CAS 33320-16-0|5-Aminolevulinic acid methyl ester|Metvix|methyl 5-amino-4-oxopentanoate|Aminolevulinic acid methyl ester|Methyl aminolevulinate|methyl aminolevulinate|5-aminolevulinic acid methyl es...

基本信息

化学结构

分子式

C₆H₁₁NO₃

分子量

145.15644

精确质量

145.07389322

电荷

InChI

InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3

InChIKey

YUUAYBAIHCDHHD-UHFFFAOYSA-N

Canonic Smiles

NCC(=O)CCC(=O)OC

Isomeric Smiles

O(C(=O)CCC(=O)CN)C

计算属性

JChem

LogD (pH = 7.4)

-1.42

LogD (pH = 5.5)

-3.10

Log P

-0.85

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

7.83

极化表面积

69.39

极化性

14.68

摩尔折射率

35.22

LOG S

0.34

数据来源

学术数据

数据来源

名称和标识

商标名

Metvix

别名

5-Aminolevulinic acid methyl esterAminolevulinic acid methyl esterMethyl aminolevulinate5-aminolevulinic acid methyl estermethyl 5-aminolevulinateaminolevulinic acid methyl esterMethyl aminolevulinatemethyl delta-aminolevulinate

IUPAC标准名

methyl 5-amino-4-oxopentanoate

IUPAC传统名

methyl aminolevulinate

名称和标识

数据登录号

CAS号

33320-16-0

PubChem SID

4650700416096432999333768

PubChem CID

DrugBank ID

CHEBI ID

MetaboLights数据库

PubMed文献链接

232126242119752422785615212548522304601422971196225829112197871122949035

CompTox数据库

DTXSID3048570

Drug Central Database

BKMS React数据库

BRENDA Ligand数据库

CHEMBL

KEGG DRUG Database

SureChEMBL数据库

ACToR数据库

维基百科标题

Methyl_Aminolevulinate

BRENDA数据库

2.3.1.37

Reaxys Registry

5921212

数据登录号

化合物性质

理化性质

溶解度

Freely soluble

疏水性(logP)

-1.2

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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]

ChEBI

CHEBI:724125

The methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydrochloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills the tumour cells.

描述信息

参考文献

PubChem文献

数据源提供

• 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

• Link

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

数据来源

• 学术数据