Ingenol-3-mebutate
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| Category | Others |
| Catalog number | BBF-04003 |
| CAS | 75567-37-2 |
| Molecular Weight | 430.53 |
| Molecular Formula | C25H34O6 |
| Purity | >98% |
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Description
Ingenol-3-mebutate is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death. It is effective for field treatment of actinic keratoses, significantly reduced head and non-head actinic keratosis lesions.
Specification
| Synonyms | PEP005; PEP-005; PEP 005; ingenol-3-angelate; Ingenol mebutate |
| Storage | Store at -20°C |
| IUPAC Name | [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate |
| Canonical SMILES | CC=C(C)C(=O)OC1C(=CC23C1(C(C(=CC(C2=O)C4C(C4(C)C)CC3C)CO)O)O)C |
| InChI | 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 |
| InChI Key | VDJHFHXMUKFKET-UHFFFAOYSA-N |
Properties
| Appearance | White to beige Solid |
| Boiling Point | 576.9±50.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.IL-1 Contributes to the Anti-Cancer Efficacy of Ingenol Mebutate.
Le TT1, Skak K2, Schroder K3, Schroder WA1, Boyle GM1, Pierce CJ1, Suhrbier A1. PLoS One. 2016 Apr 21;11(4):e0153975. doi: 10.1371/journal.pone.0153975. eCollection 2016.
Ingenol mebutate is approved for the topical treatment of actinic keratoses and may ultimately also find utility in treating skin cancers. Here we show that relapse rates of subcutaneous B16 melanoma tumours treated topically with ingenol mebutate were not significantly different in C57BL/6 and Rag1-/- mice, suggesting B and T cells do not play a major role in the anti-cancer efficacy of ingenol mebutate. Relapse rates were, however, significantly increased in MyD88-/- mice and in C57BL/6 mice treated with the anti-IL-1 agent, anakinra. Ingenol mebutate treatment induces a pronounced infiltration of neutrophils, which have been shown to have anti-cancer activity in mice. Herein we provide evidence that IL-1 promotes neutrophil recruitment to the tumour, decreases apoptosis of infiltrating neutrophils and increases neutrophil tumour killing activity. These studies suggest IL-1, via its action on neutrophils, promotes the anti-cancer efficacy of ingenol mebutate, with ingenol mebutate treatment causing both IL-1β induction and IL-1α released from keratinocytes.
2.Ingenol mebutate in the treatment of 'Hydroxyurea-induced Squamous Dysplasia': a single centre experience.
Grandi V1, Delfino C1, Pimpinelli N1. J Eur Acad Dermatol Venereol. 2016 Apr 13. doi: 10.1111/jdv.13616. [Epub ahead of print]
BACKGROUND: 'Hydroxyurea-induced Squamous Dysplasia' (HISD) is a cutaneous side-effect related to chronic oral treatment with Hydroxyurea. Ingenol mebutate gel is a topical drug approved for the treatment of multiple, non-hypertrophic actinic keratoses (AK) localized within a limited cancerization field. Since HISD may be considered as a drug-induced variant of classic AK, ingenol mebutate is likely to have therapeutic effects.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
