Ingenol
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Hodoodo CAT#: H555137

CAS#: 30220-46-3

Description: 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 Structure

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Ingenol
CAS# 30220-46-3
Instruction

Theoretical Analysis

Hodoodo Cat#: H555137
Name: Ingenol
CAS#: 30220-46-3
Chemical Formula: C20H28O5
Exact Mass: 348.19
Molecular Weight: 348.439
Elemental Analysis: C, 68.94; H, 8.10; O, 22.96

Price and Availability

Size Price Availability Quantity
25mg USD 250 2 Weeks
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
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Synonym: Ingenol,

IUPAC/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

InChi Key: VEBVPUXQAPLADL-POYOOMFHSA-N

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 348.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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: 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.

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.

4: 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.

5: 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.

6: Stockfleth E, Harwood C, Serra Guillén C, Larsson T, Østerdal ML, Skov T. Response to "Phase IV head-to-head randomised controlled trial comparing ingenol mebutate 0.015% gel with diclofenac sodium 3% gel for the treatment of actinic keratosis on the face or scalp" - reply from authors. Br J Dermatol. 2017 Dec 5. doi: 10.1111/bjd.16225. [Epub ahead of print] PubMed PMID: 29206275.

7: Malvehy J, Puig S. Response to "Phase IV head-to-head randomised controlled trial comparing ingenol mebutate 0.015% gel with diclofenac sodium 3% gel for the treatment of actinic keratosis on the face or scalp". Br J Dermatol. 2017 Dec 5. doi: 10.1111/bjd.16216. [Epub ahead of print] PubMed PMID: 29205276.

8: Lain E, Skov T, Hall A. Pharmacokinetics and Safety of Ingenol Disoxate Gel Administered Under Maximum-Use Conditions to Patients With Actinic Keratosis. Clin Drug Investig. 2017 Dec 4. doi: 10.1007/s40261-017-0608-y. [Epub ahead of print] PubMed PMID: 29204958.

9: Miyata S, Wang LY, Kitanaka S. 3EZ, 20Ac-ingenol induces cell-specific apoptosis in cyclin D1 over-expression through the activation of ATR and downregulation of p-Akt. Leuk Res. 2018 Jan;64:46-51. doi: 10.1016/j.leukres.2017.08.007. Epub 2017 Aug 24. PubMed PMID: 29179029.

10: Erlendsson AM. Exploring the use of ingenol mebutate to prevent non-melanoma skin cancer. Dan Med J. 2017 Nov;64(11). pii: B5368. PubMed PMID: 29115209.

11: Rallis E, Liakopoulou A, Christodoulopoulos C. Ingenol Mebutate for the Treatment of Intraepidermal Squamous Cell Carcinoma. J Clin Aesthet Dermatol. 2017 Jul;10(7):12-13. Epub 2017 Jul 1. PubMed PMID: 29104717; PubMed Central PMCID: PMC5605217.

12: Skroza N, Proietti I, Bernardini N, Balduzzi V, Mambrin A, Marchesiello A, Tolino E, Zuber S, La Torre G, Potenza C. Factors influencing response to ingenol mebutate therapy for actinic keratosis of face and scalp. World J Clin Oncol. 2017 Oct 10;8(5):405-411. doi: 10.5306/wjco.v8.i5.405. PubMed PMID: 29067277; PubMed Central PMCID: PMC5638716.

13: Stockfleth E, Harwood CA, Serra-Guillén C, Larsson T, Østerdal ML, Skov T. Phase IV head-to-head randomized controlled trial comparing ingenol mebutate 0•015% gel with diclofenac sodium 3% gel for the treatment of actinic keratosis on the face or scalp. Br J Dermatol. 2017 Oct 14. doi: 10.1111/bjd.16048. [Epub ahead of print] PubMed PMID: 29030864.

14: Larsen HK, Banzhaf CA, Thomsen SF, Gormsen M, Schopf RE, Haedersdal M. An exploratory, prospective, open-label trial of ingenol mebutate gel 0.05% for the treatment of external anogenital warts. J Eur Acad Dermatol Venereol. 2017 Oct 10. doi: 10.1111/jdv.14625. [Epub ahead of print] PubMed PMID: 29024025.

15: Wu DC, Guiha I, Goldman MP. A Prospective Pilot Clinical Trial to Evaluate the Efficacy and Safety of Topical Therapy with Ingenol Mebutate Gel 0.015% for Actinic Keratosis on an Expanded Area of the Chest. J Clin Aesthet Dermatol. 2017 Aug;10(8):31-36. Epub 2017 Aug 1. PubMed PMID: 28979661; PubMed Central PMCID: PMC5605212.

16: Ortega Del Olmo R, Salido-Vallejo R. Ingenol mebutate for the treatment of actinic keratosis: effectiveness and safety in 246 patients treated in real-life clinical practice. J Dermatolog Treat. 2017 Nov 8:1. doi: 10.1080/09546634.2017.1386272. [Epub ahead of print] PubMed PMID: 28956675.

17: Brambilla L, Tourlaki A, Nazzaro G. Erosive pustular dermatosis of the scalp induced by ingenol mebutate. G Ital Dermatol Venereol. 2017 Sep 8. doi: 10.23736/S0392-0488.17.05691-7. [Epub ahead of print] PubMed PMID: 28895376.

18: Handler MZ, Bloom BS, Goldberg DJ. Clinical and Histologic Evaluation of Ingenol Mebutate 0.015% Gel for the Cosmetic Improvement of Photoaged Skin. Dermatol Surg. 2017 Aug 30. doi: 10.1097/DSS.0000000000001269. [Epub ahead of print] PubMed PMID: 28858927.

19: Wang P, Lu P, Qu X, Shen Y, Zeng H, Zhu X, Zhu Y, Li X, Wu H, Xu J, Lu H, Ma Z, Zhu H. Reactivation of HIV-1 from Latency by an Ingenol Derivative from Euphorbia Kansui. Sci Rep. 2017 Aug 25;7(1):9451. doi: 10.1038/s41598-017-07157-0. PubMed PMID: 28842560; PubMed Central PMCID: PMC5573388.

20: Béres T, Dragull K, Pospíšil J, Tarkowská D, Dančák M, Bíba O, Tarkowski P, Doležal K, Strnad M. Quantitative Analysis of Ingenol in Euphorbia species via Validated Isotope Dilution Ultra-high Performance Liquid Chromatography Tandem Mass Spectrometry. Phytochem Anal. 2018 Jan;29(1):23-29. doi: 10.1002/pca.2711. Epub 2017 Aug 7. PubMed PMID: 28786149.