Paclitaxel

Paclitaxel
Clinical data
Trade names	Taxol, Abraxane, others
Other names	PTX
AHFS/Drugs.com	Monograph
MedlinePlus	a607070
License data	EU EMA: by INN; US DailyMed: Paclitaxel;
Pregnancy; category	AU: D; ;
Routes of; administration	Intravenous
ATC code	L01CD01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	6.5% (by mouth)
Protein binding	89 to 98%
Metabolism	Liver (CYP2C8 and CYP3A4)
Elimination half-life	5.8 hours
Excretion	Fecal and urinary
Identifiers
	IUPAC name (2α,4α,5β,7β,10β,13α)-4,10-Bis(acetyloxy)-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate;
CAS Number	33069-62-4 ;
PubChem CID	36314;
IUPHAR/BPS	2770;
DrugBank	DB01229 ;
ChemSpider	10368587 ;
UNII	P88XT4IS4D;
KEGG	D00491 ;
ChEBI	CHEBI:45863 ;
ChEMBL	ChEMBL428647 ;
PDB ligand	TA1 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID9023413 ;
ECHA InfoCard	100.127.725
Chemical and physical data
Formula	C47H51NO14
Molar mass	853.918 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C2[C@@]([C@]([C@H]([C@@H]3[C@]4([C@H](OC4)C[C@@H]([C@]3(C(=O)[C@@H]2OC(=O)C)C)O)OC(=O)C)OC(=O)c5ccccc5)(C[C@@H]1OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7)O)(C)C;
	InChI InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1 ; Key:RCINICONZNJXQF-MZXODVADSA-N ;
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Paclitaxel, sold under the brand name Taxol among others, is a chemotherapy medication used to treat ovarian cancer, esophageal cancer, breast cancer, lung cancer, Kaposi's sarcoma, cervical cancer, and pancreatic cancer.^[4] It is administered by intravenous injection.^[4] There is also an albumin-bound formulation.^[4]

Common side effects include hair loss, bone marrow suppression, numbness, allergic reactions, muscle pains, and diarrhea.^[4] Other side effects include heart problems, increased risk of infection, and lung inflammation.^[4] There are concerns that use during pregnancy may cause birth defects.^[5]^[4] Paclitaxel is in the taxane family of medications.^[6] It works by interference with the normal function of microtubules during cell division.^[4]

Paclitaxel was isolated in 1971 from the Pacific yew and approved for medical use in 1993.^[7]^[8] It is on the World Health Organization's List of Essential Medicines.^[9] It has been made from precursors, and through cell culture.^[8]

^ "Paclitaxel Use During Pregnancy". Drugs.com. 24 January 2019. Archived from the original on 3 December 2020. Retrieved 19 May 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 October 2023.
^ Peltier S, Oger JM, Lagarce F, Couet W, Benoît JP (June 2006). "Enhanced oral paclitaxel bioavailability after administration of paclitaxel-loaded lipid nanocapsules". Pharmaceutical Research. 23 (6): 1243–1250. doi:10.1007/s11095-006-0022-2. PMID 16715372. S2CID 231917.
^ ^a ^b ^c ^d ^e ^f ^g "Paclitaxel". The American Society of Health-System Pharmacists. Archived from the original on 14 September 2017. Retrieved 2 January 2015.
^ Berveiller P, Mir O (2012). "Taxanes during pregnancy: probably safe, but still to be optimized". Oncology. 83 (4): 239–240. doi:10.1159/000341820. PMID 22907122.
^ Chang AE, Ganz PA, Hayes DF, Kinsella T, Pass HI, Schiller JH, et al. (2007). Oncology: An Evidence-Based Approach. Springer Science & Business Media. p. 34. ISBN 9780387310565. Archived from the original on 21 December 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 512. ISBN 9783527607495. Archived from the original on 21 December 2016.
^ ^a ^b "Taxol® (NSC 125973)". National Cancer Institute. Archived from the original on 5 September 2015. Retrieved 14 February 2016. Wayback machine
^ 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] "Paclitaxel Use During Pregnancy". Drugs.com. 24 January 2019. Archived from the original on 3 December 2020. Retrieved 19 May 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 October 2023.

[bioavail-3] Peltier S, Oger JM, Lagarce F, Couet W, Benoît JP (June 2006). "Enhanced oral paclitaxel bioavailability after administration of paclitaxel-loaded lipid nanocapsules". Pharmaceutical Research. 23 (6): 1243–1250. doi:10.1007/s11095-006-0022-2. PMID 16715372. S2CID 231917.

[AHFS2015-4] ^ ^a ^b ^c ^d ^e ^f ^g "Paclitaxel". The American Society of Health-System Pharmacists. Archived from the original on 14 September 2017. Retrieved 2 January 2015.

[5] Berveiller P, Mir O (2012). "Taxanes during pregnancy: probably safe, but still to be optimized". Oncology. 83 (4): 239–240. doi:10.1159/000341820. PMID 22907122.

[6] Chang AE, Ganz PA, Hayes DF, Kinsella T, Pass HI, Schiller JH, et al. (2007). Oncology: An Evidence-Based Approach. Springer Science & Business Media. p. 34. ISBN 9780387310565. Archived from the original on 21 December 2016.

[Fis2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 512. ISBN 9783527607495. Archived from the original on 21 December 2016.

[NCI2016-8] "Taxol® (NSC 125973)". National Cancer Institute. Archived from the original on 5 September 2015. Retrieved 14 February 2016. Wayback machine

[WHO21st-9] 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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