

    59. Einecs 200-631-3

    60. Nsc 34462

    61. Rcra Waste No. U237

    62. Unii-w7kq46gj8u

    63. Uracil Mustard [usan:usp]

    64. Uracil-mustard

    65. Ai3-50439

    66. 5-[bis(2-chloroethyl)amino]pyrimidine-2,4-diol

    67. Dsstox_cid_6270

    68. Schembl4091

    69. Uramustine [mart.]

    70. Chembl1488

    71. Dsstox_rid_78084

    72. Uracil Mustard [mi]

    73. Uramustine [who-dd]

    74. Dsstox_gsid_26270

    75. Mls003899236

    76. Uracil Mustard [hsdb]

    77. Uracil Mustard [iarc]

    78. Wln: T6mvmvj En2g2g

    79. Uracil Mustard [vandf]

    80. Gtpl7621

    81. Zinc2235

    82. Dtxsid8026270

    83. Schembl19915183

    84. Bcp27982

    85. Nsc34462

    86. Tox21_111911

    87. Mfcd00233542

    88. Uracil Mustard [orange Book]

    89. Akos015850649

    90. Akos024332500

    91. Cs-5184

    92. Db00791

    93. Cas-66-75-1

    94. Uracil, 5-[bis(2-chloroethyl)-amino]-

    95. Hy-13544

    96. Nci60_003061

    97. Smr002543516

    98. Db-005369

    99. Ft-0602268

    100. 5-(bis-(2-chloroethyl)-amino)-uracil

    101. D06265

    102. Ab01273928-01

    103. 5-[bis(2-chlorethyl)amino]-2,3h)pyrimidinedione

    104. A835541

    105. 2,3h)-pyrimidinedione, 5-[bis(2-chloroethyl)amino]-

    106. 2,6-dihydroxy-5-[bis(2-chloroethyl)amino]pyrimidine

    107. Q15211075

    108. Uracil Mustard (500 Mg) (for U.s. Sale Only)

    109. 5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 252.09 g/mol
    Molecular Formula C8H11Cl2N3O2
    XLogP30.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass251.0228320 g/mol
    Monoisotopic Mass251.0228320 g/mol
    Topological Polar Surface Area61.4 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity288
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Antineoplastic Agents, Alkylating

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    URACIL MUSTARD HAS BEEN TESTED IN LAB ANIMALS AS IMMUNOSUPRESSIVE AGENT & AGAINST INFLUENZA & VACCINIA VIRUSES & CERTAIN STRAINS OF BACTERIA.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V9 236 (1975)

    IT MAY BE USED IN PALLIATIVE TREATMENT OF CHRONIC LYMPHOCYTIC LEUKEMIA, MALIGNANT LYMPHOMAS, & HODGKIN'S DISEASE. URACIL MUSTARD ALSO IS EFFECTIVE IN CHRONIC MYELOCYTIC LEUKEMIA & IMPROVEMENT HAS BEEN REPORTED IN OCCASIONAL CASES OF POLYCYTHEMIA VERA, MYCOSIS FUNGOIDES, & OVARIAN CARCINOMA.

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1117

    Uracil mustard has been used for the following indications, although use has generally been replaced by that of more effective agents: for palliative treatment of chronic lymphocytic and myelocytic leukemia; for palliative treatment of non-Hodgkin's lymphomas of the histiocytic or lymphocytic type; for palliative treatment of mycosis fungoides; for palliative treatment of the early stages of polycythemia vera before the development of leukemia or myelofibrosis. /Included in US product labeling/

    USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 2938

    For more Therapeutic Uses (Complete) data for URACIL MUSTARD (6 total), please visit the HSDB record page.

    4.2 Drug Warning

    AGENT IS CONTRAINDICATED IN PRESENCE OF PRONOUNCED LEUKOPENIA, THROMBOCYTOPENIA, OR APLASTIC ANEMIA & SHOULD NOT BE USED DURING FIRST TRIMESTER OF PREGNANCY TO AVOID POSSIBLE & POTENTIAL DAMAGING EFFECTS ON FETUS.

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1117

    SERUM URIC ACID LEVELS SHOULD BE MEASURED REGULARLY TO AVOID POSSIBLE HYPERURICEMIC NEPHROPATHY & ACUTE RENAL FAILURE. HEMATOPOIETIC EFFECTS ... ARE CUMULATIVE ... COMPLETE BLOOD CELL COUNTS SHOULD BE MADE ONCE WEEKLY DURING 1ST MO OF THERAPY ...

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1117

    EXTREME CAUTION IS INDICATED WHEN THERE IS DECR IN RBC COUNT OR HEMOGLOBIN LEVEL OF 30% OR MORE BELOW PRETREATMENT LEVEL. DRUG SHOULD BE WITHDRAWN IMMEDIATELY IF THERE IS SHARP FALL IN COUNT OF ANY OF FORMED ELEMENTS. AMBULATORY PT SHOULD NOT RECEIVE MORE THAN 1-WK SUPPLY OF DRUG @ ANY VISIT.

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1117

    URACIL MUSTARD SHOULD NOT BE ADMIN FOR SEVERAL WK AFTER COMPLETING COURSE OF TREATMENT WITH ANOTHER CYTOTOXIC DRUG OR RADIATION, SINCE IT IS ESSENTIAL TO ALLOW BONE MARROW FUNCTION TO RETURN TO SATISFACTORY LEVELS.

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1117

    For more Drug Warnings (Complete) data for URACIL MUSTARD (9 total), please visit the HSDB record page.

    4.3 Drug Indication

    Used for its antineoplastic properties.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Uracil Mustard selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Uracil Mustard-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents, Alkylating

    A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)

    5.3 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01A - Alkylating agents

    L01AD - Nitrosoureas

    L01AD08 - Uramustine

    5.4 Absorption, Distribution and Excretion

    URACIL MUSTARD IS ABSORBED QUICKLY BUT NOT COMPLETELY AFTER ORAL ADMIN IN DOGS. CONCN IN PLASMA DECLINED AFTER EITHER ORAL (2 MG/KG) OR IV (1 MG/KG) ADMIN, & NO EVIDENCE OF DRUG WAS DETECTED @ 2 HR. LESS THAN 1% OF ADMIN DOSE WAS RECOVERED UNCHANGED IN URINE.

    Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1258

    2-(14)C-URACIL MUSTARD WAS ADMIN @ DOSE OF 4 MG TO 265 WALKER CARCINOSARCOMA BEARING HOLZMAN RATS. INCORPORATION OF (14)C LABEL INTO MACROMOLECULES IN SUBCELLULAR FRACTIONS OF VARIOUS TISSUES WAS MEASURED FOR 6 HR AFTER ADMIN AND WAS GENERALLY FOUND TO BE MAXIMAL BY 1 HR & TO BE MORE EXTENSIVE IN RNA THAN IN DNA OR PROTEIN.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V9 239 (1975)

    THE REACTION OF 0.2 UMOLES/ML URACIL MUSTARD WITH HEPARINIZED HUMAN BLOOD @ 37 C IN VITRO WAS MEASURED COLORIMETRICALLY: ABOUT 50% OR ORIGINAL DRUG WAS NO LONGER DETECTABLE AFTER 30 MIN.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V9 239 (1975)

    5.5 Mechanism of Action

    After activation, it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.

    ... ITS ANTINEOPLASTIC EFFECTS ARE STRICTLY THOSE OF ITS BIS-CHLOROETHYLAMINE MOIETY.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1085

    Uracil mustard, as an alkylating agent, interferes with DNA replication and transcription of RNA, and ultimately results in the disruption of nucleic acid function.

    McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 795

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