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Podophyllin is a resinous powder obtained by precipitating an alcoholic tincture of the rhizome of American Mayapple (Podophyllum peltatum) or Podophyllum emodi by means of water acidified with hydrochloric acid. It varies in color from grayish to bright yellow or greenish-brown, the first-named being the purest. It was commonly used against genital warts because it contains antiwart lignans, although podofilox, a purified form of the main active ingredient, has become recommended due to its higher efficacy and safety.[1]

The powder is soluble in alcohol and strong solutions of alkalis, such as ammonia. Its composition is somewhat complex. There are certainly at least two resins in the powder (which is known officially as Podophylli resina), one of them being soluble and the other insoluble in ether. Each of these contains an active substance, which can be obtained in crystalline form, and is known as podophyllotoxin. It is soluble in alcohol, ether, chloroform and boiling water.

Contents

Reactivity

Alkalis decompose it into picro-podophyllic acid and picro-podophyllin, minute traces of both of which occur in a free state in the rhizome. The acid is inert, but picro-podophyllin is the active principle.

It is a crystalline body, soluble only in concentrated alcohol. Hence the inutility of the pharmacopeial tinctura podophylli, which cannot be diluted before administration. The properties of podophyllin resin vary with the reaction of the tissue with which it is in contact; where this is acid the drug is inert, the picro-podophyllin being precipitated.

The resin does not affect the unbroken skin, but may be absorbed from a raw surface, and will then cause purging. When taken internally it is both a secretory and an excretory cholagogue, but so irritating and powerful that its use in cases of jaundice is generally undesirable. Its value, however, in certain cases of constipation of hepatic origin is undeniable. It is largely used in patent medicines, usually as an auxiliary to aloes. The best method of prescribing podophyllin is in pill form.

Toxicity

In toxic doses podophyllin causes intense enteritis, with all its characteristic symptoms, and severe depression, which may end in death. The treatment is symptomatic, there being no specific antidote.

Even when podophyllin resin is used topically, it can be systemically absorbed into the body, and fatal and near-fatal reactions have been reported, particularly when it is used extensively or on mucous membranes.[2] Neither podophyllin resin nor podofilox lotion or gel is used during pregnancy because these medications can be harmful to the fetus. The most common side effects near the application site are skin reactions, including burning, redness, pain, itching, swelling. There is some concern about the mutagenicity of some of the flavonoids in podophyllin.[1]

Medical Applications

Podophyllin has been used to remove genital warts since its efficacy was first demonstrated in 1942, although the reliability of this early report has been questioned.[1] This requires one application of podophyllin resin a week to the warts by a health professional, which is then washed off after 4 to 6 hours.[1] Petroleum jelly, such as Vaseline, may be used to protect normal tissue near the warts from irritation. A health professional usually applies the resin once a week for at least 6 weeks or until warts disappear. It is unstable and therefore must be prepared shortly before use, which has possibly led to the lower efficacy shown in some clinical trials.[1]

Podophyllin is also used to treat Molluscum contagiosum in the genital area. As the molluscum lesions can sometimes be quite numerous, scarring and hypopigmentation become an issue with cryosurgery.

References

  1. ^ a b c d e Longstaff E, von Krogh G (April 2001). "Condyloma eradication: self-therapy with 0.15-0.5% podophyllotoxin versus 20-25% podophyllin preparations--an integrated safety assessment". Regul. Toxicol. Pharmacol. 33 (2): 117–37. doi:10.1006/rtph.2000.1446. PMID 11350195.  
  2. ^ von Krogh G, Longstaff E (December 2001). "Podophyllin office therapy against condyloma should be abandoned" (Registration required). Sex Transm Infect 77 (6): 409–12. doi:10.1136/sti.77.6.409. PMID 11714936. PMC 1744412. http://sti.bmj.com/cgi/content/full/77/6/409.  

Further reading

  • Kelly M, Hartwell J. L. (1954). "The biological effects and the chemical composition of podophyllin: a review.". Journal of the National Cancer Institute 14 (4): 967–1010.  
  • J. L. Hartwell, A. W. Schrecker (1951). "Components of Podophyllin. V. The Constitution of Podophyllotoxin". Journal of the American Chemical Society 73 (6): 2909–2916. doi:10.1021/ja01150a143.  
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1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

PODOPHYLLIN, a drug obtained from the rhizome of the American mandrake or may apple, Podophyllum peltatum, an herbaceous perennial belonging to the natural order Berberidaceae, indigenous in woods in Canada and the United States. The plant is about 1 ft. high, bearing two peltate, deeplydivided leaves, which are about 5 in. in diameter, and bear in the axil a solitary, stalked, white flower, about the size and shape of the garden anemone, with six or more petals and twice as many hypogynous stamens. The fruit is ripe in July, and is an oval, yellowish, fleshy berry, containing twelve or more seeds, each surrounded by a pulpy outer coat or aril. The rhizome, as met with in commerce, occurs in cylindrical pieces 2 or 3 in. long and about 4 in. in diameter, of a chocolate or purplish-brown colour, smooth, and slightly enlarged where the juncture of the leafy stem is indicated by a circular scar on the upper and a few broken rootlets on the under side. The odour is heavy and disagreeable, and the taste acrid and bitter.

Podophyllin is a resinous powder obtained by precipitating an alcoholic tincture of the rhizome by means of water acidulated with hydrochloric acid. It varies in colour from greyish to bright yellow or greenish-brown, the first-named being the purest. The powder is soluble in alcohol and strong solutions of alkalis, such as ammonia. Its composition is somewhat complex. There are certainly at least two resins in the powder (which is known officially as Podophylli resina), one of them being soluble and the other insoluble in ether. Each of these contains an active substance, which can be obtained in crystalline foi m, and is known as podophyllotoxin. It is soluble in alcohol, ether, chloroform and boiling water. Alkalis decompose it into picro-podophyllic acid and picro-podophyllin, minute traces of both of which occur in a free state in the rhizome. The acid is inert, but picro-podophyllin is the active principle. It is a crystalline body, soluble only in concentrated alcohol. Hence the inutility of the pharmacopeial tinctura podophylli, which cannot be diluted before administration. The properties of podophyllin resin vary with the reaction of the tissue with which it is in contact; where this is acid the drug is inert, the picro-podophyllin being precipitated.

The resin does not affect the unbroken skin, but may be absorbed from a raw surface, and will then cause purging. When taken internally it is both a secretory and an excretory cholagogue, but so irritant and powerful that its use in cases of jaundice is generally undesirable. Its value, however, in certain cases of constipation of hepatic origin is undeniable. It is largely used in patent medicines, usuall y as an auxiliary to aloes. The best method of prescribing podophyllin is in pill form. In toxic doses podophyllin causes intense enteritis, with all its characteristic symptoms, and severe depression, which may end in death. The treatment is symptomatic, there being no specific antidote.


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