- Mertansine
-
Mertansine 
Other namesMaytansinoid DM1
N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)-maytansineIdentifiers PubChem 11343137 Jmol-3D images Image 1 - CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)CCS)C)C)OC)(NC(=O)O2)O
- InChI=1S/C35H48ClN3O10S/c1-19-10-9-11-26(46-8)35(44)18-25(47-33(43)37-35)20(2)31-34(4,49-31)27(48-32(42)21(3)38(5)28(40)12-13-50)17-29(41)39(6)23-15-22(14-19)16-24(45-7)30(23)36/h9-11,15-16,20-21,25-27,31,44,50H,12-14,17-18H2,1-8H3,(H,37,43)/b11-9+,19-10+/t20-,21+,25+,26-,27+,31+,34+,35+/m1/s1
Key: ANZJBCHSOXCCRQ-FKUXLPTCSA-N
Properties Molecular formula C35H48ClN3O10S Molar mass 738.29 g mol−1 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Mertansine is a cytotoxic agent also known as DM1. It is a maytansinoid (that is, a derivative of maytansine).[1]
Its patent rights are owned by ImmunoGen Inc.
Uses
The following drugs are antibody-drug conjugates 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[2]
Mertansine linked to a monoclonal antibody (mab). The part where mertansine differs from its parent compound maytansine is shown red. The linker 4-mercaptovaleric acid is shown blue.Mertansine can also be linked via a more complicated structure – 4-(3-mercapto-2,5-dioxo-1-pyrrolidinylmethyl)-cylohexanecarboxylic acid or MCC –, in which case the International Nonproprietary Name of the conjugate is formed with emtansine:
References
- ^ Tijink, BM; Buter, J; De Bree, R; Giaccone, G; Lang, MS; Staab, A; Leemans, CR; Van Dongen, GA (2006). "A phase I dose escalation study with anti-CD44v6 bivatuzumab mertansine in patients with incurable squamous cell carcinoma of the head and neck or esophagus". Clinical cancer research : an official journal of the American Association for Cancer Research 12 (20 Pt 1): 6064–72. doi:10.1158/1078-0432.CCR-06-0910. PMID 17062682.
- ^ "ImmunoGen reports encouraging clinical data of IMGN901". The Medical News. 6 December 2009. http://www.news-medical.net/news/20091206/ImmunoGen-reports-encouraging-clinical-data-of-IMGN901.aspx.
- ^ National Cancer Institute: trastuzumab-MCC-DM1 antibody-drug conjugate
- ^ Immunogen: Trastuzumab-DM1
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