7-ethyl-10-hydroxycamptothecin

Also known as SN 38 lactone, 10-Hydroxy-7-ethylcamptothecin, 7-Ethyl-10-hydroxy-20(S)-camptothecin, SN 38

SN-38 is an antineoplastic drug. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold.

Chemical data

Formula: C22H20N2O5
Molecular weight: 392.4 g/mol
IUPAC name: (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)O
InChIKey: FJHBVJOVLFPMQE-QFIPXVFZSA-N
XLogP: 1.4
Polar surface area: 100 Å²
H-bond donors: 2
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule
Indications: small cell lung carcinoma, breast cancer, lung cancer, cancer

via ChEMBL · EBI

Wikidata facts

Subclass of: alkaloid
Mass: 392.137222

Show 3 more facts

chemical formula: C₂₂H₂₀N₂O₅
isomeric SMILES: CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)[C@@]5(CC)O)O
canonical SMILES: CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)C5(CC)O)O

Sources (5)

via Wikidata · CC0

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