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Identification
NameUracil mustard
Accession NumberDB00791  (APRD00130)
TypeSmall Molecule
GroupsApproved
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
5-(Di-2-chloroethyl)aminouracilNot AvailableNot Available
5-[Bis(2-chloroethyl)amino]-2,4(1H,3H)-pyrimidinedioneNot AvailableNot Available
5-[Di(beta-chloroethyl)amino]uracilNot AvailableNot Available
5-Aminouracil mustardNot AvailableNot Available
5-N,N-Bis(2-chloroethyl)aminouracilNot AvailableNot Available
Aminouracil mustardNot AvailableNot Available
Uracil mustardNot AvailableNot Available
Uracil nitrogen mustardNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Uracil Mustard Upjohn
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number66-75-1
WeightAverage: 252.098
Monoisotopic: 251.022832025
Chemical FormulaC8H11Cl2N3O2
InChI KeyIDPUKCWIGUEADI-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassNitrogen mustard compounds
Sub ClassNot Available
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Dialkylarylamine
  • Nitrogen mustard
  • Pyrimidone
  • Pyrimidine
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Tertiary amine
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed for its antineoplastic properties.
PharmacodynamicsUracil 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 actionAfter activation, it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding5%
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8672
Blood Brain Barrier+0.7711
Caco-2 permeable-0.6657
P-glycoprotein substrateSubstrate0.5716
P-glycoprotein inhibitor INon-inhibitor0.7111
P-glycoprotein inhibitor IINon-inhibitor0.9146
Renal organic cation transporterNon-inhibitor0.63
CYP450 2C9 substrateNon-substrate0.7045
CYP450 2D6 substrateNon-substrate0.7938
CYP450 3A4 substrateNon-substrate0.5662
CYP450 1A2 substrateNon-inhibitor0.8493
CYP450 2C9 substrateNon-inhibitor0.6858
CYP450 2D6 substrateNon-inhibitor0.894
CYP450 2C19 substrateInhibitor0.5511
CYP450 3A4 substrateNon-inhibitor0.7064
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6569
Ames testAMES toxic0.718
CarcinogenicityNon-carcinogens0.9019
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity3.4851 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6391
hERG inhibition (predictor II)Non-inhibitor0.5087
Pharmacoeconomics
Manufacturers
  • Shire development inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point206 dec °CPhysProp
water solubility1070 mg/LNot Available
logP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.32 mg/mLALOGPS
logP0.79ALOGPS
logP0.41ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.05ChemAxon
pKa (Strongest Basic)1.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.44 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.35 m3·mol-1ChemAxon
Polarizability22.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: unknown

Actions: intercalation

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on November 23, 2013 20:24