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Details

Stereochemistry ABSOLUTE
Molecular Formula C68H106N11O15
Molecular Weight 1317.6366
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 13
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VEDOTIN FRAGMENT

SMILES

CC[C@H](C)[C@@]([H])([C@@H](CC(=O)N1CCC[C@@]1([H])[C@@H]([C@@H](C)C(=O)N[C@H](C)[C@H](c2ccccc2)O)OC)OC)N(C)C(=O)[C@H]([C@@H](C)C)NC(=O)[C@H](C(C)C)N(C)C(=O)OCc3ccc(cc3)NC(=O)[C@H](CCCNC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)CCCCCN4C(=O)CC(C4=O)*

InChI

InChIKey=ERROR

HIDE SMILES / InChI

Molecular Formula C68H106N11O15
Molecular Weight 1317.6366
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 13
E/Z Centers 0
Optical Activity UNSPECIFIED

Vedotin fragment (Monomethyl auristatin E, MMAE; SGD-1010) is a synthetic derivative of dolastatin 10 and functions as a potent mitotic inhibitor by inhibiting tubulin polymerization. MMAE is widely used as a cytotoxic component of antibody-drug conjugates (ADCs) to treat several different cancer types. MMAE is a potent radiosensitizer. MMAE radiosensitization can be localized to tumors by targeted activatable cell-penetrating peptides.

Approval Year

PubMed

PubMed

TitleDatePubMed
Intracellular activation of SGN-35, a potent anti-CD30 antibody-drug conjugate.
2010 Feb 1
Tumor radiosensitization by monomethyl auristatin E: mechanism of action and targeted delivery.
2015 Apr 1

Sample Use Guides

Vedotin fragment (MMAE) was incubated at 1-1000 nM with cultured primary human hepatocytes for 72 h, and CYP1A2, CYP2B6, and CYP3A4 mRNA expression was assessed by quantitative reverse transcription-polymerase chain reaction and CYP-specific probe substrate by liquid chromatography coupled with mass spectrometry, along with microtubule disruption by immunofluorescence staining using anti-β-tubulin antibody and imaging. MMAE up to 10 nM had no significant effect on CYP1A2, CYP2B6, and CYP3A4 mRNA expression and activity, whereas at higher concentrations of 100- and 1000-nM MMAE, the CYP mRNA expression and activity were diminished substantially. At the clinical dose, the concentration of MMAE was 7 nM which did not show any significant CYP suppression or microtubule disruption in hepatocytes.
Substance Class Chemical
Created
by admin
on Sun Jun 27 00:33:50 UTC 2021
Edited
by admin
on Sun Jun 27 00:33:50 UTC 2021
Record UNII
Q3606FDE0B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VEDOTIN FRAGMENT
Common Name English
CONJUGATED FORM OF MC-VC-PAB-MMAE
Common Name English
VEDOTIN [USAN]
Common Name English
VEDOTIN (FRAGMENT)
Common Name English
VEDOTIN RADICAL
Common Name English
PAB-MMAE
Code English
VEDOTIN
USAN  
USAN  
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C67422
Created by admin on Sun Jun 27 00:33:52 UTC 2021 , Edited by admin on Sun Jun 27 00:33:52 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C152842
Created by admin on Sun Jun 27 00:33:52 UTC 2021 , Edited by admin on Sun Jun 27 00:33:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL2364667
Created by admin on Sun Jun 27 00:33:52 UTC 2021 , Edited by admin on Sun Jun 27 00:33:52 UTC 2021
PRIMARY
Related Record Type Details
CONJUGATE->CONJUGATE COMPONENT
CONJUGATE->CONJUGATE COMPONENT
PARENT -> DERIVATIVE
CONJUGATE->CONJUGATE COMPONENT
CONJUGATE->CONJUGATE COMPONENT
CONJUGATE->CONJUGATE COMPONENT
CONJUGATE -> TOXIN
DERIVATIVE -> PARENT
CONJUGATE->CONJUGATE COMPONENT
MOLECULAR FRAGMENT
CONJUGATE->CONJUGATE COMPONENT
CONJUGATED ANTIGEN -> CONJUGATE COMPONENT
CONJUGATE -> TOXIN
CONJUGATE->CONJUGATE COMPONENT
CONJUGATE->CONJUGATE COMPONENT