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Uramustine

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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^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)

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[edit]

^ 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.

Block microtubule assembly

Block microtubule disassembly

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Rabacfosadine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^# +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

Alkylating	Nitrogen mustards: Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# Mitomycins Plicamycin)

Other

Other/ungrouped

^‡Withdrawn from market

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