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Identification
NameMethyl aminolevulinate
Accession NumberDB00992  (APRD01105)
TypeSmall Molecule
GroupsApproved
Description

Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.

Structure
Thumb
Synonyms
5-Aminolevulinic acid methyl ester
Aminolevulinic acid methyl ester
Methyl aminolevulinate
Methyl delta-aminolevulinate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Metvixcream168 mgtopicalGalderma Canada Inc2009-06-16Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Methyl aminolevulinate hydrochloride
ThumbNot applicableDBSALT001462
Categories
UNII585NM85KYM
CAS number33320-16-0
WeightAverage: 145.1564
Monoisotopic: 145.073893223
Chemical FormulaC6H11NO3
InChI KeyInChIKey=YUUAYBAIHCDHHD-UHFFFAOYSA-N
InChI
InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
IUPAC Name
methyl 5-amino-4-oxopentanoate
SMILES
COC(=O)CCC(=O)CN
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDelta amino acids and derivatives
Alternative Parents
Substituents
  • Delta amino acid or derivatives
  • Gamma-keto acid
  • Fatty acid methyl ester
  • Fatty acid ester
  • Fatty acyl
  • Keto acid
  • Methyl ester
  • Alpha-aminoketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationFor 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).
PharmacodynamicsAfter 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 actionPhotosensitization 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.
Related Articles
AbsorptionIn vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThe 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9652
Blood Brain Barrier+0.9677
Caco-2 permeable-0.5715
P-glycoprotein substrateNon-substrate0.6238
P-glycoprotein inhibitor INon-inhibitor0.806
P-glycoprotein inhibitor IINon-inhibitor0.7456
Renal organic cation transporterNon-inhibitor0.7855
CYP450 2C9 substrateNon-substrate0.8561
CYP450 2D6 substrateNon-substrate0.7888
CYP450 3A4 substrateNon-substrate0.6617
CYP450 1A2 substrateNon-inhibitor0.5854
CYP450 2C9 inhibitorNon-inhibitor0.9022
CYP450 2D6 inhibitorNon-inhibitor0.9309
CYP450 2C19 inhibitorNon-inhibitor0.8932
CYP450 3A4 inhibitorNon-inhibitor0.8724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8936
Ames testNon AMES toxic0.8519
CarcinogenicityNon-carcinogens0.8042
BiodegradationReady biodegradable0.899
Rat acute toxicity1.7684 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8837
hERG inhibition (predictor II)Non-inhibitor0.8402
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Galderma laboratories lp
Packagers
Dosage forms
FormRouteStrength
Creamtopical168 mg
Prices
Unit descriptionCostUnit
Metvixia 16.8% cream82.2USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2215069 No2006-09-122016-03-08Canada
US6034267 No1996-03-082016-03-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityFreely solubleNot Available
logP-1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility220.0 mg/mLALOGPS
logP-1.3ALOGPS
logP-0.85ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)16.12ChemAxon
pKa (Strongest Basic)7.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.39 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.22 m3·mol-1ChemAxon
Polarizability14.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Smits T, Moor AC: New aspects in photodynamic therapy of actinic keratoses. J Photochem Photobiol B. 2009 Sep 4;96(3):159-69. doi: 10.1016/j.jphotobiol.2009.06.003. Epub 2009 Jun 13. [PubMed:19592269 ]
External Links
ATC CodesL01XD03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (597 KB)
MSDSNot Available
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antibody
General Function:
Receptor signaling protein activity
Specific Function:
High affinity receptor for the Fc region of immunoglobulins gamma. Functions in both innate and adaptive immune responses.
Gene Name:
FCGR1A
Uniprot ID:
P12314
Molecular Weight:
42631.525 Da
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:17139284 ]
  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:17016423 ]
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 01:51