Uracil mustard
Identification
- Generic Name
- Uracil mustard
- DrugBank Accession Number
- DB00791
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 252.098
Monoisotopic: 251.022832025 - Chemical Formula
- C8H11Cl2N3O2
- Synonyms
- 5-(di-2-chloroethyl)aminouracil
- 5-[bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedione
- 5-[bis(2-chloroethyl)amino]uracil
- 5-[di(β-chloroethyl)amino]uracil
- 5-aminouracil mustard
- 5-N,N-bis(2-chloroethyl)aminouracil
- Aminouracil mustard
- Uracil mustard
- Uracil nitrogen mustard
- Uramustina
- Uramustine
- Uramustinum
- External IDs
- CB-4835
- NSC-34462
- SK-19849
- U 8344
- U-8344
Pharmacology
- Indication
Used for its antineoplastic properties.
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- Pharmacodynamics
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.
- 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.
Target Actions Organism UDNA intercalationHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
5%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Uracil mustard is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Uracil mustard is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Uracil mustard is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Uracil mustard is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Uracil mustard is combined with Bupivacaine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Uracil Mustard (Upjohn)
Categories
- ATC Codes
- L01AD08 — Uramustine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Nitrogen mustard compounds
- Direct Parent
- Nitrogen mustard compounds
- Alternative Parents
- Dialkylarylamines / Pyrimidones / Aminopyrimidines and derivatives / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds show 5 more
- Substituents
- Alkyl chloride / Alkyl halide / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Dialkylarylamine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- nitrogen mustard, aminouracil (CHEBI:9884)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- W7KQ46GJ8U
- CAS number
- 66-75-1
- InChI Key
- IDPUKCWIGUEADI-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 5-[bis(2-chloroethyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione
- SMILES
- ClCCN(CCCl)C1=CNC(=O)NC1=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014929
- KEGG Drug
- D06265
- KEGG Compound
- C11686
- PubChem Compound
- 6194
- PubChem Substance
- 46506168
- ChemSpider
- 5959
- 10996
- ChEBI
- 9884
- ChEMBL
- CHEMBL1488
- ZINC
- ZINC000000002235
- Therapeutic Targets Database
- DAP000990
- PharmGKB
- PA451830
- Wikipedia
- Uramustine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Shire development inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 206 dec °C PhysProp water solubility 1070 mg/L Not Available logP 1.2 Not Available - Predicted Properties
Property Value Source Water Solubility 1.32 mg/mL ALOGPS logP 0.79 ALOGPS logP 0.41 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 8.76 Chemaxon pKa (Strongest Basic) -4.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 61.44 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 58.35 m3·mol-1 Chemaxon Polarizability 23.08 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8672 Blood Brain Barrier + 0.7711 Caco-2 permeable - 0.6657 P-glycoprotein substrate Substrate 0.5716 P-glycoprotein inhibitor I Non-inhibitor 0.7111 P-glycoprotein inhibitor II Non-inhibitor 0.9146 Renal organic cation transporter Non-inhibitor 0.63 CYP450 2C9 substrate Non-substrate 0.7045 CYP450 2D6 substrate Non-substrate 0.7938 CYP450 3A4 substrate Non-substrate 0.5662 CYP450 1A2 substrate Non-inhibitor 0.8493 CYP450 2C9 inhibitor Non-inhibitor 0.6858 CYP450 2D6 inhibitor Non-inhibitor 0.894 CYP450 2C19 inhibitor Inhibitor 0.5511 CYP450 3A4 inhibitor Non-inhibitor 0.7064 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6569 Ames test AMES toxic 0.718 Carcinogenicity Non-carcinogens 0.9019 Biodegradation Not ready biodegradable 0.9962 Rat acute toxicity 3.4851 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6391 hERG inhibition (predictor II) Non-inhibitor 0.5087
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 147.9510538 predictedDarkChem Lite v0.1.0 [M-H]- 143.31447 predictedDeepCCS 1.0 (2019) [M+H]+ 148.4148538 predictedDarkChem Lite v0.1.0 [M+H]+ 147.14577 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.9510538 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.44334 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Hartley JA, Forrow SM, Souhami RL: Effect of ionic strength and cationic DNA affinity binders on the DNA sequence selective alkylation of guanine N7-positions by nitrogen mustards. Biochemistry. 1990 Mar 27;29(12):2985-91. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:55