Uramustine

Uramustine
Clinical data
ATC code	L01AD08 (WHO) ;
Pharmacokinetic data
Protein binding	5%
Excretion	Renal
Identifiers
	IUPAC name 5-[bis(2-Chloroethyl)amino]-1H-pyrimidine-2,4-dione;
CAS Number	66-75-1 ;
PubChem CID	6194;
IUPHAR/BPS	7621;
DrugBank	DB00791 ;
ChemSpider	5959 ;
UNII	W7KQ46GJ8U;
KEGG	D06265 ;
ChEMBL	ChEMBL1488 ;
CompTox Dashboard (EPA)	DTXSID8026270 ;
ECHA InfoCard	100.000.574
Chemical and physical data
Formula	C8H11Cl2N3O2
Molar mass	252.10 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:IDPUKCWIGUEADI-UHFFFAOYSA-N ;
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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.

Chemically it is a derivative of nitrogen mustard and uracil.

References

^ 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.

Clinical data

ATC code	L01AD08 (WHO)
Pharmacokinetic data
Protein binding	5%
Excretion	Renal
Identifiers
IUPAC name 5-[bis(2-Chloroethyl)amino]-1H-pyrimidine-2,4-dione
CAS Number	66-75-1^Y
PubChem CID	6194
IUPHAR/BPS	7621
DrugBank	DB00791^N
ChemSpider	5959^N
UNII	W7KQ46GJ8U
KEGG	D06265^Y
ChEMBL	ChEMBL1488^N
CompTox Dashboard (EPA)	DTXSID8026270
ECHA InfoCard	100.000.574
Chemical and physical data
Formula	C₈H₁₁Cl₂N₃O₂
Molar mass	252.10 g·mol⁻¹
3D model (JSmol)	Interactive image
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)