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''-nitros ...

(R-NO) group and a

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

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 medic ...

(BCNU, BiCNU) *

Chlorozotocin Chlorozotocin is a nitrosourea. It is used for cancer therapy. The International Agency for Research on Cancer concluded it was "probably carcinogenic" in 1990 It is an analogue of streptozotocin Streptozotocin or streptozocin ( INN, USP) ...

* Ethylnitrosourea (ENU) *

Fotemustine Fotemustine is a nitrosourea alkylating agent used in the treatment of metastatic melanoma Melanoma is the most dangerous type of skin cancer; it develops from the melanin-producing cells known as melanocytes. It typically occurs in the ...

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 hig ...

(CCNU) *

Nimustine Nimustine () is a nitrosourea alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 evaluatio ...

(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-b ...

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 Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...

alkylating agents Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 effectin ...

and are often used in

chemotherapy Chemotherapy (often abbreviated chemo, sometimes CTX and CTx) is the type of cancer treatment that uses one or more anti-cancer drugs (list of chemotherapeutic agents, chemotherapeutic agents or alkylating agents) in a standard chemotherapy re ...

. They are

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

and thus can cross the

blood–brain barrier The blood–brain barrier (BBB) is a highly selective semipermeable membrane, semipermeable border of endothelium, endothelial cells that regulates the transfer of solutes and chemicals between the circulatory system and the central nervous system ...

, making them useful in the treatment of

brain tumor A brain tumor (sometimes referred to as brain cancer) occurs when a group of cells within the Human brain, brain turn cancerous and grow out of control, creating a mass. There are two main types of tumors: malignant (cancerous) tumors and benign ...

s such as

glioblastoma multiforme Glioblastoma, previously known as glioblastoma multiforme (GBM), is the most aggressive and most common type of cancer that originates in the brain, and has a very poor prognosis for survival. Initial signs and symptoms of glioblastoma are nons ...

. 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, pulm ...

References

External links

* * Nitrosamines Ureas {{Organic-compound-stub