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Chemistry

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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

Uracil Mustard
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

Uracil Mustard

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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DMF Number : 9908

Submission : 1992-10-14

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URACIL MUSTARD

Brand Name : URACIL MUSTARD

Dosage Form : CAPSULE;ORAL

Dosage Strength : 1MG

Packaging :

Approval Date : 1982-01-01

Application Number : 12892

Regulatory Info : DISCN

Registration Country : USA

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URACIL MUSTARD

Brand Name : URACIL MUSTARD

Dosage Form : CAPSULE;ORAL

Dosage Strength : 1MG

Approval Date : 1982-01-01

Application Number : 12892

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

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ABOUT THIS PAGE

Uracil Mustard Manufacturers

A Uracil Mustard manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Uracil Mustard, including repackagers and relabelers. The FDA regulates Uracil Mustard manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Uracil Mustard API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Uracil Mustard Suppliers

A Uracil Mustard supplier is an individual or a company that provides Uracil Mustard active pharmaceutical ingredient (API) or Uracil Mustard finished formulations upon request. The Uracil Mustard suppliers may include Uracil Mustard API manufacturers, exporters, distributors and traders.

click here to find a list of Uracil Mustard suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Uracil Mustard USDMF

A Uracil Mustard DMF (Drug Master File) is a document detailing the whole manufacturing process of Uracil Mustard active pharmaceutical ingredient (API) in detail. Different forms of Uracil Mustard DMFs exist exist since differing nations have different regulations, such as Uracil Mustard USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Uracil Mustard DMF submitted to regulatory agencies in the US is known as a USDMF. Uracil Mustard USDMF includes data on Uracil Mustard's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Uracil Mustard USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Uracil Mustard suppliers with USDMF on PharmaCompass.

Uracil Mustard GMP

Uracil Mustard Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Uracil Mustard GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Uracil Mustard GMP manufacturer or Uracil Mustard GMP API supplier for your needs.

Uracil Mustard CoA

A Uracil Mustard CoA (Certificate of Analysis) is a formal document that attests to Uracil Mustard's compliance with Uracil Mustard specifications and serves as a tool for batch-level quality control.

Uracil Mustard CoA mostly includes findings from lab analyses of a specific batch. For each Uracil Mustard CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Uracil Mustard may be tested according to a variety of international standards, such as European Pharmacopoeia (Uracil Mustard EP), Uracil Mustard JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Uracil Mustard USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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