Podophyllotoxin

Podophyllotoxin

Clinical data
Trade names	Condylox, Wartec, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684055
Pregnancy category	C
ATC code	D06BB04 (WHO)
Pharmacokinetic data
Biological 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
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
CAS Number	518-28-5 Y
PubChem (CID)	10607
DrugBank	DB01179 N
ChemSpider	10162 Y
UNII	L36H50F353 Y
KEGG	D05529 Y
ChEBI	CHEBI:50305 Y
ChEMBL	CHEMBL61 Y
ECHA InfoCard	100.007.502
Chemical and physical data
Formula	C22H22O8
Molar mass	414.405 g/mol
3D model (Jmol)	Interactive image
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 Y Key:YJGVMLPVUAXIQN-XVVDYKMHSA-N Y
NY (what is this?)

Podophyllotoxin (PPT), also known as podofilox, is a medical cream that is used to treat genital warts and molluscum contagiosum. It is not recommended in HPV infections without external warts. It can be applied either by a healthcare provider or the person themselves.

It is a non-alkaloid toxin lignan extracted from the roots and rhizomes of Podophyllum species. A less refined form known as podophyllum resin is also available; however has greater side effects.

Podophyllotoxin was isolated in 1880. In the United Kingdom a 3.5 ml of medication costs the NHS about 14.49 pounds. In the United States a course of treatment costs more than 200 USD.

Podophyllotoxin possesses a large number of medical applications and can be used as a cathartic, purgative, antiviral agent, vesicant, and antihelminthic. Additionally, podophyllotoxin and its derivatives are leads for anti-tumor agents such as etoposide and teniposide.

The most common side effects near the application site are skin reactions, including burning, redness, pain, itching, swelling. Application can be immediately followed by burning or itching. Small sores, itching and peeling skin can also follow.

Neither podophyllin resin nor podophyllotoxin lotions or gels are used during pregnancy because these medications can be harmful to the fetus.

While podophyllin, the herbal extract from which podophyllotoxin is derived, can cause enteritis and potentially fatal CNS depression, podophyllotoxin has been shown to be safe, with minimal toxicity even in large doses.