Podofilox  

Podophyllotoxin
Systematic (IUPAC) name
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
Identifiers
CAS number	518-28-5
ATC code	D06BB04
PubChem	10607
DrugBank	APRD01189
Chemical data
Formula	C22H22O8
Mol. mass	414.405 g/mol
SMILES	eMolecules & PubChem
Synonyms	(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
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. It is the main active antiwart component of podophyllin, an herbal extract of Podophyllum which used to be one of the main treatments for genital warts. It is more effective and safer than podophyllin. Podofilox can be applied by the patient whereas podophyllin is applied by the doctor.^[1]

The melting point of podophyllotoxin is 183.3 - 184.0 °C. ^[2]

Sources

It is present at concentrations of 0.3 to 1.0% by mass in the rhizome of American Mayapple (Podophyllum peltatum).^[3][4] Another common source of podophyllotoxin is 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

Uses

Podophyllotoxin is the pharmacological precursor for the important anti-cancer drug etoposide. ^[5][6]

It is also used as a gel or solution to treat genital warts.^[7]

References