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Also known as: Podophyllotoxin, 518-28-5, Condylox, Condyline, (-)-podophyllotoxin, Wartec
Molecular Formula
C22H22O8
Molecular Weight
414.4  g/mol
InChI Key
YJGVMLPVUAXIQN-XVVDYKMHSA-N
FDA UNII
L36H50F353

Podophyllotoxin
A lignan (LIGNANS) 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.
The physiologic effect of podofilox is by means of Decreased Mitosis.
1 2D Structure

Podophyllotoxin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
2.1.2 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
2.1.3 InChI Key
YJGVMLPVUAXIQN-XVVDYKMHSA-N
2.1.4 Canonical SMILES
COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
2.1.5 Isomeric SMILES
COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O
2.2 Other Identifiers
2.2.1 UNII
L36H50F353
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Condyline

2. Condylox

3. Cph86

4. Epipodophyllotoxin

5. Podocon-25

6. Podofilm

7. Podophyllotoxin

8. Podophyllotoxin, (5r-(5 Alpha,5a Alpha,8a Alpha,9 Alpha))-isomer

9. Podophyllotoxin, (5r-(5 Alpha,5a Alpha,8a Alpha,9 Beta))-isomer

10. Podophyllotoxin, (5r-(5 Alpha,5a Alpha,8a Beta,9 Alpha))-isomer

11. Podophyllotoxin, (5r-(5 Alpha,5a Beta,8a Alpha,9 Beta))-isomer

12. Wartec

13. Warticon

2.3.2 Depositor-Supplied Synonyms

1. Podophyllotoxin

2. 518-28-5

3. Condylox

4. Condyline

5. (-)-podophyllotoxin

6. Wartec

7. Podophyllinic Acid Lactone

8. Podophyllotoxin 7

9. Warticon

10. Podofilox [usan]

11. Podophyllum

12. Nsc24818

13. Chembl61

14. Mfcd00075290

15. Nsc-24818

16. (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(9),2,7-trien-12-one

17. (5r,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

18. Mls000069495

19. (5r,5ar,8ar,9r)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one

20. Chebi:50305

21. Podofilox (usan)

22. L36h50f353

23. (5r,5ar,8ar,9r)-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one

24. Ncgc00022001-05

25. Podofilm

26. Smr000059121

27. Nsc 24818

28. Dsstox_cid_25645

29. Dsstox_rid_81023

30. Dsstox_gsid_45645

31. (5r,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-isobenzofuro[5,6-f][1,3]benzodioxol-8-one

32. (5r,5ar,8ar,9r)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8h)-one

33. Podocon-25

34. Podophilox

35. (5r,5ar,8ar,9r)-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one

36. Ccris 565

37. Hsdb 7238

38. Sr-05000001749

39. Mls002702981

40. Einecs 208-250-4

41. Podofillina

42. Podophylotoxin

43. Ai3-50456

44. Mayapple Isolate

45. Unii-l36h50f353

46. Condylox (tn)

47. Cas-518-28-5

48. Podophyllotoxin,(s)

49. Prestwick_1018

50. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5r-(5alpha,5abeta,8aalpha,9alpha))-

