Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H11NO3 |
| Molecular Weight | 145.1564 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)CCC(=O)CN
InChI
InChIKey=YUUAYBAIHCDHHD-UHFFFAOYSA-N
InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
| Molecular Formula | C6H11NO3 |
| Molecular Weight | 145.1564 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00992Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021415s004lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00992
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021415s004lbl.pdf
Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy. 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. Methyl aminolevulinate is used 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).
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map00860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25048871 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | METVIXIA Approved UseMETVIXIA Cream in combination with Aktilite CL128 lamp red light illumination is indicated for treatment of thin and moderately thick, non-hyperkeratotic, non-pigmented actinic keratoses of the face and scalp in immunocompetent patients. This photodynamic therapy should be used in conjunction with appropriate lesion preparation in the physician’s office when other therapies are considered medically less appropriate. Launch Date2004 |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 g single, topical Dose: 1 g Route: topical Route: single Dose: 1 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Disc. AE: Pain localised... AEs leading to discontinuation/dose reduction: Pain localised (1%) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Pain localised | 1% Disc. AE |
1 g single, topical Dose: 1 g Route: topical Route: single Dose: 1 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Photodynamic therapy for cutaneous verrucous carcinoma. | 2007-09 |
|
| Topical methyl aminolevulinate photodynamic therapy for the treatment of folliculitis. | 2007-08 |
|
| Identification of tetrapyrrole compounds excreted by Rhodobacter sphaeroides and sources of the methyl hydrogens of bacteriochlorophyll a biosynthesized by R. sphaeroides, based on 13C-NMR spectral analysis of coproporphyrin III tetramethyl ester. | 2007-07 |
|
| The efficacy of photodynamic therapy in actinic cheilitis of the lower lip: a prospective study of 15 patients. | 2007-07 |
|
| Randomized, double-blind, prospective study to compare topical 5-aminolaevulinic acid methylester with topical 5-aminolaevulinic acid photodynamic therapy for extensive scalp actinic keratosis. | 2007-07 |
|
| Photodetection of basal cell carcinoma using methyl 5-aminolaevulinate-induced protoporphyrin IX based on fluorescence image analysis. | 2007-07 |
|
| Direct comparison of delta-aminolevulinic acid and methyl-aminolevulinate-derived protoporphyrin IX accumulations potentiated by desferrioxamine or the novel hydroxypyridinone iron chelator CP94 in cultured human cells. | 2007-06-20 |
|
| Fluorescence diagnosis of face-located basal cell carcinomas: a new dermatological procedure which may help the surgeon. | 2007-05-23 |
|
| Methyl aminolaevulinate-photodynamic therapy: a review of clinical trials in the treatment of actinic keratoses and nonmelanoma skin cancer. | 2007-05 |
|
| Photodynamic therapy: update 2006. Part 2: Clinical results. | 2007-04 |
|
| Clinical and echographic analysis of photodynamic therapy using methylaminolevulinate as sensitizer in the treatment of photodamaged facial skin. | 2007-03 |
|
| Photodynamic treatment of cutaneous leishmaniasis. | 2007-02 |
|
| Allergic contact dermatitis to methyl aminolevulinate (Metvix) cream used in photodynamic therapy. | 2007-02 |
|
| Phototoxic reaction and porphyrin fluorescence in skin after topical application of methyl aminolaevulinate. | 2007-02 |
|
| A comparative study of intense pulsed light alone and its combination with photodynamic therapy for the treatment of facial acne in Asian skin. | 2007-01 |
|
| Guidelines on the use of photodynamic therapy for nonmelanoma skin cancer: an international consensus. International Society for Photodynamic Therapy in Dermatology, 2005. | 2007-01 |
|
| Chemopreventative thoughts for photodynamic therapy. | 2007-01 |
|
| Methyl aminolevulinate-photodynamic therapy for basal cell carcinoma. | 2007-01 |
|
| Methyl aminolevulinate: actinic keratoses and Bowen's disease. | 2007-01 |
|
| Photodynamic therapy for actinic keratoses. | 2007-01 |
|
| Successful treatment of necrobiosis lipoidica diabeticorum with photodynamic therapy. | 2006-12 |
|
