Structure via PubChem · Public domain (PubChem)
lurbinectedin
Sign in to saveLurbinectedin, sold under the brand name Zepzelca, is a medication used for the treatment of small cell lung cancer.
Chemical data
- Formula
- C41H44N4O10S
- Molecular weight
- 784.9 g/mol
- IUPAC name
- [(1R,2R,3R,11S,12S,14R,26R)-5,12-dihydroxy-6,6'-dimethoxy-7,21,30-trimethyl-27-oxospiro[17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaene-26,1'-2,3,4,9-tetrahydropyrido[3,4-b]indole]-22-yl] acetate
- SMILES
- CC1=CC2=C([C@@H]3[C@@H]4[C@H]5C6=C(C(=C7C(=C6[C@@H](N4[C@H]([C@H](C2)N3C)O)COC(=O)[C@@]8(CS5)C9=C(CCN8)C2=C(N9)C=CC(=C2)OC)OCO7)C)OC(=O)C)C(=C1OC)O
- InChIKey
- YDDMIZRDDREKEP-HWTBNCOESA-N
- XLogP
- 3.9
- Polar surface area
- 190 Ų
- H-bond donors
- 4
- H-bond acceptors
- 14
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 784.278
Show 4 more facts
- Commons category
- Lurbinectedin
- canonical SMILES
- CC1=C(C(=C2C3C4C5C6=C(C(N4C(C(N3C)CC2=C1)O)COC(=O)C7(CS5)C8=C(CCN7)C9=C(N8)C=CC(=C9)OC)C1=C(C(=C6OC(=O)C)C)OCO1)O)OC
- isomeric SMILES
- CC1=C(C(=C2[C@@H]3[C@@H]4[C@H]5C6=C([C@@H](N4[C@H]([C@@H](N3C)CC2=C1)O)COC(=O)[C@@]7(CS5)C8=C(CCN7)C9=C(N8)C=CC(=C9)OC)C1=C(C(=C6OC(=O)C)C)OCO1)O)OC
- chemical formula
- C₄₁H₄₄N₄O₁₀S
Sources (2)
via Wikidata · CC0
~7 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Adverse effects
- Structure
- Synthesis
- Mechanism of action
- History
- Research
- Clinical Trials
- References
- External links
Lurbinectedin, sold under the brand name Zepzelca, is a medication used for the treatment of small cell lung cancer.
Lurbinectedin is a synthetic tetrahydropyrrolo [4,3,2-de]quinolin-8(1H)-one alkaloid analogue with potential antineoplastic activity. Lurbinectedin covalently binds to residues lying in the minor groove of DNA, which may result in delayed progression through S phase, cell cycle arrest in the G2/M phase and cell death.
Excerpted from Wikipedia’s “lurbinectedin” article, available under the CC BY-SA 4.0 licence.