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Diflomotecan

Clinical data
Trade names	Diflomotecan
Identifiers
IUPAC name (R)-5-ethyl-9,10-difluoro-5-hydroxy-4,5-dihydrooxepinoindolizinoquinoline-3,15(1H,13H)-dione
CAS Number	220997-97-7
PubChem CID	219023
ChemSpider	189858
UNII	QKT1LC4J1P
ChEBI	CHEBI:144046
ChEMBL	ChEMBL306280
CompTox Dashboard (EPA)	DTXSID201026358
Chemical and physical data
Formula	C21H16F2N2O4
Molar mass	398.366 g·mol
3D model (JSmol)	Interactive image
SMILES O=C1N2C(C3=NC(C=C(F)C(F)=C4)=C4C=C3C2)=CC((O)(CC)C5)=C1COC5=O
InChI InChI=1S/C21H16F2N2O4/c1-2-21(28)7-18(26)29-9-12-13(21)5-17-19-11(8-25(17)20(12)27)3-10-4-14(22)15(23)6-16(10)24-19/h3-6,28H,2,7-9H2,1H3/t21-/m1/s1 Key:LFQCJSBXBZRMTN-OAQYLSRUSA-N

Diflomotecan (also known as BN80905) is a chemotherapeutic agent that is a topoisomerase inhibitor (Top1). It varies from other camptothecin based Top1 inhibitors like topotecan in having a 7-membered E-ring. The oxepan-2-one ring in the homocamptothecin analogues is more stable in plasma compared to the 6-membered lactone in camptothecin. Diflomotecan was the first homocamptothecin to enter clinical trials and is currently in phase I for treating patients with sensitive small cell lung cancer (SCLC).

References

1. Bailly C (2003). "Homocamptothecins: potent topoisomerase I inhibitors and promising anticancer drugs". Critical Reviews in Oncology/Hematology. 45 (1): 91–108. doi:10.1016/s1040-8428(02)00090-2. PMID 12482574.
2. Kroep JR, Gelderblom H (2009). "Diflomotecan, a promising homocamptothecin for cancer therapy". Expert Opin Investig Drugs. 18 (1): 69–75. doi:10.1517/13543780802571674. PMID 19053883. S2CID 73027318.
3. "Diflomotecan (BN80915) Administered Once Every 3 Weeks in Treating Patients With Sensitive Small Cell Lung Cancer (SCLC) - Full Text View - ClinicalTrials.gov". clinicaltrials.gov.

• Epsilon-lactones
• Topoisomerase inhibitors