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Methyl aminolevulinate

Methyl aminolevulinate structure

CAS No:
33320-16-0
Formula:
C6H11NO3
Chemical Name:
Methyl aminolevulinate
Synonyms:
Pentanoic acid,5-amino-4-oxo-,methyl ester;Levulinic acid,5-amino-,methyl ester;Aminolevulinic acid methyl ester;5-Aminolevulinic acid methyl ester;Methyl aminolevulinate;5-Amino-4-oxopentanoic acid methyl ester;Metvixia;Visonac
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

ChEBI: 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 membran

Solid

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 prodrug and a dermatologic drug. It derives from a 5-aminolevulinic acid.|Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.|Methyl aminolevulinate is a Porphyrin Precursor.

Methyl aminolevulinate Basic Attributes

Molecular Weight：

181.61738

Exact Mass：

145.16

UNII：

585NM85KYM

DSSTox ID：

DTXSID3048570

ATC Code：

L01XD03|L - Antineoplastic and immunomodulating agents

Characteristics

PSA：

69.39000

XLogP3：

0.16770

Appearance：

Solid

Density：

1.097g/cm3

Boiling Point：

223.9ºC at 760 mmHg

Flash Point：

95.5ºC

Refractive Index：

1.444

Water Solubility：

2.20e+02 g/L

Toxicity

Toxicity Summary：

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.

Drug Information

Drug 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).|FDA Label

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.

MeSH：

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. (See all compounds classified as Photosensitizing Agents.)

Absorption：

In vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.

Mechanism of Action：

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.

MeSH Entry Terms：

5-aminolevulinic acid methyl ester|MAOP cpd

Computed Properties

Molecular Weight:145.16
XLogP3:-1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:145.07389321
Monoisotopic Mass:145.07389321
Topological Polar Surface Area:69.4
Heavy Atom Count:10
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes