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Substance Name: Podofilox [USAN]
RN: 518-28-5
UNII: L36H50F353
InChIKey: YJGVMLPVUAXIQN-XVVDYKMHSA-N

Note

  • 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.

Molecular Formula

  • C22-H22-O8

Molecular Weight

  • 414.4078
 

Classification Codes

  • Antimitotic
  • Antimitotic Agents
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Keratolytic Agents
  • Mitosis Modulators
  • Mutation Data
  • Natural Product
  • Reproductive Effect
  • Tubulin Modulators

Names and Synonyms

Name of Substance

  • Podofilox
  • Podofilox [USAN]
  • Podophyllotoxin

MeSH Heading

  • Podophyllotoxin

Synonyms

  • (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
  • AI3-50456
  • CCRIS 565
  • Condyline
  • Condylox
  • EINECS 208-250-4
  • 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))-
  • HSDB 7238
  • NSC 24818
  • Podocon-25
  • Podofilm
  • Podofilox
  • Podophilox
  • Podophyllinic acid lactone
  • Podophyllotoxin
  • Podophyllotoxin 7
  • UNII-L36H50F353
  • Wartec
  • Warticon

Systematic Names

  • 1,3,3a,4,9,9a-Hexahydro-9-hydroxy-6,7-(methylenedioxy)-4-(3',4',5'-trimethoxyphenyl)benz(f)isobenzofuran-3-one
  • 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))-
  • Podophyllotoxin

Registry Numbers

CAS Registry Number

  • 518-28-5

FDA UNII

  • L36H50F353

Other Registry Number

  • 11016-28-7

System Generated Number

  • 0000518285

Structure Descriptors

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

InChIKey

YJGVMLPVUAXIQN-XVVDYKMHSA-N

Smiles

[C@H]1(c2c([C@@H]([C@@H]3[C@@H]1C(=O)OC3)O)cc1c(c2)OCO1)c1cc(c(c(c1)OC)OC)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intramuscular 4mg/kg (4mg/kg) SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
cat LD50 intravenous 1700ug/kg (1.7mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
cat LDLo subcutaneous 300ug/kg (0.3mg/kg)   Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
cat LDLo subcutaneous 300ug/kg (0.3mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
chicken LDLo subcutaneous 6250ug/kg (6.25mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
dog LDLo subcutaneous 1mg/kg (1mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
frog LDLo parenteral 152mg/kg (152mg/kg) BEHAVIORAL: STIFFNESS Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
mouse LD50 intraperitoneal 30mg/kg (30mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 327, 1961.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01679,
mouse LD50 oral 100mg/kg (100mg/kg)   PCT Vol. #86-04062,
mouse LDLo subcutaneous 24600ug/kg (24.6mg/kg)   Toxicon. Vol. 8, Pg. 85, 1970.
pigeon LDLo subcutaneous 10mg/kg (10mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.
rabbit LD50 intravenous 5mg/kg (5mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rabbit LD50 skin 200mg/kg (200mg/kg)   PCT Vol. #86-04062,
rat LD50 intramuscular 3mg/kg (3mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rat LD50 intraperitoneal 15mg/kg (15mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rat LD50 intravenous 8700ug/kg (8.7mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.
rat LD50 skin 500mg/kg (500mg/kg)   PCT Vol. #86-04062,
rat LD50 subcutaneous 8mg/kg (8mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 77, Pg. 269, 1951.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 183 deg C   EXP
log P (octanol-water) 2.01 (none)   EXP
Water Solubility 155 mg/L 25 EST
Vapor Pressure 8.34E-15 mm Hg 25 EST
Henry's Law Constant 3.80E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.20E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.