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

Stem definitionDrug idCAS RN
4226 75567-37-2

Description:

MoleculeDescription

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:

DateAgencyCompanyOrphan
Jan. 23, 2012 FDA LEO PHARMA AS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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 termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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:

SourceCodeDescription
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)

DiseaseRelationSNOMED_IDDOID
Actinic keratosis indication 201101007 DOID:8866

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.14 acidic
pKa2 11.74 acidic
pKa3 13.75 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent 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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Protein kinase C delta type Kinase ACTIVATOR EC50 8.33 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Protein kinase C gamma type Kinase ACTIVATOR Ki 9.79 IUPHAR
Protein kinase C beta type Kinase EC50 6.84 SCIENTIFIC LITERATURE
Protein kinase C alpha type Kinase EC50 6.20 SCIENTIFIC LITERATURE
Protein kinase C epsilon type Kinase EC50 8.96 SCIENTIFIC LITERATURE
Serine/threonine-protein kinase D1 Kinase EC50 7.52 SCIENTIFIC LITERATURE

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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