Nitrosourea

Nitrosourea is both the name of a molecule, and a class of compounds that include a nitroso (R-NO) group and a urea.

Nitrosourea

Skeletal formula of a minor tautomer of nitrosourea Ball and stick model a minor tautomer of nitrosourea
Names
IUPAC name Nitrosourea
Identifiers
CAS Number	13010-20-3 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	94772 Y
PubChem CID	105035
UNII	S0W1V6314Y Y
CompTox Dashboard (EPA)	DTXSID80156337
InChI InChI=1S/CH3N3O2/c2-1(5)3-4-6/h(H3,2,3,5,6) Y Key: OSTGTTZJOCZWJG-UHFFFAOYSA-N Y
SMILES NC(=O)N=NO C(=O)(N)NN=O
Properties
Chemical formula	CH3N3O2
Molar mass	89.054 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Examples

Examples include:

• Arabinopyranosyl-N-methyl-N-nitrosourea (Aranose)
• Carmustine (BCNU, BiCNU)
• Chlorozotocin
• Ethylnitrosourea (ENU)
• Fotemustine
• Lomustine (CCNU)
• Nimustine
• N-Nitroso-N-methylurea (NMU)
• Ranimustine (MCNU)
• Semustine
• Streptozocin (Streptozotocin)

Nitrosourea compounds are DNA alkylating agents and are often used in chemotherapy.^[1] They are lipophilic and thus can cross the blood–brain barrier, making them useful in the treatment of brain tumors such as glioblastoma multiforme.^[2]

• 
  Arabinopyranosyl-N-methyl-N-nitrosourea
• 
  Carmustine
• 
  Chlorozotocin
• 
  Ethylnitrosourea
• 
  Fotemustine
• 
  Lomustine

• 
  N-Nitroso-N-methylurea
• 
  Nimustine
• 
  Ranimustine
• 
  Semustine
• 
  Streptozocin

Side effects

Some nitrosoureas (e.g. lomustine) have been associated with the development of interstitial lung disease.^[3]