ingenol mebutate   Click here for help

GtoPdb Ligand ID: 7443

Synonyms: PEP-005 | Picato®
Approved drug
ingenol mebutate is an approved drug (FDA & EMA (2012))
Comment: Ingenol mebutate is extracted from the plant Euphorbia peplus.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 104.06
Molecular weight 430.24
XLogP 3.21
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC=C(C(=O)OC1C(=CC23C1(O)C(O)C(=CC(C3=O)C1C(CC2C)C1(C)C)CO)C)C
Isomeric SMILES C/C=C(\C(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](O)C(=C[C@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)CO)C)/C
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
InChI Key VDJHFHXMUKFKET-WDUFCVPESA-N
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Summary of Clinical Use Click here for help
A gel formulation containing ingenol mebutate is indicated for the topical treatment of actinic keratoses [3-4]. Ingenol mebutate is being further investigated in clinical trials for treatment of other skin lesions, including basal cell and squamous cell skin cancers. Click this link to view ClinicalTrials.gov's list of ingenol mebutate trials.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Ingenol mebutate is a pleiotropic effector which activates protein kinase C δ (PKCδ) [2]. Activation of PKCδ induces two main processes: rapid cell death and neutrophil infiltration at the site of application [1,1].
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