Identification
NamePodophyllin
Accession NumberDB09094
TypeSmall Molecule
GroupsApproved
Description

Podophyllin is a resin extracted from the root of the plant Podophyllum sp. Berberidaceae (mandrake), which contains numerous compounds, among which podophyllotoxin. Podophyllin is the principal active component. Podophyllin arrests mitosis in metaphase.

Structure
Thumb
Synonyms
Podophyllum resin
External IDs Not Available
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Podofilm Liq 250mg/mlLiquid250 mgTopicalPaladin Labs Inc1984-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Podocon 25Tincture1 mg/4mLTopicalPaddock Laboratories, Inc.1990-09-01Not applicableUs
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Canthacur-PSLiquidTopicalPaladin Labs Inc1983-12-31Not applicableCanada
Cantharone PlusLiquidTopicalDormer Laboratories Inc.1984-12-31Not applicableCanada
Verban OntOintmentTopicalWelcker Lyster Ltd., Division Of Technilab Inc.1963-12-311999-09-17Canada
Categories
UNII16902YVY2B
CAS number9000-55-9
WeightAverage: 1693.67
Monoisotopic: 1692.547000042
Chemical FormulaC88H92O34
InChI KeyKOUZYZCESNTXJO-UHFFFAOYSA-N
InChI
InChI=1S/2C22H24O9.2C22H22O8/c2*1-27-16-4-10(5-17(28-2)21(16)29-3)18-11-6-14-15(31-9-30-14)7-12(11)20(24)13(8-23)19(18)22(25)26;2*1-25-16-4-10(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/h2*4-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26);2*4-7,13,18-20,23H,8-9H2,1-3H3
IUPAC Name
bis(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); bis(8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-2H,5H,6H,7H,8H-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid)
SMILES
COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(O)C2=CC3=C(OCO3)C=C12.COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(O)C2=CC3=C(OCO3)C=C12.COC1=CC(=CC(OC)=C1OC)C1C(C(CO)C(O)C2=CC3=C(OCO3)C=C12)C(O)=O.COC1=CC(=CC(OC)=C1OC)C1C(C(CO)C(O)C2=CC3=C(OCO3)C=C12)C(O)=O
Pharmacology
Indication

25% podophyllin (in benzoin tincture) is indicated for the removal of soft genital (venereal) warts (condylomata acuminata).

Structured Indications Not Available
Pharmacodynamics

Cell division is arrested and other cellular processes are impaired, gradually resulting in the disruption of cells and destruction of the tissue.

Mechanism of action

Podophyllin is a cytotoxic agent that has been used topically in the treatment of genital warts. It arrests mitosis in metaphase, an effect it shares with other cytotoxic agents such as the vinca alkaloids. The active agent is podophyllotoxin.

Related Articles
Absorption

Oral absorption: Podophyllum is very well and rapidly absorbed after ingestion. Dermal absorption: systemic poisoning was reported after topical application in some cases. Symptoms were delayed between 2-24 hr.

Volume of distribution

No data available.

Protein binding

No data available.

Metabolism

No data available.

Route of elimination

No data available.

Half life

No data available.

Clearance

No data available.

Toxicity
  1. LD50 (IV) Rat: 8.7 mg/kg
    1. LD50 (IP) Rat: 15 mg/kg
    2. LD50 (SC) Rat: 8 mg/kg
    3. LD50 (IM) Rat: 3 mg/kg
    4. LD50 (IP) Mouse: 30 mg/kg
    5. LD50 (SC) Mouse: 24.6 mg/kg 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. Application can be immediately followed by burning or itching. Small sores, itching and peeling skin can also follow.
Affected organisms
  • Various viruses
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Podophyllin.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Podophyllin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Podophyllin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Podophyllin.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Podophyllin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Podophyllin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Podophyllin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Podophyllin.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Podophyllin.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Podophyllin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Podophyllin.Approved, Vet Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Podophyllin.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. product info [Link]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
LiquidTopical
TinctureTopical1 mg/4mL
LiquidTopical250 mg
OintmentTopical
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.427 mg/mLALOGPS
logP1.35ALOGPS
logP0.96ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.56ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area123.91 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity107.4 m3·mol-1ChemAxon
Polarizability43.46 Å3ChemAxon
Number of Rings18ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
ClassificationNot classified
Drug created on September 16, 2015 11:36 / Updated on September 01, 2017 12:02