Nitrosourea

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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	94772 ;
PubChem CID	105035;
UNII	S0W1V6314Y ;
CompTox Dashboard (EPA)	DTXSID80156337 ;
	InChI InChI=1S/CH3N3O2/c2-1(5)3-4-6/h(H3,2,3,5,6) Key: OSTGTTZJOCZWJG-UHFFFAOYSA-N ;
	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

Nitrosoureas are organic compounds containing the subunit R₂NC(O)N(NO)R, where R can be alkyl, aryl, or H. These compounds are formally derived by the attachment of a nitroso group (NO) to the nitrogen atom of a urea R₂NC(O)NR₂. Urea is a naturally occurring, innocuous compound, but the nitrosoureas are highly active biochemically. They are sometimes uses for DNA crosslinking.

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. They are lipophilic and thus can cross the blood–brain barrier, making them useful in the treatment of brain tumors such as glioblastoma multiforme.

Side effects

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

References

↑ Kleemann, Axel (2022). "Antineoplastic and Immunomodulating Agents (L)". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–87. doi:10.1002/14356007.a05_001.pub4. ISBN 978-3-527-30385-4.
↑ "Antineop". Archived from the original on 2009-03-07. Retrieved 2009-01-24.
↑ Takimoto CH, Calvo E. "Principles of oncologic pharmacotherapy". Archived 2009-05-15 at the Wayback Machine in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer management: a multidisciplinary approach Archived 2013-10-04 at the Wayback Machine. 11 ed. 2008.
↑ 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.

External links

Nitrosourea+Compounds at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
Diseases Database (DDB): 9052

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[1] Kleemann, Axel (2022). "Antineoplastic and Immunomodulating Agents (L)". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–87. doi:10.1002/14356007.a05_001.pub4. ISBN 978-3-527-30385-4.

[urlantineop-2] "Antineop". Archived from the original on 2009-03-07. Retrieved 2009-01-24.

[3] Takimoto CH, Calvo E. "Principles of oncologic pharmacotherapy". Archived 2009-05-15 at the Wayback Machine in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer management: a multidisciplinary approach Archived 2013-10-04 at the Wayback Machine. 11 ed. 2008.

[4] 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.