Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H9NO3 |
Molecular Weight | 131.1299 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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)
Molecular Formula | C5H9NO3 |
Molecular Weight | 131.1299 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12493610 | https://www.ncbi.nlm.nih.gov/pubmed/9792218
Curator's Comment: There is low permeability of the undisrupted BBB in humans
Originator
Sources: http://www.mdpi.com/1420-3049/16/5/4140
Curator's Comment: The first report on excessive protoporphyrin accumulation and high photosensitivity after exogenous administration of ALA in humans was presented by Berlin et al. in 1956
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LEVULAN KERASTICK Approved UseThe LEVULAN KERASTICK for Topical Solution plus blue light illumination using the BLU-U Blue
Light Photodynamic Therapy Illuminator 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. Launch Date9.4452482E11 |
|||
Diagnostic | Gliolan Approved UseGliolan is indicated in adult patients for visualisation of malignant tissue during surgery for malignant
glioma (WHO grade III and IV). Launch Date1.16760956E12 |
|||
Primary | ALA Approved UseCondylomata Acuminata Launch Date1.17141117E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8239.1 μg/L |
20 mg/kg bw single, oral dose: 20 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1862.6 μg/L |
2 mg/kg bw single, oral dose: 2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
274.7 μg/L |
0.2 mg/kg bw single, oral dose: 0.2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
15.44 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11961050/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.65 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11961050/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27143.5 μg × h/L |
20 mg/kg bw single, oral dose: 20 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2901.3 μg × h/L |
2 mg/kg bw single, oral dose: 2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
424.2 μg × h/L |
0.2 mg/kg bw single, oral dose: 0.2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
13.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11961050/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11961050/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.94 h |
20 mg/kg bw single, oral dose: 20 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.84 h |
2 mg/kg bw single, oral dose: 2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.75 h |
0.2 mg/kg bw single, oral dose: 0.2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
50.1 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11961050/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
44.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11961050/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
88% |
20 mg/kg bw single, oral dose: 20 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
88% |
2 mg/kg bw single, oral dose: 2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
88% |
0.2 mg/kg bw single, oral dose: 0.2 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
AMINOLEVULINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
20 mg/kg single, oral Recommended Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: |
unhealthy, 70.5 years (range: 53–84 years) n = 61 Health Status: unhealthy Condition: primary or recurrent non-muscle-invasive bladder cancer Age Group: 70.5 years (range: 53–84 years) Sex: M+F Population Size: 61 Sources: |
Other AEs: Alanine aminotransferase increase, Hypotension... Other AEs: Alanine aminotransferase increase (grade 3, 6.6%) Sources: Hypotension (grade 3, 1.6%) Urticaria (grade 3, 1.6%) |
10 % 1 times / day multiple, topical Recommended Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: Page: p. 44 |
unhealthy n = 384 Health Status: unhealthy Sex: M+F Population Size: 384 Sources: Page: p. 44 |
Disc. AE: Application site burning, Application site pain... AEs leading to discontinuation/dose reduction: Application site burning (1 patient) Sources: Page: p. 44Application site pain (1 patient) |
100 mg single, intravenous Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: |
healthy n = 6 |
|
100 mg single, oral |
healthy n = 6 |
|
1328 mg single, intravesical Dose: 1328 mg Route: intravesical Route: single Dose: 1328 mg Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: recurrent bladder cancer Population Size: 8 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypotension | grade 3, 1.6% | 20 mg/kg single, oral Recommended Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: |
unhealthy, 70.5 years (range: 53–84 years) n = 61 Health Status: unhealthy Condition: primary or recurrent non-muscle-invasive bladder cancer Age Group: 70.5 years (range: 53–84 years) Sex: M+F Population Size: 61 Sources: |
Urticaria | grade 3, 1.6% | 20 mg/kg single, oral Recommended Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: |
unhealthy, 70.5 years (range: 53–84 years) n = 61 Health Status: unhealthy Condition: primary or recurrent non-muscle-invasive bladder cancer Age Group: 70.5 years (range: 53–84 years) Sex: M+F Population Size: 61 Sources: |
Alanine aminotransferase increase | grade 3, 6.6% | 20 mg/kg single, oral Recommended Dose: 20 mg/kg Route: oral Route: single Dose: 20 mg/kg Sources: |
unhealthy, 70.5 years (range: 53–84 years) n = 61 Health Status: unhealthy Condition: primary or recurrent non-muscle-invasive bladder cancer Age Group: 70.5 years (range: 53–84 years) Sex: M+F Population Size: 61 Sources: |
Application site burning | 1 patient Disc. AE |
10 % 1 times / day multiple, topical Recommended Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: Page: p. 44 |
unhealthy n = 384 Health Status: unhealthy Sex: M+F Population Size: 384 Sources: Page: p. 44 |
Application site pain | 1 patient Disc. AE |
10 % 1 times / day multiple, topical Recommended Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: Page: p. 44 |
unhealthy n = 384 Health Status: unhealthy Sex: M+F Population Size: 384 Sources: Page: p. 44 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Multivariate analysis of laryngeal fluorescence spectra recorded in vivo. | 2001 |
|
Multiple biosynthetic pathways for vitamin B12: variations on a central theme. | 2001 |
|
Modulator of heme biosynthesis induces apoptosis in leukemia cells. | 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 |
