Nitrosamines

thumb|150px|Structure of the nitrosamino group

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 cancers of the islets of Langerhans and used in medical research to produce an animal model for hyperglycemia and Alzheimer's in a large dose, as well as type 2 diabetes or type 1 diabetes with multiple low doses.

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 highly lipid-soluble drug, thus it crosses the blood–brain barrier. This property makes it ideal for treating brain tumors, which is its primary use, although it is also used to treat Hodgkin lymphoma as a second-line option. It has also been used in veterinary practice as a treatment for cancers in cats and dogs.

thumb | right | Structural formula of nitroso group

'''N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN'''), is an organic compound with the formula (CH3)2NNO. It is one of the simplest members of a large class of nitrosamines. It is a volatile yellow oil. NDMA has attracted wide attention as being highly hepatotoxic and a known carcinogen in laboratory animals.

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

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 but does not increase survival (over dacarbazine in the treatment of disseminated cutaneous melanoma. Median survival was 7.3 months with fotemustine versus 5.6 months with DTIC (P=.067). There was also toxicity prevalence in fotemustine arm. The main toxicity was grade 3 to 4 neutropenia (51% with fotemustine v 5% with DTIC) and thrombocytopenia (43% v 6%, re

'''N-Nitroso-N-methylurea (NMU''') is a highly reliable carcinogen, mutagen, and teratogen. NMU is an alkylating agent, and exhibits its toxicity by transferring its methyl group to nucleobases in nucleic acids, which can lead to AT:GC transition mutations.

'''N-Nitrosonornicotine (NNN''') is a tobacco-specific nitrosamine produced during the curing and processing of tobacco.

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.

Nicotine-derived nitrosamine ketone (NNK) is one of the key tobacco-specific nitrosamines (TSNAs) derived from nicotine. It plays an important role in carcinogenesis. The conversion of nicotine to NNK entails opening of the pyrrolidine ring.

'''N-Nitrosodiethylamine (NDEA''') is an organic compound with the formula Et2NNO (Et = C2H5). A member of the nitrosamines, it is a light-sensitive, volatile, clear yellow oil that is soluble in water, lipids, and other organic solvents. It has an amine or aromatic odor. It is used as gasoline and lubricant additive, antioxidant, and stabilizer for industry materials. When heated to decomposition, N-nitrosodiethylamine emits toxic fumes of nitrogen oxides. N-Nitrosodiethylamine affects DNA integrity, probably by alkylation, and is used in experimental research to induce liver tumorigenesis. I

Nimustine () is a nitrosourea alkylating agent.

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.

Alanosine (also called SDX-102) is a substance that has been studied for the treatment of pancreatic cancer. It is an antimetabolite. It is used as one of a few experimental treatments for patients with deadly pancreatic cancer when the main chemotherapeutic treatment regimen of gemcitabine is no longer useful.

'Methyl-n-amylnitrosamine' (MNAN) is a potential carcinogen It is metabolized in the liver by the enzyme CYP2A6.

chemical compound

Nitrosoproline is a nitroso derivative of the amino acid proline.

Dopastin is a chemical compound produced by the bacteria Pseudomonas No. BAC-125. It was first isolated and characterized in 1972. It is an inhibitor of the enzyme dopamine β-hydroxylase.