Docetaxel

Docetaxel
Clinical data
Trade names	Taxotere, Docecad, Docefrez, others
AHFS/Drugs.com	Monograph
MedlinePlus	a696031
License data	US DailyMed: Docetaxel;
Pregnancy; category	AU: D; ;
Routes of; administration	Intravenous
ATC code	L01CD02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: WARNINGRx-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	NA
Protein binding	>98%
Metabolism	Liver
Elimination half-life	11 hours
Excretion	Bile duct
Identifiers
	IUPAC name 1,7β,10β-trihydroxy-9-oxo-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-{(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate};
CAS Number	114977-28-5 ;
PubChem CID	148124;
IUPHAR/BPS	6809;
DrugBank	DB01248 ;
ChemSpider	130581 ;
UNII	699121PHCA;
KEGG	D07866 ;
ChEBI	CHEBI:4672 ;
ChEMBL	ChEMBL92 ;
CompTox Dashboard (EPA)	DTXSID0040464 ;
ECHA InfoCard	100.129.246
Chemical and physical data
Formula	C43H53NO14
Molar mass	807.890 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OC(C)(C)C)N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@@H]4C(=C3/[C@@H](O)C(=O)[C@]6([C@H]([C@H](OC(=O)c2ccccc2)[C@@](O)(C3(C)C)C4)[C@@]5(OC(=O)C)[C@H](OC5)C[C@@H]6O)C)/C;
	InChI InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1 ; Key:ZDZOTLJHXYCWBA-VCVYQWHSSA-N ;
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Docetaxel (DTX or DXL), sold under the brand name Taxotere among others, is a chemotherapy medication used to treat a number of types of cancer.^[6] This includes breast cancer, head and neck cancer, stomach cancer, prostate cancer and non-small-cell lung cancer.^[7] It may be used by itself or along with other chemotherapy medication.^[6] It is given by slow injection into a vein.^[6]

Common side effects include hair loss, cytopenia (low blood cell counts), numbness, shortness of breath, nausea, vomiting, and muscle pains.^[6] Other severe side effects include allergic reactions and future cancers.^[6] Docetaxel induced pneumotoxicity is also a well recognized adverse effect which has to be identified timely and treated after withholding the drug.^[8] Side effects are more common in people with liver problems.^[6] Use during pregnancy may harm the baby.^[6] Docetaxel is in the taxane family of medications.^[9] It works by disrupting the normal function of microtubules and thereby stopping cell division.^[6]

Docetaxel was patented in 1986 and approved for medical use in 1995.^[10] It is on the World Health Organization's List of Essential Medicines.^[11] Docetaxel is available as a generic medication.^[6]

^ "Docetaxel Use During Pregnancy". Drugs.com. 4 June 2020. Retrieved 29 October 2020.
^ "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.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ "Taxotere- docetaxel injection, solution, concentrate". DailyMed. 26 December 2019. Retrieved 28 October 2020.
^ "Taxotere EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 28 October 2020.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Docetaxel". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
^ "FDA Approval for Docetaxel". National Cancer Institute. 2006-10-05. Archived from the original on 21 December 2016. Retrieved 21 December 2016.
^ Hettiarachchi SM, Thilakaratne D, Dharmasena D, Rathnapala A, Abeysinghe P, Perera E (July 2021). "Docetaxel-induced interstitial lung disease among patients with breast cancer: a case series and review of literature". Respirology Case Reports. 9 (7): e00802. doi:10.1002/rcr2.802. PMC 8200505. PMID 34136263.
^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 622. ISBN 9780857111562.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 512. ISBN 9783527607495. Archived from the original on 2016-12-21.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Drugs.com_pregnancy-1] "Docetaxel Use During Pregnancy". Drugs.com. 4 June 2020. Retrieved 29 October 2020.

[FDA-AllBoxedWarnings-2] "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.

[3] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[Taxotere_FDA_label-4] "Taxotere- docetaxel injection, solution, concentrate". DailyMed. 26 December 2019. Retrieved 28 October 2020.

[Taxotere_EPAR-5] "Taxotere EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 28 October 2020.

[AHFS2016-6] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Docetaxel". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.

[NCI2014-7] "FDA Approval for Docetaxel". National Cancer Institute. 2006-10-05. Archived from the original on 21 December 2016. Retrieved 21 December 2016.

[ReferenceA-8] Hettiarachchi SM, Thilakaratne D, Dharmasena D, Rathnapala A, Abeysinghe P, Perera E (July 2021). "Docetaxel-induced interstitial lung disease among patients with breast cancer: a case series and review of literature". Respirology Case Reports. 9 (7): e00802. doi:10.1002/rcr2.802. PMC 8200505. PMID 34136263.

[BNF69-9] British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 622. ISBN 9780857111562.

[Fis2006-10] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 512. ISBN 9783527607495. Archived from the original on 2016-12-21.

[WHO21st-11] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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