Mertansine (DM1)
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MedKoo CAT#: 123212

CAS#: 139504-50-0

Description: Mertansine refers to the thiol-containing maytansinoid, DM1 (N2’-deacetyl-N2’-(3-mercapto-1-oxopropyl)maytansine) attached to a monoclonal antibody through reaction of the thiol group with an SPP (N-succinimidyl 4-(2-pyridyldithio)) linker to create an antibody-drug conjugate or ADC. Experimental ADCs with the SPP-DM1 design include lorvotuzumab mertansine. DM1 can also be linked to an antibody using the SMCC (4-(3-mercapto-2,5-dioxo-1-pyrrolidinylmethyl)-cylohexanecarboxylic acid) linker, in which case the International Nonproprietary Name of the conjugate formed contains the word emtansine. DM1 and its attachment via these linkers result from ImmunoGen Inc research. Trastuzumab emtansine (T-DM1) is an anti-HER2/neu antibody-drug conjugate.


Chemical Structure

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Mertansine (DM1)
CAS# 139504-50-0

Theoretical Analysis

MedKoo Cat#: 123212
Name: Mertansine (DM1)
CAS#: 139504-50-0
Chemical Formula: C35H48ClN3O10S
Exact Mass: 737.27489
Molecular Weight: 738.29
Elemental Analysis: C, 56.94; H, 6.55; Cl, 4.80; N, 5.69; O, 21.67; S, 4.34

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Ready to ship
25.0mg USD 202.0 Ready to ship
50.0mg USD 364.0 Ready to ship
100.0mg USD 655.0 Ready to ship
200.0mg USD 1179.0 Ready to ship
500.0mg USD 2650.0 Ready to ship
1.0g USD 4850.0 Ready to ship
2.0g USD 9150.0 2 Weeks
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Synonym: DM1; DM-1; DM 1; DM1 Compound; DM1 [Maytansinoid]; Maytansinoid DM 1; Maytansinoid DM1; Maytansinoid DM-1; UNII-DDZ29HGH0E; maytansine, Mertansine; emtansine;

IUPAC/Chemical Name: (14S,16S,33S,2R,4R,10E,12Z,14R)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-(3-mercaptopropanoyl)-N-methyl-L-alaninate

InChi Key: ANZJBCHSOXCCRQ-GCRZMMRQSA-N

InChi Code: 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

SMILES Code: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C\C=C(\CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@H]([C@]4(C1O4)C)OC(=O)[C@H](C)N(C)C(=O)CCS)C)/C)OC)(NC(=O)O2)O

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 60.0 81.26

Preparing Stock Solutions

The following data is based on the product molecular weight 738.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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15: Gurtner K, Hessel F, Eicheler W, Dörfler A, Zips D, Heider KH, Krause M, Baumann M. Combined treatment of the immunoconjugate bivatuzumab mertansine and fractionated irradiation improves local tumour control in vivo. Radiother Oncol. 2012 Mar;102(3):444-9. doi: 10.1016/j.radonc.2011.10.013. Epub 2011 Nov 17. PubMed PMID: 22100655.

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18: Rodon J, Garrison M, Hammond LA, de Bono J, Smith L, Forero L, Hao D, Takimoto C, Lambert JM, Pandite L, Howard M, Xie H, Tolcher AW. Cantuzumab mertansine in a three-times a week schedule: a phase I and pharmacokinetic study. Cancer Chemother Pharmacol. 2008 Oct;62(5):911-9. doi: 10.1007/s00280-007-0672-8. Epub 2008 Feb 27. PubMed PMID: 18301896.

19: Riechelmann H, Sauter A, Golze W, Hanft G, Schroen C, Hoermann K, Erhardt T, Gronau S. Phase I trial with the CD44v6-targeting immunoconjugate bivatuzumab mertansine in head and neck squamous cell carcinoma. Oral Oncol. 2008 Sep;44(9):823-9. doi: 10.1016/j.oraloncology.2007.10.009. Epub 2008 Jan 18. PubMed PMID: 18203652.

20: Rupp U, Schoendorf-Holland E, Eichbaum M, Schuetz F, Lauschner I, Schmidt P, Staab A, Hanft G, Huober J, Sinn HP, Sohn C, Schneeweiss A. Safety and pharmacokinetics of bivatuzumab mertansine in patients with CD44v6-positive metastatic breast cancer: final results of a phase I study. Anticancer Drugs. 2007 Apr;18(4):477-85. PubMed PMID: 17351401.



Additional Information

Mertansine is a tubulin inhibitor, meaning that it inhibits the assembly of microtubules by binding to tubulin (at the rhizoxin binding site). The monoclonal antibody binds specifically to a structure (usually a protein) occurring in a tumour, thus directing mertansine into this tumour. This concept is called targeted therapy.
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.