paclitaxel

Also known as BMS-181339-01, PAX, taxol, 5beta,20-epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine, taxol A

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

OverviewAI-generated

Paclitaxel is a chemical compound with the formula C₄₇H₅₁NO₁₄. Its mass is listed as 853.331, while its weight is recorded as 853.9. The compound carries a charge of 0 and has a stylized name written as PACLitaxel.

Chemical properties include an xlogp value of 2.5 and a topological polar surface area of 221. The molecule contains 4 hydrogen bond donors and 14 hydrogen bond acceptors. It is identified by the InChIKey RCINICONZNJXQF-MZXODVADSA-N and the PubChem CID 36314.

In academic literature, paclitaxel is the subject of 51,627 PubMed entries. The compound is also referenced by 1,066 other encyclopedia articles and has a dedicated category on Commons.

Synthesized by Vinony from 15 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.StdInChI: 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
Drug.StdInChIKey: RCINICONZNJXQF-MZXODVADSA-N
Drug.Verifiedfields: changed
Drug.verifiedrevid: 458461737
Drug.image: Taxol.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Paclitaxel-from-hydrate-xtal-Mercury-3D-sk.png
Drug.image_class2: bg-transparent
Drug.tradename: Taxol, Abraxane, others
Drug.MedlinePlus: a607070
Drug.DailyMedID: Paclitaxel
Drug.pregnancy_AU: D
Drug.routes_of_administration: Intravenous
Drug.ATC_prefix: L01
Drug.ATC_suffix: CD01
Drug.legal_AU: S4
Drug.legal_CA: Rx-only

via Wikipedia infobox

Chemical data

Formula: C47H51NO14
Molecular weight: 853.9 g/mol
IUPAC name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
InChIKey: RCINICONZNJXQF-MZXODVADSA-N
XLogP: 2.5
Polar surface area: 221 Å²
H-bond donors: 4
H-bond acceptors: 14
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1992
Admin. routes: parenteral
Indications: breast carcinoma, gastric adenocarcinoma, gastric carcinoma, melanoma

via ChEMBL · EBI

Research

51,627 papers

nab-Paclitaxel mechanisms of action and delivery.Journal of controlled release : official journal of the Controlled Release Society · 2013
Paclitaxel's Mechanistic and Clinical Effects on Breast Cancer.Biomolecules · 2019
Progress in research on paclitaxel and tumor immunotherapy.Cellular & molecular biology letters · 2019
Cytotoxic studies of paclitaxel (Taxol) in human tumour cell lines.British journal of cancer · 1993
Post-genomic illumination of paclitaxel biosynthesis.Nature plants · 2024

via PubMed

Wikidata facts

Mass: 853.331
Manufacturer: Pfizer

Show 11 more facts

chemical formula: C₄₇H₅₁NO₁₄
World Health Organisation international non-proprietary name: paclitaxel
medical condition treated: squamous cell carcinoma of the lung
isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
canonical SMILES: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
Commons category: Paclitaxel
subject has role: essential medicine
stylized name: PACLitaxel
significant drug interaction: phenytoin
legal status (medicine): boxed warning
has characteristic: natural product

Sources (11)

via Wikidata · CC0

~31 min read

Encyclopedic overview

22 sections

Contents

Medical use
Similar compounds
Restenosis
Side effects
Mechanism of action
Chemistry
Production
Bark processing
Semisynthesis
Biosynthesis
Total synthesis
History
Plant screening program
Early clinical trials, supply and the transfer to BMS
Society and culture
Legal status
Economics
Research
Additional images
References
Bibliography
External links

{{Infobox drug | Verifiedfields = changed | verifiedrevid = 458461737 | image = Taxol.svg | image_class = skin-invert-image | width = 250 | alt = | caption = | image2 = Paclitaxel-from-hydrate-xtal-Mercury-3D-sk.png | image_class2 = bg-transparent | alt2 = | pronounce = | tradename = Taxol, Abraxane, others | Drugs.com = | MedlinePlus = a607070 | DailyMedID = Paclitaxel | pregnancy_AU = D | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Intravenous | class = | ATC_prefix = L01 | ATC_suffix = CD01 | ATC_supplemental = | legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =

Excerpted from Wikipedia’s “paclitaxel” article, available under the CC BY-SA 4.0 licence.