Maytansinoid DM4 | Ravtansine | Soravtansine | CAS#796073-69-3 | Antibody Drug Conjugate

MedKoo Cat#: 206839 | Name: Maytansinoid DM4

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Maytansinoid DM4, a chemical derivative of maytansine, 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.

Chemical Structure

Maytansinoid DM4

CAS#796073-69-3

Theoretical Analysis

MedKoo Cat#: 206839

Name: Maytansinoid DM4

CAS#: 796073-69-3

Chemical Formula: C38H54ClN3O10S

Exact Mass: 779.3218

Molecular Weight: 780.37

Elemental Analysis: C, 58.49; H, 6.98; Cl, 4.54; N, 5.38; O, 20.50; S, 4.11

Price and Availability

Size	Price	Availability
5mg	USD 120.00	Ready to ship
10mg	USD 200.00	Ready to ship
25mg	USD 450.00	Ready to ship
50mg	USD 750.00	Ready to ship
100mg	USD 1,350.00	Ready to ship

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Related CAS #

796073-69-3 DM4 hydrate

Synonym

Maytansinoid DM4; DM4; Ravtansine; Soravtansine

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

Appearance

Solid powder

Purity

>95% (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

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

More Info

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

Certificate of Analysis

View CoA: current batch, Lot#X7P06R08

View CoA: current batch, Lot#A9T09K05

QC Data

View QC data: current batch, Lot#A9T09K05

View QC data: current batch, Lot#X7P06R08

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 780.37 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.

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

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.