Structure via PubChem · Public domain (PubChem)
lurtotecan
Sign in to saveLurtotecan is a semi-synthetic analog of camptothecin with antineoplastic activity. Liposomal lurtotecan was in clinical trials as a treatment for topotecan-resistant ovarian cancer, but was discontinued.
Chemical data
- Formula
- C28H30N4O6
- Molecular weight
- 518.6 g/mol
- IUPAC name
- (18S)-18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.03,12.05,10.015,24.017,22]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione
- SMILES
- CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC6=C(C=C5N=C4C3=C2)OCCO6)CN7CCN(CC7)C)O
- InChIKey
- RVFGKBWWUQOIOU-NDEPHWFRSA-N
- XLogP
- 0.3
- Polar surface area
- 105 Ų
- H-bond donors
- 1
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- neoplasm, small cell lung carcinoma, ovarian neoplasm, head and neck malignant neoplasia
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 518.217
- Has use
- medication
Show 5 more facts
- chemical formula
- C₂₈H₃₀N₄O₆
- canonical SMILES
- CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC6=C(C=C5N=C4C3=C2)OCCO6)CN7CCN(CC7)C)O
- isomeric SMILES
- CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC6=C(C=C5N=C4C3=C2)OCCO6)CN7CCN(CC7)C)O
- subject has role
- antineoplastic
- Commons category
- Lurtotecan
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Lurtotecan is a semi-synthetic analog of camptothecin with antineoplastic activity. Liposomal lurtotecan was in clinical trials as a treatment for topotecan-resistant ovarian cancer, but was discontinued.
==Synthesis== thumb|center|600px|class=skin-invert-image|Lurtotecan synthesis Heck reaction Mitsunobu reaction Potassium osmate Sharpless asymmetric dihydroxylation Swern oxidation
Excerpted from Wikipedia’s “lurtotecan” article, available under the CC BY-SA 4.0 licence.