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Details

Stereochemistry ACHIRAL
Molecular Formula C6H11NO3
Molecular Weight 145.1567
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYL AMINOLEVULINATE

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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
METVIXIA

Approved Use

METVIXIA 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 Date

1.09079999E12
Doses

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Can autofluorescence demarcate basal cell carcinoma from normal skin? A comparison with protoporphyrin IX fluorescence.
2001 Aug-Sep
5-Aminolaevulinic acid methyl ester transport on amino acid carriers in a human colon adenocarcinoma cell line.
2001 Feb
Selective distribution of porphyrins in skin thick basal cell carcinoma after topical application of methyl 5-aminolevulinate.
2001 Sep 15
Photodynamic therapy using topical methyl 5-aminolevulinate compared with cryotherapy for actinic keratosis: A prospective, randomized study.
2002 Aug
Weekly topical application of methyl aminolevulinate followed by light exposure delays the appearance of UV-induced skin tumours in mice.
2002 Jul
Protoporphyrin IX fluorescence kinetics in UV-induced tumours and normal skin of hairless mice after topical application of 5-aminolevulinic acid methyl ester.
2002 May
Metvix (PhotoCure).
2002 Nov
Photosensitizing effect of protoporphyrin IX in pigmented melanoma of mice.
2002 Sep 27
Clinical efficacy of methyl aminolevulinate (Metvix) photodynamic therapy.
2003
The role of light in the treatment of non-melanoma skin cancer using methyl aminolevulinate.
2003
Comparative in vitro percutaneous penetration of 5-aminolevulinic acid and two of its esters through excised hairless mouse skin.
2003
[An unsurpassed duo in control of skin cancer. Metvix and Aktilite].
2003
Photodynamic therapy with topical methyl aminolevulinate for actinic keratosis: results of a prospective randomized multicenter trial.
2003 Feb
A study of 5-aminolevulinic acid and its methyl ester used in in vitro and in vivo systems of human bladder cancer.
2003 Feb
Treatment of cutaneous leishmaniasis by photodynamic therapy.
2003 Jun
[In actinic keratosis and basal cell carcinoma. The power of light heals without scars].
2003 Mar 27
Gateways to clinical trials.
2003 May
Pain associated with photodynamic therapy using 5-aminolevulinic acid or 5-aminolevulinic acid methylester on tape-stripped normal skin.
2003 Sep
Discrete choice experiment to derive willingness to pay for methyl aminolevulinate photodynamic therapy versus simple excision surgery in basal cell carcinoma.
2004
[Eliminating light-induced skin cancer without operation].
2004
Topical methyl aminolevulinate.
2004
A randomized controlled clinical trial of topical photodynamic therapy with methyl aminolaevulinate in the treatment of actinic keratoses in transplant recipients.
2004 Jul
Iontophoretic delivery of 5-aminolevulinic acid and its methyl ester using a carbopol gel as vehicle.
2004 Jul 23
Transdermal delivery from a lipid sponge phase--iontophoretic and passive transport in vitro of 5-aminolevulinic acid and its methyl ester.
2004 Nov 24
Gateways to clinical trials.
2005 Jun
[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
Gateways to clinical trials.
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
Morphine gel 0.3% does not relieve pain during topical photodynamic therapy: a randomized, double-blind, placebo-controlled study.
2006
Topical photodynamic therapy for prevention of new skin lesions in renal transplant recipients.
2006
Gateways to clinical trials.
2006 Jan-Feb
Gateways to clinical trials.
2006 May
Topical application of 5-aminolaevulinic acid, methyl 5-aminolaevulinate and hexyl 5-aminolaevulinate on normal human skin.
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
Topical methyl aminolaevulinate photodynamic therapy for treatment of facial acne vulgaris: results of a randomized, controlled study.
2006 Sep
Allergic contact dermatitis to methyl aminolevulinate (Metvix) cream used in photodynamic therapy.
2007 Feb
Chemopreventative thoughts for photodynamic therapy.
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
Methyl aminolaevulinate-photodynamic therapy: a review of clinical trials in the treatment of actinic keratoses and nonmelanoma skin cancer.
2007 May
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
0.5-2mM Methyl aminolevulinate induced formation of porphyrin in malignant cells (HS192T) and human FLS from RA and OA patients.
Name Type Language
METHYL AMINOLEVULINATE
MI   VANDF   WHO-DD  
Systematic Name English
PENTANOIC ACID, 5-AMINO-4-OXO-, METHYL ESTER
Common Name English
METVIX
Brand Name English
METHYL AMINOLEVULINATE [VANDF]
Common Name English
METHYL 5-AMINOLEVULINATE
Common Name English
METHYL AMINOLEVULINATE [WHO-DD]
Common Name English
METHYL 5-AMINO-4-OXOPENTANOATE
Systematic Name English
METHYL AMINOLEVULINATE [MI]
Common Name English
METHYL AMINOLAEVULINATE
Common Name English
Classification Tree Code System Code
NDF-RT N0000171207
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
WHO-ATC L01XD03
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
NDF-RT N0000171207
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
NCI_THESAURUS C1420
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
NDF-RT N0000171207
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
NDF-RT N0000171207
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
WHO-VATC QL01XD03
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
NDF-RT N0000175846
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
Code System Code Type Description
EVMPD
SUB22645
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
FDA UNII
585NM85KYM
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
DRUG BANK
DB00992
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
RXCUI
337068
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY RxNorm
MESH
C475457
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
EPA CompTox
33320-16-0
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
PUBCHEM
157922
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
DRUG CENTRAL
168
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
MERCK INDEX
M7360
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
METHYL AMINOLEVULINATE
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
NCI_THESAURUS
C76305
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY
CAS
33320-16-0
Created by admin on Fri Jun 25 23:11:33 UTC 2021 , Edited by admin on Fri Jun 25 23:11:33 UTC 2021
PRIMARY