51. Podofillina [italian]

52. Podophyllotoxin (ban)

53. Podophyllotoxin, 95%

54. Spectrum_000199

55. Podofilox [hsdb]

56. Opera_id_1397

57. Prestwick0_000782

58. Prestwick1_000782

59. Prestwick2_000782

60. Prestwick3_000782

61. Spectrum2_000878

62. Spectrum4_000592

63. Spectrum5_001368

64. Podofilox [vandf]

65. Upcmld-dp035

66. Podophyllotoxin [mi]

67. Schembl42243

68. Bspbio_000884

69. Bspbio_002352

70. Kbiogr_001084

71. Kbioss_000679

72. Mls001148204

73. Mls002172467

74. Mls006010754

75. Mls006011412

76. Bidd:gt0123

77. Divk1c_000292

78. Unii-16902yvy2b

79. Spbio_000955

80. Spbio_002823

81. Bpbio1_000974

82. Ccris 4391

83. Podofilox [orange Book]

84. Podophyllotoxin [mart.]

85. Dtxsid3045645

86. Podophyllotoxin [who-dd]

87. Upcmld-dp035:001

88. Upcmld-dp035:002

89. Bcbcmap01_000165

90. Hms500o14

91. Kbio1_000292

92. Kbio2_000679

93. Kbio2_003247

94. Kbio2_005815

95. Amy2648

96. Ninds_000292

97. 16902yvy2b

98. Hms1570m06

99. Hms2093p16

100. Hms2097m06

101. Hms2235a23

102. Hms3259j19

103. Hms3714m06

104. Pharmakon1600-02300332

105. (5r,5ar,8ar,9r)-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5ah)-one

106. 9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one

107. Albb-020906

108. Bcp24085

109. Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5r-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.))-

110. Podophyllotoxin, Analytical Standard

111. Zinc3861806

112. Einecs 232-546-2

113. Tox21_110874

114. Tox21_202922

115. B18-5c

116. Bbl033695

117. Bdbm50035218

118. Ccg-39894

119. Nsc759591

120. Stk801918

121. Podophyllotoxin [ep Monograph]

122. Akos000265559

123. Tox21_110874_1

124. Ac-1656

125. Cs-1185

126. Db01179

127. Ks-1281

128. Nc00675

129. Nd-1185

130. Nsc-759591

131. Sdccgmls-0066888.p001

132. Idi1_000292

133. Smp1_000243

134. Ncgc00022001-03

135. Ncgc00022001-07

136. Ncgc00022001-08

137. Ncgc00022001-09

138. Ncgc00022001-10

139. Ncgc00022001-11

140. Ncgc00022001-13

141. Ncgc00022001-14

142. Ncgc00260468-01

143. (5r,9r,5ar,8ar)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,9,5a,8a-pentahydro-2h -isobenzofurano[5',6'-2,1]benzo[4,5-d]1,3-dioxolan-6-one

144. 1,3,3a,4,9,9a-hexahydro-9-hydroxy-6,7-(methylenedioxy)-4-(3',4',5'-trimethoxyphenyl)benz(f)isobenzofuran-3-one

145. Hy-15552

146. Nci60_001981

147. Rd4-6269

148. P1771

149. En300-52746

150. D05529

151. P-6980

152. 518p285

153. A828801

154. Q421193

155. Sr-01000003030

156. Sr-01000003030-3

157. Sr-05000001749-1

158. Sr-05000001749-2

159. Brd-k47869605-001-05-6

160. Brd-k47869605-001-18-9

161. Z1258578359

162. (10r,11r,15r,16r)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0?,?.0??,??]hexadeca-1(9),2,7-trien-12-one

163. (10r,11r,15r,16r)-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

164. (5r,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-isobenzofuro[6,5-f][1,3]benzodioxol-8-one

165. (5r,5ar,8ar,9r)-5-oxidanyl-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

166. 11016-28-7

167. 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one, [5r-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]

168. Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5r,5ar,8ar,9r)-

169. Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5r-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]-

170. Naphtho[2,3-dioxole-6-carboxylic Acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl-, .gamma.-lactone

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 414.4 g/mol
Molecular Formula C22H22O8
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass414.13146766 g/mol
Monoisotopic Mass414.13146766 g/mol
Topological Polar Surface Area92.7 Ų
Heavy Atom Count30
Formal Charge0
Complexity629
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCondylox
PubMed HealthPodofilox (On the skin)
Drug ClassesKeratolytic
Drug LabelCondylox is the brand name of podofilox, an antimitotic drug which can be chemically synthesized or purified from the plant families Coniferae and Berberidaceae (e.g. species of Juniperus and Podophyllum). Condylox 0.5% Solution is formulated for top...
Active IngredientPodofilox
Dosage FormGel; Solution
RouteTopical
Strength0.5%
Market StatusPrescription
CompanyWatson Pharms

2 of 4  
Drug NamePodofilox
Drug LabelPodofilox Topical Solution 0.5% is an antimitotic drug which can be chemically synthesized or purified from the plant families Coniferae and Berberidaceae (e.g. species of Juniperus and Podophyllum). Podofilox Topical Solution 0.5% is formulated for...
Active IngredientPodofilox
Dosage FormSolution
RouteTopical
Strength0.5%
Market StatusPrescription
CompanyPrecision Dermat; Paddock

