Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01160)
Name
Ingenol mebutate
Synonyms    Click to Show/Hide the Synonyms of This API
Ingenol mebutate; Picato; 3-Angeloylingenol; Ingenol 3-angelate; 3-Ingenyl angelate; PEP-005; 75567-37-2; Ingenol-3-angelate; PEP005; PEP 005; UNII-7686S50JAH; 7686S50JAH; AGN 204332; (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[E][10]annulen-6-yl (2Z)-2-methylbut-2-enoate; C25H34O6; Euphorbia factor H1; Picato (TN); Euphorbia factor An1; Ingenol mebutate [USAN:INN]; ingenol-mebutate; ingenoli mebutas; [dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] (Z)-2-methylbut-2-enoate; mebutate d'ingenol; mebutato de ingenol; Ingenol-3- angelate; Ingenol mebutate (USAN); GTPL7443; SCHEMBL2526605; CHEMBL1863513; CHEBI:66913; HSDB 8308; BDBM50470108; LMFA07010911; AKOS024457952; ZINC100037855; ACN-035815; DB05013; Ingenol-3-angelate, >=95% (HPLC); D09393; Q426386; (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a- methanocyclopenta(a)cyclopropa(e)cyclodecen-6-yl (2Z)-2-methylbut-2-enoate; (2Z)-2-Methyl-2-butenoic acid (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2 ,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydro xymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-metha nocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester; (2Z)-2-Methyl-2-butenoic acid (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester; 2-Butenoic acid, 2-methyl-, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta(a)cyclopropa(e)cyclodecen-6-yl ester, (2Z)-
Clinical Status
Approved
PubChem CID
6918670
Formula
C25H34O6
Canonical 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
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
InChIKey
VDJHFHXMUKFKET-WDUFCVPESA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6918670"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 430.5 Topological Polar Surface Area 104
XlogP 2 Complexity 926
Heavy Atom Count 31 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Ingenol Mebutate 0.015% gel Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Isopropyl Alcohol; Hydroxyethyl Cellulose; Citric Acid Monohydrate; Sodium Citrate; Benzyl Alcohol; Purified Water
                   Dosage Form Gel
                   Company Leo Labs
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [1]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [2]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [3]
          Ingenol Mebutate 0.05% gel Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Isopropyl Alcohol; Hydroxyethyl Cellulose; Citric Acid Monohydrate; Sodium Citrate; Benzyl Alcohol; Purified Water
                   Dosage Form Gel
                   Company Leo Labs
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [1]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [2]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [3]
References
1 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
2 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
3 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.

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