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( T o p )
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A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
Systematic IUPAC name
(4 R R S R S S 10 ]annulene
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
C[C@@H]1CCC[C@@]2([C@@H]1C[C@@H]3CC[C@H]([C@@H](C3(C )C)CC2)C)C
C 20 H 36
−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Taxanes are a class of diterpenes . They were originally identified from plants of the genus Taxus 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.
Production [ edit ]
As their name suggests, taxanes were first derived from natural sources, but some have been semisynthesized . Paclitaxel was originally derived from the Pacific yew tree.[4] [5] chiral centres—taxol has 11 of these.
Recently, the presence of taxanes in the shells and leaves of Corylus avellana [6] [7]
Mechanism of action [ edit ]
Mechanism of action of taxanes
The principal mechanism of action of the taxane class of drugs is the disruption of microtubule function. Microtubules are essential to cell division, and taxanes stabilize GDP -bound tubulin in the microtubule, thereby inhibiting the process of cell division as depolymerization is prevented. Thus, in essence, taxanes are mitotic inhibitors . In contrast to the taxanes, the vinca alkaloids prevent mitotic spindle formation through inhibition of tubulin polymerization . Both taxanes and vinca alkaloids are, therefore, named spindle poisons or mitosis poisons, but they act in different ways. Taxanes are also thought to be radiosensitizing .
Substances [ edit ]
Hongdoushans A–C are oxygenated taxane diterpenes, isolated from the wood of Taxus wallichiana C 29 H 44 O 7 C 27 H 40 O 7 C 27 H 42 O 6 in vitro .[8] Taxuspines A–D have been isolated from Taxus .[9] [10] [11] [12]
Taxuspine B
Hongdoushan A
Taxanes are usually treated as synonymous with taxoids . The name "taxol" began as a common noun (analogous with other terms in which a genus name root was suffixed with -ol or -in international nonproprietary name of the compound is paclitaxel.
See also [ edit ]
References [ edit ]
^ 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 .
^ Hacker, Miles (2009). "Adverse Drug Reactions". Pharmacology . pp. 327–352. doi :10.1016/B978-0-12-369521-5.00013-0 . ISBN 9780123695215
^ Weaver, Beth A.; Bement, William (2014). "How Taxol/paclitaxel kills cancer cells" . Molecular Biology of the Cell . 25 18 ): 2677–2681. doi :10.1091/mbc.e14-04-0916 ISSN 1059-1524 . PMC 4161504 PMID 25213191 .
^ Ottaggio, Laura; Bestoso, Federica; Armirotti, Andrea; Balbi, Alessandro; Damonte, Gianluca; Mazzei, Mauro; Sancandi, Monica; Miele, Mariangela (2008). "Taxanes from Shells and Leaves of Corylus avellana". Journal of Natural Products . 71 1 ): 58–60. doi :10.1021/np0704046 . PMID 18163585 .
^ Hoffman, Angela M; Shahidi, Fereidoon (January 2009). "Paclitaxel and other taxanes in hazel" . Journal of Functional Foods . 1 1 ): 33–37. doi :10.1016/j.jff.2008.09.004
^ Banskota AH, Usia T, Tezuka Y, Kouda K, Nguyen NT, Kadota S (2002). "Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis". J Nat Prod . 65 11 ): 1700–2. doi :10.1021/np020235j . PMID 12444707 .
^ CID 10417482 from PubChem
^ CID 5321744 from PubChem
^ CID 100991639 from PubChem
^ CID 5321746 from PubChem
External links [ edit ]
taxanes at Wikimedia Commons
Vinflunine §
Vinorelbine # )
Block microtubule disassembly
Docetaxel #
Larotaxel
Ortataxel †
Paclitaxel #
Tesetaxel )
Epothilones Ixabepilone )
Raltitrexed )
Carmofur
Doxifluridine
Floxuridine
Fluorouracil #
Tegafur (+gimeracil/oteracil ))
Etirinotecan pegol †
Exatecan
Gimatecan
Irinotecan #
Lurtotecan ‡
Rubitecan ‡
Silatecan §
Topotecan )
Teniposide )
Amrubicin †
Daunorubicin # (+cytarabine )
Doxorubicin #
Epirubicin
Idarubicin
Pirarubicin
Valrubicin
Zorubicin )
Anthracenediones Losoxantrone
Mitoxantrone
Pixantrone )
Amsacrine
Bisantrene
Crisnatol
Menogaril §
Trofosfamide )
Chlorambucil #
Melphalan (Melphalan flufenamide )
Prednimustine
Uramustine
Cisplatin #
Dicycloplatin
Nedaplatin
Oxaliplatin #
Satraplatin
Hydrazines Procarbazine # )
Etoglucid
Mitobronitol
Pipobroman
Triazenes Dacarbazine #
Mitozolomide §
Temozolomide )
Bleomycin #
Mitomycins
Plicamycin )
Efaproxiral
Methyl aminolevulinate
Padeliporfin
Porphyrin derivatives Porfimer sodium
Talaporfin
Temoporfin
Verteporfin )
Palbociclib
Ribociclib
Seliciclib † )
PrI
PhI Anagrelide )
IMPDI Tiazofurin § )
LI Masoprocol )
PARP inhibitor Fuzuloparib
Niraparib +abiraterone acetate
Olaparib
Rucaparib )
HDAC Belinostat
Entinostat
Panobinostat
Romidepsin
Vorinostat )
PIKI (Pi3K)Alpelisib
Copanlisib
Duvelisib
Idelalisib
Umbralisib ‡ )
Retinoid X receptor Bexarotene )
Sex steroid Testolactone )
Aflibercept
Arsenic trioxide
Asparagine depleters Asparaginase # /Pegaspargase )
Axicabtagene ciloleucel
Belzutifan
Bexarotene
Brexucabtagene autoleucel
Celecoxib
Ciltacabtagene autoleucel
Demecolcine
Denileukin diftitox
Eflornithine
Elesclomol §
Elsamitrucin
Enasidenib
Epacadostat
Eribulin
Estramustine
Glasdegib
Idecabtagene vicleucel
Imetelstat
Ivosidenib
Lifileucel
Lonidamine
Lucanthone
Lurbinectedin
Mitoguazone
Mitotane
Navitoclax
Oblimersen †
Omacetaxine mepesuccinate
Plitidepsin
Retinoids Alitretinoin
Tretinoin # )
Selinexor
Sitimagene ceradenovec
Sotorasib
Tagraxofusp
Talimogene laherparepvec
Tazemetostat
Tebentafusp
Tiazofurine
Tigilanol tiglate
Tisagenlecleucel
Trabectedin
Veliparib
Venetoclax
Verdinexor
Vosaroxin
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Taxane&oldid=1220549324 " C a t e g o r i e s : ● M i c r o t u b u l e i n h i b i t o r s ● M i t o t i c i n h i b i t o r s ● T a x a n e s H i d d e n c a t e g o r i e s : ● P u b C h e m I D ( C I D ) n o t i n W i k i d a t a ● A r t i c l e s w i t h o u t E B I s o u r c e ● A r t i c l e s w i t h o u t K E G G s o u r c e ● A r t i c l e s w i t h o u t U N I I s o u r c e ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● C o m m o n s c a t e g o r y l i n k i s o n W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 2 4 A p r i l 2 0 2 4 , a t 1 4 : 0 9 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
Media related to taxanes at Wikimedia Commons
