ingenol mebutate Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	4226	75567-37-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: picato PEP005 Ingenol 3-angelate 3-Angeloylingenol 3-Ingenyl angelate ingenol mebutate	protein kinase C agonist and antineoplastic Molecular weight: 430.54 Formula: C25H34O6 CLOGP: 3.41 LIPINSKI: 0 HAC: 6 HDO: 3 TPSA: 104.06 ALOGS: -3.19 ROTB: 4 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Drug dosage:

None

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
Jan. 23, 2012	FDA	LEO PHARMA AS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Application site vesicles	840.87	115.22	118	1188	1376	53346384
Application site erythema	710.19	115.22	120	1186	4971	53342789
Application site pain	516.51	115.22	89	1217	4094	53343666
Incorrect product administration duration	481.32	115.22	97	1209	10527	53337233
Application site swelling	270.82	115.22	39	1267	535	53347225
Product administered at inappropriate site	270.58	115.22	48	1258	2574	53345186
Application site scab	259.01	115.22	33	1273	163	53347597
Application site exfoliation	183.26	115.22	26	1280	317	53347443
Application site discharge	158.60	115.22	21	1285	146	53347614
Application site pustules	144.47	115.22	16	1290	13	53347747
Application site reaction	126.33	115.22	21	1285	756	53347004

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Application site erythema	307.98	198.13	51	596	2292	32510587
Application site pain	200.53	198.13	34	613	1740	32511139
Incorrect product administration duration	200.34	198.13	39	608	4339	32508540

Pharmacologic Action:

Source	Code	Description
ATC	D06BX02	DERMATOLOGICALS ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE CHEMOTHERAPEUTICS FOR TOPICAL USE Other chemotherapeutics
FDA PE	N0000009176	Increased Cellular Death
FDA EPC	N0000184015	Cell Death Inducer
CHEBI has role	CHEBI:35610	cytostatic

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Actinic keratosis	indication	201101007	DOID:8866

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.14	acidic
pKa2	11.74	acidic
pKa3	13.75	acidic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.015%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	8536163	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.015%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	8716271	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.015%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	8735375	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.015%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	9820959	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.015%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	9861603	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.05%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	8536163	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.05%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	8716271	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.05%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	8735375	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.05%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	9820959	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.05%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	9861603	Dec. 18, 2026	USE OF INGENOL MEBUTATE TO TREAT ACTINIC KERATOSIS
0.015%	PICATO	LEO LABS	N202833	Jan. 23, 2012	DISCN	GEL	TOPICAL	9789078	May 15, 2033	TOPICAL TREATMENT OF ACTINIC KERATOSIS OF THE FACE OR SCALP USING MORE THAN ONE TREATMENT COURSE OF INGENOL MEBUTATE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Protein kinase C delta type	Kinase	Q05655	KPCD_HUMAN	ACTIVATOR	EC50	8.33		SCIENTIFIC LITERATURE	SCIENTIFIC LITERATURE
Protein kinase C gamma type	Kinase	P05129	KPCG_HUMAN	ACTIVATOR	Ki	9.79		IUPHAR
Protein kinase C beta type	Kinase	P05771	KPCB_HUMAN		EC50	6.84		SCIENTIFIC LITERATURE
Protein kinase C alpha type	Kinase	P17252	KPCA_HUMAN		EC50	6.20		SCIENTIFIC LITERATURE
Protein kinase C epsilon type	Kinase	Q02156	KPCE_HUMAN		EC50	8.96		SCIENTIFIC LITERATURE
Serine/threonine-protein kinase D1	Kinase	Q15139	KPCD1_HUMAN		EC50	7.52		SCIENTIFIC LITERATURE

External reference:

ID	Source
D09393	KEGG_DRUG
30220-46-3	SECONDARY_CAS_RN
4031406	VANDF
4031407	VANDF
CHEBI:66913	CHEBI
CHEMBL1863513	ChEMBL_ID
C486592	MESH_SUPPLEMENTAL_RECORD_UI
C008125	MESH_SUPPLEMENTAL_RECORD_UI
7443	IUPHAR_LIGAND_ID
9006	INN_ID
DB05013	DRUGBANK_ID
7686S50JAH	UNII
6918670	PUBCHEM_CID
442042	PUBCHEM_CID
IC77UZI9G8	UNII
1242806	RXNORM
187013	MMSL
28281	MMSL
014146	NDDF
710279008	SNOMEDCT_US
715552008	SNOMEDCT_US
C2825682	UMLSCUI
C0063537	UMLSCUI
CHEMBL2165402	ChEMBL_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Picato	HUMAN PRESCRIPTION DRUG LABEL	1	50222-502	GEL	150 ug	TOPICAL	NDA	26 sections
Picato	HUMAN PRESCRIPTION DRUG LABEL	1	50222-503	GEL	500 ug	TOPICAL	NDA	26 sections