Aminolevulinic acid

Identification

Summary

Aminolevulinic acid is a porphyrin precursor used to treat actinic keratosis of the face, scalp, and upper extremities, as well as to visualize a glioma.

Brand Names
Ameluz, Gliolan, Levulan
Generic Name
Aminolevulinic acid
DrugBank Accession Number
DB00855
Background

A compound produced from succinyl-CoA and glycine as an intermediate in heme synthesis. It is used as a photochemotherapy for actinic keratosis. [PubChem]

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 131.1299
Monoisotopic: 131.058243159
Chemical Formula
C5H9NO3
Synonyms
  • 5-ALA
  • 5-Aminolevulinic acid
  • ácido 5-aminolevulínico
  • Aminolevulinic acid
  • dALA
  • δ-ALA
  • δ-aminolevulinic acid
External IDs
  • EINECS 226-679-5
  • NSC 18509

Pharmacology

Indication

As a topical gel, aminolevulinic acid (ALA) is indicated for lesion-directed and field-directed treatment of actinic keratoses (AKs) of mild-to-moderate severity on the face and scalp in combination with photodynamic therapy (PDT) using BF-RhodoLED® lamp, a narrowband, red light illumination source.5 As a topical solution, ALA can also be used for the same indication mentioned previously in addition to AKs of the upper extremities, but in conjunction with blue light illumination using the BLU-U Blue Light Photodynamic Therapy Illuminator.6 Finally, ALA is also available as an oral solution to be used as an adjunct for the visualization of glioma during surgery.7

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofActinic cheilitis••• •••••
Adjunct therapy in treatment ofActinic keratoses of the face••••••••••••••••••••
Adjunct therapy in treatment ofActinic keratoses of the face•••••••••••••••
Adjunct therapy in treatment ofActinic keratoses of the scalp••••••••••••••••••••
Adjunct therapy in treatment ofActinic keratoses of the scalp•••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

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).

TargetActionsOrganism
ADelta-aminolevulinic acid dehydratase
inducer
Humans
Absorption

Oral bioavailability is 50-60%.

Topical gel

Pharmacokinetics (PK) of aminolevulinic acid (ALA) and PpIX was evaluated in a trial of 12 adult subjects with mild to moderate AK with at least 10 AK lesions on the face or forehead. A single dose of one entire tube of ALA (2 grams) was applied under occlusion for 3 hours followed by photodynamic therapy (PDT) to a total area of 20 cm2. The mean ± SD baseline plasma ALA and PpIX concentrations were 20.16 ± 16.53 ng/mL and 3.27 ± 2.40 ng/mL, respectively. In most subjects, an up to 2.5-fold increase of ALA plasma concentrations was observed during the first 3 hours after ALA application. The mean ± SD area under the concentration time curve (AUC0-t) and maximum concentration (Cmax) for baseline corrected ALA (n=12) were 142.83 ± 75.50 ng.h/mL and 27.19 ± 20.02 ng/mL, respectively. The median Tmax (time at which Cmax occurred) was 3 hours.

Topical solution

Two human pharmacokinetic (PK) studies were conducted in subjects with minimally to moderately thick actinic keratoses on the upper extremities, having at least 6 lesions on one upper extremity and at least 12 lesions on the other upper extremity. A single dose comprising of two topical applications of ALA topical solution (each containing 354 mg ALA HCl) were directly applied to the lesions and occluded for 3 hours prior to light treatment.

The first PK study was conducted in 29 subjects and PK parameters of ALA were assessed. The baseline corrected mean ± SD of the maximum concentration (Cmax) of ALA was 249.9 ± 694.5 ng/mL and the median Tmax was 2 hours post dose. The mean ± SD exposure to ALA, as expressed by area under the concentration time curve (AUCt) was 669.9 ± 1610 ng·hr/mL. The mean ± SD elimination half-life (t1/2) of ALA was 5.7 ± 3.9 hours.

A second PK study was conducted in 14 subjects and PK parameters of ALA and PpIX were measured. The baseline corrected PpIX concentrations were negative in at least 50% of samples in 50% (7/14) subjects and AUC could not be estimated reliably. The baseline-corrected mean ± SD of Cmax for ALA and PpIX was 95.6 ± 120.6 ng/mL and 0.95 ± 0.71 ng/mL, respectively. The median Tmax of ALA and PpIX was 2 hours post dose and 12 hours post dose, respectively. The mean AUCt of ALA was 261.1 ± 229.3 ng·hr/mL. The mean ± SD t1/2 of ALA was 8.5 ± 6.7 hours.

