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 |
|---|---|---|---|---|
| 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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| Uracil mustard revisited. | 1999 May 15 |
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| Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A. | 2002 Aug 15 |
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| Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis. | 2002 May |
|
| Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus. | 2002 Nov-Dec |
|
| Galanthamine pattern in Narcissus confusus plants. | 2003 Dec |
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| Antimalarial activity screening of some alkaloids and the plant extracts from Amaryllidaceae. | 2003 Dec |
|
| Alkaloids in Bulgarian Pancratium maritimum L. | 2004 Jan-Feb |
|
| Intraspecific variability in the alkaloid metabolism of Galanthus elwesii. | 2004 Mar |
|
| Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids. | 2004 Sep |
|
| Analysis of Amaryllidaceae alkaloids from Narcissus by GC-MS and capillary electrophoresis. | 2006 Sep 11 |
|
| Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids. | 2007 Apr |
|
| Alkaloid variability in Leucojum aestivum from wild populations. | 2007 Sep-Oct |
|
| A new tyrosinase inhibitor from Crinum yemense as potential treatment for hyperpigmentation. | 2008 May |
|
| Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design. | 2009 Apr |
|
| Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida. | 2009 Jan |
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| Design, synthesis, and analysis of minor groove binder pyrrolepolyamide-2'-deoxyguanosine hybrids. | 2010 |
|
| Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells. | 2010 Jul 23 |
| Substance Class |
Chemical
Created
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admin
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Fri Dec 15 15:29:06 GMT 2023
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| Record UNII |
W7KQ46GJ8U
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| Record Status |
Validated (UNII)
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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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L01AD08
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m11306
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SUB11383MIG
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100000076643
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66-75-1
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URAMUSTINE
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