NameMethyl aminolevulinate
Accession NumberDB00992  (APRD01105)
TypeSmall Molecule

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

5-Aminolevulinic acid methyl ester
Aminolevulinic acid methyl ester
Methyl aminolevulinate
Methyl delta-aminolevulinate
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Methyl aminolevulinate hydrochloride7S73606O1A 79416-27-6UJYSYPVQHFNBML-UHFFFAOYSA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MetvixCream168 mgTopicalGalderma2009-06-16Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CAS number33320-16-0
WeightAverage: 145.1564
Monoisotopic: 145.073893223
Chemical FormulaC6H11NO3
methyl 5-amino-4-oxopentanoate

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).

Structured Indications

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.

TargetKindPharmacological actionActionsOrganismUniProt ID
High affinity immunoglobulin gamma Fc receptor IProteinunknown
HumanP12314 details
Related Articles

In 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

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
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Methyl aminolevulinate.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Methyl aminolevulinate.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Methyl aminolevulinate.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Methyl aminolevulinate.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Methyl aminolevulinate.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Methyl aminolevulinate.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Methyl aminolevulinate.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Methyl aminolevulinate.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Methyl aminolevulinate.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Methyl aminolevulinate.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Methyl aminolevulinate.Approved, Vet Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Methyl aminolevulinate.Approved, Investigational
Food InteractionsNot Available
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 — Methyl aminolevulinate
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (597 KB)
MSDSNot Available
Clinical Trials
Clinical Trials
1CompletedTreatmentBasal Cell Carcinoma of the Skin / Pain / Recurrent Skin Cancer1
1, 2CompletedTreatmentActinic Keratosis (AK)1
1, 2CompletedTreatmentCervical Dysplasia1
1, 2RecruitingTreatmentBasal Cell Carcinoma (BCC) / Neoplasms, Basal Cell / Photochemotherapy / Photosensitizing Agents1
2CompletedTreatmentFacial Photodamage1
3Active Not RecruitingTreatmentBasal Cell Carcinoma (BCC)1
3CompletedTreatmentActinic Keratosis (AK)3
3CompletedTreatmentSkin Aging1
3RecruitingTreatmentActinic Keratosis (AK)1
4Active Not RecruitingTreatmentActinic Keratosis (AK) / Natural Daylight Photodynamic Therapy1
4CompletedTreatmentActinic Keratoses (gr I-III) / Multiple Actinic Keratoses1
Not AvailableNo Longer AvailableNot AvailableBasal Cell Carcinoma (BCC) / Field Actinic Keratoses / Squamous Cell Carcinoma (SCC)1
Not AvailableRecruitingTreatmentActinic Keratosis (AK)1
Not AvailableRecruitingTreatmentSquamous Cell Carcinoma (SCC) / Superficial Basal Cell Carcinoma1
  • Galderma laboratories lp
Dosage forms
CreamTopical168 mg
Unit descriptionCostUnit
Metvixia 16.8% cream82.2USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2215069 No2006-09-122016-03-08Canada
US6034267 No1996-03-082016-03-08Us
Experimental Properties
water solubilityFreely solubleNot Available
logP-1.2Not Available
Predicted Properties
Water Solubility220.0 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
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
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 )
Mass Spec (NIST)Not Available
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
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 ParentsGamma-keto acids and derivatives / Fatty acid methyl esters / Methyl esters / Alpha-amino ketones / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
SubstituentsDelta amino acid or derivatives / Gamma-keto acid / Fatty acid ester / Fatty acid methyl ester / Keto acid / Fatty acyl / Alpha-aminoketone / Methyl ester / Carboxylic acid ester / Ketone
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsdelta-amino acid ester (CHEBI:724125 )


Pharmacological action
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:
Uniprot ID:
Uniprot Name:
High affinity immunoglobulin gamma Fc receptor I
Molecular Weight:
42631.525 Da
  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 ]
Drug created on June 13, 2005 07:24 / Updated on July 27, 2017 16:01