nitrosourea

{{Chembox

| ImageFileL1 = Nitrosourea.svg

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageSizeL1 = 121

| ImageNameL1 = Skeletal formula of a minor tautomer of nitrosourea

| ImageFileR1 = Nitrosourea-3D-balls.png

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageSizeR1 = 121

| ImageNameR1 = Ball and stick model a minor tautomer of nitrosourea

| IUPACName = Nitrosourea

| Section1 = {{Chembox Identifiers

| CASNo = 13010-20-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S0W1V6314Y

| PubChem = 105035

| ChemSpiderID = 94772

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| SMILES = NC(=O)N=NO

| SMILES1 = C(=O)(N)NN=O

| StdInChI = 1S/CH3N3O2/c2-1(5)3-4-6/h(H3,2,3,5,6)

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OSTGTTZJOCZWJG-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

| Section2 = {{Chembox Properties

| C=1 | H=3 | N=3 | O=2

}}

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

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.{{cite web |url=http://faculty.swosu.edu/scott.long/phcl/antineop.htm |title=Antineop |access-date=2009-01-24 |url-status=dead |archive-url=https://web.archive.org/web/20090307052941/http://faculty.swosu.edu/scott.long/phcl/antineop.htm |archive-date=2009-03-07 }} They are lipophilic and thus can cross the blood–brain barrier, making them useful in the treatment of brain tumors such as glioblastoma multiforme.Takimoto CH, Calvo E. [http://www.cancernetwork.com/cancer-management-11/chapter03/article/10165/1402628 "Principles of oncologic pharmacotherapy".] in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) [http://www.cancernetwork.com/cancer-management-11/ Cancer management: a multidisciplinary approach]. 11 ed. 2008.

File:Aranose (Haworth).svg|Arabinopyranosyl-N-methyl-N-nitrosourea

File:Carmustine.svg|Carmustine

File:Chlorozotocin (Haworth).svg|Chlorozotocin

File:ENU.svg|Ethylnitrosourea

File:Fotemustine.svg|Fotemustine

File:Lomustine.svg|Lomustine

File:N-Nitroso-N-methylurea.svg|N-Nitroso-N-methylurea

File:Nimustine.svg|Nimustine

File:Ranimustine (Haworth).svg|Ranimustine

File:Semustine.svg|Semustine

File:Streptozocin (Haworth).svg|Streptozocin

Side effects

Some nitrosoureas (e.g. lomustine) have been associated with the development of interstitial lung disease.{{cite journal |vauthors=Tucci E, Verdiani P, Di Carlo S, Sforza V |title=Lomustine (CCNU)-induced pulmonary fibrosis |journal=Tumori |volume=72 |issue=1 |pages=95–8 |year=1986 |doi=10.1177/030089168607200114 |pmid=3952821|s2cid=33327504 }}

References

External links

{{MeshName|Nitrosourea+Compounds}}
{{DiseasesDB|9052}}

Category:Nitrosamines

Category:Ureas