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Details

Stereochemistry ACHIRAL
Molecular Formula C5H9NO3
Molecular Weight 131.1299
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINOLEVULINIC ACID

SMILES

NCC(=O)CCC(O)=O

InChI

InChIKey=ZGXJTSGNIOSYLO-UHFFFAOYSA-N
InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)

HIDE SMILES / InChI

Description

Aminolevulinic Acid is the first compound in the porphyrin synthesis pathway. The metabolism of aminolevulinic acid (ALA) is the first step in the biochemical pathway resulting in heme synthesis. Aminolevulinic acid is not a photosensitizer, but rather a metabolic precursor of protoporphyrin IX (PpIX), which is a photosensitizer. The synthesis of ALA is normally tightly controlled by feedback inhibition of the enzyme, ALA synthetase, presumably by intracellular heme levels. ALA, when provided to the cell, bypasses this control point and results in the accumulation of PpIX, which is converted into heme by ferrochelatase through the addition of iron to the PpIX nucleus. Marketed under the brand name LEVULAN KERASTICK for Topical Solution plus blue light illumination using the BLU-U Blue Light Photodynamic Therapy Illuminator, it is indicated for the treatment of minimally to moderately thick actinic keratoses (Grade 1 or 2, see table 2 for definition) of the face or scalp. Aminolevulinic acid is also being studied in the treatment of other conditions and types of cancer. An orally-administered in vivo diagnostic agent, Aminolevulinic acid, is used in photodynamic diagnosis (PDD) whose aim is to help doctors visualize the tumor tissue during surgical resection of malignant glioma, it is already sold in over 20 European countries including Germany and the U.K. According to the presumed mechanism of action, photosensitization following application of aminolevulinic acid (ALA) topical solution occurs through the metabolic conversion of ALA to protoporphyrin IX (PpIX), which accumulates in the skin to which aminolevulinic acid has been applied. When exposed to light of appropriate wavelength and energy, the accumulated PpIX produces a photodynamic reaction, a cytotoxic process dependent upon the simultaneous presence of light and oxygen. The absorption of light results in an excited state of the porphyrin molecule, and subsequent spin transfer from PpIX to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals. Photosensitization of actinic (solar) keratosis lesions using aminolevulinic acid, plus illumination with the BLU-UTM Blue Light Photodynamic Therapy Illuminator (BLU-U), is the basis for aminolevulinic acid photodynamic therapy (PDT).

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
LEVULAN KERASTICK
Primary
ALA
Diagnostic
Gliolan
PMID

