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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
Structure of METHYL AMINOLEVULINATE HYDROCHLORIDE

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

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

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

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
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
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
Photosensitizing effect of protoporphyrin IX in pigmented melanoma of mice.
2002 Sep 27
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
[In actinic keratosis and basal cell carcinoma. The power of light heals without scars].
2003 Mar 27
Gateways to clinical trials.
2003 May
Discrete choice experiment to derive willingness to pay for methyl aminolevulinate photodynamic therapy versus simple excision surgery in basal cell carcinoma.
2004
Topical methyl aminolevulinate.
2004
[Photodynamic therapy of cutaneous leishmaniasis. A promising new therapeutic modality].
2004 Apr
Photodynamic therapy for subungual Bowen's disease.
2004 Aug
[Photodynamic therapy with methylaminooxopentanoate (Metvix) and a broad band light source (PhotoDyn 501): practical experiences in problem-patients with actinic keratoses and basal cell carcinomas].
2004 Dec
Iontophoretic delivery of 5-aminolevulinic acid and its methyl ester using a carbopol gel as vehicle.
2004 Jul 23
A randomized multicenter study to compare two treatment regimens of topical methyl aminolevulinate (Metvix)-PDT in actinic keratosis of the face and scalp.
2005
Photodynamic therapy with topical methyl aminolaevulinate for 'difficult-to-treat' basal cell carcinoma.
2005 Apr
Methyl aminolaevulinate photodynamic therapy for Bowen's disease: a practical option?
2005 Feb
Methyl aminolaevulinate photodynamic therapy in practice: treatment protocol.
2005 Feb
Topical photodynamic therapy for Bowen's disease.
2005 Feb
Gateways to clinical trials.
2005 Jun
Gateways to clinical trials.
2005 May
Photodynamic therapy and imiquimod immunotherapy for basal cell carcinomas.
2005 Sep-Oct
Successful treatment of disseminated superficial actinic porokeratosis with methyl aminolevulinate-photodynamic therapy.
2006
Multiple large surface photodynamic therapy sessions with topical methylaminolaevulinate in PTCH heterozygous mice.
2006 Apr
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
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
Gateways to clinical trials.
2006 Jan-Feb
Gateways to clinical trials.
2006 Jun
A case of focal dermal hypoplasia (Goltz) syndrome with exophytic granulation tissue treated by curettage and photodynamic therapy.
2006 Mar
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 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
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
Photodynamic therapy for actinic keratoses.
2007 Jan
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
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 Fri Dec 15 15:48:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:48:49 GMT 2023
Record UNII
7S73606O1A
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYL AMINOLEVULINATE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
Methyl aminolevulinate hydrochloride [WHO-DD]
Common Name English
Methyl 5-amino-4-oxopentanoate hydrochloride
Systematic Name English
METHYL AMINOLEVULINATE HYDROCHLORIDE [USAN]
Common Name English
METHYL AMINOLEVULINATE HCL
INCI  
INCI  
Official Name English
P-1202
Code English
METHYL AMINOLEVULINATE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
METHYL-5-AMINOLEVULINATE HYDROCHLORIDE
Common Name English
METVIXIA
Brand Name English
METHYL AMINOLEVULINATE HYDROCHLORIDE [MI]
Common Name English
METHYL AMINOLEVULINATE HCL [INCI]
Common Name English
METHYL AMINOLEVULINATE HYDROCHLORIDE [MART.]
Common Name English
METHYLAMINOLEVULINATE HYDROCHLORIDE
Common Name English
PENTANOIC ACID, 5-AMINO-4-OXO-, METHYL ESTER, HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1420
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
Code System Code Type Description
USAN
NN-79
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
SMS_ID
100000089567
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
NCI_THESAURUS
C76893
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
RXCUI
1300479
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
279-151-1
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
DAILYMED
7S73606O1A
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
MERCK INDEX
m7360
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1096562
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
CAS
79416-27-6
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
FDA UNII
7S73606O1A
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
CHEBI
60641
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
PUBCHEM
157921
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID4045630
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
DRUG BANK
DBSALT001462
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
EVMPD
SUB21579
Created by admin on Fri Dec 15 15:48:49 GMT 2023 , Edited by admin on Fri Dec 15 15:48:49 GMT 2023
PRIMARY
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