Methyl aminolevulinate is a porphyrin precursor used to treat non-hyperkeratotic, non-pigmented actinic keratosis of the face and scalp.
- Brand Names
- Metvix, Metvixia
- Generic Name
- Methyl aminolevulinate
- DrugBank Accession Number
Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.
- Small Molecule
- Approved, Investigational
- Average: 145.1564
- Chemical Formula
- 5-aminolevulinic acid methyl ester
- Aminolevulinato de metilo
- Aminolevulinic acid methyl ester
- methyl 5-aminolevulinate
- Methyl aminolevulinate
- Methyl delta-aminolevulinate
- methyl δ-aminolevulinate
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).Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.
- Associated Conditions
- Contraindications & Blackbox Warnings
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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.
In vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.
- Volume of distribution
- Protein binding
- Not Available
- Route of elimination
- Adverse Effects
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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.
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Padeliporfin Methyl aminolevulinate may increase the photosensitizing activities of Padeliporfin. Tretinoin The risk or severity of adverse effects can be increased when Tretinoin is combined with Methyl aminolevulinate.Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more
- Food Interactions
- No interactions found.
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Methyl aminolevulinate hydrochloride 7S73606O1A 79416-27-6 UJYSYPVQHFNBML-UHFFFAOYSA-N
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Metvix Cream 168 mg / g Topical Galderma 2009-06-16 Not applicable Metvixia Cream 168 mg/1g Topical Penn Pharmaceutical Services Ltd. 2007-10-02 Not applicable Metvixia Cream 168 mg/1g Topical Galderma 2004-07-27 2012-11-29
- ATC Codes
- L01XD03 — Methyl aminolevulinate
- Drug Categories
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Keto Acids
- Levulinic Acids
- Misc. Skin and Mucous Membrane Agents
- Photosensitizing Agents
- Photosensitizing Agents for Phototherapy
- Porphyrin Precursor
- Radiation-Sensitizing Agents
- Sensitizers Used in Photodynamic/radiation Therapy
- Chemical TaxonomyProvided by Classyfire
- This 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.
- Organic compounds
- Super Class
- Organic acids and derivatives
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Delta amino acids and derivatives
- Alternative Parents
- Gamma-keto acids and derivatives / Fatty acid methyl esters / Methyl esters / Alpha-amino ketones / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
- Aliphatic acyclic compound / Alpha-aminoketone / Amine / Carbonyl group / Carboxylic acid ester / Delta amino acid or derivatives / Fatty acid ester / Fatty acid methyl ester / Fatty acyl / Gamma-keto acid
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- delta-amino acid ester (CHEBI:724125)
- Affected organisms
- Humans and other mammals
- CAS number
- InChI Key
- IUPAC Name
- methyl 5-amino-4-oxopentanoate
- General References
- 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. [Article]
- FDA label
- Download (597 KB)
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Other Actinic Keratosis (AK) 1 4 Completed Treatment Actinic Keratosis (AK) / Natural Daylight Photodynamic Therapy 1 4 Completed Treatment Multiple Actinic Keratoses 1 4 Recruiting Treatment Cutaneous Squamous Cell Carcinoma in Situ (CSCCis) 1 4 Unknown Status Treatment Superficial Basal Cell Carcinoma 1 3 Completed Treatment Actinic Keratosis (AK) 6 3 Completed Treatment Basal Cell Carcinoma (BCC) 2 3 Completed Treatment Skin Aging 1 2 Completed Treatment Acne Vulgaris 2 2 Completed Treatment Facial Photodamage 1
- Galderma laboratories lp
- Galderma Laboratories
- Penn Pharmaceutical Services Ltd.
- Dosage Forms
Form Route Strength Cream Topical Cream Cutaneous 160 MG/G Cream Topical 168 mg / g Cream Topical 16 % w/w Cream Topical 16 g Cream Topical 168 mg/1g Cream Cutaneous 160.000 mg
Unit description Cost Unit Metvixia 16.8% cream 82.2USD gDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2215069 No 2006-09-12 2016-03-08 US6034267 No 2000-03-07 2016-03-08
- Experimental Properties
Property Value Source water solubility Freely soluble Not Available logP -1.2 Not Available
- Predicted Properties
Property Value Source Water Solubility 220.0 mg/mL ALOGPS logP -1.3 ALOGPS logP -0.85 Chemaxon logS 0.18 ALOGPS pKa (Strongest Acidic) 17.16 Chemaxon pKa (Strongest Basic) 7.83 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 69.39 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 35.22 m3·mol-1 Chemaxon Polarizability 14.55 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon
- Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9652 Blood Brain Barrier + 0.9677 Caco-2 permeable - 0.5715 P-glycoprotein substrate Non-substrate 0.6238 P-glycoprotein inhibitor I Non-inhibitor 0.806 P-glycoprotein inhibitor II Non-inhibitor 0.7456 Renal organic cation transporter Non-inhibitor 0.7855 CYP450 2C9 substrate Non-substrate 0.8561 CYP450 2D6 substrate Non-substrate 0.7888 CYP450 3A4 substrate Non-substrate 0.6617 CYP450 1A2 substrate Non-inhibitor 0.5854 CYP450 2C9 inhibitor Non-inhibitor 0.9022 CYP450 2D6 inhibitor Non-inhibitor 0.9309 CYP450 2C19 inhibitor Non-inhibitor 0.8932 CYP450 3A4 inhibitor Non-inhibitor 0.8724 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8936 Ames test Non AMES toxic 0.8519 Carcinogenicity Non-carcinogens 0.8042 Biodegradation Ready biodegradable 0.899 Rat acute toxicity 1.7684 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8837 hERG inhibition (predictor II) Non-inhibitor 0.8402
- Mass Spec (NIST)
- Not Available
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at June 13, 2005 13:24 / Updated at September 25, 2023 18:32