maytansine

Also known as NSC-153858, NSC 153858

Maitansine (INN), or maytansine (USAN), is a cytotoxic agent. It inhibits the assembly of microtubules by binding to tubulin at the rhizoxin binding site. The maytansine binding site and binding mode has been characterized.

Chemical data

Formula: C34H46ClN3O10
Molecular weight: 692.2 g/mol
IUPAC name: [(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate
SMILES: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)\C)OC)(NC(=O)O2)O
InChIKey: WKPWGQKGSOKKOO-RSFHAFMBSA-N
XLogP: 2
Polar surface area: 156 Å²
H-bond donors: 2
H-bond acceptors: 10
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Research

1,444 papers

Maytansine.Cancer treatment reviews · 1978
Biomimetic Nanoerythrosome-Coated Aptamer-DNA Tetrahedron/Maytansine Conjugates: pH-Responsive and Targeted Cytotoxicity for HER2-Positive Breast Cancer.Advanced materials (Deerfield Beach, Fla.) · 2022
New insights into the anticancer therapeutic potential of maytansine and its derivatives.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2023
Strategies and challenges for the next generation of antibody-drug conjugates.Nature reviews. Drug discovery · 2017
Bridging the maytansine and vinca sites: Cryptophycins target β-tubulin's T5-loop.The Journal of biological chemistry · 2024

via PubMed

Wikidata facts

Mass: 691.287

Show 6 more facts

chemical formula: C₃₄H₄₆ClN₃O₁₀
canonical SMILES: CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)C)C)C)OC)(NC(=O)O2)O
found in taxon: Gymnosporia emarginata
isomeric SMILES: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)\C)OC)(NC(=O)O2)O
World Health Organisation international non-proprietary name: maitansine
Commons category: Maitansine

Sources (2)

via Wikidata · CC0

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