Taxane

Taxane
Names
	IUPAC name Taxane
	Systematic IUPAC name (4R,4aR,6S,9R,10S,12aS)-4,9,12a,13,13-Pentamethyltetradecahydro-6,10-methanobenzo[10]annulene
Identifiers
CAS Number	1605-68-1;
3D model (JSmol)	Interactive image;
ChemSpider	7827751;
PubChem CID	9548828;
	InChI InChI=1S/C20H36/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h14-18H,6-13H2,1-5H3/t14-,15-,16+,17+,18-,20+/m1/s1 Key: DKPFODGZWDEEBT-QFIAKTPHSA-N; InChI=1S/C20H36/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h14-18H,6-13H2,1-5H3/t14-,15-,16+,17+,18-,20+/m1/s1 Key: DKPFODGZWDEEBT-QFIAKTPHSA-N;
	SMILES C[C@@H]1CCC[C@@]2([C@@H]1C[C@@H]3CC[C@H]([C@@H](C3(C)C)CC2)C)C;
Properties
Chemical formula	C20H36
Molar mass	276.508 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Taxanes are a class of diterpenes. They were originally identified from plants of the genus Taxus (yews), and feature a taxadiene core. Paclitaxel (Taxol) and docetaxel (Taxotere) are widely used as chemotherapy agents.^[2]^[3] Cabazitaxel was FDA approved to treat hormone-refractory prostate cancer.

Taxanes present difficulties in formulation as medicines because they are poorly soluble in water.

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1540. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ Hagiwara, H.; Sunada, Y. (2004). "Mechanism of taxane neurotoxicity". Breast Cancer (Tokyo, Japan). 11 (1): 82–85. doi:10.1007/BF02968008. PMID 14718798. S2CID 22096988.
^ Rowinsky, MD, Eric K. (February 1997). "The Development and Clinical Utility of the Taxane Class of Antimicrotubule Chemotherapy Agents". Annual Review of Medicine. 48 (1): 353–374. doi:10.1146/annurev.med.48.1.353. PMID 9046968.

Names

IUPAC name Taxane^[1]
Systematic IUPAC name (4R,4aR,6S,9R,10S,12aS)-4,9,12a,13,13-Pentamethyltetradecahydro-6,10-methanobenzo[10]annulene
Identifiers
CAS Number	1605-68-1
3D model (JSmol)	Interactive image
ChemSpider	7827751
PubChem CID	9548828
InChI InChI=1S/C20H36/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h14-18H,6-13H2,1-5H3/t14-,15-,16+,17+,18-,20+/m1/s1 Key: DKPFODGZWDEEBT-QFIAKTPHSA-N InChI=1S/C20H36/c1-14-7-6-11-20(5)12-10-17-15(2)8-9-16(13-18(14)20)19(17,3)4/h14-18H,6-13H2,1-5H3/t14-,15-,16+,17+,18-,20+/m1/s1 Key: DKPFODGZWDEEBT-QFIAKTPHSA-N
SMILES C[C@@H]1CCC[C@@]2([C@@H]1C[C@@H]3CC[C@H]([C@@H](C3(C)C)CC2)C)C
Properties
Chemical formula	C₂₀H₃₆
Molar mass	276.508 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references