Ingenol disoxate | CAS#1383547-60-1

MedKoo Cat#: 206446 | Name: Ingenol disoxate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ingenol disoxate, also known as LEO43204, is a Novel 4-Isoxazolecarboxylate Ester of Ingenol with Improved Properties for Treatment of Actinic Keratosis and Other Non-Melanoma Skin Cancers. Ingenol is a natural product found in the sap of the plant Euphorbia peplus and an inducer of cell death.

Chemical Structure

Ingenol disoxate

CAS#1383547-60-1

Theoretical Analysis

MedKoo Cat#: 206446

Name: Ingenol disoxate

CAS#: 1383547-60-1

Chemical Formula: C28H37NO7

Exact Mass: 499.2570

Molecular Weight: 499.60

Elemental Analysis: C, 67.31; H, 7.47; N, 2.80; O, 22.42

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

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Synonym

Ingenol disoxate; LEO43204; LEO 43204; LEO-43204.

IUPAC/Chemical Name

(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 3,5-diethylisoxazole-4-carboxylate

InChi Key

GLIUZQUNUNICGS-XUBYYPQFSA-N

InChi Code

InChI=1S/C28H37NO7/c1-7-18-20(19(8-2)36-29-18)25(33)35-24-13(3)11-27-14(4)9-17-21(26(17,5)6)16(23(27)32)10-15(12-30)22(31)28(24,27)34/h10-11,14,16-17,21-22,24,30-31,34H,7-9,12H2,1-6H3/t14-,16+,17-,21+,22-,24+,27+,28+/m1/s1

SMILES Code

[H][C@]1(C[C@H]2C)C(C)([C@@]([C@@](C([C@]23C=C([C@@H]([C@@]43O)OC(C5=C(CC)ON=C5CC)=O)C)=O)(C=C([C@H]4O)CO)[H])1[H])C

Appearance

Solid powder

Purity

>98% (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, not in water

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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ingenol disoxate, also known as LEO43204, is a Novel 4-Isoxazolecarboxylate Ester of Ingenol with Improved Properties for Treatment of Actinic Keratosis and Other Non-Melanoma Skin Cancers.

In vitro activity:

Ingenol disoxate was profiled against selected PKC isoforms representing both subgroups in a biochemical radiometric activation assay. Ingenol disoxate and ingenol mebutate activated all tested PKC isoforms (βII, δ, η, ε) in the low nanomolar range with similar potency and relative efficacy (Table 3). Ingenol disoxate also activated PKCα (EC50 0.5 nM), PKCγ (EC50 0.9 nM) and PKCθ (EC50 11 nM) with high affinity. Reference: Dermatol Ther (Heidelb). 2016 Dec;6(4):599-626. https://pubmed.ncbi.nlm.nih.gov/27503482/

In vivo activity:

In comparison, vehicle-treated tumors grew rapidly and exceeded 250 mm3 in all animals within 10 days. Most notably, the antitumor efficacy of 0.1% ingenol disoxate was significantly superior compared to 0.1% ingenol mebutate (P < 0.0036) with 90% of animals remaining tumor free at 3 months which is to be compared with a median survival time of 16 days and 45% overall tumor free survival in the ingenol mebutate treatment group. Reference: Dermatol Ther (Heidelb). 2016 Dec;6(4):599-626. https://pubmed.ncbi.nlm.nih.gov/27503482/

Preparing Stock Solutions

The following data is based on the product molecular weight 499.60 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.

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:

1. Bertelsen M, Stahlhut M, Grue-Sørensen G, Liang X, Christensen GB, Skak K, Engell KM, Högberg T. Ingenol Disoxate: A Novel 4-Isoxazolecarboxylate Ester of Ingenol with Improved Properties for Treatment of Actinic Keratosis and Other Non-Melanoma Skin Cancers. Dermatol Ther (Heidelb). 2016 Dec;6(4):599-626. doi: 10.1007/s13555-016-0137-2. Epub 2016 Aug 8. PMID: 27503482; PMCID: PMC5120626.

In vitro protocol:

In vivo protocol:

1: Bertelsen M, Stahlhut M, Grue-Sørensen G, Liang X, Christensen GB, Skak K, Engell KM, Högberg T. Ingenol Disoxate: A Novel 4-Isoxazolecarboxylate Ester of Ingenol with Improved Properties for Treatment of Actinic Keratosis and Other Non-Melanoma Skin Cancers. Dermatol Ther (Heidelb). 2016 Dec;6(4):599-626. PubMed PMID: 27503482. 2: Sinnya S, Tan JM, Prow TW, Primiero C, McEniery E, Selmer J, Østerdal ML, Soyer HP. A randomized, phase IIa exploratory trial to assess the safety and preliminary efficacy of LEO 43204 in patients with actinic keratosis. Br J Dermatol. 2016 Feb;174(2):305-11. doi: 10.1111/bjd.14245. PubMed PMID: 26499175.