|
Endoscopic detection of transitional cell carcinoma with 5-aminolevulinic acid: results of 1012 fluorescence endoscopies. | 2001 Apr |
|
Photodynamic therapy vs. cryosurgery of basal cell carcinomas: results of a phase III clinical trial. | 2001 Apr |
|
Porphyric enzymes in hamster Harderian gland, a model of damage by porphyrins and their precursors. A chronobiological study on the role of sex differences. | 2001 Apr 16 |
|
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 |
|
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 |
|
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 |
|
Survival of two patients with severe delta-aminolaevulinic acid dehydratase deficiency porphyria. | 2001 Feb |
|
5-Aminolaevulinic acid methyl ester transport on amino acid carriers in a human colon adenocarcinoma cell line. | 2001 Feb |
|
Photodynamic diagnosis with 5-aminolevulinic acid in the treatment of secondary urethral tumors: first in vitro and in vivo results. | 2001 Feb |
|
Uroporphyria in Hfe mutant mice given 5-aminolevulinate: a new model of Fe-mediated porphyria cutanea tarda. | 2001 Feb |
|
Suppression of the induction of long-term depression by carbon monoxide in rat cerebellar slices. | 2001 Feb |
|
Porphyrin bleaching and PDT-induced spectral changes are irradiance dependent in ALA-sensitized normal rat skin in vivo. | 2001 Jan |
|
Immunological and viral factors associated with the response of vulval intraepithelial neoplasia to photodynamic therapy. | 2001 Jan 1 |
|
[Diagnostic difficulties in acute intermittent porphyria with neurological manifestations: apropos of 2 cases]. | 2001 Jan 1-15 |
|
Photodynamic therapy with 5-aminolevulinic acid induces apoptosis and caspase activation in malignant T cells. | 2001 Jan-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 |
|
Photodynamic therapy of actinic keratoses with topical aminolevulinic acid hydrochloride and fluorescent blue light. | 2001 Jul |
|
Photosensitization and mechanism of cytotoxicity induced by the use of ALA derivatives in photodynamic therapy. | 2001 Jul 20 |
|
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 |
|
Role of 5-aminolevulinic acid in the diagnosis and treatment of superficial bladder cancer: improvement in diagnostic sensitivity. | 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 |
|
Circular permutation of 5-aminolevulinate synthase. Mapping the polypeptide chain to its function. | 2001 Jun 1 |
|
Evidence for direct interaction between enzyme I(Ntr) and aspartokinase to regulate bacterial oligopeptide transport. | 2001 Jun 15 |
|
[Are new treatments always effective ?]. | 2001 Jun-Jul |
|
[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 |
|
Bowen's disease, solar keratoses and superficial basal cell carcinomas treated by photodynamic therapy using a large-field incoherent light source. | 2001 Mar |
|
Endoscopic fluorescence detection of low and high grade dysplasia in Barrett's oesophagus using systemic or local 5-aminolaevulinic acid sensitisation. | 2001 Mar |
|
[Fluorescence cytology of the urinary bladder]. | 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 |
|
Antioxidants inhibit indoleamine 2,3-dioxygenase in IFN-gamma-activated human macrophages: posttranslational regulation by pyrrolidine dithiocarbamate. | 2001 May 15 |
|
Expression of PEPT2 peptide transporter mRNA and protein in glial cells of rat dorsal root ganglia. | 2001 May 25 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Can also be used orally for visualisation of malignant tissue during surgery for malignant glioma (WHO grade III and IV): the recommended dose is 20 mg 5-ALA HCl per kilogram body weight. http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000744/WC500021790.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27764515
Curator's Comment: Glioma cells, seeded at the bottom of 96-well plates and incubated with ALA (10 ug/ml) for 6 h, were exposed to the sinusoidal US pulses with a resonance frequency of 1 MHz, 1000 µs duration, 0.4 duty-cycle, and average acoustic power varying from 2 W to 6 W. Ultrasound waves were generated by a flat circular piezoelectric transducer with a diameter of 25 mm. Cell viability was determined by MTT assay.
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 18:01:22 UTC 2022
by
admin
on
Fri Dec 16 18:01:22 UTC 2022
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Record UNII |
88755TAZ87
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175846
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FDA ORPHAN DRUG |
387312
Created by
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FDA ORPHAN DRUG |
710519
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WHO-ATC |
L01XD04
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NDF-RT |
N0000171207
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CFR |
21 CFR 862.1060
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NCI_THESAURUS |
C1420
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WHO-VATC |
QL01XD04
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NDF-RT |
N0000171207
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NDF-RT |
N0000171207
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FDA ORPHAN DRUG |
811521
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NDF-RT |
N0000171207
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EU-Orphan Drug |
EU/3/16/1811
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88755TAZ87
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17549
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D000622
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AMINOLEVULINIC ACID
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4784
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88755TAZ87
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DTXSID8048490
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C234
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M1713
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SUB12853MIG
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106-60-5
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DB00855
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155002
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ALTERNATIVE | |||
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203-414-1
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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