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Compound Detail

CHEMBL1863513

INGENOL MEBUTATE
💊 Approved Drug
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💊 Approved Drug
C/C=C(/C)C(=O)O[C@H]1C(C)=C[C@]23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@]12O)[C@H]1[C@@H](C[C@H]3C)C1(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1863513
Name INGENOL MEBUTATE
Phase Approved
Structure Type MOL
InChI Key VDJHFHXMUKFKET-WDUFCVPESA-N
Therapeutic ✓ Yes

Known Names

AGN 204332 AGN204332 Ingenol mebutate Mebutate d'ingenol Mebutato de ingenol PEP-005 PEP005 Picato
7
Targets
15
Activities
1
Assay Types
0
PK Parameters
20
Publications
8
Known Names
11
Indications
1
Mechanisms

Molecular Properties

430.5
MW (Da)
2.33
ALogP
6
HBA
3
HBD
104.1
PSA (Ų)
0.36
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2010
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Withdrawn Natural Product First in Class
USAN Year 2008

Extended Properties

Molecular Formula C25H34O6
MW 430.54
Aromatic Rings 0
Heavy Atoms 31
NP-Likeness 3.62

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Keratosis, Actinic Carcinoma Carcinoma, Basal Cell Carcinoma, Squamous Cell Condylomata Acuminata Keratosis Keratosis, Seborrheic Skin Diseases Cheilitis Warts Molluscum Contagiosum

ATC Classification

D06BX02
ingenol mebutate
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

Drug Warnings

Withdrawn
carcinogenicity
Increased risk of skin cancer, particularly squamous cell carcinoma
Country: European Union; Canada   Year: 2020
Withdrawn
carcinogenicity
Increased risk of skin cancer, particularly squamous cell carcinoma
Country: European Union; Canada   Year: 2020
Withdrawn
carcinogenicity
Increased risk of non-melanoma skin cancer
Country: European Union; Canada   Year: 2020

Activity Summary

EC50 15 meas. best 8.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protein kinase C delta type
CHEMBL2996
 EC50 8.39 8.39 4.1 2
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.38 8.205 4.2 4
Unchecked
CHEMBL612545
 EC50 8.06 8.06 8.7 2
Human immunodeficiency virus 2
CHEMBL380
 EC50 8.05 8.05 9.0 1
Keratinocyte
CHEMBL613995
 EC50 7.99 7.97 10.3 4
Protein kinase C (PKC)
CHEMBL2093867
 EC50 7.14 7.14 72.5 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.64 4.64 22900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protein kinase C delta type EC50 = 4.1 nM 8.39 Activation of PKCdelta (unknown origin) using phosphatidylserine as substrate 23993332
Protein kinase C delta type EC50 = 4.1 nM 8.39 Activation of PKCdelta (unknown origin) after 40 mins 24332494
Human immunodeficiency virus 1 EC50 = 4.2 nM 8.38 Reactivation of latent HIV1 infected in human U1 cells assessed as increase in p... 30031972
Human immunodeficiency virus 1 EC50 = 4.5 nM 8.35 Antiviral activity against Human immunodeficiency virus 1 NL4-3 infected in huma... 30031972
Human immunodeficiency virus 1 EC50 = 4.8 nM 8.32 Reactivation of latent HIV1 infected in human U1 cells assessed as increase in p... 29541372
Unchecked EC50 = 8.7 nM 8.06 Induction of oxidative burst in polymorphonuclear leukocytes (unknown origin) is... 23993332
Unchecked EC50 = 8.7 nM 8.06 Immunostimulatory activity in polymorphonuclear leukocytes (unknown origin) asse... 24332494
Human immunodeficiency virus 2 EC50 = 9.0 nM 8.05 Antiviral activity against HIV2 ROD infected in MT4 cells assessed as cell viabi... 25970561
Keratinocyte EC50 = 10.3 nM 7.99 Induction of IL-8 release in human primary epidermal keratinocytes after 6 hrs b... 23993332
Keratinocyte EC50 = 10.3 nM 7.99 Induction of proimflammatory activity in human primary epidermal keratinocytes a... 24332494
Keratinocyte EC50 = 11.2 nM 7.95 Induction of TNFalpha release in human primary epidermal keratinocytes after 6 h... 23993332
Keratinocyte EC50 = 11.2 nM 7.95 Induction of proimflammatory activity in human primary epidermal keratinocytes a... 24332494
Human immunodeficiency virus 1 EC50 = 17.0 nM 7.77 Antiviral activity against HIV1 3B infected in MT4 cells assessed as cell viabil... 25970561
Protein kinase C (PKC) EC50 = 72.5 nM 7.14 Activation of PKC in human platelet assessed as induction of platelet aggregatio... 27731641
NON-PROTEIN TARGET EC50 = 22900.0 nM 4.64 Antiviral activity against chikungunya virus Indian ocean strain 899 infected in... 25970561

Literature References

PubMed DOI Target Context # Activities
27731641 10.1021/acs.jnatprod.6b00603 Protein kinase C (PKC) 31
26225771 10.1371/journal.ppat.1005066 Unchecked 22
23993332 10.1016/j.bmcl.2013.08.038 Keratinocyte 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
29541372 10.1021/acsmedchemlett.8b00012 Human immunodeficiency virus 1 3
30031972 10.1016/j.ejmech.2018.07.020 Human immunodeficiency virus 1 3
25970561 10.1021/acs.jnatprod.5b00073 Unchecked 3
24332494 10.1016/j.bmcl.2013.11.073 Keratinocyte 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
27731641 10.1021/acs.jnatprod.6b00603 Protein kinase C alpha type 2
27731641 10.1021/acs.jnatprod.6b00603 Protein kinase C beta type 2
27731641 10.1021/acs.jnatprod.6b00603 Protein kinase C delta type 2
23993332 10.1016/j.bmcl.2013.08.038 Unchecked 2
29541372 10.1021/acsmedchemlett.8b00012 Unchecked 2
26225771 10.1371/journal.ppat.1005066 U1 2
24332494 10.1016/j.bmcl.2013.11.073 Protein kinase C delta type 1
24332494 10.1016/j.bmcl.2013.11.073 HeLa 1
25970561 10.1021/acs.jnatprod.5b00073 NON-PROTEIN TARGET 1
26225771 10.1371/journal.ppat.1005066 Inhibitor of nuclear factor kappa-B kinase subunit beta 1

Data from ChEMBL 36 via Core Engine