DT-Web

DB00855 - Aminolevulinic acid


Identification
Name Aminolevulinic acid
Accession Number DB00855 (APRD00793, DB05277)
Type small molecule
Description A compound produced from succinyl-CoA and glycine as an intermediate in heme synthesis. It is used as a photochemotherapy for actinic keratosis. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 131.1299
Groups approved
Monoisotopic Weight 131.058243159
Pharmacology
Indication Aminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.
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).
Absorption Oral bioavailability is 50-60%.
Protein binding Not Available
Biotransformation Following topical administration, synthesis into protoporphyrin IX takes place in situ in the skin.
Route of elimination Not Available
Toxicity Solution overdose have not been reported.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Delta-aminolevulinic acid dehydratase
Name Delta-aminolevulinic acid dehydratase
Gene Name ALAD
Pharmacological action yes
Actions inducer
References
  • Sakai T: Biomarkers of lead exposure. Ind Health. 2000 Apr;38(2):127-42. - Pubmed
  • 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. - Pubmed
  • 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. - Pubmed
  • 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. - Pubmed
  • 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. - Pubmed
  • 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. - Pubmed
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 1.3761

Transporters


Oligopeptide transporter, small intestine isoform
Name Oligopeptide transporter, small intestine isoform
Gene Name SLC15A1
Actions inhibitor
References
  • 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. - Pubmed
  • 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. - Pubmed
  • 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. - Pubmed
  • 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. - Pubmed
  • 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. - Pubmed
DTHybrid score 0.5175
Oligopeptide transporter, kidney isoform
Name Oligopeptide transporter, kidney isoform
Gene Name SLC15A2
Actions inhibitor
References
  • 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. -
  • 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. - Pubmed
DTHybrid score 0.5073