PMID

TitleDatePMID
An affordable, portable fluorescence imaging device for skin lesion detection using a dual wavelength approach for image contrast enhancement and aminolaevulinic acid-induced protoporphyrin IX. Part II. In vivo testing.
2001
An affordable, portable fluorescence imaging device for skin lesion detection using a dual wavelength approach for image contrast enhancement and aminolaevulinic acid-induced protoporphyrin IX. Part I. Design, spectral and spatial characteristics.
2001
Modulator of heme biosynthesis induces apoptosis in leukemia cells.
2001 Apr
The porphyrias: genetic and acquired aspects.
2001 Apr
Fluorescence staining of oral cancer using a topical application of 5-aminolevulinic acid: fluorescence microscopic studies.
2001 Apr
Topical photodynamic therapy at low fluence rates--theory and practice.
2001 Apr
Routine experimental system for defining conditions used in photodynamic therapy and fluorescence photodetection of (non-) neoplastic epithelia.
2001 Apr
Evaluation of different photosensitizers for use in photochemical gene transfection.
2001 Apr
Photodynamic therapy of feline superficial squamous cell carcinoma using topical 5-aminolaevulinic acid.
2001 Apr
[Photodynamic therapy of dysplasias and early carcinomas in Barrett esophagus with a diode laser system--a pilot study].
2001 Apr 15
Spectrophotometric microassay for delta-aminolevulinate dehydratase in dried-blood spots as confirmation for hereditary tyrosinemia type I.
2001 Aug
Correlation between lead exposure indicators and sister chromatid exchange (SCE) frequencies in lymphocytes from inorganic lead exposed workers.
2001 Aug
Peripheral neuropathy in chronic occupational inorganic lead exposure: a clinical and electrophysiological study.
2001 Aug
Recognition and transport characteristics of nonpeptidic compounds by basolateral peptide transporter in Caco-2 cells.
2001 Aug
Anticarcinogenic actions of melatonin which involve antioxidative processes: comparison with other antioxidants.
2001 Aug
Antitumor effect of 5-aminolevulinic acid-mediated photodynamic therapy can be enhanced by the use of a low dose of photofrin in human tumor xenografts.
2001 Aug 1
Evaluation of protoporphyrin IX production, phototoxicity and cell death pathway induced by hexylester of 5-aminolevulinic acid in Reh and HPB-ALL cells.
2001 Aug 10
Fluorescence spectroscopy of normal mouse skin exposed to 5-aminolaevulinic acid and red light.
2001 Aug 15
Photodynamic therapy with topical delta-aminolaevulinic acid for the treatment of plantar warts.
2001 Aug 15
In vivo pharmacokinetics of protoporphyrin IX accumulation following intracutaneous injection of 5-aminolevulinic acid.
2001 Aug 15
5-Aminolevulinic acid inhibits [3H]muscimol binding to human and rat brain synaptic membranes.
2001 Feb
Melatonin prevents delta-aminolevulinic acid-induced oxidative DNA damage in the presence of Fe2+.
2001 Feb
The photosensitizing effect of the photoproduct of protoporphyrin IX.
2001 Jul
5-Aminolaevulinic acid-mediated photodynamic therapy in multidrug resistant leukemia cells.
2001 Jul
Some articles should just not be published.
2001 Jul
Photodynamic therapy of actinic keratoses with topical aminolevulinic acid hydrochloride and fluorescent blue light.
2001 Jul
On the promoting action of tamoxifen in a model of hepatocarcinogenesis induced by p-dimethylaminoazobenzene in CF1 mice.
2001 Jul
Photosensitization and mechanism of cytotoxicity induced by the use of ALA derivatives in photodynamic therapy.
2001 Jul 20
Mechanistic basis for suicide inactivation of porphobilinogen synthase by 4,7-dioxosebacic acid, an inhibitor that shows dramatic species selectivity.
2001 Jul 27
Photobiological activity of exogenous and endogenous porphyrin derivatives in Escherichia coli and Enterococcus hirae cells.
2001 Jun
Effect of photodynamic therapy on urinary bladder function: an experimental study with rats.
2001 Jun
Topical 5-aminolaevulinic acid photodynamic therapy for tumour-stage mycosis fungoides.
2001 Jun
Systemic photodynamic therapy with aminolaevulinic acid delays the appearance of ultraviolet-induced skin tumours in mice.
2001 Jun
Role of 5-aminolevulinic acid in the diagnosis and treatment of superficial bladder cancer: improvement in diagnostic sensitivity.
2001 Jun
High efficiency of 5-aminolevulinate-photodynamic treatment using UVA irradiation.
2001 Jun
Clinical experience with 5-aminolevulinic acid and photodynamic therapy for refractory superficial bladder cancer.
2001 Jun
Optimization of differential photodynamic effectiveness between normal and tumor urothelial cells using 5-aminolevulinic acid-induced protoporphyrin IX as sensitizer.
2001 Jun 1
[Are new treatments always effective ?].
2001 Jun-Jul
Iontophoretic delivery of 5-aminolevulinic acid (ALA): effect of pH.
2001 Mar
[Experimental 5-aminolevulinic acid-induced photodynamic therapy (ALA-PDT) of oral carcinomas. Procedures in treatment of solid tumors and elucidation of cell death].
2001 Mar
Abortive assembly of succinate-ubiquinone reductase (complex II) in a ferrochelatase-deficient mutant of Escherichia coli.
2001 May
[Fluorescence cytology of the urinary bladder].
2001 May
Photodynamic therapy for Bowen's disease (squamous cell carcinoma in situ) of the digit.
2001 May
A quantitative assessment of protoporphyrin IX metabolism and phototoxicity in human skin following dose-controlled delivery of the prodrugs 5-aminolaevulinic acid and 5-aminolaevulinic acid-n-pentylester.
2001 May
Fluorescence detection of cervical intraepithelial neoplasia for photodynamic therapy with the topical agents 5-aminolevulinic acid and benzoporphyrin-derivative monoacid ring.
2001 May
Zinc mesoporphyrin represses induced hepatic 5-aminolevulinic acid synthase and reduces heme oxygenase activity in a mouse model of acute hepatic porphyria.
2001 May
Photomodification of the electrical properties of the plasma membrane: a comparison between 6 different membrane-active photosensitizers.
2001 May 1
Antioxidants inhibit indoleamine 2,3-dioxygenase in IFN-gamma-activated human macrophages: posttranslational regulation by pyrrolidine dithiocarbamate.
2001 May 15
Diagnosing cancer in vivo.
2001 May 18
Expression of PEPT2 peptide transporter mRNA and protein in glial cells of rat dorsal root ganglia.
2001 May 25
Patent