Oral solution

In 12 healthy subjects, the absolute bioavailability of ALA following the recommended dose of ALA solution was 100.0% + 1.1 with a range of 78.5% to 131.2%. Maximum ALA plasma concentrations were reached with a median of 0.8 hour (range 0.5 – 1.0 hour).

Volume of distribution

In healthy volunteers, the administration of aminolevulinic acid resulted in a volume of distribution of 9.3 ± 2.8 L intravenously and 14.5 ± 2.5 orally.[11961050]

Protein binding

In in vitro experiments using aminolevulinic acid (ALA) concentrations up to approximately 25% of the maximal concentration that occurs in plasma following the recommended dose of ALA solution, the mean protein binding of ALA was 12%.7

Metabolism

Exogenous aminolevulinic acid (ALA) is metabolized to PpIX, but the fraction of administered ALA that is metabolized to PpIX is unknown. The average plasma AUC of PpIX is less than 6% of that of ALA.7

Route of elimination

In 12 healthy subjects, excretion of parent aminolevulinic acid (ALA) in urine in the 12 hours following administration of the recommended dose of ALA solution was 34 + 8% (mean + std dev) with a range of 27% to 57%.7

Half-life

The mean ± SD elimination half-life (t1/2) of aminolevulinic acid was 5.7 ± 3.9 hours for the topical solution formulation and the mean half-life was 0.9 ± 1.2 hours for the oral solution formulation.6,7 In another pharmacokinetic studies with 6 healthy volunteers using a 128 mg dose, the mean half-life was 0.70 ± 0.18 h after the oral dose and 0.83 ± 0.05 h after the intravenous dose.8

Clearance

Not Available

Adverse Effects
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Toxicity

There are no available human data on aminolevulinic acid (ALA) in pregnant women to inform a drug-associated risk of adverse developmental outcomes. In animal reproduction studies, no adverse developmental effects were observed with oral ALA HCl administration to pregnant rabbits during organogenesis at doses 3 times the maximum recommended human oral dose.7

No carcinogenicity testing has been carried out using ALA. No evidence of mutagenic effects was seen in four studies conducted with ALA to evaluate this potential. In the Salmonella-Escherichia coli/mammalian microsome reverse mutation assay (Ames mutagenicity assay), no increases in the number of revertants were observed with any of the tester strains. In the Salmonella-Escherichia coli/mammalian microsome reverse mutation assay in the presence of solar light radiation (Ames mutagenicity assay with light), ALA did not cause an increase in the number of revertants per plate of any of the tester strains in the presence or absence of simulated solar light. In the L5178Y TK± mouse lymphoma forward mutation assay, ALA was evaluated as negative with and without metabolic activation under the study conditions. PpIX formation was not demonstrated in any of these in vitro studies. In the in vivo mouse micronucleus assay, ALA was considered negative under the study exposure conditions. In contrast, at least one report in the literature has noted genotoxic effects in cultured rat hepatocytes after ALA exposure with PpIX formation. Other studies have documented oxidative DNA damage in vivo and in vitro as a result of ALA exposure.6

No assessment of effects of ALA HCl on fertility has been performed in laboratory animals. It is unknown what effects systemic exposure to ALA HCl might have on fertility or reproductive function.6

