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Ingenol Mebutate

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Also known as AGN 204332AGN204332Mebutate d'ingenolMebutato de ingenolPEP-005PEP005PicatoIngenol 3A

Summary

Ingenol Mebutate (CHEMBL1863513) is an approved small molecule (ATC D06BX02) targeting PRKCA, PRKCB, and PRKCG; indicated across 11 conditions including actinic keratosis and basal cell carcinoma.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: D06BX02
  • Targets: 5 (PRKCA, PRKCB, PRKCG…)
  • Indications: 11 conditions
  • Clinical trials: 31
  • Chemistry: 430.5 Da · C25H34O6

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1863513
NameIngenol Mebutate
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID6918670
ATCD06BX02
Molecular formulaC25H34O6
Molecular weight430.5
InChIKeyVDJHFHXMUKFKET-WDUFCVPESA-N

SMILES: C/C=C(/C)\C(=O)O[C@H]1C(=C[C@@]23[C@@]1([C@@H](C(=C[C@H](C2=O)[C@H]4[C@H](C4(C)C)C[C@H]3C)CO)O)O)C

IUPAC name: [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate

Also known as: AGN 204332, AGN204332, Ingenol mebutate, Mebutate d’ingenol, Mebutato de ingenol, PEP-005, PEP005, Picato, INGENOL MEBUTATE, Ingenol 3A, Ingenol Mebutate

Patent coverage: 560 distinct patent families (1,475 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
PRKCAprotein kinase C alphaActivation9.520.7%P17252
PRKCBprotein kinase C betaActivation9.980.1%P05771
PRKCGprotein kinase C gammaActivation9.790%P05129
PRKCDprotein kinase C deltaActivation9.420.2%Q05655
PRKCEprotein kinase C epsilonActivation9.773.3%Q02156

Broader ChEMBL bioactivity targets: 2 (assay-derived). Sample: Protein kinase C (PKC), Protein kinase C delta type.

Bioactivity

ChEMBL activities: 3 potent at pChembl ≥ 5 of 3 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
PRKCD8.39EC504.1nMCHEMBL_ACT_13459788
PRKCD8.39EC504.1nMCHEMBL_ACT_13880715
PRKD37.14EC5072.5nMCHEMBL_ACT_18194741

Target pathways

Aggregated over 5 target gene(s): PRKCA, PRKCB, PRKCG, PRKCD, PRKCE.

Top Reactome pathways

97 total, by targets touching each:

PathwayTargetsGenes
Hemostasis5PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
Signal Transduction5PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
Signaling by GPCR5PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
GPCR downstream signalling5PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
G alpha (z) signalling events5PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
Platelet activation, signaling and aggregation5PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
DAG and IP3 signaling4PRKCA, PRKCD, PRKCE, PRKCG
Intracellular signaling by second messengers4PRKCA, PRKCD, PRKCE, PRKCG
Signaling by Receptor Tyrosine Kinases4PRKCA, PRKCB, PRKCD, PRKCE
Opioid Signalling3PRKCA, PRKCD, PRKCG
Calmodulin induced events3PRKCA, PRKCD, PRKCG
Ca-dependent events3PRKCA, PRKCD, PRKCG
CaM pathway3PRKCA, PRKCD, PRKCG
G-protein mediated events3PRKCA, PRKCD, PRKCG
PLC beta mediated events3PRKCA, PRKCD, PRKCG
Neurotransmitter receptors and postsynaptic signal transmission3PRKCA, PRKCB, PRKCG
Transmission across Chemical Synapses3PRKCA, PRKCB, PRKCG
Neuronal System3PRKCA, PRKCB, PRKCG
Disinhibition of SNARE formation3PRKCA, PRKCB, PRKCG
Signaling by ERBB23PRKCA, PRKCD, PRKCE
SHC1 events in ERBB2 signaling3PRKCA, PRKCD, PRKCE
Immune System3PRKCB, PRKCD, PRKCE
Signaling by VEGF3PRKCA, PRKCB, PRKCD
Signaling by Rho GTPases3PRKCA, PRKCB, PRKCD
RHO GTPase Effectors3PRKCA, PRKCB, PRKCD
Signaling by WNT3PRKCA, PRKCB, PRKCG
Beta-catenin independent WNT signaling3PRKCA, PRKCB, PRKCG
Trafficking of AMPA receptors3PRKCA, PRKCB, PRKCG
Glutamate binding, activation of AMPA receptors and synaptic plasticity3PRKCA, PRKCB, PRKCG
PCP/CE pathway3PRKCA, PRKCB, PRKCG

