methyl 5-amino-4-oxopentanoate

• ChemBase编号: 866
• 分子式: C6H11NO3
• 平均质量: 145.15644
• 单一同位素质量: 145.07389322
• SMILES: O(C(=O)CCC(=O)CN)C
• Canonical SMILES: NCC(=O)CCC(=O)OC
• InChI: InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
• InChIKey: YUUAYBAIHCDHHD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl 5-amino-4-oxopentanoate
• IUPAC传统名: methyl aminolevulinate
• 商标名: Metvix
• 别名: 5-Aminolevulinic acid methyl ester; Aminolevulinic acid methyl ester; Methyl aminolevulinate

登记号

• CAS号: 33320-16-0
• PubChem SID: 46507004; 160964329
• PubChem CID: 157922

理论计算性质

JChem

• Acid pKa: 16.117233
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -3.1040556
• LogD (pH = 7.4): -1.416226
• Log P: -0.8470932
• 摩尔折射率: 35.2169 cm^3
• 极化性: 14.204587 Å^3
• 极化表面积: 69.39 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.3
• LOG S: 0.18
• 溶解度: 2.20e+02 g/l

分子性质

理化性质

• 溶解度: Freely soluble
• 疏水性(logP): -1.2

详细说明

DrugBank - DB00992

• Drug Groups: approved
• Description: Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.
• Indication: For topical use, in combination with 570 to 670 nm wavelength red light illumination, in the treatment of non-hyperkeratotic actinic keratoses of the face and scalp in immunocompetent patients when used in conjunction with lesion preparation (debridement using a sharp dermal curette).
• Pharmacology: After topical application of methyl aminolevulinate, porphyrins will accumulate intracellularly in the treated skin lesions. The intracellular porphyrins (including PpIX) are photoactive, fluorescing compounds and, upon light activation in the presence of oxygen, singlet oxygen is formed which causes damage to cellular compartments, in particular the mitochondria. Light activation of accumulated porphyrins leads to a photochemical reaction and thereby phototoxicity to the light-exposed target cells.
• Toxicity: The severity of local phototoxic reactions such as erythema, pain and burning sensation may increase in case of prolonged application time or very high light intensity.
• Affected Organisms: Humans and other mammals
• Absorption: In vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.
• References: [Link] ; Smits T, Moor AC: New aspects in photodynamic therapy of actinic keratoses. J Photochem Photobiol B. 2009 Sep 4;96(3):159-69. Epub 2009 Jun 13. [Pubmed]
• External Links: Wikipedia; Drugs.com

参考文献

• Link
• Smits T, Moor AC: New aspects in photodynamic therapy of actinic keratoses. J Photochem Photobiol B. 2009 Sep 4;96(3):159-69. Epub 2009 Jun 13. Pubmed