Ingenol mebutate

Ingenol mebutate
Clinical data
Trade namesPicato
Other namesPEP005, ingenol-3-angelate
AHFS/Drugs.comMonograph
MedlinePlusa613008
Pregnancy
category
  • AU: B3
Routes of
administration		Topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailabilitynot absorbed when used topically
Identifiers
  • (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclpropa[e][10]annulen-6-yl (2Z)-2-methylbut-2-enoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.214.695 Edit this at Wikidata
Chemical and physical data
FormulaC25H34O6
Molar mass430.541 g·mol−1
3D model (JSmol)
  • C/C=C(/C)\C(=O)O[C@H]1C(C)=C[C@]23[C@]1(O)[C@H](O)C(CO)=C[C@H](C3=O)[C@H]4[C@H](C4(C)C)C[C@H]2C
  • InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
  • Key:VDJHFHXMUKFKET-WDUFCVPESA-N

Ingenol mebutate, sold under the brand name Picato, is a substance that is found in the sap of the plant Euphorbia peplus,[1] commonly known as petty spurge, and is an inducer of apoptosis. This compound was isolated first from this plant in 2000.[2] A gel formulation of the drug has been approved by the U.S. Food and Drug Administration (FDA)[3] and by the European Medicines Agency (EMA)[4] for the topical treatment of actinic keratosis. Two different strengths of the gel have been approved for use on either the face and scalp (0.015%) or the trunk and extremities (0.05%), respectively.[5] In 2020 the drug was withdrawn from the market in the EU.[6]

  1. ^ Cite error: The named reference Fallen was invoked but never defined (see the help page).
  2. ^ Hohmann J, Evanics F, Berta L, Bartók T (April 2000). "Diterpenoids from Euphorbia peplus". Planta Medica. 66 (3): 291–294. doi:10.1055/s-2000-8568. PMID 10821064. S2CID 260249228.
  3. ^ Cite error: The named reference Drugs@FDA was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference EMA was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Approved label was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference EMA-withdrawal was invoked but never defined (see the help page).