Ingenol ((-)-Ingenol)
(Synonyms: 巨大戟醇; (-)-Ingenol) 目录号 : GC32870
A PKC activator
Cas No.:30220-46-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus.1 It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro.2,3 Most ingenol esters are tumor-promoting.4 However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.5
1.Wender, P.A., Koehler, K.F., Sharkey, N.A., et al.Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogsProc. Natl. Acad. Sci. USA83(12)4214-4218(1986) 2.Hasler, C.M., Acs, G., and Blumberg, P.M.Specific binding to protein kinase C by ingenol and its induction of biological responsesCancer Res.52(1)202-208(1992) 3.Vogg, G., Mattes, E., Rothenburger, J., et al.Tumor promoting diterpenes from Euphorbia leuconeura LPhytochemistry51(2)289-295(1999) 4.Nelson, T.J., and Alkon, D.L.Neuroprotective versus tumorigenic protein kinase C activatorsTrends Biochem. Sci.34(3)136-145(2009) 5.Lebwohl, M., Swanson, N., Anderson, L.L., et al.Ingenol mebutate gel for actinic keratosisN. Engl. J. Med.366(11)1010-1019(2012)
| Cas No. | 30220-46-3 | SDF | |
| 别名 | 巨大戟醇; (-)-Ingenol | ||
| Canonical SMILES | O[C@@]([C@@H](C(CO)=C[C@@]1([H])[C@H](C2(C)C)[C@H]2C3)O)([C@H]4O)[C@]([C@@H]3C)(C=C4C)C1=O | ||
| 分子式 | C20H28O5 | 分子量 | 348.43 |
| 溶解度 | DMSO : 100 mg/mL (287.00 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.87 mL | 14.3501 mL | 28.7002 mL |
| 5 mM | 0.574 mL | 2.87 mL | 5.74 mL |
| 10 mM | 0.287 mL | 1.435 mL | 2.87 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Ingenol Mebutate: Expanded Utility
J Drugs Dermatol 2020;19(2):156-161.PMID:32129959DOI:10.36849/JDD.2020.4731.
Ingenol mebutate (IM) is a novel drug that was developed for the treatment of actinic keratosis (AK). The drug works by a dual mechanism of action -- a rapid induction of cell death by necrosis along with a delayed neutrophil-mediated cellular cytotoxicity response.¹ Currently, IM is available as a 0.015% or 0.05% topical gel and has only been FDA-approved for the treatment of actinic keratosis. However, IM has also been extensively used off-label, and found to be efficacious in the treatment of multiple other skin disorders. In this review, we discuss the current literature that provides evidence for the successful use of Ingenol mebutate as treatment for dermatologic disorders beyond actinic keratosis. J Drugs Dermatol. 2020;19(2)156-161. doi:10.36849/JDD.2020.4731
Ingenol Mebutate and the Treatment of Actinic Keratosis
J Drugs Dermatol 2021 Jan 1;20(1):102-104.PMID:33400406DOI:10.36849/JDD.5328.
Actinic keratoses (AKs) are common skin lesions association with increased exposure to ultraviolet radiation; these lesions have the potential to transform into squamous cell carcinomas (SCCs).1.
Ingenol mebutate gel 0.015% and 0.05%: in actinic keratosis
Drugs 2012 Dec 24;72(18):2397-405.PMID:23231025DOI:10.2165/11470090-000000000-00000.
Ingenol mebutate is the main active constituent of sap from the plant Euphorbia peplus, which has traditionally been used as a home remedy for various skin conditions. Ingenol mebutate gel is approved in the US, EU, Australia and Brazil for the topical treatment of actinic keratosis. A short course of field-directed therapy with topical Ingenol mebutate gel was effective in the treatment of actinic keratoses on the face or scalp (Ingenol mebutate gel 0.015% once daily for 3 consecutive days) and on the trunk or extremities (Ingenol mebutate gel 0.05% once daily for 2 consecutive days), according to the results of four randomized, double-blind, vehicle-controlled, multicentre studies. Significantly higher complete clearance rates (primary endpoint) and partial clearance rates were seen at day 57 in patients receiving Ingenol mebutate gel than in those receiving vehicle gel. Treatment with Ingenol mebutate gel was generally associated with sustained clearance of actinic keratoses in the longer term. Topical Ingenol mebutate gel was generally well tolerated in the treatment of patients with actinic keratoses on the face or scalp and on the trunk or extremities. Application-site conditions were the most commonly occurring adverse events.
Ingenol mebutate: a promising treatment for actinic keratoses and nonmelanoma skin cancers
J Cutan Med Surg 2013 May-Jun;17(3):173-9.PMID:23673300DOI:10.2310/7750.2012.12050.
Background: A new treatment for actinic keratoses, Ingenol mebutate, was recently approved by the US Food and Drug Administration. Objective: To review the mechanisms of action, efficacy and safety data, and practical recommendations for Ingenol mebutate. Methods: The PubMed and clinicaltrials.gov databases were searched in March/April 2012 using the terms PEP005, Ingenol mebutate, and Ingenol 3-angelate. The abstracts from the Annual Scientific Meeting of the Australian College of Dermatologists (2009-2011) and the Annual Meeting of the American Academy of Dermatology (2009-2012) were also searched. Results: Due to its multiple mechanisms of action, Ingenol mebutate treatment resulted in short- and long-term efficacy similar to other topical treatments for actinic keratoses in a shorter period of 2 or 3 days. This short therapy would reduce the duration of adverse events. Premarketing trials for treatment of nonmelanoma skin cancers also showed promising results for Ingenol mebutate. Conclusion: Ingenol mebutate is a convenient, safe, and effective intervention for precancerous and cancerous skin conditions.
Topical Ingenol Mebutate: A New Treatment Modality for Multiple Actinic Keratoses and Field Cancerization
Anticancer Agents Med Chem 2017;17(10):1304-1311.PMID:28270072DOI:10.2174/1871520617666170213130523.
Background: Ingenol mebutate gel is a recent stirring weapon recommended for the treatment of multiple actinic keratoses (AKs) and field cancerization. This review brings a summary of recent data on the treatment of AKs with Ingenol mebutate (IM) providing critical commentary with regard to drug's characteristics, drug's safety profile, treatment regimen, treatment outcome, patient compliance, AK recurrence, costeffectiveness and cost-utility, as well as guidelines for the management of the treatment of AK. Method: We undertook a structured search of bibliographic databases for peer-reviewed scientific articles, including review articles, original research articles as well as case report articles based on inclusion/exclusion criteria. Reports on Ingenol mebutate from U.S. Food and Drug Administration and European Medical Agency were also included. Results: Sixty-six papers were included in this review. We report current data on Ingenol mebutate chemical properties, pharmacology, efficacy, safety, and tolerability, potential new indications in dermatology, costeffectiveness, and cost-utility analysis. Conclusion: Treatment of AKs is necessary in order to prevent possible transition to invasive SCC. Although the mechanism of action of Ingenol mebutate is not fully elucidated, dual mechanism of action is presumed. Ingenol mebutate is an effective and cost-saving topical agent for the treatment of AK, especially multiple AKs and field cancerization, with acceptable safety profile. It may also have perspective in dermatology regarding the treatment of superficial BCC, Bowen disease, actinic cheilitis, and anogenital warts that has to be evaluated in clinical trials. Patients' adherence to recommended treatment regimen and auspicious safety profile make this drug attractive.