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 | ? |
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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]
[edit] 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
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]
[edit] References
- ^ Longstaff E, von Krogh G (April 2001). "Condyloma eradication: self-therapy with 0.15-0.5% podophyllotoxin versus 20-25% podophyllin preparations--an integrated safety assessment". Regul. Toxicol. Pharmacol. 33 (2): 117–37. doi:10.1006/rtph.2000.1446. PMID 11350195.
- ^ "Podophyllum (PIM 427)". http://www.inchem.org/documents/pims/pharm/pim427.htm. Retrieved 2007-12-03.
- ^ 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.
- ^ 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. http://linkinghub.elsevier.com/retrieve/pii/S0041010104001953.
- ^ Damayanthi Y, Lown JW (June 1998). "Podophyllotoxins: current status and recent developments". Curr. Med. Chem. 5 (3): 205–52. PMID 9562603.
- ^ 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.
