Podophyllotoxin

Podophyllotoxin
Clinical data
Trade names	Condylox, Wartec, others
Other names	(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
AHFS/Drugs.com	Monograph
MedlinePlus	a684055
Pregnancy; category	C;
ATC code	D07BB04 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	1.0 to 4.5 hours.
Identifiers
	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;
CAS Number	518-28-5 ;
PubChem CID	10607;
DrugBank	DB01179 ;
ChemSpider	10162 ;
UNII	L36H50F353;
KEGG	D05529 ;
ChEBI	CHEBI:50305 ;
ChEMBL	ChEMBL61 ;
CompTox Dashboard (EPA)	DTXSID3045645 ;
ECHA InfoCard	100.007.502
Chemical and physical data
Formula	C22H22O8
Molar mass	414.410 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	183.3 to 184 °C (361.9 to 363.2 °F)
	SMILES COc1cc(cc(c1OC)OC)[C@@H]2c3cc4c(cc3[C@@H]([C@@H]5[C@@H]2C(=O)OC5)O)OCO4;
	InChI InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1 ; Key:YJGVMLPVUAXIQN-XVVDYKMHSA-N ;
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Podophyllotoxin (PPT) is the active ingredient in Podofilox, a medical cream used to treat genital warts and molluscum contagiosum. It is not recommended for HPV infections without external warts. It can be applied either by a healthcare provider or the patient themselves.

Podophyllotoxin is a non-alkaloid lignan extracted from the roots and rhizomes of plants of the genus Podophyllum. A less refined form known as podophyllum resin is also available, but has greater side effects.

Podophyllotoxin was first isolated in pure form in 1880 by Valerian Podwyssotzki (1818 – 28 January 1892), a Polish-Russian privatdozent at the University of Dorpat (now Tartu, Estonia) and assistant at the Pharmacological Institute there.

PPT is on the World Health Organization's List of Essential Medicines.