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Identification
Name Methyl aminolevulinate
Accession Number DB00992 (APRD01105)
Type small molecule
Groups approved
Description

Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 5-Aminolevulinic acid methyl ester
  • Aminolevulinic acid methyl ester
Brand names
  • Metvix
Brand name mixtures Not Available
Categories
  • Antineoplastic Agents
CAS number 33320-16-0
Weight Average: 145.1564
Monoisotopic: 145.073893223
Chemical Formula C6H11NO3
InChI Key InChIKey=YUUAYBAIHCDHHD-UHFFFAOYSA-N
InChI
InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
Plain Text
IUPAC Name
methyl 5-amino-4-oxopentanoate
SMILES
COC(=O)CCC(=O)CN
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
  • Carboxylic Acids and Derivatives
  • Keto-Acids
Substructures
  • Amino Acids
  • Carboxylic Acids and Derivatives
  • Acetates
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Ethers
  • Keto-Acids
  • Ketones
Pharmacology
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).
Pharmacodynamics 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 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.
Absorption In vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Galderma laboratories lp
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Metvixia 16.8% cream 82.2 USD g
Patents
Country Patent Number Approved Expires
United States 6034267 1996-03-08 2016-03-08
Canada 2215069 2006-09-12 2016-03-08
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Freely soluble PhysProp
logP -1.2 PhysProp
Predicted Properties
Property Value Source
water solubility 2.20e+02 g/l ALOGPS
logP -1.30 ALOGPS
logP -0.85 ChemAxon Molconvert
logS 0.18 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 69.39 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 35.22 ChemAxon Molconvert
polarizability 14.55 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Link
  2. 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
Resource Link
PubChem Compound 157922 Link_out
PubChem Substance 46507004 Link_out
ChemSpider 138950 Link_out
ChEBI 724125 Link_out
ChEMBL 724125 Link_out
Therapeutic Targets Database DAP001024 Link_out
Drug Product Database 0 Link_out
Drugs.com http://www.drugs.com/mtm/methyl-aminolevulinate-topical.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Methyl_aminolevulinate Link_out
ATC Codes
  • L01XD03
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (597 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. High affinity immunoglobulin gamma Fc receptor I

Pharmacological action: unknown
Actions: antibody

Binds to the Fc region of immunoglobulins gamma. High affinity receptor

Organism class: human
UniProt ID: P12314 Link_out
Gene: FCGR1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on August 04, 2011 23:12

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.