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Identification
- Summary
Podofilox is a topical agent used for the treatment of external genital warts and perianal warts.
- Brand Names
- Condylox
- Generic Name
- Podofilox
- DrugBank Accession Number
- DB01179
- Background
A lignan found in podophyllin resin from the roots of podophyllum plants. It is a potent spindle poison, toxic if taken internally, and has been used as a cathartic. It is very irritating to skin and mucous membranes, has keratolytic actions, has been used to treat warts and keratoses, and may have antineoplastic properties, as do some of its congeners and derivatives.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Podofilox (DB01179)
- Weight
- Average: 414.4053
Monoisotopic: 414.13146768 - Chemical Formula
- C22H22O8
- Synonyms
- (−)-podophyllotoxin
- Podofilox
- Podophyllinic acid lactone
- Podophyllotoxin
- PPT
Pharmacology
- Indication
For treatment of external genital warts (Condyloma acuminatum).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of External genital warts •••••••••••• •••• •••••••• Treatment of Perianal warts •••••••••••• ••• Treatment of Perianal warts •••••••••••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Podofilox, also called podophyllotoxin, is a purer and more stable form of podophyllin in which only the biologically active portion of the compound is present. Podofilox is used to remove certain types of warts on the outside skin of the genital areas.
- Mechanism of action
The exact mechanism of action is not well understood. It does appear, however, that it and its derivatives may bind and inhibit topoisomerase II during the late S and early G2 stage. The drug may bind and stabilize the temporary break caused by the enzyme. This disrupts the reparation of the break through which the double-stranded DNA passes, and consequently stops DNA unwinding and replication
Target Actions Organism ADNA topoisomerase 2-beta modulatorHumans ATubulin alpha-4A chain inhibitorHumans ATubulin beta chain inhibitorHumans ADNA topoisomerase 2-alpha inhibitorHumans - Absorption
Topical application of 0.05 mL of 0.5% podofilox solution to external genitalia did not result in detectable serum levels. Applications of 0.1 to 1.5 mL resulted in peak serum levels of 1 to 17 ng/mL one to two hours after application.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
1.0 to 4.5 hours.
- Clearance
Not Available
- Adverse Effects
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Not Available
- 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.No interactions found.
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Podophyllotoxin 7
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Condyline Solution 0.5 % Topical Sanofi Aventis Deutschland Gmb H 1992-12-31 2021-08-25 Canada 
Condylox Solution 5 mg/1mL Topical Watson Labs 2007-03-31 2007-03-31 US 
Condylox Gel 5 mg/1g Topical Oclassen Dermatologics 2007-05-03 2007-09-14 US Condylox Solution 5 mg/1mL Topical Actavis Pharma, Inc. 1990-12-13 2018-02-28 US Condylox Gel 5 mg/1g Topical Actavis Pharma Company 1997-03-13 2018-12-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Podofilox Solution 5 mg/1mL Topical bryant ranch prepack 1990-12-13 Not applicable US Podofilox Solution 5 mg/1mL Topical Oceanside Pharmaceuticals 2010-07-21 2017-07-31 US Podofilox Solution 5 mg/1mL Topical Physicians Total Care, Inc. 2010-11-12 Not applicable US Podofilox Solution 5 mg/1mL Topical Padagis US LLC 2002-01-29 Not applicable US Podofilox Solution 5 mg/1mL Topical Metacon Labs 2010-07-21 2014-08-31 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image WARTEC CREAM 0.15% w/w Cream 0.15 % w/w Topical Glaxosmithkline Consumer Healthcare Ulc 2001-07-16 Not applicable Singapore 
WARTEC SOLUTION 0.5% w/v Solution 0.5 % w/v Topical Glaxosmithkline Consumer Healthcare Ulc 2001-07-16 Not applicable Singapore
Categories
- ATC Codes
- D06BB04 — Podophyllotoxin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).