Dominant GO biological processes

GO termTargets
protein phosphorylation5
intracellular signal transduction5
apoptotic process4
positive regulation of insulin secretion3
protein kinase C signaling3
signal transduction3
mitotic nuclear membrane disassembly2
cell adhesion2
learning or memory2
response to toxic substance2
negative regulation of glial cell apoptotic process2
regulation of mRNA stability2
positive regulation of angiogenesis2
chromatin remodeling2
regulation of transport2

Indications & clinical

Indications

11 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
actinic keratosis4MONDO:0005173EFO:0002496
basal cell carcinoma2MONDO:0020804EFO:0004193
skin disorder2MONDO:0005093EFO:0000701
squamous cell carcinoma2MONDO:0005096EFO:0000707
seborrheic keratosis2MONDO:0008420EFO:0005584
anogenital human papillomavirus infection2MONDO:0005647EFO:0007147
keratosis2MONDO:0006566EFO:1000720
carcinoma2MONDO:0004993EFO:0000313
cheilitis1MONDO:0002102MONDO:0002102
common wart1MONDO:0001209EFO:0009662
molluscum contagiosum0MONDO:0005855EFO:0007375

Clinical trials

Total trials: 31.

Phase distribution

PhaseTrials
PHASE211
PHASE17
Not specified6
PHASE43
PHASE32
EARLY_PHASE12

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02251652PHASE4COMPLETEDSafety and Efficacy of Ingenol Mebutate 0.05% Gel When Used After Cryotherapy in the Hypertrophic Actinic Keratoses
NCT02281682PHASE4UNKNOWNIM Versus 5-FU Versus IMI Versus MAL-PDT in Treatment of Actinic Keratosis
NCT02990221PHASE4COMPLETEDEfficacy of Ingenol Mebutate on Actinic Keratoses and Field Cancerization vs Cryotherapy
NCT02361216PHASE3COMPLETEDEfficacy and Safety of Ingenol Mebutate Gel for Actinic Keratosis Applied on Large Area on Face, Scalp or Chest
NCT02473848PHASE3TERMINATEDIngenol Mebutate Gel 0.05% in Kidney Transplant Recipients With Actinic Keratoses
NCT00107965PHASE2COMPLETEDStudy to Determine the Safety of Two Applications of PEP005 Topical Gel to Actinic Keratoses
NCT00108121PHASE2COMPLETEDStudy to Determine the Safety of Two Applications of PEP005 Topical Gel to Nodular Basal Cell Carcinoma
NCT00108134PHASE2COMPLETEDStudy to Determine the Safety of Two Applications of PEP005 Topical Gel to Superficial Basal Cell Carcinoma
NCT00239135PHASE2COMPLETEDStudy to Determine the Maximum Tolerated Dose and Safety of PEP005 Topical Gel
NCT00329121PHASE2COMPLETEDStudy to Determine the Safety of Two Applications of PEP005 Topical Gel to Cutaneous Squamous Cell Carcinoma In Situ
NCT00375739PHASE2COMPLETEDStudy to Determine the Safety of PEP005 0.025% and 0.05% Topical Gel in Patients With Actinic Keratoses
