Podophyllin

Identification

Name
Podophyllin
Accession Number
DB09094
Type
Small Molecule
Groups
Approved
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Podofilm Liq 250mg/mlLiquid250 mgTopicalPaladin Labs Inc1984-12-31Not applicableCanada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Podocon 25Tincture1 mg/4mLTopicalPaddock Laboratories, Inc.1990-09-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Canthacur-PSPodophyllin (5 %) + Cantharidin (1 %) + Salicylic acid (30 %)LiquidTopicalPaladin Labs Inc1983-12-31Not applicableCanada
Cantharone PlusPodophyllin (2 %) + Cantharidin (1 %) + Salicylic acid (30 %)LiquidTopicalDormer Laboratories Inc.1984-12-31Not applicableCanada
Verban OntPodophyllin (2 g) + Colchicine (100 mg)OintmentTopicalWelcker Lyster Ltd., Division Of Technilab Inc.1963-12-311999-09-17Canada
Categories
UNII
16902YVY2B
CAS number
9000-55-9
Weight
Average: 1693.67
Monoisotopic: 1692.547000042
Chemical Formula
C88H92O34
InChI Key
KOUZYZCESNTXJO-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.

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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Podophyllin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Podophyllin.Experimental
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
CymarinCymarin may decrease the cardiotoxic activities of Podophyllin.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Podophyllin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Podophyllin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Podophyllin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) 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
GitoformateGitoformate may decrease the cardiotoxic activities of Podophyllin.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Podophyllin.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Podophyllin.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Podophyllin.Experimental, Investigational
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
PeruvosidePeruvoside may decrease the cardiotoxic activities of Podophyllin.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Podophyllin.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Podophyllin.Approved, Investigational
Food Interactions
Not Available

References

General References
  1. product info [Link]
External Links
PubChem Compound
11979494
PubChem Substance
310265021
ChemSpider
10152781
AHFS Codes
  • 84:92.00 — Misc. Skin and Mucous Membrane Agents

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidTopical
TinctureTopical1 mg/4mL
LiquidTopical250 mg
OintmentTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position.
Kingdom
Organic compounds
Super Class
Lignans, neolignans and related compounds
Class
Aryltetralin lignans
Sub Class
9,9p-dihydroxyaryltetralin lignans
Direct Parent
9,9p-dihydroxyaryltetralin lignans
Alternative Parents
Naphthalenecarboxylic acids / Tetralins / Benzodioxoles / Phenoxy compounds / Anisoles / Methoxybenzenes / Alkyl aryl ethers / Secondary alcohols / Acetals / Oxacyclic compounds
show 6 more
Substituents
9,9p-dihydroxyaryltetralin lignan / 2-naphthalenecarboxylic acid / 2-naphthalenecarboxylic acid or derivatives / Tetralin / Benzodioxole / Methoxybenzene / Phenol ether / Phenoxy compound / Anisole / Alkyl aryl ether
show 18 more
Molecular Framework
Not Available
External Descriptors
Not Available

Drug created on September 16, 2015 11:36 / Updated on November 22, 2017 12:38