- Kingdom
- Organic compounds
- Super Class
- Lignans, neolignans and related compounds
- Class
- Lignan lactones
- Sub Class
- Podophyllotoxins
- Direct Parent
- Podophyllotoxins
- Alternative Parents
- Aryltetralin lignans / Furanonaphthodioxoles / Tetralins / Benzodioxoles / Phenoxy compounds / Anisoles / Methoxybenzenes / Alkyl aryl ethers / Gamma butyrolactones / Tetrahydrofurans show 8 more
- Substituents
- 1-aryltetralin lignan / Acetal / Alcohol / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Benzenoid / Benzodioxole / Carbonyl group / Carboxylic acid derivative show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- lignan, furonaphthodioxole (CHEBI:50305) / Phenylpropanoids, Lignans, Phytotoxins (C10874)
- Affected organisms
- Condyloma acuminatum
Chemical Identifiers
- UNII
- L36H50F353
- CAS number
- 518-28-5
- InChI Key
- YJGVMLPVUAXIQN-XVVDYKMHSA-N
- InChI
- InChI=1S/C22H22O8/c1-25-16-4-10(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/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
- IUPAC Name
- (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one
- SMILES
- [H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015310
- KEGG Compound
- C10874
- PubChem Compound
- 10607
- PubChem Substance
- 46505716
- ChemSpider
- 10162
- BindingDB
- 50035218
- 8463
- ChEBI
- 50305
- ChEMBL
- CHEMBL61
- ZINC
- ZINC000003861806
- Therapeutic Targets Database
- DNC001139
- PharmGKB
- PA450993
- PDBe Ligand
- POD
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Podophyllotoxin
- PDB Entries
- 1sa1
- MSDS
- Download (55.9 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment External Anogenital Warts 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- DPT Laboratories Ltd.
- Oclassen Pharmaceuticals Inc.
- Paddock Labs
- Physicians Total Care Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Solution Topical 0.5 % Gel Topical 5 mg/1g Solution Topical 5 mg/1mL Solution Topical 0.5 g Gel Topical 0.5 g Cream Topical Liquid Topical 5 mg / mL Solution Topical Cream Topical 0.15 g Solution Topical 5 mg Cream Topical 0.15 % w/w Solution Topical 0.5 % w/v - Prices
Unit description Cost Unit Podofilox 0.5% Solution 3.5ml Bottle 105.99USD bottle Condylox 0.5% gel 97.73USD g Wartec 0.5 % Solution 14.26USD solution DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 228 °C PhysProp water solubility 100 mg/L (at 25 °C) MERCK INDEX (1996) logP 1.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.114 mg/mL ALOGPS logP 2.37 ALOGPS logP 1.62 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 14.02 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 92.68 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 103.9 m3·mol-1 Chemaxon Polarizability 41.78 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9939 Blood Brain Barrier - 0.5388 Caco-2 permeable + 0.849 P-glycoprotein substrate Non-substrate 0.5382 P-glycoprotein inhibitor I Inhibitor 0.5455 P-glycoprotein inhibitor II Inhibitor 0.6709 Renal organic cation transporter Non-inhibitor 0.8403 CYP450 2C9 substrate Non-substrate 0.8241 CYP450 2D6 substrate Non-substrate 0.8911 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7468 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.91 Biodegradation Not ready biodegradable 0.8596 Rat acute toxicity 3.0013 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9871 hERG inhibition (predictor II) Non-inhibitor 0.9081
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 209.6356744 predictedDarkChem Lite v0.1.0 [M-H]- 213.1269744 predictedDarkChem Lite v0.1.0 [M-H]- 210.6550744 predictedDarkChem Lite v0.1.0 [M-H]- 188.72331 predictedDeepCCS 1.0 (2019) [M+H]+ 209.8348744 predictedDarkChem Lite v0.1.0 [M+H]+ 213.3609744 predictedDarkChem Lite v0.1.0 [M+H]+ 211.5788744 predictedDarkChem Lite v0.1.0 [M+H]+ 191.11888 predictedDeepCCS 1.0 (2019) [M+Na]+ 209.9266744 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.8249744 predictedDarkChem Lite v0.1.0 [M+Na]+ 210.7155744 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.0314 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Key decatenating enzyme that alters DNA topology by binding to two double-stranded DNA molecules, generating a double-stranded break in one of the strands, passing the intact strand through the broken strand, and religating the broken strand. Plays a role in B-cell differentiation
