Identification Name Uracil mustard Accession Number DB00791 (APRD00130) Type Small Molecule Groups Approved Description
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. [PubChem]
5-(Di-2-chloroethyl)aminouracil 5-[Bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedione 5-[Di(beta-chloroethyl)amino]uracil 5-Aminouracil mustard 5-N,N-Bis(2-chloroethyl)aminouracil Aminouracil mustard Uracil mustard Uracil nitrogen mustard Uramustine External IDs NSC-34462 / U-8344 Product Ingredients Not Available Approved Prescription Products Not Available Approved Generic Prescription Products Not Available Approved Over the Counter Products Not Available Unapproved/Other Products Not Available International Brands
Name Company Uracil Mustard Upjohn Brand mixtures Not Available Categories UNII W7KQ46GJ8U CAS number 66-75-1 Weight Average: 252.098 Monoisotopic: 251.022832025 Chemical Formula C 8H 11Cl 2N 3O 2 InChI Key IDPUKCWIGUEADI-UHFFFAOYSA-N InChI
Used for its antineoplastic properties.
Structured Indications Not Available 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 Kind Pharmacological action Actions Organism UniProt ID DNA Nucleotide unknown
Human not applicable details Related Articles Absorption Not Available Volume of distribution Not Available Protein binding
Metabolism Not Available Route of elimination Not Available Half life Not Available Clearance Not Available Toxicity Not Available Affected organisms Pathways Not Available Pharmacogenomic Effects/ADRs Not Available Interactions Drug Interactions
Drug Interaction Drug group Acetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Uracil mustard. Approved Bevacizumab Bevacizumab may increase the cardiotoxic activities of Uracil mustard. Approved, Investigational Cabazitaxel The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Uracil mustard. Approved Cyclophosphamide Cyclophosphamide may increase the cardiotoxic activities of Uracil mustard. Approved, Investigational Deslanoside Deslanoside may decrease the cardiotoxic activities of Uracil mustard. Approved Digitoxin Digitoxin may decrease the cardiotoxic activities of Uracil mustard. Approved Digoxin Digoxin may decrease the cardiotoxic activities of Uracil mustard. Approved Docetaxel The risk or severity of adverse effects can be increased when Docetaxel is combined with Uracil mustard. Approved, Investigational Oleandrin Anvirzel may decrease the cardiotoxic activities of Uracil mustard. Experimental Ouabain Ouabain may decrease the cardiotoxic activities of Uracil mustard. Approved Paclitaxel The risk or severity of adverse effects can be increased when Paclitaxel is combined with Uracil mustard. Approved, Vet Approved Trastuzumab Trastuzumab may increase the cardiotoxic activities of Uracil mustard. Approved, Investigational Food Interactions Not Available References Synthesis Reference Not Available General References Not Available External Links ATC Codes Not Available AHFS Codes Not Available PDB Entries Not Available FDA label Not Available MSDS Not Available Clinical Trials Clinical Trials Not Available Pharmacoeconomics Manufacturers 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 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
ADMET data is predicted using
, a free tool for evaluating chemical ADMET properties. (
Spectra Mass Spec (NIST) Not Available Spectra Taxonomy Description This compound belongs to the class of chemical entities known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom. Kingdom Chemical entities Super Class Organic compounds Class Organic nitrogen compounds Sub Class Organonitrogen compounds Direct Parent Nitrogen mustard compounds Alternative Parents Dialkylarylamines / Pyrimidones / Aminopyrimidines and derivatives / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Alkyl chlorides show 5 more Substituents Nitrogen mustard / Tertiary aliphatic/aromatic amine / Dialkylarylamine / Aminopyrimidine / Pyrimidone / Hydropyrimidine / Pyrimidine / Heteroaromatic compound / Vinylogous amide / Lactam / Tertiary amine / Urea / Organoheterocyclic compound / Azacycle / Alkyl halide / Organooxygen compound / Organochloride / Organohalogen compound / Organic oxygen compound / Hydrocarbon derivative / Organic oxide / Alkyl chloride / Organopnictogen compound / Amine / Aromatic heteromonocyclic compound show 15 more Molecular Framework Aromatic heteromonocyclic compounds External Descriptors nitrogen mustard, aminouracil ( CHEBI:9884 )