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Podophyllotoxin
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Systematic (IUPAC) name
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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
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Identifiers
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CAS number
| 518-28-5
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ATC code
| D06BB04
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PubChem
| 10607
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DrugBank
| APRD01189
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Chemical data
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Formula | C22H22O8
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Mol. mass | 414.405 g/mol
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Pharmacokinetic data
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Bioavailability | ?
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Metabolism | ?
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Half life | 1.0 to 4.5 hours.
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Excretion | ?
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Therapeutic considerations
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Pregnancy cat.
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?
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Legal status
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Routes
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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 is the rhizomes of Podophyllum hexandrum Royle (Berberidaceae).
Additional recommended knowledge
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. [1]
Podophyllotoxin is the pharmacological base for the important anti-cancer drug etoposide. [2]
It is also used as a gel or solution to treat genital warts.[3]
References
- ^ Podophyllum (PIM 427). Retrieved on 2007-12-03.
- ^ 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.
- ^ 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.
- 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.
Antivirals, other than for HIV (primarily J05, also S01AD and D06BB) |
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Anti-herpesvirus (DNA, I) | guanine analogues (Aciclovir, Famciclovir, Ganciclovir, Penciclovir, Valaciclovir, Valganciclovir) • nucleoside analogues (Idoxuridine, Trifluridine, Vidarabine) • Cidofovir • Docosanol • Fomivirsen • Foscarnet • Tromantadine |
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HPV/MC (DNA, I) | Imiquimod • Podophyllotoxin |
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Hepatitis B (DNA, VII) | Adefovir dipivoxil • Interferon alfa-2b • Pegylated interferon alfa-2a • Lamivudine • Entecavir • Telbivudine • Tenofovir† |
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Hepatitis C (RNA, IV) | Ribavirin • Taribavirin |
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Picornavirus (RNA, IV) | Pleconaril |
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Anti-influenza agents (RNA, V) | Arbidol
adamantane derivatives/M2 inhibitors (Amantadine, Rimantadine)
neuraminidase inhibitors (Oseltamivir, Peramivir†, Zanamivir) |
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HIV (Reverse, VI) | See HIV pharm |
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Other antiviral agents | general (Inosine, Interferon) |
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†Undergoing clinical trials, not FDA approved. |
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