3D model (JSmol)
|Molar mass||738.29 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Mertansine, also called DM1 (and in some of its forms emtansine), is a thiol-containing maytansinoid that for therapeutic purposes is attached to a monoclonal antibody through reaction of the thiol group with a linker structure to create an antibody-drug conjugate (ADC).
Mechanism of action
Uses and chemistry
The following (experimental) drugs are antibody-drug conjugates (ADC) combining monoclonal antibodies with mertansine as the cytotoxic component. Mertansine is linked via 4-mercaptovaleric acid.
- Bivatuzumab mertansine
- Cantuzumab mertansine
- Lorvotuzumab mertansine (IMGN901) for CD56 positive cancers, for example multiple myeloma
DM1 can also be linked via a more complicated structure – 4-(3-mercapto-2,5-dioxo-1-pyrrolidinylmethyl)-cylohexanecarboxylic acid or SMCC –, in which case the International Nonproprietary Name of the conjugate formed contains the word emtansine. The abbreviation comes from the chemical designation "succinimidyl-trans-4-(maleimidylmethyl) cyclohexane-1-carboxylate" which is used in the primary literature as well as by the World Health Organization (WHO) despite the fact that the linker contains only one imide group according to the WHO.
DM1 and its attachment via these linkers result from ImmunoGen Inc research.
An example is:
- National Cancer Institute: Definition of Maytansine
- "International Nonproprietary Names (INN) for pharmaceutical substances: Names for radicals, groups & others" (PDF). WHO. 2012: 66f.
- "International Nonproprietary Names for Pharmaceutical Substances (INN): List 89" (PDF). WHO. 2003: 188.
- "ImmunoGen reports encouraging clinical data of IMGN901". The Medical News. 6 December 2009.
- "Clinical pharmacology of trastuzumab emtansine (T-DM1): an antibody–drug conjugate in development for the treatment of HER2-positive cancer". Cancer Chemother Pharmacol. 69 (5): 1229–1240. May 2012. doi:10.1007/s00280-011-1817-3. PMC . PMID 22271209.
- "International Nonproprietary Names for Pharmaceutical Substances (INN): List 103" (PDF). WHO. 2010: 172.
- National Cancer Institute: trastuzumab-MCC-DM1 antibody-drug conjugate
- ImmunoGen: Trastuzumab-DM1 Archived 2010-10-20 at the Wayback Machine.