NCT00427050PHASE2COMPLETEDA Study to Determine the Optimal Tolerated Regime and Safety of PEP005 Topical Gel
NCT00432185PHASE2COMPLETEDTo Determine the Maximum Tolerated Dose Level (MTD) of PEP005 Topical Gel in Patients With sBCC
NCT01998984PHASE2COMPLETEDEfficacy and Safety of Ingenol Mebutate Gel 0.06% When Applied Once Daily for 2, 3 or 4 Consecutive Days to a Treatment Area of Approximately 250 cm2 on Trunk and Extremities in Subjects With Actinic Keratosis
NCT02377999PHASE2COMPLETEDSafety and Efficacy of Repeat Use of Picato® 0.05% in the Treatment of Anogenital Warts
NCT03546166PHASE2COMPLETEDStudy Evaluating the Efficacy and Safety of 0.05% Ingenol Mebutate (Picato® 500) in the Treatment of Basal Cell Carcinoma
NCT00544258PHASE1COMPLETEDPharmacokinetic Study to Evaluate the Extent of Systemic Absorption of PEP005
NCT00546611PHASE1WITHDRAWNThe Purpose of This Study is to Determine Whether Topical Application of PEP005 is Safe for the Treatment of Common Wart(s)
NCT01449513PHASE1COMPLETEDPEP005 Gel - Biological Effects in Actinic Keratosis Assessed by Reflectance Confocal Microscopy
NCT01836367PHASE1COMPLETEDIngenol Mebutate 0.015% Gel in the Treatment of Actinic Keratoses (AK) on the Face and Scalp
NCT02124239PHASE1COMPLETEDPharmacokinetics of Ingenol Mebutate Gel in Actinic Keratosis Under Maximum Use Conditions
NCT02411851PHASE1COMPLETEDTreatment of Actinic Keratoses (AK) on the Face
NCT02748902PHASE1COMPLETEDExploratory Study of Efficacy and Safety of Ingenol Mebutate 0.05% Gel for Common Warts on the Hands.
NCT01735942EARLY_PHASE1WITHDRAWNIngenol Mebutate Compared to Cryotherapy for the Treatment of Skin Lesions
NCT03336372EARLY_PHASE1WITHDRAWNPicato for the Treatment of Molluscum Contagiosum in Immunocompromised Patients
NCT02090465Not specifiedCOMPLETEDAssessment of Treatment Success and Quality of Life in Patients With Actinic Keratoses Under Therapy With Ingenol Mebutate in a Period of 8 Weeks
NCT02242747Not specifiedCOMPLETEDSafety and Tolerability Study of Ingenol Mebutate Compared to 5-FU to Treat Facial Actinic Keratosis
NCT02362152Not specifiedCOMPLETEDThe Real Life Topical Field Treatment of Actinic Keratosis Study
NCT02421471Not specifiedCOMPLETEDPMS to Evaluate the Safety and Efficacy of Picato® Gel
NCT02594436Not specifiedCOMPLETEDThe Use of Picato® (Ingenol Mebutate) to Treat Actinic Keratosis in Standard Clinical Practice
NCT04202445Not specifiedCOMPLETEDTreatMent of ActInic KerAtosis Lesions : pharmacoepiDemiological Study of the Impact in Real Life of ingenOl Mebutate Gel (Picato®) on Patients Satisfaction

