Maytansinoid DM4
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MedKoo CAT#: 206839

CAS#: 796073-69-3

Description: Maytansinoid DM4, a chemical derivative of maytansine, and is a potent and selective cytotoxic agent with promising anticancer properties. Anticancer properties of maytansinoids have been attributed to their ability to disrupt microtubule function. Maytansinoid DM4 can be use to make antibody drug conjugates such as Anetumab ravtansine (BAY 94-9343) and Indatuximab ravtansine (BT062). Note: the correct CAS# for Maytansinoid DM4 is 796073-69-3. Many websites and vendor, including Sci-Finder wrongly assigned Maytansinoid DM4's CAS# as 799840-96-3.


Price and Availability

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2mg
USD 250
25mg
USD 1450
Size
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5mg
USD 450
50mg
USD 2250
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10mg
USD 650
1g
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Maytansinoid DM4 purity > 95%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 500mg may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206839
Name: Maytansinoid DM4
CAS#: 796073-69-3
Chemical Formula: C38H54ClN3O10S
Exact Mass: 779.3218
Molecular Weight: 780.371
Elemental Analysis: C, 58.49; H, 6.98; Cl, 4.54; N, 5.38; O, 20.50; S, 4.11


Related CAS #: 796073-69-3   799840-96-3 (wrong CAS#)    

Synonym: Maytansinoid DM4; DM4.

IUPAC/Chemical Name: (14S,16S,32S,33S,2R,4S,10E,12E,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-(4-mercapto-4-methylpentanoyl)-N-methyl-L-alaninate

InChi Key: JFCFGYGEYRIEBE-YVLHJLIDSA-N

InChi Code: InChI=1S/C38H54ClN3O10S/c1-21-12-11-13-28(49-10)38(47)20-27(50-35(46)40-38)22(2)33-37(6,52-33)29(51-34(45)23(3)41(7)30(43)14-15-36(4,5)53)19-31(44)42(8)25-17-24(16-21)18-26(48-9)32(25)39/h11-13,17-18,22-23,27-29,33,47,53H,14-16,19-20H2,1-10H3,(H,40,46)/b13-11+,21-12+/t22-,23+,27+,28-,29+,33+,37+,38+/m1/s1

SMILES Code: C/C(CC1=CC(OC)=C(Cl)C(N(C(C[C@]([C@]2(C)O[C@H]2[C@@H]3C)([H])OC([C@@H](N(C(CCC(C)(C)S)=O)C)C)=O)=O)C)=C1)=C\C=C\[C@@H](OC)[C@](NC4=O)(C[C@]3([H])O4)O


Technical Data

Appearance:
Solid powder

Purity:
>95% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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

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).

Harmonized System Code:
293490


Additional Information

Note: many websites and vendor, including Sci-Finder wrongly assigned Maytansinoid DM4's CAS# as 799840-96-3.
CAS#799840-96-3 has one more methyl group compared to the correct Maytansinoid DM4 structure.
CAS#799840-96-3 Smile code: C/C(CC1=CC(OC)=C(Cl)C(N(C(C[C@]([C@]2(C)O[C@H]2C3(C)C)([H])OC([C@@H](N(C(CCC(C)(C)S)=O)C)C)=O)=O)C)=C1)=C\C=C\[C@@H](OC)[C@](NC4=O)(C[C@]3([H])O4)O
CAS#799840-96-3 Inchi: InChI=1S/C39H56ClN3O10S/c1-22-13-12-14-27(50-11)39(48)21-29(52-35(47)41-39)37(5,6)34-38(7,53-34)28(51-33(46)23(2)42(8)30(44)15-16-36(3,4)54)20-31(45)43(9)25-18-24(17-22)19-26(49-10)32(25)40/h12-14,18-19,23,27-29,34,48,54H,15-17,20-21H2,1-11H3,(H,41,47)/b14-12+,22-13+/t23-,27+,28-,29-,34-,38-,39-/m0/s1
CAS#799840-96-3 Inchi key: SVVGCFZPFZGWRG-OTKBOCOUSA-N
Chemical Formula: C39H56ClN3O10S
Exact Mass: 793.3375
Molecular Weight: 794.40
Elemental Analysis: C, 58.97; H, 7.11; Cl, 4.46; N, 5.29; O, 20.14; S, 4.04

Common used maytansinoid derivatives are Ansamitocin, Mertansine/emtansine (DM1), ravtansine/soravtansine (DM4)
DM4 attached with ImmunoGen's SPDB linker is called "ravtansine"
indatuximab ravtansine(BT062) targeting multiple myeloma,
anetumab ravtansine(BAY94-9343) targeting mesothelin (to treat mesothelioma), starting phase II trial in 2016
coltuximab ravtansine (SAR3419) targeting CD19 to treat acute lymphoblastic leukemia (ALL).
DM4 attached with ImmunoGen's sSPDB linker is called "soravtansine": mirvetuximab soravtansine


References

1: Schönfeld K, Zuber C, Pinkas J, Häder T, Bernöster K, Uherek C. Indatuximab ravtansine (BT062) combination treatment in multiple myeloma: pre-clinical studies. J Hematol Oncol. 2017 Jan 11;10(1):13. doi: 10.1186/s13045-016-0380-0. PubMed PMID: 28077160; PubMed Central PMCID: PMC5225632.

