Mustards are alkylating agents that are chemically similar to the mustard agents used in chemical warfare.

Cyclophosphamide

Brand/Trade Names: Cytoxan, Neosar, Endoxan, Cytophosphane

Manufacturers: Transo-Pharm USA, Fermion Oy, Orion Corporation. Johnson Matthey, Jiangsu Hengrui Medicine Co.

Formula: C₇H₁₅Cl₂N₂O₂P

Mechanism: Alkylating

Class: Mustard

Administration: Intravenous, oral

Notes: Prodrug that converts to active drug inside the body.  Approved by the FDA in 1959.  Used for treatment of ovarian cancer, retinoblastoma, chronic myelogenous leukemia, Hodgkin’s disease, multiple myeloma, mycosis fungoides, neuroblastoma, Non-Hodgkin lymphoma, acute lymphoblastic leukemia,  acute monocytic leukemia, acute myeloid leukemia, breast cancer, chronic granulocytic leukemia. and chronic lymphocytic leukemia

Chlorambucil

Brand/Trade Names: Leukeran

Manufacturers: Biophore India Pharmaceuticals, Sionc Pharmaceuticals, SGMR Pharmaceuticals, Farmhispania S.A.

Formula: C₁₄H₁₉Cl₂NO₂

Mechanism: Alkylating

Class: Mustard

Administration: Intravenous, oral

Notes:  Approved by FDA in 1957.  Used in treatment of Chronic lymphocytic leukemia, Hodgkin’s disease, and Non-Hodgkin’s lymphoma .

Mechlorethamine

Brand/Trade Names: Mustargen, Mechlorethamine Hydrochloride, mustine, nitrogen mustard, and HN2

Manufacturer: Sigma-Aldrich Corporation

Formula: C₅H₁₁Cl₂N

Mechanism: Alkylating

Class: Mustard

Administration: Intravenous, topical

Notes:  Approved by the FDA in 2013.  Used for treatment of lymphoma, leukemia, bronchogenic carcinoma, and mycosis fungoides.

Bendamustine

Brand/Trade Names: Ribomustin, Treanda, and 4-[5-[Bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid.

Manufacturers: Teva Pharmaceuticals, Biophore India Pharmaceuticals, Dr Reddy’s Laboratories, Beijing Huikand Boyuan Chemical Techm,  Euticals.

Formula: C₁₆H₂₁Cl₂N₃O₂

Mechanism: Alkylating

Class: Mustard

Administration: Intravenous

Notes:  Approved by the FDA in 2008.  More. Used for treatment of B-cell non-Hodgkin lymphoma and chronic lymphocytic leukemia.  More on bendamustine.

Estramustine

Brand/Trade Names: Emcyt, Estracit

Manufacturers: Cipla, Excella, Pamakemu Asia, Pfizer 

Formula: C₂₃H₃₁Cl₂NO₃

Mechanism: Alkylating

Class: Mustard

Administration: Oral

Notes:  Approved by the FDA in 1981.  Used in treatment of prostate cancer.

Other Effects

Since alkylating agents are designed and intended to destroy human cells (tumors are, after all, collections of abnormal human cells of a particular type), inevitably non-cancerous cells will be destroyed as well. The most common toxicities (side-effects) that occur as a consequence of alkylating agent administration used as cancer chemotherapy are related to the destruction of normal cells. Alkylating agents are known to cause a dose-dependent destruction of certain cells of the immune system. In the treatment of autoimmune diseases, this is occasionally an advantage (such as with cyclophosphamide), but in cancer treatment it can cause severe immunosuppression. This state makes cancer patients treated with these drugs particularly susceptible to certain infections, including infections by microorganisms that do not often infect people with a normal immune system (e.g. fungi). Another common side-effect related to cellular destruction affects rapidly dividing cells, such as mucosal cells. This becomes clinically apparent in damage done to the oral mucosa and to the lining of the gastrointestinal tract—bleeding gums and copius, sometimes bloody diarrhea can occur. Poor absorption of nutrients across the gastrointestinal tract can take place as well.