Nitrosourea

Nitrosourea
IUPAC name Nitrosourea
Identifiers
CAS number	13010-20-3 N
PubChem	105035
ChemSpider	94772 Y
Jmol-3D images	Image 1 Image 2
SMILES NC(=O)N=NO C(=O)(N)NN=O
InChI InChI=1S/CH3N3O2/c2-1(5)3-4-6/h(H3,2,3,5,6) Y Key: OSTGTTZJOCZWJG-UHFFFAOYSA-N Y
Properties
Molecular formula	CH3N3O2
Molar mass	89.05 g mol−1
Exact mass	89.022526355 g mol-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Urea

Streptozotocin

ENU

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:

• Carmustine
• Lomustine
• Semustine
• Ethylnitrosourea (ENU)
• 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]

Side effects

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

References

1. ^ "Antineop". http://faculty.swosu.edu/scott.long/phcl/antineop.htm. 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. PMID 3952821. 

External links

• MeSH Nitrosourea+Compounds
• DDB 9052

DNA replication
inhibitor

DNA precursors/ antimetabolites (S phase)	Folic acid dihydrofolate reductase inhibitor (Aminopterin, Methotrexate, Pemetrexed, Pralatrexate) • thymidylate synthase inhibitor (Raltitrexed, Pemetrexed) Purine adenosine deaminase inhibitor (Pentostatin) halogenated/ribonucleotide reductase inhibitors (Cladribine, Clofarabine, Fludarabine) thiopurine (Thioguanine, Mercaptopurine) Pyrimidine thymidylate synthase inhibitor (Fluorouracil, Capecitabine, Tegafur, Carmofur, Floxuridine) DNA polymerase inhibitor (Cytarabine) ribonucleotide reductase inhibitor (Gemcitabine) hypomethylating agent (Azacitidine, Decitabine) Deoxyribonucleotide ribonucleotide reductase inhibitor (Hydroxycarbamide)
Topoisomerase inhibitors (S phase)	I Camptotheca (Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan) II Podophyllum (Etoposide, Teniposide) II+Intercalation Anthracyclines (Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin) • Anthracenediones (Mitoxantrone, Pixantrone)
Crosslinking of DNA (CCNS)	Alkylating Nitrogen mustards: Mechlorethamine • Cyclophosphamide (Ifosfamide, Trofosfamide) • Chlorambucil (Melphalan, Prednimustine) • Bendamustine • Uramustine • Estramustine Nitrosoureas: Carmustine • Lomustine (Semustine) • Fotemustine • Nimustine • Ranimustine • Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan, Treosulfan) Aziridines: Carboquone • ThioTEPA • Triaziquone • Triethylenemelamine Alkylating-like Platinum (Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin) Nonclassical Hydrazines (Procarbazine) • Triazenes (Dacarbazine, Temozolomide) • Altretamine • Mitobronitol Intercalation Streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin)

Photosensitizers/PDT

Aminolevulinic acid/Methyl aminolevulinate • Efaproxiral • Porphyrin derivatives (Porfimer sodium, Talaporfin, Temoporfin, Verteporfin)

Other

Enzyme inhibitors	FI (Tipifarnib)  • CDK inhibitors (Alvocidib, Seliciclib) • PrI (Bortezomib) • PhI (Anagrelide) • IMPDI (Tiazofurine) • LI (Masoprocol) • PARP inhibitor (Olaparib) • HDAC (Vorinostat, Romidepsin)
Receptor antagonists	ERA (Atrasentan) • retinoid X receptor (Bexarotene) • sex steroid (Testolactone)
Other/ungrouped	Amsacrine • Trabectedin • retinoids (Alitretinoin, Tretinoin) • Arsenic trioxide • asparagine depleters (Asparaginase/Pegaspargase) • Celecoxib • Demecolcine • Elesclomol • Elsamitrucin • Etoglucid • Lonidamine • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)

M: NEO tsoc, mrkr tumr, epon, para drug (L1i/1e/V03)