Ingenol

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.

Product information

CAS Number: 30220-46-3

Molecular Weight: 348.43

Formula: C20H28O5

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][10]annulen-11-one

Smiles: CC1(C)[C@@H]2C[C@@H](C)[C@]34C=C(C)[C@H](O)[C@@]3(O)[C@H](O)C(CO)=C[C@@H]([C@H]12)C4=O

InChiKey: VEBVPUXQAPLADL-POYOOMFHSA-N

InChi: 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

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

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.

References:

1. 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.
2. 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.
3. 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.

Products are for research use only. Not for human use.