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Rubitecan

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Rubitecan
Rubitecan.svg
Clinical data
Trade namesOrathecin
Other names9-Nitrocamptothecin
9-NC
9-nitro-20(S)-camptothecin
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
Routes of
administration
Oral (capsules)
ATC code
  • None
Legal status
Legal status
  • Application withdrawn
Pharmacokinetic data
Bioavailability25–30% (rubitecan and 9-AC; in dogs)
Protein binding97% (rubitecan), 65% (9-AC)
MetabolismProbably CYP-dependent
Metabolites9-Aminocamptothecin (9-AC)
Elimination half-life15–18 hours (rubitecan), 18–22 hours (9-AC)
ExcretionBile and feces (major proportion), urine (the minor one)[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC20H15N3O6
Molar mass393.349 g/mol g·mol−1
3D model (JSmol)
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Rubitecan (INN, marketing name Orathecin) is an oral topoisomerase inhibitor, developed by SuperGen (now Astex Pharmaceuticals, Inc.; a member of the Otsuka Group).

History

On January 27, 2004, SuperGen announced that it has completed the submission of an NDA for rubitecan to the US FDA,[2] and was accepted for filing on March 2004.[3]

In January 2005, and under the direction of then-CEO James Manuso, SuperGen withdrew the NDA for rubitecan, based on feedback indicating that the current data package would not be sufficient to gain US approval,[4] and on January 2006, the Marketing Authorization Application (MAA) filed with the European Medicines Agency (EMA) was also withdrawn.[5]

The name Rubitecan is a portmanteau of SuperGen's founder, Dr. Joseph Rubinfeld, and the chemical name 9-Nitrocamptothecin.

Synthesis

Large scale production of Rubitecan has encountered problems. The direct nitration of camptothecin results in regioselectivity problems. One way that has been used to synthesize Rubitecan is to nitrate 10-hydroxycamptothecin than remove the hydroxyl functional group.[6]

Use as Anti-Cancer Drug

Rubitecan is a compound used extensively in cancer research. Rubitecan is an effective drug against pancreatic cancer and other solid tumors. One major problem is the lack of oral bioavailability due to low permeability and poor water solubility. One study shows 9-NC-SD through Soluplus1-based solid dispersion system is a much more effective delivery method than free 9-NC.[7]

References


Latest research - Rubitecan

PubMed
Clinical trials
 

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