| Intraindividual, right-left comparison of topical methyl aminolaevulinate-photodynamic therapy and cryotherapy in subjects with actinic keratoses: a multicentre, randomized controlled study. | 2006-11 |
|
| Photodynamic therapy using a methyl ester of 5-aminolevulinic acid in recurrent Paget's disease of the vulva: a pilot study. | 2006-11 |
|
| Gateways to clinical trials. | 2006-10 |
|
| Topical application of 5-aminolaevulinic acid, methyl 5-aminolaevulinate and hexyl 5-aminolaevulinate on normal human skin. | 2006-10 |
|
| Economic evaluation of methyl aminolaevulinate-based photodynamic therapy in the management of actinic keratosis and basal cell carcinoma. | 2006-10 |
|
| A study comparing endogenous protoporphyrin IX induced by 5-ALA and ALA-methyl ester with exogenous PpIX and PpIX dimethyl ester in photodynamic diagnosis of human nasopharyngeal carcinoma xenografts. | 2006-10 |
|
| Photodynamic therapy with methylaminolevulinate as a valuable treatment option for unilesional cutaneous T-cell lymphoma. | 2006-10 |
|
| Nonablative skin resurfacing: the role of PDT. | 2006-09 |
|
| Topical methyl aminolaevulinate photodynamic therapy for treatment of facial acne vulgaris: results of a randomized, controlled study. | 2006-09 |
|
| Topical photodynamic therapy: an introduction for nurses. | 2006-08-29 |
|
| The effect of folic acid on porphyrin synthesis in tumors and normal skin of mice treated with 5-aminolevulinic acid or methyl 5-aminolevulinate. | 2006-08 |
|
| Gateways to clinical trials. | 2006-06 |
|
| Topical photodynamic therapy with methyl aminolevulinate to treat sebaceous hyperplasia in an organ transplant recipient. | 2006-06 |
|
| The effect of skin permeation enhancers on the formation of porphyrins in mouse skin during topical application of the methyl ester of 5-aminolevulinic acid. | 2006-05-01 |
|
| Gateways to clinical trials. | 2006-05 |
|
| [Dynamic phototherapy in dermatology: current uses and future perspectives]. | 2006-05 |
|
| Photodynamic therapy of acne vulgaris using methyl aminolaevulinate: a blinded, randomized, controlled trial. | 2006-05 |
|
| Photodynamic therapy induces less pain in patients treated with methyl aminolevulinate compared to aminolevulinic acid. | 2006-04 |
|
| Photodynamic therapy of acne vulgaris using 5-aminolevulinic acid versus methyl aminolevulinate. | 2006-04 |
|
| Multiple large surface photodynamic therapy sessions with topical methylaminolaevulinate in PTCH heterozygous mice. | 2006-04 |
|
| 5-Aminolevulinic acid derivatives in photomedicine: Characteristics, application and perspectives. | 2006-03-18 |
|
| Gateways to clinical trials. | 2006-03-17 |
|
| A case of focal dermal hypoplasia (Goltz) syndrome with exophytic granulation tissue treated by curettage and photodynamic therapy. | 2006-03 |
|
| Photodynamic therapy and imiquimod immunotherapy for basal cell carcinomas. | 2006-01-10 |
|
| The temperature dependence of porphyrin production in Propionibacterium acnes after incubation with 5-aminolevulinic acid (ALA) and its methyl ester (m-ALA). | 2006-01 |
|
| Morphine gel 0.3% does not relieve pain during topical photodynamic therapy: a randomized, double-blind, placebo-controlled study. | 2006 |
|
| Successful treatment of disseminated superficial actinic porokeratosis with methyl aminolevulinate-photodynamic therapy. | 2006 |
|
| Topical photodynamic therapy for prevention of new skin lesions in renal transplant recipients. | 2006 |
|
| Fluorescence diagnosis and photodynamic therapy in dermatology from experimental state to clinic standard methods. | 2006 |
Patents
Sample Use Guides
Using a spatula, apply a layer of METVIXIA Cream (Methyl aminolevulinate) about 1 mm thick to the lesion and the surrounding 5 mm of normal skin. Do not apply more than one gram (half tube) of METVIXIA Cream per treatment session.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25048871
0.5-2mM Methyl aminolevulinate induced formation of porphyrin in malignant cells (HS192T) and human FLS from RA and OA patients.
| Substance Class |
Chemical
Created
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585NM85KYM
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585NM85KYM
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DB00992
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337068
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m7360
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METHYL AMINOLEVULINATE
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100000087993
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33320-16-0
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