Nitrosourea is both the name of a molecule, and a class of compounds that include a

nitroso In organic chemistry, nitroso refers to a functional group in which the nitric oxide () group is attached to an organic moiety. As such, various nitroso groups can be categorized as ''C''-nitroso compounds (e.g., nitrosoalkanes; ), ''S''-nitroso ...

(R-NO) group and a

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

Examples

Examples include: * Arabinopyranosyl-''N''-methyl-''N''-nitrosourea (Aranose) *

Carmustine Carmustine, sold under the brand name BiCNU among others, is a medication used mainly for chemotherapy. It is a nitrogen mustard β-chloro- nitrosourea compound used as an alkylating agent. Description Carmustine is an orange-yellow solid medica ...

(BCNU, BiCNU) *

Chlorozotocin Chlorozotocin is a nitrosourea 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) * Ca ...

* Ethylnitrosourea (ENU) *

Fotemustine Fotemustine is a nitrosourea alkylating agent used in the treatment of metastatic melanoma. It is available in Europe but has not been approved by the United States FDA. A study has shown that fotemustine produces improved response rates and but ...

Lomustine Lomustine (INN); abbreviated as CCNU; original brand name CeeNU, now marketed as Gleostine) is an alkylating nitrosourea compound used in chemotherapy. It is closely related to semustine and is in the same family as streptozotocin. It is a highl ...

(CCNU) *

Nimustine Nimustine () is a nitrosourea alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalent ...

* ''N''-Nitroso-''N''-methylurea (NMU) *

Ranimustine Ranimustine (INN, marketed under the tradename Cymerin; also known as MCNU) is a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia and polycythemia vera. It has never been filed for FDA evaluation in ...

(MCNU) *

Semustine Semustine (1- (2-Chloroethyl)-3-(trans-4-methylcyclohexyl)- 1-nitrosourea, MeCCNU) is an alkylating nitrosourea compound used in chemotherapy treatment of various types of tumours. Due to its lipophilic property, semustine can cross the blood-br ...

Streptozocin Streptozotocin or streptozocin (INN, USP) (STZ) is a naturally occurring alkylating antineoplastic agent that is particularly toxic to the insulin-producing beta cells of the pancreas in mammals. It is used in medicine for treating certain canc ...

(Streptozotocin) Nitrosourea compounds are DNA

alkylating agents Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecti ...

and are often used in

chemotherapy Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemothe ...

. They are

lipophilic Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves li ...

and thus can cross the blood–brain barrier, making them useful in the treatment of

brain tumor A brain tumor occurs when abnormal cells form within the brain. There are two main types of tumors: malignant tumors and benign (non-cancerous) tumors. These can be further classified as primary tumors, which start within the brain, and secon ...

s such as

glioblastoma multiforme Glioblastoma, previously known as glioblastoma multiforme (GBM), is one of the most aggressive types of cancer that begin within the brain. Initially, signs and symptoms of glioblastoma are nonspecific. They may include headaches, personality cha ...

. File:Aranose (Haworth).svg, Arabinopyranosyl-''N''-methyl-''N''-nitrosourea File:Carmustine.svg,

File:Chlorozotocin (Haworth).svg,

File:ENU.svg, Ethylnitrosourea File:Fotemustine.svg,

File:Lomustine.svg,

File:N-Nitroso-N-methylurea.svg, ''N''-Nitroso-''N''-methylurea File:Nimustine.svg,

File:Ranimustine (Haworth).svg,

File:Semustine.svg,

File:Streptozocin (Haworth).svg,

Side effects

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

interstitial lung disease Interstitial lung disease (ILD), or diffuse parenchymal lung disease (DPLD), is a group of respiratory diseases affecting the interstitium (the tissue and space around the alveoli (air sacs)) of the lungs. It concerns alveolar epithelium, pul ...

References

External links

* * Nitrosamines Ureas {{Organic-compound-stub