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

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Podophyllin (DB09094)

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Weight

Average: 1693.67
Monoisotopic: 1692.547000042

Chemical Formula

C₈₈H₉₂O₃₄

Synonyms

• Podofillina
• Podophyllum (resin)
• Podophyllum resin

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Pharmacology

Indication

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

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Soft genital warts		••••••••••••

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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

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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

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Podocon 25	Tincture	1 mg/4mL	Topical	bryant ranch prepack	1990-09-01	Not applicable
Podocon 25	Tincture	1 mg/4mL	Topical	Padagis US LLC	1990-09-01	Not applicable
Podofilm Liq 250mg/ml	Liquid	250 mg / mL	Topical	Paladin Labs Inc.	1984-12-31	2021-07-28

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
PODOFILM WART TREATMENT 25%	Liquid	25 %	Topical	MEDICELL PHARMACEUTICAL (S) PTE. LTD.	1991-04-06	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
CANTHACUR PS %1,%5,%30 TOPIKAL SOLUSYON 7,5 ML	Podophyllin (51 mg/ml) + Cantharidin (10.2 mg/ml) + Salicylic acid (306 mg/ml)	Solution	Topical	ASSOS İLAÇ KİMYA GIDA ÜRÜNLERİ ÜRETİM VE TİC. A.Ş.	2005-06-10	Not applicable
Canthacur-PS	Podophyllin (5 %) + Cantharidin (1 %) + Salicylic acid (30 %)	Liquid	Topical	Paladin Labs Inc	1983-12-31	2017-05-30
Cantharone Plus	Podophyllin (2 %) + Cantharidin (1 %) + Salicylic acid (30 %)	Liquid	Topical	Dormer Laboratories Inc.	1984-12-31	Not applicable
PODOPHYLLIN PAINT, CO.	Podophyllin (25 g/100mL) + Benzoin resin (100 mL/100mL)	Solution		บริษัท วิทยาศรม จำกัด	1987-04-23	Not applicable
Verban Ont	Podophyllin (2 g / 100 g) + Colchicine (100 mg / 100 g)	Ointment	Topical	Welcker Lyster Ltd., Division Of Technilab Inc.	1963-12-31	1999-09-17

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Cantharidin 1% / Podophyllum Resin 5% / Salicylic Acid 30%	Podophyllin (5 g/100g) + Cantharidin (1 g/100g) + Salicylic acid (30 g/100g)	Liquid	Topical	Sincerus Florida, LLC	2019-05-17	Not applicable
Podocon 25	Podophyllin (1 mg/4mL)	Tincture	Topical	Padagis US LLC	1990-09-01	Not applicable
Podocon 25	Podophyllin (1 mg/4mL)	Tincture	Topical	bryant ranch prepack	1990-09-01	Not applicable

Categories

Drug Categories

• Antineoplastic Agents
• Antineoplastic Agents, Phytogenic
• Biological Products
• Caustics
• Complex Mixtures
• Compounds used in a research, industrial, or household setting
• Cytotoxins
• Dermatologicals
• Keratolytic Agents
• Misc. Skin and Mucous Membrane Agents
• Noxae
• Plant Extracts
• Plant Preparations
• Toxic Actions

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 / Carboxylic acids / Monocarboxylic acids and derivatives / Carbonyl compounds / Primary alcohols / Hydrocarbon derivatives / Organic oxides

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Substituents

2-naphthalenecarboxylic acid / 2-naphthalenecarboxylic acid or derivatives / 9,9p-dihydroxyaryltetralin lignan / Acetal / Alcohol / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Benzenoid / Benzodioxole / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Ether / Hydrocarbon derivative / Methoxybenzene / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound / Oxacycle / Phenol ether / Phenoxy compound / Primary alcohol / Secondary alcohol / Tetralin

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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]

External Links

PubChem Compound

11979494

PubChem Substance

310265021

ChemSpider

10152781

RxNav

8462

Wikipedia

Podophyllum_resin

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Unknown Status	Treatment	Condylomata Acuminata	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Solution	Topical
Liquid	Topical
Solution	Cutaneous	250.000 mg
Tincture	Topical	1 mg/4mL
Solution	Topical	25 %
Liquid	Topical	250 mg / mL
Liquid	Topical	25 %
Solution
Powder	Not applicable	1 g/1g
Ointment	Topical
Solution	Cutaneous	0.250 g

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.427 mg/mL	ALOGPS
logP	1.35	ALOGPS
logP	0.96	Chemaxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.56	Chemaxon
pKa (Strongest Basic)	-2.6	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	9	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	123.91 Å2	Chemaxon
Rotatable Bond Count	20	Chemaxon
Refractivity	107.4 m3·mol-1	Chemaxon
Polarizability	43.46 Å3	Chemaxon
Number of Rings	18	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	375.1923	predicted	DeepCCS 1.0 (2019)
[M+H]+	376.84546	predicted	DeepCCS 1.0 (2019)
[M+Na]+	383.00232	predicted	DeepCCS 1.0 (2019)

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Drug created at September 16, 2015 17:36 / Updated at April 18, 2024 09:15