Pathways
PathwayCategory
Glycine and Serine MetabolismMetabolic
Porphyrin MetabolismMetabolic
Non-Ketotic HyperglycinemiaDisease
SarcosinemiaDisease
Acute Intermittent PorphyriaDisease
Porphyria Variegata (PV)Disease
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
Hereditary Coproporphyria (HCP)Disease
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
Dimethylglycine Dehydrogenase DeficiencyDisease
Hyperglycinemia, Non-KetoticDisease
3-Phosphoglycerate Dehydrogenase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AmbroxolThe risk or severity of methemoglobinemia can be increased when Aminolevulinic acid is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Aminolevulinic acid is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Aminolevulinic acid is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Aminolevulinic acid is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Aminolevulinic acid is combined with Bupivacaine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Aminolevulinic acid hydrochlorideV35KBM8JGR5451-09-2ZLHFONARZHCSET-UHFFFAOYSA-N
International/Other Brands
Levulan (DUSA Pharmaceuticals, Inc.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AmeluzGel100 mg/1gTopicalBiofrontera Inc.2016-08-26Not applicableUS flag
AmeluzGel78 mg/gCutaneousBiofrontera Bioscience Gmb H2016-09-08Not applicableEU flag
GleolanPowder, for solution1500 mg/1OralNx Development Corp2018-03-14Not applicableUS flag
GleolanPowder, for solution1500 mg/1OralMedexus Pharma, Inc.2018-04-14Not applicableUS flag
GleolanPowder, for solution1.5 g / vialOralMedexus Inc2021-02-22Not applicableCanada flag

Categories

ATC Codes
L01XD04 — Aminolevulinic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Delta amino acids and derivatives
Alternative Parents
Gamma-keto acids and derivatives / Short-chain keto acids and derivatives / Alpha-amino ketones / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Alpha-aminoketone / Amine / Amino acid / Carbonyl group / Carboxylic acid / Delta amino acid or derivatives / Gamma-keto acid / Hydrocarbon derivative / Keto acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
delta-amino acid, 4-oxo monocarboxylic acid (CHEBI:17549) / Amino fatty acids (LMFA01100055)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
88755TAZ87
CAS number
106-60-5
InChI Key
ZGXJTSGNIOSYLO-UHFFFAOYSA-N
InChI
InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
IUPAC Name
5-amino-4-oxopentanoic acid
SMILES
NCC(=O)CCC(O)=O

References

Synthesis Reference

Takashi Ebata, Hiroshi Kawakami, Katsuya Matsumoto, Koshi Koseki, Hajime Matsushita, "Method of preparing an acid additional salt of delta-aminolevulinic acid." U.S. Patent US5284973, issued July, 1974.

US5284973
General References
  1. Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ: Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial. Lancet Oncol. 2006 May;7(5):392-401. [Article]
  2. Kennedy JC, Marcus SL, Pottier RH: Photodynamic therapy (PDT) and photodiagnosis (PD) using endogenous photosensitization induced by 5-aminolevulinic acid (ALA): mechanisms and clinical results. J Clin Laser Med Surg. 1996 Oct;14(5):289-304. [Article]
  3. Dalton JT, Yates CR, Yin D, Straughn A, Marcus SL, Golub AL, Meyer MC: Clinical pharmacokinetics of 5-aminolevulinic acid in healthy volunteers and patients at high risk for recurrent bladder cancer. J Pharmacol Exp Ther. 2002 May;301(2):507-12. doi: 10.1124/jpet.301.2.507. [Article]
  4. FDA Approved Drug Products: AMELUZ (aminolevulinic acid hydrochloride) topical gel, 10% (October 2023) [Link]
  5. FDA Approved Drug Products: AMELUZ (aminolevulinic acid hydrochloride) gel, 10%, for topical use [Link]
  6. FDA Approved Drug Products: LEVULAN KERASTICK (aminolevulinic acid HCl) for topical solution, 20% [Link]
  7. FDA Approved Drug Products: GLEOLAN [aminolevulinic acid hydrochloride (ALA HCl)] for oral solution [Link]
  8. FDA Approved Drug Products: LEVULAN®KERASTICK™ (aminolevulinic acid HCl) for Topical Solution, 20% [Link]
Human Metabolome Database
HMDB0001149
KEGG Compound
C00430
PubChem Compound
137
PubChem Substance
46506856
ChemSpider
134
BindingDB
50240386
RxNav
155002
ChEBI
356416
ChEMBL
CHEMBL601
ZINC
ZINC000003782550
Therapeutic Targets Database
DAP000314
PharmGKB
PA10015
PDBe Ligand
FVT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Aminolevulinic_acid
PDB Entries
6h7u / 6hzp
FDA label
Download (195 KB)
MSDS
Download (72.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentActinic Cheilitis1
4CompletedTreatmentActinic Keratosis (AK)2
4CompletedTreatmentActinic Keratosis (AK) / Natural Daylight Photodynamic Therapy1
4CompletedTreatmentHutchinson's Melanotic Freckle1
4CompletedTreatmentMultiple Actinic Keratoses1