- Specific Function
- ATP binding
- Gene Name
- TOP2B
- Uniprot ID
- Q02880
- Uniprot Name
- DNA topoisomerase 2-beta
- Molecular Weight
- 183265.825 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Tubulin is the major constituent of microtubules, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin
- Specific Function
- GTP binding
- Gene Name
- TUBA4A
- Uniprot ID
- P68366
- Uniprot Name
- Tubulin alpha-4A chain
- Molecular Weight
- 49923.995 Da
References
- Labruere R, Gautier B, Testud M, Seguin J, Lenoir C, Desbene-Finck S, Helissey P, Garbay C, Chabot GG, Vidal M, Giorgi-Renault S: Design, synthesis, and biological evaluation of the first podophyllotoxin analogues as potential vascular-disrupting agents. ChemMedChem. 2010 Dec 3;5(12):2016-25. doi: 10.1002/cmdc.201000305. [Article]
- Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [Article]
- Kim ND, Park ES, Kim YH, Moon SK, Lee SS, Ahn SK, Yu DY, No KT, Kim KH: Structure-based virtual screening of novel tubulin inhibitors and their characterization as anti-mitotic agents. Bioorg Med Chem. 2010 Oct 1;18(19):7092-100. doi: 10.1016/j.bmc.2010.07.072. Epub 2010 Aug 6. [Article]
- Screpanti E, Santaguida S, Nguyen T, Silvestri R, Gussio R, Musacchio A, Hamel E, De Wulf P: A screen for kinetochore-microtubule interaction inhibitors identifies novel antitubulin compounds. PLoS One. 2010 Jul 15;5(7):e11603. doi: 10.1371/journal.pone.0011603. [Article]
- Alam MA, Naik PK: Applying linear interaction energy method for binding affinity calculations of podophyllotoxin analogues with tubulin using continuum solvent model and prediction of cytotoxic activity. J Mol Graph Model. 2009 Jun-Jul;27(8):930-43. doi: 10.1016/j.jmgm.2009.02.003. Epub 2009 Feb 20. [Article]
- Clark PI: Clinical pharmacology and schedule dependency of the podophyllotoxin derivatives. Semin Oncol. 1992 Apr;19(2 Suppl 6):20-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Tubulin is the major constituent of microtubules, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin
- Specific Function
- GTP binding
- Gene Name
- TUBB
- Uniprot ID
- P07437
- Uniprot Name
- Tubulin beta chain
- Molecular Weight
- 49670.515 Da
References
- Wolff J, Knipling L, Cahnmann HJ, Palumbo G: Direct photoaffinity labeling of tubulin with colchicine. Proc Natl Acad Sci U S A. 1991 Apr 1;88(7):2820-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Key decatenating enzyme that alters DNA topology by binding to two double-stranded DNA molecules, generating a double-stranded break in one of the strands, passing the intact strand through the broken strand, and religating the broken strand (PubMed:17567603, PubMed:18790802, PubMed:22013166, PubMed:22323612). May play a role in regulating the period length of BMAL1 transcriptional oscillation (By similarity)
- Specific Function
- ATP binding
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
References
- Iida A, Kano M, Kubota Y, Koga K, Tomioka K: Podophyllotoxin aza-analogue, a novel DNA topoisomerase II inhibitor. Chem Pharm Bull (Tokyo). 2000 Apr;48(4):486-9. [Article]
- Zhang YL, Shen YC, Wang ZQ, Chen HX, Guo X, Cheng YC, Lee KH: Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II. J Nat Prod. 1992 Aug;55(8):1100-11. [Article]
- Terada T, Fujimoto K, Nomura M, Yamashita J, Kobunai T, Takeda S, Wierzba K, Yamada Y, Yamaguchi H: Antitumor agents. I. DNA topoisomerase II inhibitory activity and the structural relationship of podophyllotoxin derivatives as antitumor agents. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2720-7. [Article]
- Kamal A, Gayatri NL, Reddy DR, Mohan Reddy PS, Arifuddin M, Dastidar SG, Kondapi AK, Rajkumar M: Synthesis and biological evaluation of new 4beta-anilino- and 4beta-imido-substituted podophyllotoxin congeners. Bioorg Med Chem. 2005 Nov 15;13(22):6218-25. Epub 2005 Aug 2. [Article]
- Ruckdeschel JC: Etoposide in the management of non-small cell lung cancer. Cancer. 1991 Jan 1;67(1 Suppl):250-3. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 13, 2024 00:22