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
Skeletal formula of a minor tautomer of nitrosourea
Ball and stick model a minor tautomer of nitrosourea
Ball and stick model a minor tautomer of nitrosourea
Names
IUPAC name
Nitrosourea
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/CH3N3O2/c2-1(5)3-4-6/h(H3,2,3,5,6) checkY
    Key: OSTGTTZJOCZWJG-UHFFFAOYSA-N checkY
  • NC(=O)N=NO
  • C(=O)(N)NN=O
Properties
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:

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]

Side effects

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

References
  1. "Antineop". Archived from the original on 2009-03-07. Retrieved 2009-01-24.
  2. Takimoto CH, Calvo E. "Principles of oncologic pharmacotherapy". in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer management: a multidisciplinary approach. 11 ed. 2008.
  3. Tucci E, Verdiani P, Di Carlo S, Sforza V (1986). "Lomustine (CCNU)-induced pulmonary fibrosis". Tumori. 72 (1): 95–8. doi:10.1177/030089168607200114. PMID 3952821. S2CID 33327504.
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