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

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
Topical methyl aminolaevulinate photodynamic therapy in patients with basal cell carcinoma prone to complications and poor cosmetic outcome with conventional treatment.
2003 Dec
[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
Discrete choice experiment to derive willingness to pay for methyl aminolevulinate photodynamic therapy versus simple excision surgery in basal cell carcinoma.
2004
Effectiveness of different light sources for 5-aminolevulinic acid photodynamic therapy.
2004
[Eliminating light-induced skin cancer without operation].
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
Allergic contact dermatitis to 5-aminolaevulinic acid methylester but not to 5-aminolaevulinic acid after photodynamic therapy.
2004 Jan
Photodynamic therapy using topical methyl aminolevulinate vs surgery for nodular basal cell carcinoma: results of a multicenter randomized prospective trial.
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
Iontophoretic delivery of 5-aminolevulinic acid and its methyl ester using a carbopol gel as vehicle.
2004 Jul 23
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
Photodynamic therapy with topical methyl aminolaevulinate for 'difficult-to-treat' basal cell carcinoma.
2005 Apr
Methyl aminolaevulinate photodynamic therapy in practice: treatment protocol.
2005 Feb
Practical aspects of methyl aminolaevulinate photodynamic therapy.
2005 Feb
Topical photodynamic therapy for Bowen's disease.
2005 Feb
Clinical efficacy of methyl aminolaevulinate photodynamic therapy in basal cell carcinoma and solar keratosis.
2005 Feb
Pain, pain relief and other practical issues in photodynamic therapy.
2005 Feb
Photodynamic therapy.
2005 Feb
Gateways to clinical trials.
2005 Jun
Kinetics of protoporphyrin IX formation in rat oral mucosa and skin after application of 5-aminolevulinic acid and its methylester.
2005 Mar-Apr
[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
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
Photodynamic therapy induces less pain in patients treated with methyl aminolevulinate compared to aminolevulinic acid.
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
Treatment of basal cell carcinoma with topical methylaminolaevulinate photodynamic therapy in an organ-transplant recipient.
2006 Jan
Gateways to clinical trials.
2006 Jan-Feb
Gateways to clinical trials.
2006 Jun
Topical photodynamic therapy with methyl aminolevulinate to treat sebaceous hyperplasia in an organ transplant recipient.
2006 Jun
Gateways to clinical trials.
2006 May
Photodynamic therapy of acne vulgaris using methyl aminolaevulinate: a blinded, randomized, controlled trial.
2006 May
Gateways to clinical trials.
2006 Oct
Topical application of 5-aminolaevulinic acid, methyl 5-aminolaevulinate and hexyl 5-aminolaevulinate on normal human skin.
2006 Oct
Economic evaluation of methyl aminolaevulinate-based photodynamic therapy in the management of actinic keratosis and basal cell carcinoma.
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
Topical methyl aminolaevulinate photodynamic therapy for treatment of facial acne vulgaris: results of a randomized, controlled study.
2006 Sep
Phototoxic reaction and porphyrin fluorescence in skin after topical application of methyl aminolaevulinate.
2007 Feb
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
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
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
  • Download
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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