2: Reichert JM. Antibodies to watch in 2017. MAbs. 2017 Feb/Mar;9(2):167-181. doi: 10.1080/19420862.2016.1269580. Epub 2016 Dec 14. PubMed PMID: 27960628; PubMed Central PMCID: PMC5297518.

3: Hassan R, Thomas A, Alewine C, Le DT, Jaffee EM, Pastan I. Mesothelin Immunotherapy for Cancer: Ready for Prime Time? J Clin Oncol. 2016 Dec;34(34):4171-4179. Epub 2016 Oct 31. PubMed PMID: 27863199.

4: Zhao XY, Subramanyam B, Sarapa N, Golfier S, Dinter H. Novel Antibody Therapeutics Targeting Mesothelin In Solid Tumors. Clin Cancer Drugs. 2016 Oct;3(2):76-86. PubMed PMID: 27853672; PubMed Central PMCID: PMC5080863.

5: Coiffier B, Thieblemont C, de Guibert S, Dupuis J, Ribrag V, Bouabdallah R, Morschhauser F, Navarro R, Le Gouill S, Haioun C, Houot R, Casasnovas O, Holte H, Lamy T, Broussais F, Payrard S, Hatteville L, Tilly H. A phase II, single-arm, multicentre study of coltuximab ravtansine (SAR3419) and rituximab in patients with relapsed or refractory diffuse large B-cell lymphoma. Br J Haematol. 2016 Jun;173(5):722-30. doi: 10.1111/bjh.13992. Epub 2016 Mar 24. PubMed PMID: 27010483.

6: Robak P, Robak T. Management of Multiple Myeloma with Second-Generation Antibody-Drug Conjugates. BioDrugs. 2016 Apr;30(2):87-93. doi: 10.1007/s40259-016-0165-6. Review. PubMed PMID: 26927803.

7: Kantarjian HM, Lioure B, Kim SK, Atallah E, Leguay T, Kelly K, Marolleau JP, Escoffre-Barbe M, Thomas XG, Cortes J, Jabbour E, O'Brien S, Bories P, Oprea C, Hatteville L, Dombret H. A Phase II Study of Coltuximab Ravtansine (SAR3419) Monotherapy in Patients With Relapsed or Refractory Acute Lymphoblastic Leukemia. Clin Lymphoma Myeloma Leuk. 2016 Mar;16(3):139-45. doi: 10.1016/j.clml.2015.12.004. Epub 2015 Dec 21. PubMed PMID: 26775883.

8: Sondergeld P, van de Donk NW, Richardson PG, Plesner T. Monoclonal antibodies in myeloma. Clin Adv Hematol Oncol. 2015 Sep;13(9):599-609. Review. PubMed PMID: 26452191.

9: Sher T, Gertz MA. Antibody based immunotherapy for multiple myeloma: it's about time. Leuk Lymphoma. 2015 Dec 16:1-7. [Epub ahead of print] PubMed PMID: 26373636.

10: Hong EE, Erickson H, Lutz RJ, Whiteman KR, Jones G, Kovtun Y, Blanc V, Lambert JM. Design of Coltuximab Ravtansine, a CD19-Targeting Antibody-Drug Conjugate (ADC) for the Treatment of B-Cell Malignancies: Structure-Activity Relationships and Preclinical Evaluation. Mol Pharm. 2015 Jun 1;12(6):1703-16. doi: 10.1021/acs.molpharmaceut.5b00175. Epub 2015 Apr 27. PubMed PMID: 25856201.

11: Golfier S, Kopitz C, Kahnert A, Heisler I, Schatz CA, Stelte-Ludwig B, Mayer-Bartschmid A, Unterschemmann K, Bruder S, Linden L, Harrenga A, Hauff P, Scholle FD, Müller-Tiemann B, Kreft B, Ziegelbauer K. Anetumab ravtansine: a novel mesothelin-targeting antibody-drug conjugate cures tumors with heterogeneous target expression favored by bystander effect. Mol Cancer Ther. 2014 Jun;13(6):1537-48. doi: 10.1158/1535-7163.MCT-13-0926. Epub 2014 Apr 8. PubMed PMID: 24714131.

12: Robak T, Robak E. Current Phase II antibody-drug conjugates for the treatment of lymphoid malignancies. Expert Opin Investig Drugs. 2014 Jul;23(7):911-24. doi: 10.1517/13543784.2014.908184. Epub 2014 Apr 7. Review. PubMed PMID: 24708159.