Rubitecan

Rubitecan

Clinical data
Trade names	Orathecin
Routes of administration	Oral (capsules)
ATC code	None
Legal status
Legal status	Application withdrawn
Pharmacokinetic data
Bioavailability	25–30% (rubitecan and 9-AC; in dogs)
Protein binding	97% (rubitecan), 65% (9-AC)
Metabolism	Probably -dependent
Metabolites	9-Aminocamptothecin (9-AC)
Biological half-life	15–18 hours (rubitecan), 18–22 hours (9-AC)
Excretion	Bile and feces (major proportion), urine (the minor one)
Identifiers
IUPAC name (4S)-4-Ethyl-4-hydroxy-11-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
Synonyms	9-Nitrocamptothecin Camptogen (19S)-19-Ethyl-19-hydroxy-10-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
CAS Number	91421-42-0 Y
PubChem CID	472335
ChemSpider	414807 N
UNII	H19C446XXB
KEGG	D04031 N
ChEBI	CHEBI:90225 N
ChEMBL	CHEMBL77305 N
Chemical and physical data
Formula	C20H15N3O6
Molar mass	393.349 g/mol
3D model (Jmol)	Interactive image
SMILES CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5[N+](=O)[O-])N=C4C3=C2)O
InChI InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1 N Key:VHXNKPBCCMUMSW-FQEVSTJZSA-N N
NY (what is this?)

Rubitecan (INN, marketing name Orathecin) is an oral topoisomerase inhibitor, developed by Supergen.

On January 27, 2004, Supergen announced that it has completed the submission of an NDA for rubitecan to the US FDA, and was accepted for filing on March 2004.

On January 2005, Supergen withdrew the NDA for rubitecan, based on feedback indicating that the current data package would not be sufficient to gain US approval, and on January 2006, the Marketing Authorization Application (MAA) filed with the European Medicines Agency (EMA) was also withdrawn.