U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

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

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

2004
Doses

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
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
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 Mon Mar 31 18:01:34 GMT 2025
Edited
by admin
on Mon Mar 31 18:01:34 GMT 2025
Record UNII
585NM85KYM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METVIX
Preferred Name English
METHYL AMINOLEVULINATE
MI   VANDF   WHO-DD  
Systematic Name English
METHYLAMINOLEVULINATE
Common Name English
PENTANOIC ACID, 5-AMINO-4-OXO-, METHYL ESTER
Common 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 Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
WHO-ATC L01XD03
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
NDF-RT N0000171207
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
NCI_THESAURUS C1420
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
NDF-RT N0000171207
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
NDF-RT N0000171207
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
WHO-VATC QL01XD03
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
NDF-RT N0000175846
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
Code System Code Type Description
CHEBI
724125
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
DAILYMED
585NM85KYM
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
EVMPD
SUB22645
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
FDA UNII
585NM85KYM
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
DRUG BANK
DB00992
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
RXCUI
337068
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY RxNorm
MESH
C475457
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID3048570
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
PUBCHEM
157922
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
DRUG CENTRAL
168
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
MERCK INDEX
m7360
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
METHYL AMINOLEVULINATE
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
SMS_ID
100000087993
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
NCI_THESAURUS
C76305
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
CAS
33320-16-0
Created by admin on Mon Mar 31 18:01:34 GMT 2025 , Edited by admin on Mon Mar 31 18:01:34 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY