Ingenol Mebutate


Catalog No. size PriceQuantity
M6794-2 2mg solid $120
M6794-10 10mg solid $488

Description

Cas:75567-37-2

Product Information

Ingenol mebutate, also known as ingenol-3-angelate, is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death. Ingenol Mebutate was approved for the topical treatment of actinic keratosis. Ingenol mebutate has also been found to be useful for reactivating latent HIV virus in cells taken from individuals who have tested negative for signs of the disease following extended courses of anti-retroviral drugs, raising the possibility that this drug may be used to expose the last traces of virus, and thus potentially provide a permanent cure for HIV infection.

 

Chemical Formula: C25H34O6

 

Exact Mass: 430.23554

 

Molecular Weight: 430.53

 

Elemental Analysis:C, 69.74; H, 7.96; O, 22.30

 

Synonym: 

 

PEP005

PEP-005

PEP 005

ingenol-3-angelate

Ingenol mebutate

trade name Picato

 

Chemical Name:

(Z)-(1aS,5R,5aS,6S,9R)-5,5a-dihydroxy-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-6-yl 2-methylbut-2-enoate

 

InChi Key:

VDJHFHXMUKFKET-RGSPJFHZSA-N

 

InChi Code:

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

 

Smiles Code:

C/C=C(C)\C(O[C@H]1C(C)=CC23[C@]1(O)[C@H](O)C(CO)=CC(C3=O)[C@]4([H])C(C4(C)C)C[C@H]2C)=O

 

Technical Data:

 

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 soluble in water.

Shelf Life: >5 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

 

In Vitro:

Ingenol Mebutate (Ingenol 3-angelate) is an active ingredient in Euphorbia peplus, acting as a potent PKC activator, with Kis of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively. Ingenol Mebutate also EC50s of 13 ± 2.4 nM (PKC-α), 4.37 ± 0.4 nM (PKC-βI), 10.5 ± 2.2 nM (PKC-βII), 38.6 ± 2.9 nM (PKC-δ), 1.08 ± 0.01 nM (PKC-ε), 0.9 ± 0.13 nM (PKC-μ) in WEHI-231 cells, 198 ± 12.5 nM (PKC-α), 69.1 ± 8.2 nM (PKC-βI), 4.6 ± 0.4 nM (PKC-ε) and 1 nM (PKC-μ) in HOP-92 cells, 635 ± 245 nM (PKC-α), 146 ± 35 nM (PKC-βI), 4.7 ± 0.7 nM (PKC-δ), 1.1 ± 0.5 nM (PKC-ε), and 30 nM (PKC-μ) in Colo-205 cells. Ingenol Mebutate sensitizes WEHI-231 cells, HOP-92 and Colo-205 cells, with IC50s of 1.41 ± 0.255 nM, 3.24 ± 2.01 nM, and 11.9 ± 1.307 nM, respectively. Ingenol Mebutate (PEP005; 20 nM) actions are PKC-δ dependent, induces apoptosis in primary AML marrow blasts but not in normal myeloblasts. Ingenol Mebutate (PEP005) activates PKCδ and inhibits PKCα. Colo205-R cells (IC50: >10 μM) are >300-fold more resistant to Ingenol Mebutate than parental Colo205-S cells.

 

 

References

 

  1. Bobyr I, Campanati A, Consales V, Giangiacomi M, Diotallevi F, Offidani A. Granuloma faciale successfully treated with ingenol mebutate. Dermatol Ther. 2016 Jun 30. doi: 10.1111/dth.12368. [Epub ahead of print] PubMed PMID: 27364361.

 

  1. Bettencourt MS. Tolerability of Ingenol Mebutate Gel, 0.05%, for Treating Patients with Actinic Keratosis on the Scalp in a Community Dermatology Practice. J Clin Aesthet Dermatol. 2016 Mar;9(3):20-4. Epub 2016 Mar 1. PubMed PMID: 27354884; PubMed Central PMCID: PMC4896817.

 

  1. Bobyr I, Campanati A, Consales V, Giuliodori K, Scalise A, Offidani A. Efficacy, safety and tolerability of field treatment of actinic keratosis with ingenol mebutate 0.015 % gel: a single center case series. Springerplus. 2016 May 14;5:627. doi: 10.1186/s40064-016-2290-6. eCollection 2016. PubMed PMID: 27330893; PubMed Central PMCID: PMC4870479.

 

  1. Monfrecola G, Scalvenzi M, Costa C, Cantelli M, Fabbrocini G. Ingenol mebutate for pigmented superficial basal cell carcinomas: evaluation by confocal microscopy. G Ital Dermatol Venereol. 2016 Jun 10. [Epub ahead of print] PubMed PMID: 27284778.

 

  1. Flórez Á, Batalla A, de la Torre C. Management of actinic cheilitis using ingenol mebutate gel: A report of seven cases. J Dermatolog Treat. 2016 May 31:1-3. [Epub ahead of print] PubMed PMID: 27241280.

 

  1. Braun SA, Gerber PA. Successful treatment of perianal condylomata acuminata with ingenol mebutate gel. J Dtsch Dermatol Ges. 2016 Jun;14(6):616-7. doi: 10.1111/ddg.12879. Epub 2016 May 17. PubMed PMID: 27187666.

 

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

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