Patent

Sample Use Guides

In Vivo Use Guide
LEVULAN KERASTICK for Topical Solution 20% (aminolevulinic acid HCl) is intended for direct application to individual lesions diagnosed as actinic keratoses and not to perilesional skin. This product is not intended for application by patients or unqualified medical personnel. Application should involve either scalp or face lesions, but not both simultaneously. The recommended treatment frequency is: one application of the LEVULAN KERASTICK Topical Solution and one dose of illumination per treatment site per 8­ week treatment session. Each individual LEVULAN KERASTICK should be used for only one patient. Photodynamic therapy for actinic keratoses with LEVULAN KERASTICK for Topical Solution is a two stage process involving a) application of the product to the target lesions with LEVULAN KERASTICK Topical Solution, followed 14 to 18 hours later by b) illumination with blue light using the BLU-U Blue Light Photodynamic Therapy Illuminator. The second visit, for illumination, must take place in the 14-18 hour window following application.
Route of Administration: Topical
In Vitro Use Guide
Aminolevulinic acid (10 ug/ml) mediated sonosensitization of rat RG2 glioma cells in vitro. ALA-mediated SDT evokes cytotoxic effects of low intensity US on rat RG2 glioma cells in vitro.
Name Type Language
AMINOLEVULINIC ACID
VANDF   WHO-DD  
Systematic Name English
5-ALA
Common Name English
DELTA-AMINOLEVULINIC ACID
Systematic Name English
PENTANOIC ACID, 5-AMINO-4-OXO-
Common Name English
AMINOLEVULINIC ACID [VANDF]
Common Name English
5-AMINOLEVULINIC ACID
MART.  
Common Name English
AMINOLEVULINATE
Systematic Name English
5-AMINOLEVULINIC ACID [MART.]
Common Name English
5-AMINO-4-OXOPENTANOIC ACID
Systematic Name English
AMINOLEVULINIC ACID [WHO-DD]
Common Name English
.DELTA.-AMINOLEVULINIC ACID [MI]
Common Name English
LEVULINIC ACID, 5-AMINO-
Systematic Name English
.DELTA.-AMINOLEVULINIC ACID
MI  
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175846
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
WHO-ATC L01XD04
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
NDF-RT N0000171207
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
CFR 21 CFR 862.1060
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
WHO-VATC QL01XD04
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
NDF-RT N0000171207
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
NDF-RT N0000171207
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
NDF-RT N0000171207
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
Code System Code Type Description
MESH
D000622
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
WIKIPEDIA
AMINOLEVULINIC ACID
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
IUPHAR
4784
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
EPA CompTox
106-60-5
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
NCI_THESAURUS
C234
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
MERCK INDEX
M1713
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY Merck Index
EVMPD
SUB12853MIG
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
CAS
106-60-5
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
DRUG BANK
DB00855
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
RXCUI
683
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY
RXCUI
155002
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
ALTERNATIVE
ECHA (EC/EINECS)
203-414-1
Created by admin on Tue Mar 06 12:35:35 UTC 2018 , Edited by admin on Tue Mar 06 12:35:35 UTC 2018
PRIMARY