Paclitaxel

Paclitaxel

Clinical data
Trade names	Taxol, Abraxane, Onxol, others
AHFS/Drugs.com	Monograph
Pregnancy category	US: D (Evidence of risk)
Routes of administration	IV
ATC code	L01CD01 (WHO) L01CD03 (WHO) (paclitaxel poliglumex)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	6.5% (by mouth)
Protein binding	89 to 98%
Metabolism	Liver (CYP2C8 and CYP3A4)
Biological 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 Y
PubChem (CID)	36314
IUPHAR/BPS	2770
DrugBank	DB01229 Y
ChemSpider	10368587 Y
UNII	P88XT4IS4D Y
KEGG	D00491 Y
ChEBI	CHEBI:45863 Y
ChEMBL	CHEMBL428647 N
PDB ligand ID	TA1 (PDBe, RCSB PDB)
ECHA InfoCard	100.127.725
Chemical and physical data
Formula	C47H51NO14
Molar mass	853.906 g/mol
3D model (Jmol)	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 Y Key:RCINICONZNJXQF-MZXODVADSA-N Y
NY (what is this?)

Paclitaxel (PTX), sold under the brand name Taxol among others, is a chemotherapy medication used to treat a number of types of cancer. This includes ovarian cancer, breast cancer, lung cancer, Kaposi sarcoma, cervical cancer, and pancreatic cancer. It is given by injection into a vein. There is also an albumin bound formulation.

Common side effects include hair loss, bone marrow suppression, numbness, allergic reactions, muscle pains, and diarrhea. Other serious side effects include heart problems, increased risk of infection, and lung inflammation. Use during pregnancy may result in harm to the baby. Paclitaxel is in the taxane family of medications. It works by interference with the normal function of microtubules during cell division.

Paclitaxel was first isolated in 1971 from the Pacific yew and approved for medical use in 1993. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 7.06 to 13.48 USD per 100 mg vial. This amount in the United Kingdom costs the NHS about 66.85 pounds. It is now manufactured by cell culture.