# Mertansine

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**Mertansine**, also called **DM1** (and [in some of its forms](#Emtansine) **emtansine**), is a [thiol](/source/Thiol)-containing [maytansinoid](/source/Maytansinoid) that for therapeutic purposes is attached to a [monoclonal antibody](/source/Monoclonal_antibody) through reaction of the thiol group with a linker structure to create an [antibody-drug conjugate](/source/Antibody-drug_conjugate) (ADC).[1]

ADCs with this design include [trastuzumab emtansine](/source/Trastuzumab_emtansine), [lorvotuzumab mertansine](/source/Lorvotuzumab_mertansine), and [cantuzumab mertansine](/source/Cantuzumab_mertansine). Some are still experimental; others are in regular clinical use.[citation needed]

## Mechanism of action

Mertansine is a [tubulin inhibitor](/source/Tubulin_inhibitor), meaning that it inhibits the assembly of [microtubules](/source/Microtubule) by binding to [tubulin](/source/Tubulin) (at the [rhizoxin](/source/Rhizoxin) binding site).[2]

The monoclonal antibody binds specifically to a structure (usually a [protein](/source/Protein)) occurring in a tumour, thus directing mertansine into this tumour. This concept is called [targeted therapy](/source/Targeted_therapy).[citation needed]

## 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.[3]

ADCs include:

- [Bivatuzumab mertansine](/source/Bivatuzumab_mertansine)
- [Cantuzumab mertansine](/source/Cantuzumab_mertansine)[4]
- [Lorvotuzumab mertansine](/source/Lorvotuzumab_mertansine) (IMGN901) for [CD56](/source/CD56) positive cancers, for example [multiple myeloma](/source/Multiple_myeloma)[5]

## Emtansine

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](/source/International_Nonproprietary_Name) of the conjugate formed contains the word **emtansine**. The abbreviation comes from the chemical designation "succin**imidyl**-*trans*-4-(male**imidyl**methyl) cyclohexane-1-carboxylate" which is used in the primary literature[6] as well as by the [World Health Organization](/source/World_Health_Organization) (WHO)[7] despite the fact that the linker contains only one [imide](/source/Imide) group according to the WHO.[3]

DM1 and its attachment via these linkers result from [ImmunoGen Inc](/source/ImmunoGen) research.

An example is:

- [Trastuzumab emtansine](/source/Trastuzumab_emtansine) (T-DM1), an anti-[HER2/neu](/source/HER2/neu) antibody-drug conjugate[8][9]

## References

1. Zámečník, Josef (2019). "18 – Prediktivní patologie". *Patologie* (in Czech). Vol. 1. Praha: PRAGER PUBLISHING. p. 276. ISBN 978-80-270-6457-1.

1. [National Cancer Institute](/source/National_Cancer_Institute): [Definition of Maytansine](http://www.cancer.gov/Templates/drugdictionary.aspx?CdrID=39492)

1. ["International Nonproprietary Names (INN) for pharmaceutical substances: Names for radicals, groups & others"](https://www.who.int/medicines/services/inn/Radical_Book_2012.pdf). WHO. 2012. pp. 66f.

1. ["International Nonproprietary Names for Pharmaceutical Substances (INN): List 89"](https://www.who.int/medicines/publications/druginformation/innlists/PL89.pdf). WHO. 2003. p. 188.

1. ["ImmunoGen reports encouraging clinical data of IMGN901"](https://www.news-medical.net/news/20091206/ImmunoGen-reports-encouraging-clinical-data-of-IMGN901.aspx). The Medical News. 6 December 2009.

1. Girish, Sandhya; Gupta, Manish; Wang, Bei; Lu, Dan; Krop, Ian E.; Vogel, Charles L.; Burris Iii, Howard A.; Lorusso, Patricia M.; Yi, Joo-Hee; Saad, Ola; Tong, Barbara; Chu, Yu-Waye; Holden, Scott; Joshi, Amita (May 2012). "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. [doi:10.1007/s00280-011-1817-3](https://doi.org/10.1007/s00280-011-1817-3). [PMC 3337408](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3337408). [PMID 22271209](https://pubmed.ncbi.nlm.nih.gov/22271209)

1. ["International Nonproprietary Names for Pharmaceutical Substances (INN): List 103"](https://www.who.int/medicines/publications/druginformation/INN_PL103.pdf). WHO. 2010. p. 172.

1. National Cancer Institute: [trastuzumab-MCC-DM1 antibody-drug conjugate](http://www.cancer.gov/drugdictionary/?CdrID=564399)

1. [ImmunoGen: Trastuzumab-DM1](http://www.immunogen.com/wt/page/trastuzumab_DM1) [Archived](https://web.archive.org/web/20101020064034/http://www.immunogen.com/wt/page/trastuzumab_DM1) 2010-10-20 at the Wayback Machine

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Adapted from the Wikipedia article [Mertansine](https://en.wikipedia.org/wiki/Mertansine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Mertansine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.