| Chemical Information | |
| Antiviral agent ID | DrugRepV_4216 | |
| Antiviral agent name | Ingenol-3-mebutate |  |
| 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 |  |
| SMILES (canonical) | CC=C(C)C(=O)OC1C(=CC23C1(C(C(=CC(C2=O)C4C(C4(C)C)CC3C)CO)O)O)C | |
| SMILES (isomeric) | 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 | |
| Molecular Formula | C25H34O6 | |
| Molecular Weight (g/mol) | 430.541 | |
| InChl | 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 | |
| Common Name | Ingenol mebutate | |
| Synonyms | 3-Angeloylingenol|3-Ingenyl angelate| Ingenol 3-angelate| Ingenol mebutate| Ingenol mebutato| Ingenoli mebutas| Mébutate d'ingénol| Mebutato de ingenol | |
| Structural Information | |
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| Clinical Information | |
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Category | Dermatologicals
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Primary Indication (Clinical trial phases) | Approved
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| Biological Information | |
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Primary Indication (Disease Category) | Non Infectious Disease
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Primary Indication (Disease) | Actinic keratosis
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Secondary Indication | Chikungunya virus (CHIKV) NA NA |   |
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Secondary Indication (Approaches) | Experimental | |
| Secondary Indication (Methods) | In-vitro | |
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Secondary Indication (Model system) [cell lines/ animal models] | Vero
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Secondary Indication (Mode of drug delivery) | Culture
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Secondary Indication (Drug concentration) | 22.9 ± 5.2 μM
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Secondary Indication (Cell based assay) | Cytopathic effect (CPE) assay
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Secondary Indication (Change) | Decrease
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Secondary Indication (Type of Inhibition) | EC50 [ 50 % ] | |
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Reference | Nothias-Scaglia LF, Pannecouque C, Renucci F, Delang L, Neyts J, Roussi F, Costa J, Leyssen P, Litaudon M, Paolini J..Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication..J Nat Prod. 2015 Jun 26;78(6):1277-83. doi: 10.1021/acs.jnatprod.5b00073. Epub 2015 May 13. PMID:25970561
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Comment | Pearson analysis performed with the anti-CHIKV and anti-HIV data sets demonstrated a linear relationship, which supported the hypothesis made that PKC may be an important target in CHIKV replication.
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