Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H11Cl2N3O2 |
Molecular Weight | 252.098 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClCCN(CCCl)C1=CNC(=O)NC1=O
InChI
InChIKey=IDPUKCWIGUEADI-UHFFFAOYSA-N
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)
Molecular Formula | C8H11Cl2N3O2 |
Molecular Weight | 252.098 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Uramustine (INN) or uracil mustard is a chemotherapy drug which belongs to the class of alkylating agents. It is used in lymphatic malignancies such as non-Hodgkin's lymphoma. 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. 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. The DNA damage leads to apoptosis of the affected cells. Chemically it is a derivative of nitrogen mustard and uracil.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | URACIL MUSTARD Approved UseURACIL MUSTARD is used in the palliative treatment of symptomatic Chronic Lymphocytic leukemia |
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Palliative | URACIL MUSTARD Approved UseURACIL MUSTARD is effective for palliative treatment of Lymphomas of the histiocytic or lymphocytic type |
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Palliative | URACIL MUSTARD Approved UseURACIL MUSTARD is used in the palliative treatment of patients with chronic myelogenous leukemia |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14088966/ |
single |
URACIL MUSTARD plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Acute leukemia following treatment of polycythemia vera and essential thrombocythemia with uracil mustard. | 1988 May |
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Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis. | 2002 May |
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Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus. | 2002 Nov-Dec |
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Intraspecific variability in the alkaloid metabolism of Galanthus elwesii. | 2004 Mar |
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Alkaloid variability in Leucojum aestivum from wild populations. | 2007 Sep-Oct |
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Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida. | 2009 Jan |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 17:13:20 UTC 2022
by
admin
on
Fri Dec 16 17:13:20 UTC 2022
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Record UNII |
W7KQ46GJ8U
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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IARC | Uracil mustard | ||
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NCI_THESAURUS |
C697
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WHO-ATC |
L01AD08
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W7KQ46GJ8U
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10996
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200-631-3
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1351
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C918
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M11306
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SUB11383MIG
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34462
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66-75-1
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URAMUSTINE
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D014499
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CHEMBL1488
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DTXSID8026270
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ACTIVE MOIETY |