Pharmacoeconomics

Manufacturers
  • Dusa pharmaceuticals inc
Packagers
  • Dusa Pharmaceuticals
Dosage Forms
FormRouteStrength
PatchTopical8 MG
Plaster8 mg
GelCutaneous78 mg/g
GelTopical100 mg/1g
Powder, for solutionOral1.5 g / vial
Powder, for solutionOral1500 mg/1
Powder, for solutionOral30 mg/ml
Kit; powder, for solutionTopical354 mg/1.5mL
Powder, for solutionTopical20 %
Prices
Unit descriptionCostUnit
Levulan kerastick170.25USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5422093No1995-06-062009-07-28US flag
US5954703No1999-09-212017-10-31US flag
US6709446No2004-03-232018-05-01US flag
US7723910No2010-05-252019-06-17US flag
US8216289No2012-07-102018-05-01US flag
US8758418No2014-06-242018-05-01US flag
US6559183No2003-05-062019-11-12US flag
US10357567No2019-07-232038-01-12US flag
US11077192No2021-08-032038-01-12US flag
US11135293No2021-10-052038-01-12US flag
US11235169No2020-10-152040-10-15US flag
US11540981No2008-02-072028-02-07US flag
US11571478No2018-01-122038-01-12US flag
US11690914No2018-01-122038-01-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)156-158 °CNot Available
water solubilityVery solubleNot Available
logP-1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility173.0 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.3Chemaxon
logS0.12ALOGPS
pKa (Strongest Acidic)4.05Chemaxon
pKa (Strongest Basic)7.84Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area80.39 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity30.45 m3·mol-1Chemaxon
Polarizability12.55 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9162
Blood Brain Barrier+0.7482
Caco-2 permeable-0.7802
P-glycoprotein substrateNon-substrate0.6653
P-glycoprotein inhibitor INon-inhibitor0.9515
P-glycoprotein inhibitor IINon-inhibitor0.7522
Renal organic cation transporterNon-inhibitor0.9017
CYP450 2C9 substrateNon-substrate0.8819
CYP450 2D6 substrateNon-substrate0.8314
CYP450 3A4 substrateNon-substrate0.7939
CYP450 1A2 substrateNon-inhibitor0.9219
CYP450 2C9 inhibitorNon-inhibitor0.9561
CYP450 2D6 inhibitorNon-inhibitor0.9608
CYP450 2C19 inhibitorNon-inhibitor0.9406
CYP450 3A4 inhibitorNon-inhibitor0.9187
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9784
Ames testNon AMES toxic0.8884
CarcinogenicityNon-carcinogens0.8377
BiodegradationReady biodegradable0.9445
Rat acute toxicity1.1726 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9186
hERG inhibition (predictor II)Non-inhibitor0.8944
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0fki-2910000000-12bd38ce6e25c61b8e60
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00dr-4900000000-c11a861a1638dd2c20d8
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00dr-2911000000-d5b5567862328f5a46cd
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00dr-3900000000-538e027ec9932b3f56a5
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)GC-MSsplash10-00di-9500000000-c0d571fa1aa74cf69ea6
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS; 1 MEOX)GC-MSsplash10-00di-9600000000-d0a9f31de64870117dfe
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-00di-1911000000-117a44ade2fd70812e5c
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-00dr-2900000000-635a7d4012b9ef5150f9
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-9000000000-b1941f10190ebb6e1343
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fki-2910000000-12bd38ce6e25c61b8e60
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-4900000000-c11a861a1638dd2c20d8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-2911000000-d5b5567862328f5a46cd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-3900000000-538e027ec9932b3f56a5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9500000000-c0d571fa1aa74cf69ea6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9600000000-d0a9f31de64870117dfe
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-1911000000-117a44ade2fd70812e5c
GC-MS Spectrum - GC-MSGC-MSsplash10-00dr-2900000000-635a7d4012b9ef5150f9
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0udi-5900000000-cf9a0266243b1a1d0f73
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000i-9000000000-995eb11961b16f254be2
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0fb9-9000000000-64b1ef51cceb8d346f52
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-01q9-1900000000-a5686c059e357bc14e96
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-9300000000-8e219c18bb0fd0837d82
