Podophyllotoxin
| 220px | |
| 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 | |
| ATC code | D06 |
| PubChem | |
| DrugBank | |
| 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.
Antibiotics and chemotherapeutics for dermatological use (D06) | |
|---|---|
| Antibiotics: tetracycline and derivatives | Demeclocycline - Chlortetracycline - Oxytetracycline - Tetracycline |
| Antibiotics: other | Fusidic acid - Chloramphenicol - Neomycin - Bacitracin - Gentamicin - Tyrothricin - Mupirocin - Nadifloxacin - Virginiamycin - Rifaximin - Amikacin |
| Chemotherapeutics: sulfonamides | Silver sulfadiazine - Sulfathiazole - Mafenide - Sulfamethizole - Sulfanilamide - Sulfamerazine |
| Chemotherapeutics: antivirals | Idoxuridine - Tromantadine - Aciclovir - Podophyllotoxin - Inosine - Penciclovir - Lysozyme - Ibacitabine - Edoxudine - Imiquimod - Docosanol |
| Chemotherapeutics: other | Metronidazole |
Antivirals, other than for HIV (primarily J05, also S01AD and D06BB) | |
|---|---|
| Anti-herpesvirus (DNA, I) | guanine analogues (Aciclovir, Famciclovir, Ganciclovir, Penciclovir, Valaciclovir, Valganciclovir) • nucleoside analogues (Idoxuridine, Trifluridine, Vidarabine) • Cidofovir • Docosanol • Fomivirsen • Foscarnet • Tromantadine |
| HPV/MC (DNA, I) | Imiquimod • Podophyllotoxin |
| Hepatitis B (DNA, VII) | Adefovir • Interferon alfa-2b • Pegylated interferon alfa-2a • Entecavir • Lamivudine • Telbivudine • Tenofovir† |
| Hepatitis C (RNA, IV) | Pegylated interferon alpha • Ribavirin • Taribavirin† • Boceprevir† |
| Picornavirus (RNA, IV) | Pleconaril† |
| Anti-influenza agents (RNA, V) | Arbidol
adamantane derivatives/M2 inhibitors (Amantadine, Rimantadine) neuraminidase inhibitors (Oseltamivir, Zanamivir, Peramivir†) |
| HIV (Reverse, VI) | See HIV pharm |
| Other antiviral agents | general (Inosine, Interferon) |
| †Undergoing clinical trials, not FDA approved. | |
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