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
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
*
Ethylnitrosourea
ENU, also known as ''N''-ethyl-''N''-nitrosourea (chemical formula C3H7N3O2), is a highly potent mutagen. For a given gene in mice, ENU can induce 1 new mutation in every 700 loci. It is also toxic at high doses.
The chemical is an alkylating ...
(ENU)
*
Fotemustine
*
Lomustine (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 equivale ...
*
''N''-Nitroso-''N''-methylurea (NMU)
*
Ranimustine (MCNU)
*
Semustine
*
Streptozocin (Streptozotocin)
Nitrosourea compounds are
DNA alkylating agents and are often used in
chemotherapy.
They are
lipophilic 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 prevents solutes in the circulating blood from ''non-selectively'' crossing into the extracellular fluid of ...
, making them useful in the treatment of
brain tumors such as
glioblastoma multiforme.
File:Aranose (Haworth).svg, Arabinopyranosyl-''N''-methyl-''N''-nitrosourea
File:Carmustine.svg, 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 ...
File:Chlorozotocin (Haworth).svg, Chlorozotocin
File:ENU.svg, Ethylnitrosourea
ENU, also known as ''N''-ethyl-''N''-nitrosourea (chemical formula C3H7N3O2), is a highly potent mutagen. For a given gene in mice, ENU can induce 1 new mutation in every 700 loci. It is also toxic at high doses.
The chemical is an alkylating ...
File:Fotemustine.svg, Fotemustine
File:Lomustine.svg, Lomustine
File:N-Nitroso-N-methylurea.svg, ''N''-Nitroso-''N''-methylurea
File:Nimustine.svg, 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 equivale ...
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.
References
External links
*
*
Nitrosamines
Ureas
{{Organic-compound-stub