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.^[1] 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.^[2] They are lipophilic and thus can cross the blood–brain barrier, making them useful in the treatment of brain tumors such as glioblastoma multiforme.^[3]

Side effects

Some nitrosoureas (e.g. lomustine) have been associated with the development of interstitial lung disease.^[4]

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.

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