Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.
Chemical Formula: C20H28O5
Exact Mass: 348.1937
Molecular Weight: 348.439
Elemental Analysis: C, 68.94; H, 8.10; O, 22.96
Chemical Name: (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e]annulen-11-one
InChi Code: InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-,19+,20-/m1/s1
Smiles Code: CC([C@@H]1O)=C[C@@]23[C@]1(O)[C@H](O)C(CO)=C[C@]([C@@]4([H])[C@@](C4(C)C)([H])C[C@H]3C)([H])C2=O
Appearance: Solid powder
Purity: >95% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2914.40.9000
Ingenol is a PKC activator, with a Ki of 30 μM. Ingenol induces ornithine decarboxylase activity (1, 3 mM), and causes morphological changes (1 mM) in primary mouse epidermal keratinocytes. Ingenol (125 μM, 250 μM, 500 μM, 1 mM) also inhibits cell-cell communication.
- Wang D, Liu P. Ingenol-3-Angelate Suppresses Growth of Melanoma Cells and Skin Tumor Development by Downregulation of NF-κB-Cox2 Signaling. Med Sci Monit. 2018 Jan 25;24:486-502. PubMed PMID: 29368698.
- Pampena R, Benati E, Borsari S, Bombonato C, Lombardi M, Raucci M, Mirra M, Lallas A, Apalla Z, Papadimitriou I, Moscarella E, Kyrgidis A, Argenziano G, Pellacani G, Longo C. Tracking actinic keratosis of face and scalp treated with 0.015% ingenol mebutate to identify clinical and dermoscopic predictors of treatment response. J Eur Acad Dermatol Venereol. 2018 Jan 22. doi: 10.1111/jdv.14803. [Epub ahead of print] PubMed PMID: 29356164.
- Kim YC, Yang JY, Yoon JS, Jo SJ, Ahn HH, Song KH, Lee DY, Chung KY, Won YH, Kim IH. A multi-centre, open, investigator initiated phase IV clinical trial to evaluate the efficacy and safety of ingenol mebutate gel, 0.015% on the face and scalp, and 0.05% on the trunk and extremities, in Korean patients with actinic keratosis (PERFECT). Br J Dermatol. 2018 Jan 20. doi: 10.1111/bjd.16368. [Epub ahead of print] PubMed PMID: 29355904.
- Markowitz O, Wang K, Levine A, Schwartz M, Minhas S, Feldman E, Siegel DM. Noninvasive Long-term Monitoring of Actinic Keratosis and Field Cancerization Following Treatment with Ingenol Mebutate Gel 0.015. J Clin Aesthet Dermatol. 2017 Oct;10(10):28-33. Epub 2017 Oct 1. PubMed PMID: 29344318; PubMed Central PMCID: PMC5749696.
- Parker CG, Kuttruff CA, Galmozzi A, Jørgensen L, Yeh CH, Hermanson DJ, Wang Y, Artola M, McKerrall SJ, Josyln CM, Nørremark B, Dünstl G, Felding J, Saez E, Baran PS, Cravatt BF. Chemical Proteomics Identifies SLC25A20 as a Functional Target of the Ingenol Class of Actinic Keratosis Drugs. ACS Cent Sci. 2017 Dec 27;3(12):1276-1285. doi: 10.1021/acscentsci.7b00420. Epub 2017 Dec 6. PubMed PMID: 29296668; PubMed Central PMCID: PMC5746860.
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