Mertansine

Mertansine
Other names Maytansinoid DM1 N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)-maytansine
Identifiers
	PubChem	11343137
	Jmol-3D images	Image 1
SMILES 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 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 N Key: ANZJBCHSOXCCRQ-FKUXLPTCSA-N N
Properties
Molecular formula	C35H48ClN3O10S
Molar mass	738.29 g mol−1
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 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:

• Trastuzumab emtansine (T-DM1), an anti-HER2/neu antibody-drug conjugate^[3][4]

References