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

62 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
TAMOXIFENChEMBL + PubChemPhase 4 (approved)PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
MIDOSTAURINChEMBLPhase 4 (approved)PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
ALVOCIDIBChEMBLPhase 3PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
ENZASTAURINChEMBLPhase 3PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
FASUDILChEMBLPhase 3PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
RUBOXISTAURINChEMBLPhase 3PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
SURAMINChEMBLPhase 3PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
DAROVASERTIBChEMBLPhase 2PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
EDELFOSINEChEMBLPhase 2PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
PHORBOL MYRISTATEChEMBLPhase 2PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
SOTRASTAURINChEMBLPhase 2PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
UCN-01ChEMBLPhase 2PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
UPROSERTIBChEMBLPhase 2PRKCA, PRKCB, PRKCD, PRKCE, PRKCG
BelzutifanPubChemApprovedPRKCA, PRKCB, PRKCD, PRKCE, PRKCG
IdelalisibPubChemApprovedPRKCA, PRKCB, PRKCD, PRKCE, PRKCG
CAPIVASERTIBChEMBL + PubChemPhase 4 (approved)PRKCA, PRKCB, PRKCD, PRKCG
AfatinibPubChemApprovedPRKCA, PRKCB, PRKCD, PRKCE
CrizotinibPubChemApprovedPRKCA, PRKCB, PRKCD, PRKCE
GanciclovirPubChemApprovedPRKCB, PRKCD, PRKCE, PRKCG
PazopanibPubChemApprovedPRKCA, PRKCB, PRKCD, PRKCE
SelumetinibPubChemApprovedPRKCA, PRKCB, PRKCD, PRKCE
ABEMACICLIBChEMBLPhase 4 (approved)PRKCA, PRKCB, PRKCD
BARICITINIBChEMBLPhase 4 (approved)PRKCA, PRKCB, PRKCD
LESTAURTINIBChEMBLPhase 3PRKCA, PRKCD, PRKCE
DECERNOTINIBChEMBLPhase 2PRKCA, PRKCB, PRKCD
LY-2090314ChEMBLPhase 2PRKCB, PRKCD, PRKCG
ZOTIRACICLIBChEMBLPhase 2PRKCA, PRKCB, PRKCD
BinimetinibPubChemApprovedPRKCA, PRKCB, PRKCD
dacomitinibPubChemApprovedPRKCA, PRKCB, PRKCD
FostamatinibPubChemApprovedPRKCA, PRKCB, PRKCD
GefitinibPubChemApprovedPRKCB, PRKCD, PRKCE
regorafenibPubChemApprovedPRKCA, PRKCB, PRKCD
TrametinibPubChemApprovedPRKCA, PRKCB, PRKCD
BOSUTINIBChEMBLPhase 4 (approved)PRKCD, PRKCE
PACRITINIBChEMBLPhase 4 (approved)PRKCA, PRKCB
RUXOLITINIBChEMBLPhase 4 (approved)PRKCA, PRKCE
TOFACITINIBChEMBLPhase 4 (approved)PRKCA, PRKCD
AFURESERTIBChEMBLPhase 3PRKCA, PRKCB
CURCUMINChEMBLPhase 3PRKCD, PRKCE
AT-9283ChEMBLPhase 2PRKCA, PRKCB
BMS-690514ChEMBLPhase 2PRKCA, PRKCD
BMS-754807ChEMBLPhase 2PRKCA, PRKCD
BRYOSTATIN 1ChEMBLPhase 2PRKCA, PRKCD
CENISERTIBChEMBLPhase 2PRKCD, PRKCG
DORAMAPIMODChEMBLPhase 2PRKCB, PRKCD
LAUROGUADINEChEMBLPhase 2PRKCD, PRKCG
R-406ChEMBLPhase 2PRKCD, PRKCG
FEDRATINIBChEMBL + PubChemPhase 4 (approved)PRKCE
ENTRECTINIBChEMBLPhase 4 (approved)PRKCG
GILTERITINIBChEMBLPhase 4 (approved)PRKCA
SUNITINIBChEMBLPhase 4 (approved)PRKCA
CRENOLANIBChEMBLPhase 3PRKCD
DOVITINIBChEMBLPhase 3PRKCD
RIPASUDILChEMBLPhase 3PRKCD
ACETOSIDEChEMBLPhase 2PRKCA
APITOLISIBChEMBLPhase 2PRKCA
ILORASERTIBChEMBLPhase 2PRKCD
PELITINIBChEMBLPhase 2PRKCD
SAR-407899 FREE BASEChEMBLPhase 2PRKCD
SCH-900776ChEMBLPhase 2PRKCD

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot