Cabazitaxel

Cabazitaxel

Systematic (IUPAC) name
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(Acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate
Clinical data
Trade names	Jevtana
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611009
Licence data	EMA:Link, US FDA:link
Pregnancy category	US: D (Evidence of risk)
Legal status	UK: POM (Prescription only) US: ℞-only
Routes of administration	Intravenous
Identifiers
CAS Number	183133-96-2 N
ATC code	L01CD04 (WHO)
PubChem	CID: 9854073
IUPHAR/BPS	6798
DrugBank	DB06772 Y
ChemSpider	8029779 Y
UNII	51F690397J Y
ChEBI	CHEBI:63584 N
ChEMBL	CHEMBL1201748 N
Chemical data
Formula	C45H57NO14
Molecular mass	835.93 g/mol
SMILES CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)OC)C)OC
InChI InChI=1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35, N Key:BMQGVNUXMIRLCK-OAGWZNDDSA-N Y
NY (what is this?)  (verify)

Cabazitaxel (previously XRP-6258, trade name Jevtana) is a semi-synthetic derivative of a natural taxoid. It was developed by Sanofi-Aventis and was approved by the U.S. FDA for the treatment of hormone-refractory prostate cancer on June 17, 2010. It is a microtubule inhibitor, and the fourth taxane to be approved as a cancer therapy.

Cabazitaxel in combination with prednisone is a treatment option for hormone-refractory prostate cancer following docetaxel-based treatment.

Clinical trials

In a phase III trial with 755 men for the treatment of castration-resistant prostate cancer, median survival was 15.1 months for patients receiving cabazitaxel versus 12.7 months for patients receiving mitoxantrone. Cabazitaxel was associated with more grade 3–4 neutropenia (81.7%) than mitoxantrone (58%).

External links

• Cabazitaxel - Official web site of manufacturer.
• Cabazitaxel Prescribing Information - Official prescribing information.
• U.S. National Library of Medicine: Drug Information Portal - Cabazitaxel