Podophyllin

Identification

Summary

Podophyllin is a cytotoxic agent used for the removal of soft genital (venereal) warts (condylomata acuminata).

Brand Names
Cantharone Plus
Generic Name
Podophyllin
DrugBank Accession Number
DB09094
Background

Podophyllin is a resin extracted from the roots of Podophyllum peltatum (American mandrake) and Podophyllum emodi, which contains numerous compounds, amongst which is podophyllin (as well as the drug podophyllotoxin). Podophyllin is the principal active component. Podophyllin arrests mitosis in metaphase.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 1693.67
Monoisotopic: 1692.547000042
Chemical Formula
C88H92O34
Synonyms
  • Podofillina
  • Podophyllum (resin)
  • Podophyllum resin

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

Adverse Effects
Adverseeffects
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Toxicity
  1. LD50 (IV) Rat: 8.7 mg/kg
  2. LD50 (IP) Rat: 15 mg/kg
  3. LD50 (SC) Rat: 8 mg/kg
  4. LD50 (IM) Rat: 3 mg/kg
  5. LD50 (IP) Mouse: 30 mg/kg
  6. 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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Products2
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Podocon 25Tincture1 mg/4mLTopicalPaddock Laboratories, LLC1990-09-01Not applicableUS flag
Podocon 25Tincture1 mg/4mLTopicalbryant ranch prepack1990-09-01Not applicableUS flag
Podofilm Liq 250mg/mlLiquid250 mg / mLTopicalPaladin Labs Inc.1984-12-312021-07-28Canada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PODOFILM WART TREATMENT 25%Liquid25 %TopicalMEDICELL PHARMACEUTICAL (S) PTE. LTD.1991-04-06Not applicable
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CANTHACUR PS %1,%5,%30 TOPIKAL SOLUSYON 7,5 MLPodophyllin (51 mg/ml) + Cantharidin (10.2 mg/ml) + Salicylic acid (306 mg/ml)SolutionTopicalASSOS İLAÇ KİMYA GIDA ÜRÜNLERİ ÜRETİM VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Canthacur-PSPodophyllin (5 %) + Cantharidin (1 %) + Salicylic acid (30 %)LiquidTopicalPaladin Labs Inc1983-12-312017-05-30Canada flag
Cantharone PlusPodophyllin (2 %) + Cantharidin (1 %) + Salicylic acid (30 %)LiquidTopicalDormer Laboratories Inc.1984-12-31Not applicableCanada flag
PODOPHYLLIN PAINT, CO.Podophyllin (25 g/100mL) + Benzoin (100 mL/100mL)Solutionบริษัท วิทยาศรม จำกัด1987-04-23Not applicableThailand flag
Verban OntPodophyllin (2 g / 100 g) + Colchicine (100 mg / 100 g)OintmentTopicalWelcker Lyster Ltd., Division Of Technilab Inc.1963-12-311999-09-17Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Cantharidin 1% / Podophyllum Resin 5% / Salicylic Acid 30%Podophyllin (5 g/100g) + Cantharidin (1 g/100g) + Salicylic acid (30 g/100g)LiquidTopicalSincerus Florida, LLC2019-05-17Not applicableUS flag
Podocon 25Podophyllin (1 mg/4mL)TinctureTopicalPaddock Laboratories, LLC1990-09-01Not applicableUS flag
Podocon 25Podophyllin (1 mg/4mL)TinctureTopicalbryant ranch prepack1990-09-01Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-naphthalenecarboxylic acid / 2-naphthalenecarboxylic acid or derivatives / 9,9p-dihydroxyaryltetralin lignan / Acetal / Alcohol / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Benzenoid / Benzodioxole
show 18 more
Molecular Framework
Not Available
External Descriptors
Not Available
Affected organisms
  • Various viruses

Chemical Identifiers

UNII
16902YVY2B
CAS number
9000-55-9
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

References

General References
  1. product info [Link]
PubChem Compound
11979494
PubChem Substance
310265021
ChemSpider
10152781
RxNav
8462
Wikipedia
Podophyllum_resin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Not Yet RecruitingTreatmentCondylomata Acuminata1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionTopical
LiquidTopical
TinctureTopical1 mg/4mL
SolutionTopical
LiquidTopical250 mg / mL
LiquidTopical25 %
Solution
PowderNot applicable1 g/1g
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

Drug created on September 16, 2015 17:36 / Updated on October 20, 2021 19:48