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Mafodotin [Usan]

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2 API Suppliers, 2 USDMF

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Synopsis

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Chemistry

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Also known as: Schembl13342952, Dtxsid90235521

Molecular Formula

C₄₉H₇₆N₆O₁₁

Molecular Weight

925.2 g/mol

InChI Key

ORFNVPGICPYLJV-MPEKCWBXSA-N

Depatuxizumab/Denintuzumab mafodotin has been used in trials studying the treatment of Lymphoma, Gliosarcoma, Glioblastoma, Malignant Glioma, Squamous Cell Tumors, and Glioblastoma Multiforme.

1 2D Structure

Mafodotin [Usan]

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[(2R)-3-[(2S)-1-[(3R,4S,5S)-4-[[(2S)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoyl-methylamino]-3-methylbutanoyl]amino]-3-methylbutanoyl]-methylamino]-3-methoxy-5-methylheptanoyl]pyrrolidin-2-yl]-3-methoxy-2-methylpropanoyl]amino]-3-phenylpropanoic acid

2.1.2 InChI

InChI=1S/C49H76N6O11/c1-12-32(6)44(37(65-10)29-41(59)54-27-19-22-36(54)45(66-11)33(7)46(60)50-35(49(63)64)28-34-20-15-13-16-21-34)53(9)48(62)42(30(2)3)51-47(61)43(31(4)5)52(8)38(56)23-17-14-18-26-55-39(57)24-25-40(55)58/h13,15-16,20-21,24-25,30-33,35-37,42-45H,12,14,17-19,22-23,26-29H2,1-11H3,(H,50,60)(H,51,61)(H,63,64)/t32-,33+,35-,36-,37+,42-,43-,44-,45?/m0/s1

2.1.3 InChI Key

ORFNVPGICPYLJV-MPEKCWBXSA-N

2.1.4 Canonical SMILES

CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(CC2=CC=CC=C2)C(=O)O)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C(=O)CCCCCN3C(=O)C=CC3=O

2.1.5 Isomeric SMILES

CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1C([C@@H](C)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(C)C(=O)CCCCCN3C(=O)C=CC3=O

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. Schembl13342952

2. Dtxsid90235521

2.3 Create Date

2013-04-19

3 Chemical and Physical Properties

Molecular Formula	C₄₉H₇₆N₆O₁₁
Molecular Weight	925.2 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	27
Exact Mass	924.55720726 g/mol
Monoisotopic Mass	924.55720726 g/mol
Topological Polar Surface Area	212 Å²
Heavy Atom Count	66
Formal Charge	0
Complexity	1680
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

No approved indication.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Selectively targets cancer cells expressing mutant epidermal growth factor receptor (EGFR) vIII or over expressing wild type EGFR. Depatuxizumab mafodotin acts on these cells to inhibit microtuble polymerization thus disrupting mitosis and vesicular trafficking

5.2 Mechanism of Action

Depatuxizumab is a chimeric monoclonal antibody for EGFR which is linked to monomethyl aurastatin F via a maleimidocaproyl linker (mafodotin). Once delivered to the cancer cell, the mafodotin component is able to bind to tubulin and inhibit the exchange of GDP for GTP necessary for the polymerization of tubulin subunits to form microtubules. The inhibition of microtubule polymerization disrupts mitosis and interferes with vesicle trafficking in the cancer cell.

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