D-아미노레불린산메틸에스테르염산염

Methyl Aminolevulinate

HCID 157922

기본 정보

CAS
33320-16-0
표준 SMILES
COC(=O)CCC(=O)CN
InChIKey
YUUAYBAIHCDHHD-UHFFFAOYSA-N
분자식
C6H11NO3
평균 분자량
145.16 g/mol
단동위원소 질량
145.07389321

개요

Methyl 5-aminolevulinate is 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. It has a role as an antineoplastic agent, a photosensitizing agent, a dermatologic drug and a prodrug. It is functionally related to a 5-aminolevulinic acid.

이름 및 식별자

우선 이름
Methyl Aminolevulinate
IUPAC
methyl 5-amino-4-oxopentanoate
현지명
D-아미노레불린산메틸에스테르염산염
영어명
D-Aminolevulinicacidmethylesterhydrochloride
분자식
C6H12ClNO3
분자량
181.61738

이름 및 동의어

Methyl aminolevulinatemethyl 5-amino-4-oxopentanoate33320-16-0methyl 5-aminolevulinate5-Aminolevulinic acid methyl estermethyl aminolaevulinatemethyl delta-aminolevulinateMAOP cpdMethylaminolevulinatePentanoic acid, 5-amino-4-oxo-, methyl ester585NM85KYMMethyl-5-aminolevulinate
이름 더 보기
D-아미노레불린산메틸에스테르염산염D-AminolevulinicacidmethylesterHCl
DTXSID3048570CHEBI:724125RefChem:157787DTXCID4028202MetvixAminolevulinic acid methyl esterNCGC00018251-03UNII-585NM85KYM

데이터베이스 식별자

CAS
33320-16-0
PubChem CID
157922
DTXSID
DTXSID3048570
ChEMBL
CHEMBL1096562
ChEBI
CHEBI:724125
UNII
585NM85KYM
Nikkaji
J313.797J

물성

구조 계산 물성

XLogP
-1
극성 표면적
69.4 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
10

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.2
Solubility · 2건

Freely soluble

2.20e+02 g/L

Physical DescriptionSolid

물리화학적 성질

LogP
-0.57 · -0.570 (est)

화학 및 산업

약리 정보

ATC Code · 3건

L01XD03

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Pharmacodynamics · 1건

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.

Mechanism of Action · 1건

Photosensitization following application of methyl aminolevulinate cream occurs through the metabolic conversion of methyl aminolevulinate (prodrug) to photoactive porphyrins (PAP), which accumulates in the skin lesions to which the cream has been applied. When exposed to light of appropriate wavelength and energy, the accumulated photoactive porphyrins produce a photodynamic reaction, resulting in a cytotoxic process dependent upon the simultaneous presence of oxygen. The absorption of light results in an excited state of porphyrin molecules, and subsequent spin transfer from photoactive porphyrins to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals.

FDA Pharmacological Classification · 5건

585NM85KYM

METHYL AMINOLEVULINATE

Established Pharmacologic Class [EPC] - Porphyrin Precursor

Chemical Structure [CS] - Porphyrinogens

Methyl aminolevulinate is a Porphyrin Precursor.

MeSH Pharmacological Classification · 1건

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.

Absorption, Distribution and ExcretionIn vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.

공급사11 곳

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
추가 설명 · 1건

정의ChEBI: 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 hydro hloride 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 t e tumour cells.

관련 반응

5건

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