3 of 4  
Drug NameCondylox
PubMed HealthPodofilox (On the skin)
Drug ClassesKeratolytic
Drug LabelCondylox is the brand name of podofilox, an antimitotic drug which can be chemically synthesized or purified from the plant families Coniferae and Berberidaceae (e.g. species of Juniperus and Podophyllum). Condylox 0.5% Solution is formulated for top...
Active IngredientPodofilox
Dosage FormGel; Solution
RouteTopical
Strength0.5%
Market StatusPrescription
CompanyWatson Pharms

4 of 4  
Drug NamePodofilox
Drug LabelPodofilox Topical Solution 0.5% is an antimitotic drug which can be chemically synthesized or purified from the plant families Coniferae and Berberidaceae (e.g. species of Juniperus and Podophyllum). Podofilox Topical Solution 0.5% is formulated for...
Active IngredientPodofilox
Dosage FormSolution
RouteTopical
Strength0.5%
Market StatusPrescription
CompanyPrecision Dermat; Paddock

4.2 Therapeutic Uses

Antiviral (topical)

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1355


Podofilox is indicated for the treatment of condyloma acuminatum of the external genital areas; the gel, but not the solution, may be used for perianal warts. Neither the gel nor the solution should be used to treat warts on mucous membranes, including membranous areas of the urethra, rectum, and vagina. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2337


4.3 Drug Warning

Because of the potential for adverse local reactions, the recommended dose, frequency of application, and duration of treatment of topical podofilox should not be exceeded. There is no evidence that applying podofilox more frequently than recommended would increase efficacy; however, more frequent application would be expected to increase the risk of local adverse reactions and increase systemic absorption of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3455


Pregnancy risk category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2337


Podofilox generally is well tolerated when applied topically. In clinical studies evaluating topical podofilox in otherwise healthy adults 18 years of age or older with external genital and/or perianal warts caused by human papillomavirus, up to 6% of patients discontinued the drug because of adverse local reactions; however, serious systemic effects have not been reported to date.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3455


Adverse local reactions, including burning, pain, inflammation, erosion, and pruritus, commonly occur at the site of application of podofilox 0.5% gel or 0.5% solution. These reactions usually are mild to moderate in severity; however, severe local reactions have been reported, especially during the first 2 weeks of therapy. Adverse local reactions generally resolve within 4 weeks following completion of topical podofilox therapy.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3455


For more Drug Warnings (Complete) data for PODOFILOX (9 total), please visit the HSDB record page.


4.4 Drug Indication

For treatment of external genital warts (Condyloma acuminatum).


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)


Keratolytic Agents

Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases. (See all compounds classified as Keratolytic Agents.)


Tubulin Modulators

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PODOFILOX
5.3.2 FDA UNII
L36H50F353
5.3.3 Pharmacological Classes
Decreased Mitosis [PE]
5.4 ATC Code

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BB - Antivirals

D06BB04 - Podophyllotoxin


5.5 Absorption, Distribution and Excretion

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.


Small amounts of podofilox may be absorbed systemically following topical application. In a study in adults with anogenital warts caused by human papillomavirus, topical application of 0.05 mL of podofilox 0.5% solution to external genitalia did not result in detectable serum concentrations of the drug; however, topical application of 0.1-1.5mL of the solution resulted in peak serum concentrations of 1-17 ng/mL at 1-2 hours after application.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3456


5.6 Biological Half-Life

1.0 to 4.5 hours.


The serum elimination half-life of podofilox is estimated to range from 1-4.5 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3456


5.7 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


The exact mechanism of action for podofilox is unknown. Podofilox is a potent mitotoxic agent that inhibits cell mitosis; cell division stops, other cellular processes are impaired, necrosis occurs, and the affected tissues gradually erode.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2337


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27-Feb-2021
08-Feb-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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DOSAGE - SOLUTION;TOPICAL - 0.5%

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DOSAGE - GEL;TOPICAL - 0.5%

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