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Podophyllotoxin



Podophyllotoxin
Systematic (IUPAC) name
5,8,8a,9-Tetrahydro-9-hydroxy-5- (3,4,5-trimethoxylphenyl) furo [3',4':6,7] naphtho [2,3,d]-1,3-dioxol-6(5aH)-one
Identifiers
CAS number 518-28-5
ATC code D06BB04
PubChem 10607
DrugBank APRD01189
Chemical data
Formula C22H22O8 
Mol. mass 414.405 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life 1.0 to 4.5 hours.
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status
Routes  ?

Podophyllotoxin, otherwise known as podofilox, is a non-alkaloid toxin in the lignan family present at concentrations of 0.3 to 1.0% by mass in the rhizome of American Mayapple (Podophyllum peltatum). Another common source of podophyllotoxin is the rhizomes of Podophyllum hexandrum Royle (Berberidaceae).

Additional recommended knowledge

It is synthetised biologically from two molecules of coniferyl alcohol by phenolic oxidative coupling and a series of oxidations, reductions and methylations

The melting point of Podophyllotoxin is 183.3 - 184.0 °C. [1]

Podophyllotoxin is the pharmacological base for the important anti-cancer drug etoposide. [2]

It is also used as a gel or solution to treat genital warts.[3]

References

  1. ^ Podophyllum (PIM 427). Retrieved on 2007-12-03.
  2. ^ Gordaliza M, García PA, del Corral JM, Castro MA, Gómez-Zurita MA (2004). "Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives". Toxicon 44 (4): 441–59. doi:10.1016/j.toxicon.2004.05.008. PMID 15302526.
  3. ^ Xie FM, Zeng K, Chen ZL, et al (2007). "[Treatment of recurrent condyloma acuminatum with solid lipid nanoparticle gel containing podophyllotoxin: a randomized double-blinded, controlled clinical trial]" (in Chinese). Nan Fang Yi Ke Da Xue Xue Bao 27 (5): 657–9. PMID 17545082.
  • Canel, C; Moraes, RM; Dayan, FE; Ferreira, D (2000). "Molecules of Interest: Podophyllotoxin". Phytochemistry 54 (2): 115-120.
  • J. L. Hartwell, A. W. Schrecker (1951). "Components of Podophyllin. V. The Constitution of Podophyllotoxin". Journal of the American Chemical Society 73 (6): 2909 - 2916. doi:10.1021/ja01150a143.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Podophyllotoxin". A list of authors is available in Wikipedia.
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