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McMMAE, also known as monomethyl auristatin E, is a potent antineoplastic agent that functions by inhibiting cell division through the obstruction of tubulin polymerization. It is primarily utilized as a cytotoxic component in antibody-drug conjugates (ADCs) for cancer treatment, ensuring that it is specifically targeted to cancer cells to minimize the impact on healthy cells.

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  • L-Valinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-N-methyl-L-valyl- N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenyl ethyl]amino]-1-methoxy-2-methyl-3-oxopr

    Cas No: 863971-24-8

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  • L-Valinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-N-methyl-L-valyl- N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenyl ethyl]amino]-1-methoxy-2-methyl-3-oxopropy

    Cas No: 863971-24-8

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  • 863971-24-8 Structure
  • Basic information

    1. Product Name: McMMAE
    2. Synonyms: Mc MMAE;McMMAE;Mc-MMAE;37: PN: WO2007140371 PAGE: 273 claimed sequence;Maleimidocaproyl-monomethylauristatin E
    3. CAS NO:863971-24-8
    4. Molecular Formula: C49H78N6O10
    5. Molecular Weight: 911.17782
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 863971-24-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 1025.2±65.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.144±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: 13.63±0.46(Predicted)
    10. CAS DataBase Reference: McMMAE(CAS DataBase Reference)
    11. NIST Chemistry Reference: McMMAE(863971-24-8)
    12. EPA Substance Registry System: McMMAE(863971-24-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 863971-24-8(Hazardous Substances Data)

863971-24-8 Usage

Uses

Used in Cancer Treatment:
McMMAE is used as a cytotoxic component in antibody-drug conjugates (ADCs) for the treatment of cancer. Its application is based on its ability to inhibit cell division, making it a crucial element in targeted cancer therapies.
Used in the Development of ADCs:
McMMAE is used as a key component in the development of antibody-drug conjugates, which are designed to deliver the cytotoxic agent directly to cancer cells. This targeted approach enhances the efficiency and safety of cancer treatments by minimizing the impact on healthy cells.
Used in the Treatment of Lymphomas:
McMMAE is used in the formulation of Brentuximab vedotin, a well-known ADC that is approved for the treatment of certain types of lymphomas. The ADC combines the cytotoxic properties of McMMAE with a specific antibody that targets cancer cells, improving the therapeutic outcomes for patients with these conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 863971-24-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,6,3,9,7 and 1 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 863971-24:
(8*8)+(7*6)+(6*3)+(5*9)+(4*7)+(3*1)+(2*2)+(1*4)=208
208 % 10 = 8
So 863971-24-8 is a valid CAS Registry Number.

863971-24-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name Maleimidocaproyl-monomethylauristatin E

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:863971-24-8 SDS

863971-24-8Downstream Products

863971-24-8Relevant articles and documents

Antibody-drug conjugate using ionized CYS-linker-mmae as the potent payload shows optimal therapeutic safety

Fan, Shiyong,Li, Wei,Liu, Lianqi,Wang, Yanming,Xiao, Dian,Xie, Fei,Zhong, Wu,Zhou, Xinbo

, (2020/04/01)

Monomethyl auristatin E (MMAE) is the most popular and widely used cytotoxin in the development of antibody-drug conjugates (ADCs). However, current MMAE-based ADCs are all constructed using cleavable linkers, and this design concept still has insurmountable drawbacks. Their potential instabilities and lipophilic MMAE-induced “bystander effect” inevitably increase the toxicity to normal tissues. Herein, we overturn previous negative views of MMAE-based ADCs with non-cleavable linkers and propose using ionized L-Cysteine (Cys)-linker-MMAE as a novel payload, which can ingeniously enrich and enter tumor cells through receptor-mediated endocytosis of antibodies while its lower permeability helps to avoid further off-target toxicity. We demonstrate that Cys-linker-MMAE maintains high potency similar to free MMAE at the tubulin molecular level and can also be efficiently released in target cells. As a result, the preferred ADC (mil40-15) not only exhibits ideal plasma stability and maintains potent cytotoxicity as MMAE (IC50: 10?11 M), but also shows improved safety with lower bystander toxicity (IC50: 10?9 M), its maximum tolerated dose approaching the level of the naked antibody (160 mg/kg). This study indicated that Cys-linker-MMAE has the potential as a potent payload for ADCs, which is expected to provide novel strategies for the development of MMAE-based ADCs.

BIOLOGICAL MATERIALS AND USES THEREOF

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Page/Page column 75, (2016/06/06)

The invention provides compounds comprising a therapeutic agent coupled to a carrier molecule, with a minimum coupling ratio of 5: 1; wherein the carrier molecule is (i) an antibody fragment or derivative thereof or (ii) an antibody mimetic or derivative thereof; and wherein the therapeutic agents are coupled onto a lysine amino acid residue; and further wherein the therapeutic agent is not a photosensitising agent. There is also provided uses, methods relating to such compounds, as well as processes for their manufacture.

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