Predictions


Id Partner name Gene Name Score
2356 Delta-aminolevulinic acid dehydratase hemB 1.3761
3613 Delta-aminolevulinic acid dehydratase hemB 1.3761
3674 Delta-aminolevulinic acid dehydratase hemB 1.3761
244 Angiotensin-converting enzyme ACE 0.1747
633 Penicillin-binding proteins 1A/1B pbpA 0.1007
383 Glycine amidinotransferase, mitochondrial GATM 0.0998
118 Organic cation/carnitine transporter 2 SLC22A5 0.0813
1729 Solute carrier family 22 member 6 SLC22A6 0.071
1 Peptidoglycan synthetase ftsI ftsI 0.0442
4155 Peptidoglycan synthetase ftsI ftsI 0.0442
645 Penicillin-binding protein 1A mrcA 0.0413
5805 Penicillin-binding protein 1A ponA 0.0413
6185 Penicillin-binding protein 1A mrcA 0.0413
6799 Penicillin-binding protein 1A pbpA 0.0413
6142 Solute carrier family 22 member 8 SLC22A8 0.037
471 Sodium- and chloride-dependent neutral and basic amino acid transporter B(0+) SLC6A14 0.036
1385 Angiotensin-converting enzyme 2 ACE2 0.035
587 Serum albumin ALB 0.0315
543 Penicillin-binding protein 1B mrcB 0.0309
6186 Penicillin-binding protein 1B ponB 0.0309
6822 Penicillin-binding protein 1b pbp1b 0.0309
6844 Penicillin-binding protein 1b pbp1b 0.0309
1588 Multidrug resistance protein 1 ABCB1 0.028
234 Plasminogen PLG 0.0246
1757 Myeloperoxidase MPO 0.0242
115 Penicillin-binding protein 2 mrdA 0.0235
6069 Penicillin-binding protein 2 mrdA 0.0235
6118 Penicillin-binding protein 2 penA 0.0235
6187 Penicillin-binding protein 2 pbpA 0.0235
6686 Penicillin-binding protein 2 pbp2 0.0235
6939 Penicillin-binding protein 2 mrdA 0.0235
7163 Penicillin-binding protein 2 pbpA 0.0235
6067 Penicillin binding protein 2a mecA 0.0233
3923 Cholinesterase BCHE 0.0203
230 ATP-binding cassette transporter sub-family C member 8 ABCC8 0.0203
2544 Bacterial leucyl aminopeptidase Not Available 0.0198
1024 Solute carrier family 22 member 11 SLC22A11 0.0197
4512 Cytochrome P450 3A4 CYP3A4 0.0178
4604 Liver carboxylesterase 1 CES1 0.0175
6016 Cytochrome P450 2C19 CYP2C19 0.0172
3917 Methylenetetrahydrofolate reductase MTHFR 0.0164
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0155
3060 Leukotriene A-4 hydrolase LTA4H 0.0149
6143 Solute carrier family 22 member 7 SLC22A7 0.0135
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.013
4119 Cytochrome P450 2D6 CYP2D6 0.0127
159 Penicillin-binding protein 2B penA 0.0123
6121 Penicillin-binding protein 2B penA 0.0123
4252 Penicillin-binding protein 5 dacA 0.0117
4757 Cytochrome P450 2C9 CYP2C9 0.0117
738 Monocarboxylate transporter 1 SLC16A1 0.0104
332 Beta-lactamase blaZ 0.0102
2478 Beta-lactamase ampC 0.0102
2613 Beta-lactamase ampC 0.0102
2635 Beta-lactamase ampC 0.0102
2700 Beta-lactamase penP 0.0102
5445 Beta-lactamase blaB 0.0102
6019 Beta-lactamase SHV-7 0.0102
6701 Beta-lactamase cphA 0.0102
509 Thymidine kinase TK 0.0101
570 Thymidine kinase TK 0.0101
2559 Thymidine kinase TK 0.0101
3430 Thymidine kinase tdk 0.0101
3518 Thymidine kinase TK 0.0101
5301 Thymidine kinase tdk 0.0101
5771 Thymidine kinase ORF36 0.0101
7009 Thymidine kinase ORF36 0.0101
3810 Catechol O-methyltransferase COMT 0.0092
3760 Penicillin-binding protein 5 precursor dacA 0.0091
709 ATP-sensitive inward rectifier potassium channel 1 KCNJ1 0.0089
3426 Glutamine synthetase glnA 0.0089
3987 Glutamine synthetase GLUL 0.0089
6184 D-alanyl-D-alanine carboxypeptidase dacC dacC 0.0088
338 DNA polymerase UL30 0.0087
379 DNA polymerase UL54 0.0087
697 DNA polymerase ORF28 0.0087
2482 DNA polymerase 43 0.0087
4104 DNA polymerase BALF5 0.0087
6140 Ileal sodium/bile acid cotransporter SLC10A2 0.0084
867 Penicillin-binding protein 3 pbpC 0.0083
6119 Penicillin-binding protein 3 pbp3 0.0083
7154 Penicillin-binding protein 3 pbp3 0.0083
7157 Penicillin-binding protein 3 LMHCC_2184 0.0083
7162 Penicillin-binding protein 3 pbpB 0.0083
7172 Penicillin-binding protein 3 pbp3 0.0083
6113 MecA PBP2' (penicillin binding protein 2') mecA 0.0082
20 Prostaglandin G/H synthase 1 PTGS1 0.0078
318 Alpha-2A adrenergic receptor ADRA2A 0.0071
1141 Sialidase-1 NEU1 0.0068
64 Neuraminidase NA 0.0068
641 Neuraminidase NA 0.0068
2676 Neuraminidase NA 0.0068
3026 Neuraminidase NA 0.0068
3519 Neuraminidase NA 0.0068
6007 Neuraminidase NA 0.0068
2164 Multidrug resistance-associated protein 4 ABCC4 0.0063
6160 Solute carrier organic anion transporter family member 3A1 SLCO3A1 0.006
6154 Multidrug and toxin extrusion protein 1 SLC47A1 0.0059
6153 Solute carrier organic anion transporter family member 4A1 SLCO4A1 0.0059
632 Alpha-1B adrenergic receptor ADRA1B 0.0056
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0054
5482 Sialidase-2 NEU2 0.0052
556 Alpha-1A adrenergic receptor ADRA1A 0.005
6106 Cytochrome P450 2C18 CYP2C18 0.0048
707 72 kDa type IV collagenase MMP2 0.0048
833 Organic cation/carnitine transporter 1 SLC22A4 0.0048
2461 D-alanyl-D-alanine carboxypeptidase Not Available 0.0046
5756 D-alanyl-D-alanine carboxypeptidase dac 0.0046
3961 G protein-activated inward rectifier potassium channel 4 KCNJ5 0.0046
4924 Cytochrome P450 2C8 CYP2C8 0.0043
65 Matrix metalloproteinase-9 Not Available 0.0039
521 ATP-binding cassette transporter sub-family C member 9 ABCC9 0.0038
132 ATP-binding cassette sub-family A member 1 ABCA1 0.0035
2184 Cystic fibrosis transmembrane conductance regulator CFTR 0.0034
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0033
4118 Cytochrome P450 3A5 CYP3A5 0.0033
866 Large neutral amino acids transporter small subunit 2 SLC7A8 0.0032
238 Peroxisome proliferator-activated receptor gamma PPARG 0.0031
1181 Alpha-1-acid glycoprotein 1 ORM1 0.003
781 ATP-sensitive inward rectifier potassium channel 11 KCNJ11 0.003
245 Large neutral amino acids transporter small subunit 1 SLC7A5 0.0029
3876 Aromatic-L-amino-acid decarboxylase DDC 0.0029
6107 Cytochrome P450 3A7 CYP3A7 0.0024
163 D(1B) dopamine receptor DRD5 0.0024
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0023
432 D(4) dopamine receptor DRD4 0.0023
638 D(3) dopamine receptor DRD3 0.0022
6151 Monocarboxylate transporter 10 SLC16A10 0.0022
776 Bile salt export pump ABCB11 0.0022
862 Multidrug resistance-associated protein 1 ABCC1 0.002
23 D(1A) dopamine receptor DRD1 0.002
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0019
831 D(2) dopamine receptor DRD2 0.0018
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0018
631 3-hydroxy-3-methylglutaryl-coenzyme A reductase HMGCR 0.0017
3387 3-hydroxy-3-methylglutaryl-coenzyme A reductase mvaA 0.0017
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0015
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0014
6157 Solute carrier organic anion transporter family member 1B3 SLCO1B3 0.0014
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0014
6024 Cytochrome P450 1A1 CYP1A1 0.0011
6030 Cytochrome P450 2B6 CYP2B6 0.0011
4200 Cytochrome P450 1A2 CYP1A2 0.0009
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