Uramustine

Uramustine (INN) or uracil mustard is a chemotherapy drug which belongs to the class of alkylating agents.[1] It is used in lymphatic malignancies such as non-Hodgkin's lymphoma. It works by damaging DNA, primarily in cancer cells that preferentially take up the uracil due to their need to make nucleic acids during their rapid cycles of cell division. The DNA damage leads to apoptosis of the affected cells. Bone marrow suppression and nausea are the main side effects.

Uramustine
Clinical data
ATC code
Pharmacokinetic data
Protein binding5%
ExcretionRenal
Identifiers
IUPAC name
  • 5-[bis(2-Chloroethyl)amino]-1H-pyrimidine-2,4-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.574
Chemical and physical data
FormulaC8H11Cl2N3O2
Molar mass252.10 g·mol−1
3D model (JSmol)
SMILES
  • O=C1C(\N(CCCl)CCCl)=C/NC(=O)N1
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) N
  • Key:IDPUKCWIGUEADI-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Chemically it is a derivative of nitrogen mustard and uracil.

References

  1. Ghorani-Azam A, Balali-Mood M (2015). "Clinical pharmacology and toxicology of mustard compounds.". In Balali-Mood M, Abdollahi M (eds.). Basic and clinical toxicology of mustard compounds. Cham: Springer. p. 74. ISBN 978-3-319-23874-6.


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