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).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map00860 |
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 n = 383 Health Status: unhealthy Condition: actinic keratosis Age Group: adult Population Size: 383 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 n = 383 Health Status: unhealthy Condition: actinic keratosis Age Group: adult Population Size: 383 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Reader's letter concerning K. Kreutzer, B.Bonnekoh, I. Franke, H. Gollnick. Photodynamic therapy with methylaminooxopentanoate (Metvix) and a broad band light source (Photdyn 501): practical experiences in problem patients with actinic keratoses and basal cell carcinomas. JDDG 2004,12:992-999]. | 2005 May |
|
| Influence of light exposure on the kinetics of protoporphyrin IX formation in normal skin of hairless mice after application of 5-aminolevulinic acid methyl ester. | 2005 Nov |
|
| Photodynamic therapy and imiquimod immunotherapy for basal cell carcinomas. | 2005 Sep-Oct |
|
| 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 |
|
| Photodynamic therapy induces less pain in patients treated with methyl aminolevulinate compared to aminolevulinic acid. | 2006 Apr |
|
| Photodynamic therapy of acne vulgaris using 5-aminolevulinic acid versus methyl aminolevulinate. | 2006 Apr |
|
| Multiple large surface photodynamic therapy sessions with topical methylaminolaevulinate in PTCH heterozygous mice. | 2006 Apr |
|
| Topical photodynamic therapy: an introduction for nurses. | 2006 Aug 10-Sep 13 |
|
| Successful treatment of necrobiosis lipoidica diabeticorum with photodynamic therapy. | 2006 Dec |
|
| Porphyrin formation in actinic keratosis and basal cell carcinoma after topical application of methyl 5-aminolevulinate. | 2006 Feb |
|
| The temperature dependence of porphyrin production in Propionibacterium acnes after incubation with 5-aminolevulinic acid (ALA) and its methyl ester (m-ALA). | 2006 Jan |
|
| Treatment of basal cell carcinoma with topical methylaminolaevulinate photodynamic therapy in an organ-transplant recipient. | 2006 Jan |
|
| Gateways to clinical trials. | 2006 Jan-Feb |
|
| 5-Aminolevulinic acid derivatives in photomedicine: Characteristics, application and perspectives. | 2006 Jul-Aug |
|
| Gateways to clinical trials. | 2006 Jun |
|
| Topical photodynamic therapy with methyl aminolevulinate to treat sebaceous hyperplasia in an organ transplant recipient. | 2006 Jun |
|
| A case of focal dermal hypoplasia (Goltz) syndrome with exophytic granulation tissue treated by curettage and photodynamic therapy. | 2006 Mar |
|
| Gateways to clinical trials. | 2006 May |
|
| [Dynamic phototherapy in dermatology: current uses and future perspectives]. | 2006 May |
|
| Photodynamic therapy of acne vulgaris using methyl aminolaevulinate: a blinded, randomized, controlled trial. | 2006 May |
|
| 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 May 1 |
|
| Intraindividual, right-left comparison of topical methyl aminolaevulinate-photodynamic therapy and cryotherapy in subjects with actinic keratoses: a multicentre, randomized controlled study. | 2006 Nov |
|
| Photodynamic therapy using a methyl ester of 5-aminolevulinic acid in recurrent Paget's disease of the vulva: a pilot study. | 2006 Nov |
|
| Gateways to clinical trials. | 2006 Oct |
|
| Topical application of 5-aminolaevulinic acid, methyl 5-aminolaevulinate and hexyl 5-aminolaevulinate on normal human skin. | 2006 Oct |
|
| Economic evaluation of methyl aminolaevulinate-based photodynamic therapy in the management of actinic keratosis and basal cell carcinoma. | 2006 Oct |
|
| 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 Oct |
|
| Photodynamic therapy with methylaminolevulinate as a valuable treatment option for unilesional cutaneous T-cell lymphoma. | 2006 Oct |
|
| Nonablative skin resurfacing: the role of PDT. | 2006 Sep |
|
| Topical methyl aminolaevulinate photodynamic therapy for treatment of facial acne vulgaris: results of a randomized, controlled study. | 2006 Sep |
|
| Topical methyl aminolevulinate photodynamic therapy for the treatment of folliculitis. | 2007 Aug |
|
| Photodynamic treatment of cutaneous leishmaniasis. | 2007 Feb |
|
| Allergic contact dermatitis to methyl aminolevulinate (Metvix) cream used in photodynamic therapy. | 2007 Feb |
|
| Phototoxic reaction and porphyrin fluorescence in skin after topical application of methyl aminolaevulinate. | 2007 Feb |
|
| A comparative study of intense pulsed light alone and its combination with photodynamic therapy for the treatment of facial acne in Asian skin. | 2007 Jan |
|
| Guidelines on the use of photodynamic therapy for nonmelanoma skin cancer: an international consensus. International Society for Photodynamic Therapy in Dermatology, 2005. | 2007 Jan |
|
| Chemopreventative thoughts for photodynamic therapy. | 2007 Jan |
|
| Methyl aminolevulinate: actinic keratoses and Bowen's disease. | 2007 Jan |
|
| Photodynamic therapy for actinic keratoses. | 2007 Jan |
|
| 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 Jul |
|
| The efficacy of photodynamic therapy in actinic cheilitis of the lower lip: a prospective study of 15 patients. | 2007 Jul |
|
| 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 Jul |
|
| Photodetection of basal cell carcinoma using methyl 5-aminolaevulinate-induced protoporphyrin IX based on fluorescence image analysis. | 2007 Jul |
|
| Clinical and echographic analysis of photodynamic therapy using methylaminolevulinate as sensitizer in the treatment of photodamaged facial skin. | 2007 Mar |
|
| Fluorescence diagnosis of face-located basal cell carcinomas: a new dermatological procedure which may help the surgeon. | 2007 Mar-Apr |
|
| Methyl aminolaevulinate-photodynamic therapy: a review of clinical trials in the treatment of actinic keratoses and nonmelanoma skin cancer. | 2007 May |
|
| Photodynamic therapy for cutaneous verrucous carcinoma. | 2007 Sep |
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
| Substance Class |
Chemical
Created
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| Record UNII |
585NM85KYM
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Validated (UNII)
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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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C76305
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33320-16-0
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TARGET -> AGONIST |
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ACTIVE MOIETY |
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