Ingenol mebutate

Ingenol mebutate
Clinical data
Trade names	Picato
Other names	PEP005, ingenol-3-angelate
AHFS/Drugs.com	Monograph
MedlinePlus	a613008
Pregnancy; category	AU: B3;
Routes of; administration	Topical
ATC code	D06BX02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	not absorbed when used topically
Identifiers
	IUPAC name (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	75567-37-2;
PubChem CID	6918670;
DrugBank	DB05013;
ChemSpider	26325194;
UNII	7686S50JAH;
KEGG	D09393;
ChEBI	CHEBI:66913 ;
CompTox Dashboard (EPA)	DTXSID301025610 ;
ECHA InfoCard	100.214.695
Chemical and physical data
Formula	C25H34O6
Molar mass	430.541 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 isolated from the sap of the plant Euphorbia peplus, that is an inducer of apoptosis. This compound was first discovered in the year 2000. A gel formulation of the drug has been approved by the U.S. Food and Drug Administration (FDA) and by the European Medicines Agency (EMA) 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. In 2020 the drug was withdrawn from the market in the EU.