Paclitaxel

Paclitaxel
Clinical data
Trade namesTaxol, Abraxane, others
Other namesPTX
AHFS/Drugs.comMonograph
MedlinePlusa607070
License data
Pregnancy
category
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability6.5% (by mouth)[10]
Protein binding89 to 98%
MetabolismLiver (CYP2C8 and CYP3A4)
Elimination half-life5.8 hours
ExcretionFecal and urinary
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.127.725 Edit this at Wikidata
Chemical and physical data
FormulaC47H51NO14
Molar mass853.918 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:RCINICONZNJXQF-MZXODVADSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[11] It is administered by intravenous injection.[11] There is also an albumin-bound formulation.[11]

Common side effects include hair loss, bone marrow suppression, numbness, allergic reactions, muscle pains, and diarrhea.[11] Other side effects include heart problems, increased risk of infection, and lung inflammation.[11] There are concerns that use during pregnancy may cause birth defects.[12][11] Paclitaxel is in the taxane family of medications.[13] It works by interference with the normal function of microtubules during cell division.[11]

Paclitaxel was isolated in 1971 from the Pacific yew and approved for medical use in 1993.[14][15] It is on the World Health Organization's List of Essential Medicines.[16] It has been made from precursors, and through cell culture.[15]

  1. ^ "Paclitaxel Use During Pregnancy". Drugs.com. 24 January 2019. Archived from the original on 3 December 2020. Retrieved 19 May 2020.
  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.
  3. ^ "Taxol (paclitaxel) injection". DailyMed. Retrieved 28 July 2024.
  4. ^ "Abraxane- paclitaxel injection, powder, lyophilized, for suspension". DailyMed. 31 October 2022. Retrieved 28 July 2024.
  5. ^ "Abraxane EPAR". European Medicines Agency (EMA). 11 January 2008. Retrieved 30 August 2024.
  6. ^ Cite error: The named reference Naveruclif EPAR was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Apexelsin EPAR was invoked but never defined (see the help page).
  8. ^ "Naveruclif PI". Union Register of medicinal products. 8 January 2024. Retrieved 28 July 2024.
  9. ^ "Apexelsin PI". Union Register of medicinal products. 26 July 2024. Retrieved 28 July 2024.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 512. ISBN 9783527607495. Archived from the original on 21 December 2016.
  15. ^ a b "Taxol (NSC 125973)". National Cancer Institute. Archived from the original on 5 September 2015. Retrieved 14 February 2016. Wayback machine
  16. ^ 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.