valrubicin
Trade name: valstar
Approved
Sep 25, 1998
Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the bladder. Valrubicin is an anthracycline that affects a variety of inter-related biological functions, most of which involve nucleic acid metabolism. It readily penetrates into cells, where after DNA intercalation, it inhibits the incorporation of nucleosides into nucleic acids, causes extensive chromosomal damage, and arrests cell cycle in G2. Although valrubicin does not bind strongly to DNA, a principal mechanism of its action, mediated by valrubicin metabolites, is interference with the normal DNA breaking-resealing action of DNA topoisomerase II. Valrubicin is FDA approved drug, sold under the trade name Valstar. — NCATS
Clinical trial activity
7 trials · 9 clinical orgs · 5 marketing orgs
Earliest trial started Nov 1, 1993 (NCT01316874)
Timeline
1990s
- Jan 1, 1993
Endo Pharmaceuticals — Earliest Phase 2 Sponsor(trial)
- May 23, 1994
Orphan Drug Designation
- Jan 1, 1996
Anthra Pharmaceuticals — Earliest Phase 3 Sponsor(trial)
- Sep 25, 1998
Anthra Pharmaceuticals — Earliest FDA Approval
- Sep 25, 1998
Endo Pharmaceuticals — NDA Secondary Org
- Sep 25, 1998
Anthra Pharmaceuticals — NDA Organization
- Sep 25, 1998
Endo Pharmaceuticals — Marketing Organization
- Sep 25, 1998
DuPont — NDA Secondary Org
2010s
- Jan 1, 2012
Earliest Phase 1 Sponsor(trial)
- Apr 19, 2019
Hikma — Marketing Organization
- Apr 19, 2019
Custopharm Inc — Marketing Organization
Indications
Mechanism of action
- DNA topoisomerase II alphaINHIBITOR
TOP2A inhibitor
- DNAINHIBITOR
DNA inhibitor
Approval history
- approvedPriority reviewSep 25, 1998
Chemistry & pharmacology
SMILES
CCCCC(=O)OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O2)C3=C(C1)C(O)=C4C(=O)C5=CC=CC(OC)=C5C(=O)C4=C3O- Mol. weight
- 723.6437 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Prescription Only
Oral
No
Parenteral
Yes
Topical
No
Sources
- WikipediaValrubicin ↗
- NCATS2C6NUM6878 ↗
- ChEMBLCHEMBL1096885 ↗
Also known as
- 2-oxo-2-[(2s,4s)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-({2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
- 2-oxo-2-[(2s,4s)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-({2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracen-2-yl]ethyl pentanoate
- (2s-cis)-pentanoic acid, 2-(1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-((2,3,6-trideoxy-3-((trifluoroacetyl)amino)-alpha-l-lyxo-hexopyranosyl)oxy)-2-naphth acenyl)-2-oxoethyl ester
- (8s, 10s)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-(2,2,2-trifluoroacetamido)-α-l-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione 8²-valerate
- (8s, 10s)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-(2,2,2-trifluoroacetamido)-α-l-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione 8²-valerate
- ad 32
- ad-32
- ad-32
- ad-32
- ad-32
- nsc-246131
- n-trifluoroacetyladriamycin 14-valerate
- n-trifluoroacetyladriamycin 14-valerate
- n-trifluoroacetyldoxorubicin 14-valerate
- paladin brand of valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicin
- valrubicina
- valrubicina
- valrubicine
- valrubicine
- valrubicinum
- valrubicinum
- valstar
- valstar
- valstar
- valstar
- valstar
- valtaxin
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT01438112 | Phase 2/Phase 3 (Phase 3) | Mar 1, 2014 | Cold Genesys, Inc. |
| NCT01606345 | Phase 1 | Jul 1, 2012 | Endo Pharmaceuticals, University of South Florida |
| NCT01310803 | Phase 3 | May 1, 2011 | Endo Pharmaceuticals, University of South Florida |
| NCT00003759 | Phase 2 | Nov 1, 1998 | Anthra Pharmaceuticals, University of Texas at Houston |
| NCT00003129 | Phase 2 | Jul 1, 1998 | Eastern Cooperative Oncology Group, National Cancer Institute (NCI), Northwestern University |
| NCT00003725 | Phase 3 | Dec 1, 1996 | Anthra Pharmaceuticals, University of California, San Francisco |
| NCT01316874 | Phase 2/Phase 3 (Phase 3) | Nov 1, 1993 | Endo Pharmaceuticals |
Organizations
Research & Development (9)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Endo Pharmaceuticals | For profit | 3 | 2 | 2 | 1993 |
| Anthra Pharmaceuticals | For profit | 2 | 2 | 2 | 1996 |
| University of South Florida | Academic/Hospital | 2 | 1 | 2 | 2011 |
| Cold Genesys, Inc. | For profit | 1 | 1 | 1 | 2014 |
| Eastern Cooperative Oncology Group | Academic/Hospital | 1 | 1 | 1 | 1998 |
| National Cancer Institute (NCI) | Government | 1 | 0 | 1 | 1998 |
| Northwestern University | Academic/Hospital | 1 | 0 | 1 | 1998 |
| University of California, San Francisco | Academic/Hospital | 1 | 0 | 1 | 1996 |
| University of Texas at Houston | Academic/Hospital | 1 | 0 | 1 | 1998 |
Marketing (6)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Anthra Pharmaceuticals | For profit | NDA | Sep 25, 1998 |
| Custopharm Inc | For profit | MKTG | Apr 19, 2019 |
| DuPont | For profit | NDA2 | Sep 25, 1998 |
| Endo Pharmaceuticals | For profit | NDA2 | Sep 25, 1998 |
| Endo Pharmaceuticals | For profit | MKTG | Sep 25, 1998 |
| Hikma | For profit | MKTG | Apr 19, 2019 |