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Technical details about Podophyllum Resin, learn more about the structure, uses, toxicity, action, side effects and more

Podophyllum Resin

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

4 Suppliers, 1 EU WC, 5 NDC API, 4 Listed Suppliers

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1 Dossiers, 1 Canada

RELATED EXCIPIENT COMPANIES

Suppliers, 3 Kerry, 2 BASF, 1 Pfanstiehl, 1 Roquette, 1 Actylis, 1 Gangwal Chemicals

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3 Coating Systems & Additives, 3 Co-Processed Excipients, 2 Thickeners and Stabilizers, 2 Taste Masking, 2 Granulation, 2 Direct Compression, 1 Fillers, Diluents & Binders, 1 Parenteral, 1 Controlled & Modified Release

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1 DOSSIERS // FDF

Podophyllum Resin
Chemistry
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1. Also known as: Podophyllum resin, 9000-55-9, 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid;5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one, Podophylline, Podophyllin from podophyllum emodii, Db09094

Molecular Formula

C₈₈H₉₂O₃₄

Molecular Weight

1693.6 g/mol

InChI Key

KOUZYZCESNTXJO-UHFFFAOYSA-N

Caustic extract from the roots of Podophyllum peltatum and P. emodi. It contains PODOPHYLLOTOXIN and its congeners and is very irritating to mucous membranes and skin. Podophyllin is a violent purgative that may cause CNS damage and teratogenesis. It is used as a paint for warts, skin neoplasms, and senile keratoses.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid;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/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

2.1.3 InChI Key

KOUZYZCESNTXJO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O.COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O.COC1=CC(=CC(=C1OC)OC)C2C(C(C(C3=CC4=C(C=C23)OCO4)O)CO)C(=O)O.COC1=CC(=CC(=C1OC)OC)C2C(C(C(C3=CC4=C(C=C23)OCO4)O)CO)C(=O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Podophyllum Resin

2. Resin, Podophyllum

2.2.2 Depositor-Supplied Synonyms

1. Podophyllum Resin

2. 9000-55-9

3. 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic Acid;5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

4. Podophylline

5. Podophyllin From Podophyllum Emodii

6. Db09094

7. Q22075831

2.3 Create Date

2007-01-09

3 Chemical and Physical Properties

Molecular Formula	C₈₈H₉₂O₃₄
Molecular Weight	1693.6 g/mol
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	34
Rotatable Bond Count	20
Exact Mass	1692.5470000 g/mol
Monoisotopic Mass	1692.5470000 g/mol
Topological Polar Surface Area	433 Å²
Heavy Atom Count	122
Formal Charge	0
Complexity	1240
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	16
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	4

4 Drug and Medication Information

4.1 Drug Indication

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

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cell division is arrested and other cellular processes are impaired, gradually resulting in the disruption of cells and destruction of the tissue.

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.)

Caustics

Strong alkaline chemicals that destroy soft body tissues resulting in a deep, penetrating type of burn, in contrast to corrosives, that result in a more superficial type of damage via chemical means or inflammation. Caustics are usually hydroxides of light metals. SODIUM HYDROXIDE and potassium hydroxide are the most widely used caustic agents in industry. Medically, they have been used externally to remove diseased or dead tissues and destroy warts and small tumors. The accidental ingestion of products (household and industrial) containing caustic ingredients results in thousands of injuries per year. (See all compounds classified as Caustics.)

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.)

5.3 Absorption, Distribution and Excretion

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.

Route of Elimination

No data available.

Volume of Distribution

No data available.

Clearance

No data available.

5.4 Metabolism/Metabolites

No data available.

5.5 Biological Half-Life

No data available.

5.6 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.

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