Cabazitaxel: Difference between revisions

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Revision as of 12:21, 21 October 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified and watched fields - updated 'ChEBI_Ref', 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit		Revision as of 13:09, 11 November 2011 edit undoBeetstra (talk \| contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'StdInChI', 'CAS_number').Next edit →
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	<!--Identifiers-->		<!--Identifiers-->
	\| CAS_number_Ref = {{cascite\|correct\|??}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 183133-96-2		\| CAS_number = <!-- blanked - oldvalue: 183133-96-2 -->
	\| ATC_prefix = None		\| ATC_prefix = None
	\| ATC_suffix =		\| ATC_suffix =
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	\| UNII = 51F690397J		\| UNII = 51F690397J
	\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}		\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| ChEMBL = 1201748		\| ChEMBL = <!-- blanked - oldvalue: 1201748 -->

	<!--Chemical data-->
	\| C=45 \| H=57 \| N=1 \| O=14		\| C=45 \| H=57 \| N=1 \| O=14
	\| molecular_weight = 835.93 g/mol		\| molecular_weight = 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		\| 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
	\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
	\| StdInChI = 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,		\| StdInChI = 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(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1
	\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
	\| StdInChIKey = BMQGVNUXMIRLCK-OAGWZNDDSA-N		\| StdInChIKey = BMQGVNUXMIRLCK-OAGWZNDDSA-N

Revision as of 13:09, 11 November 2011

Pharmaceutical compound

Cabazitaxel
Clinical data

AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611009
License data	EU EMA: by INN US FDA: Cabazitaxel
Routes of administration	Intravenous
ATC code	None
Legal status
Legal status	UK: POM (Prescription only) US: WARNINGRx-only
Identifiers
IUPAC name (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(Acetyloxy)-15-{amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracycloheptadec-13-ene-2-yl benzoate
PubChem CID	9854073
DrugBank	DB06772
ChemSpider	8029779
UNII	51F690397J
CompTox Dashboard (EPA)	DTXSID40171389
ECHA InfoCard	100.205.741
Chemical and physical data
Formula	C₄₅H₅₇NO₁₄
Molar mass	835.93 g/mol g·mol
3D model (JSmol)	Interactive image
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(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1 Key:BMQGVNUXMIRLCK-OAGWZNDDSA-N
(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. Food and Drug Administration (FDA) for the treatment of hormone-refractory prostate cancer on June 17, 2010. It is a microtubule inhibitor.

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

Clinical trials

In a phase III trial with 755 men for the treatment of hormone-refractory 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%).

References

"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
http://www.cancer.gov/drugdictionary/?CdrID=534131
"Jevtana (cabazitaxel) Injection Approved by U.S. FDA After Priority Review" (Press release). sanofi-aventis. 2010-06-17. Retrieved June 17, 2010.
"Cabazitaxel Effective for Hormone Refractory Prostate Cancer After Failure of Taxotere".

External links

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

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine Vincristine Vindesine Vinflunine Vinorelbine)
Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel Larotaxel Ortataxel Paclitaxel Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Rabacfosadine Thiopurine (Mercaptopurine Tioguanine)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine Carmofur Doxifluridine Floxuridine Fluorouracil Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Belotecan Camptothecin Cositecan Etirinotecan pegol Exatecan Gimatecan Irinotecan Lurtotecan Rubitecan Silatecan Topotecan)
II	Podophyllum (Etoposide Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin Daunorubicin (+cytarabine) Doxorubicin Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Losoxantrone Mitoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Bendamustine Chlormethine Cyclophosphamide (Ifosfamide Trofosfamide) Chlorambucil Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin Cisplatin Dicycloplatin Nedaplatin Oxaliplatin Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine Mitozolomide Temozolomide)
Intercalation	Streptomyces (Dactinomycin Bleomycin Mitomycins Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib) CDK inhibitors (Abemaciclib Alvocidib Palbociclib Ribociclib Seliciclib) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin) LI (Masoprocol) PARP inhibitor (Fuzuloparib Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Inavolisib Umbralisib) IDH (Enasidenib Ivosidenib Olutasidenib Vorasidenib)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Eflornithine Elesclomol Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idecabtagene vicleucel Imetelstat Lifileucel Lisocabtagene maraleucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Nadofaragene firadenovec Navitoclax Obecabtagene autoleucel Oblimersen Omacetaxine mepesuccinate Plitidepsin Tabelecleucel Retinoids (Alitretinoin Tretinoin) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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