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0avr-9000000000-b0d0d9b25a36e5c49f2a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a4i-9000000000-96cc61ad07db2c38c952
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0a4i-9000000000-7b8165e702ac7e6d5f34
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-01p9-8900000000-0b739a89ed524e47e3a2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-1ffb96adb6268888f722
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-1ffb96adb6268888f722
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-1900000000-a5686c059e357bc14e96
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-9300000000-8e219c18bb0fd0837d82
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0avr-9000000000-1815084304ee39158706
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-aa34f5a936aed90b0dcf
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-9000000000-7b8165e702ac7e6d5f34
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01p9-8900000000-0b739a89ed524e47e3a2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01qi-5900000000-573b2d0e58e1b3691feb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p9-9500000000-470318e0f465172ca30b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aor-9000000000-d3d78a662cd0621435c9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ap0-9000000000-ecac678901fc3ba11991
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-1515a9d989ff97c41c92
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-77a3202f19a380737553
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-126.8395
predicted
DarkChem Lite v0.1.0
[M-H]-126.8794
predicted
DarkChem Lite v0.1.0
[M-H]-124.17047
predicted
DeepCCS 1.0 (2019)
[M+H]+127.9837
predicted
DarkChem Lite v0.1.0
[M+H]+127.6611
predicted
DarkChem Lite v0.1.0
[M+H]+126.991
predicted
DeepCCS 1.0 (2019)
[M+Na]+126.8661
predicted
DarkChem Lite v0.1.0
[M+Na]+126.9513
predicted
DarkChem Lite v0.1.0
[M+Na]+135.49904
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Zinc ion binding
Specific Function
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
Gene Name
ALAD
Uniprot ID
P13716
Uniprot Name
Delta-aminolevulinic acid dehydratase
Molecular Weight
36294.485 Da
References
  1. Sakai T: Biomarkers of lead exposure. Ind Health. 2000 Apr;38(2):127-42. [Article]
  2. Vajpayee P, Tripathi RD, Rai UN, Ali MB, Singh SN: Chromium (VI) accumulation reduces chlorophyll biosynthesis, nitrate reductase activity and protein content in Nymphaea alba L. Chemosphere. 2000 Oct;41(7):1075-82. [Article]
  3. Tomas-Zapico C, Martinez-Fraga J, Rodriguez-Colunga MJ, Tolivia D, Hardeland R, Coto-Montes A: Melatonin protects against delta-aminolevulinic acid-induced oxidative damage in male Syrian hamster Harderian glands. Int J Biochem Cell Biol. 2002 May;34(5):544-53. [Article]
  4. Frere F, Schubert WD, Stauffer F, Frankenberg N, Neier R, Jahn D, Heinz DW: Structure of porphobilinogen synthase from Pseudomonas aeruginosa in complex with 5-fluorolevulinic acid suggests a double Schiff base mechanism. J Mol Biol. 2002 Jul 5;320(2):237-47. [Article]
  5. Flora SJ, Kannan GM, Pant BP, Jaiswal DK: Combined administration of oxalic acid, succimer and its analogue for the reversal of gallium arsenide-induced oxidative stress in rats. Arch Toxicol. 2002 Jun;76(5-6):269-76. Epub 2002 Apr 23. [Article]
  6. Akagi R, Yasui Y, Harper P, Sassa S: A novel mutation of delta-aminolaevulinate dehydratase in a healthy child with 12% erythrocyte enzyme activity. Br J Haematol. 1999 Sep;106(4):931-7. [Article]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Terada T, Sawada K, Irie M, Saito H, Hashimoto Y, Inui K: Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2. Pflugers Arch. 2000 Sep;440(5):679-84. [Article]
  2. Doring F, Walter J, Will J, Focking M, Boll M, Amasheh S, Clauss W, Daniel H: Delta-aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications. J Clin Invest. 1998 Jun 15;101(12):2761-7. [Article]
  3. Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Doring F, Walter J, Will J, Focking M, Boll M, Amasheh S, Clauss W, Daniel H: Delta-aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications. J Clin Invest. 1998 Jun 15;101(12):2761-7. [Article]
  2. Terada T, Sawada K, Irie M, Saito H, Hashimoto Y, Inui K: Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2. Pflugers Arch. 2000 Sep;440(5):679-84. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55