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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
Metvix (PhotoCure).
2002 Nov
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
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
Gateways to clinical trials.
2003 Sep
[Eliminating light-induced skin cancer without operation].
2004
Topical methyl aminolevulinate.
2004
[Photodynamic therapy of cutaneous leishmaniasis. A promising new therapeutic modality].
2004 Apr
Allergic contact dermatitis to 5-aminolaevulinic acid methylester but not to 5-aminolaevulinic acid after photodynamic therapy.
2004 Jan
A randomized controlled clinical trial of topical photodynamic therapy with methyl aminolaevulinate in the treatment of actinic keratoses in transplant recipients.
2004 Jul
Gateways to clinical trials.
2004 Jul-Aug
Transdermal delivery from a lipid sponge phase--iontophoretic and passive transport in vitro of 5-aminolevulinic acid and its methyl ester.
2004 Nov 24
Clinical efficacy of methyl aminolaevulinate photodynamic therapy in basal cell carcinoma and solar keratosis.
2005 Feb
Gateways to clinical trials.
2005 Jun
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
Gateways to clinical trials.
2006 Jan-Feb
5-Aminolevulinic acid derivatives in photomedicine: Characteristics, application and perspectives.
2006 Jul-Aug
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
[Dynamic phototherapy in dermatology: current uses and future perspectives].
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
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
Photodynamic therapy: update 2006. Part 2: Clinical results.
2007 Apr
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-photodynamic therapy for basal cell carcinoma.
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
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
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 May-Jun
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
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