Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H11NO3.ClH |
Molecular Weight | 181.617 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC(=O)CCC(=O)CN
InChI
InChIKey=UJYSYPVQHFNBML-UHFFFAOYSA-N
InChI=1S/C6H11NO3.ClH/c1-10-6(9)3-2-5(8)4-7;/h2-4,7H2,1H3;1H
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 |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
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 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 |
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Topical methyl aminolaevulinate photodynamic therapy in patients with basal cell carcinoma prone to complications and poor cosmetic outcome with conventional treatment. | 2003 Dec |
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[In actinic keratosis and basal cell carcinoma. The power of light heals without scars]. | 2003 Mar 27 |
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Gateways to clinical trials. | 2003 May |
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Gateways to clinical trials. | 2003 Sep |
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Discrete choice experiment to derive willingness to pay for methyl aminolevulinate photodynamic therapy versus simple excision surgery in basal cell carcinoma. | 2004 |
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Effectiveness of different light sources for 5-aminolevulinic acid photodynamic therapy. | 2004 |
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[Eliminating light-induced skin cancer without operation]. | 2004 |
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Topical methyl aminolevulinate. | 2004 |
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[Photodynamic therapy of cutaneous leishmaniasis. A promising new therapeutic modality]. | 2004 Apr |
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Photodynamic therapy for subungual Bowen's disease. | 2004 Aug |
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Allergic contact dermatitis to 5-aminolaevulinic acid methylester but not to 5-aminolaevulinic acid after photodynamic therapy. | 2004 Jan |
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Photodynamic therapy using topical methyl aminolevulinate vs surgery for nodular basal cell carcinoma: results of a multicenter randomized prospective trial. | 2004 Jan |
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A randomized controlled clinical trial of topical photodynamic therapy with methyl aminolaevulinate in the treatment of actinic keratoses in transplant recipients. | 2004 Jul |
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Iontophoretic delivery of 5-aminolevulinic acid and its methyl ester using a carbopol gel as vehicle. | 2004 Jul 23 |
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Gateways to clinical trials. | 2004 Jul-Aug |
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Transdermal delivery from a lipid sponge phase--iontophoretic and passive transport in vitro of 5-aminolevulinic acid and its methyl ester. | 2004 Nov 24 |
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Photodynamic therapy with topical methyl aminolaevulinate for 'difficult-to-treat' basal cell carcinoma. | 2005 Apr |
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Methyl aminolaevulinate photodynamic therapy in practice: treatment protocol. | 2005 Feb |
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Practical aspects of methyl aminolaevulinate photodynamic therapy. | 2005 Feb |
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Topical photodynamic therapy for Bowen's disease. | 2005 Feb |
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Clinical efficacy of methyl aminolaevulinate photodynamic therapy in basal cell carcinoma and solar keratosis. | 2005 Feb |
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Pain, pain relief and other practical issues in photodynamic therapy. | 2005 Feb |
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Photodynamic therapy. | 2005 Feb |
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Gateways to clinical trials. | 2005 Jun |
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Kinetics of protoporphyrin IX formation in rat oral mucosa and skin after application of 5-aminolevulinic acid and its methylester. | 2005 Mar-Apr |
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[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 |
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Morphine gel 0.3% does not relieve pain during topical photodynamic therapy: a randomized, double-blind, placebo-controlled study. | 2006 |
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Successful treatment of disseminated superficial actinic porokeratosis with methyl aminolevulinate-photodynamic therapy. | 2006 |
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Photodynamic therapy induces less pain in patients treated with methyl aminolevulinate compared to aminolevulinic acid. | 2006 Apr |
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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 Aug |
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Topical photodynamic therapy: an introduction for nurses. | 2006 Aug 10-Sep 13 |
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Successful treatment of necrobiosis lipoidica diabeticorum with photodynamic therapy. | 2006 Dec |
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Treatment of basal cell carcinoma with topical methylaminolaevulinate photodynamic therapy in an organ-transplant recipient. | 2006 Jan |
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Gateways to clinical trials. | 2006 Jan-Feb |
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Gateways to clinical trials. | 2006 Jun |
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Topical photodynamic therapy with methyl aminolevulinate to treat sebaceous hyperplasia in an organ transplant recipient. | 2006 Jun |
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Gateways to clinical trials. | 2006 May |
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Photodynamic therapy of acne vulgaris using methyl aminolaevulinate: a blinded, randomized, controlled trial. | 2006 May |
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Gateways to clinical trials. | 2006 Oct |
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Topical application of 5-aminolaevulinic acid, methyl 5-aminolaevulinate and hexyl 5-aminolaevulinate on normal human skin. | 2006 Oct |
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Economic evaluation of methyl aminolaevulinate-based photodynamic therapy in the management of actinic keratosis and basal cell carcinoma. | 2006 Oct |
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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 |
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Topical methyl aminolaevulinate photodynamic therapy for treatment of facial acne vulgaris: results of a randomized, controlled study. | 2006 Sep |
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Phototoxic reaction and porphyrin fluorescence in skin after topical application of methyl aminolaevulinate. | 2007 Feb |
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Guidelines on the use of photodynamic therapy for nonmelanoma skin cancer: an international consensus. International Society for Photodynamic Therapy in Dermatology, 2005. | 2007 Jan |
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Chemopreventative thoughts for photodynamic therapy. | 2007 Jan |
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Methyl aminolevulinate-photodynamic therapy for basal cell carcinoma. | 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 |
|
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
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
by
admin
on
Edited
Fri Dec 15 15:48:49 GMT 2023
by
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on
Fri Dec 15 15:48:49 GMT 2023
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Record UNII |
7S73606O1A
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Record Status |
Validated (UNII)
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Record Version |
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C1420
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100000089567
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C76893
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1300479
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279-151-1
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7S73606O1A
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m7360
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CHEMBL1096562
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SUB21579
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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