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Ingenol mebutate (Molecule of the Month for November 2018)

Ingenol-3-angelate, PEP005, Picato

Ingenol mebutate is a substance that is found in the sap of the plant Euphorbia peplus, commonly known as milkweed, and is an inducer of cell death.

A gel formulation of the drug has been approved by the U.S. Food and Drug Administration (FDA)[2] and by the European Medicines Agency (EMA) for the topical treatment of actinic keratosis. Actinic keratosis (AK) is a pre-cancerous area of thick, scaly, or crusty skin. These growths are more common in fair-skinned people and those who are frequently in the sun. They are believed to form when skin gets damaged by ultraviolet (UV) radiation from the sun or indoor tanning beds, usually over the course of decades. Given their pre-cancerous nature, if left untreated they may turn into a type of skin cancer called squamous cell carcinoma. Untreated lesions have up to a 20% risk of progression to squamous cell carcinoma, so treatment by a dermatologist is recommended.

Results from four multicenter, randomized, double-blind studies have shown that ingenol mebutate gel applied topically, for 2 to the trunk or 3 days to the face or scalp, is effective for field treatment of actinic keratoses. Irritation of the application site is very common. The various types of irritation include redness, scaling, crusting, pain, severe itching, and sometimes infection. Additional possible side effects include eye irritation, such as periorbital edema (3% of patients in studies), headaches (2%) and nasopharyngitis (running nose, 2%). The mechanism by which ingenol mebutate causes cell death is still not fully understood.

Formal Chemical Name (IUPAC)
(1S,4S,5R,6R,9S,10R,12R,14R)-4,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[,5.010,12]pentadeca-2,7-dien-5-yl (2Z)-2-methyl-2-butenoate



Picture of Ingenol mebutate 3D model

click on the picture of  Ingenol mebutate above to interact
with the 3D model of the
Ingenol mebutate structure
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Picture of Ingenol mebutate

C25 H34 O6

Update by Karl Harrison
(Molecule of the Month for November 2018 )

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