Podophyllotoxin

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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.

?

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 are the rhizomes of Podophyllum hexandrum Royle (Berberidaceae).

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.

Podophyllotoxin is the pharmacological base for the important anti-cancer drug Etoposide.

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

References

  • 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.
nl:Podofyllotoxine

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