Details of the Drug

General Information of Drug (ID: DMS4BLQ)

Drug Name
Aminolevulinic acid hci
Synonyms
Aminolevulinic acid; 5-Aminolevulinic acid; 5-Amino-4-oxopentanoic acid; 106-60-5; 5-Aminolevulinate; delta-aminolevulinic acid; Pentanoic acid, 5-amino-4-oxo-; Aladerm; 5-Amino-4-oxovaleric acid; Kerastick; Ameluz; Aminolevulinate; 5-ALA; delta-ALA; 5-Amino-4-oxopentanoate; 5-amino-levulinate; 5-amino-levulinic acid; 5-amino-4-oxo-pentanoic acid; CCRIS 8958; UNII-88755TAZ87; EINECS 203-414-1; Levulinic acid, 5-amino-; CHEMBL601; 4-oxo-5-amino-pentanoic acid; CHEBI:17549; ZGXJTSGNIOSYLO-UHFFFAOYSA-N; 88755TAZ87; Levulan (TN)
Indication
Disease Entry ICD 11 Status REF
Acne vulgaris ED80 Approved [1]
Actinic keratosis EK90.0 Approved [2]
Astrocytoma 2A00.0Y Approved [3]
Glioblastoma 2A00 Approved [4]
Malignant glioma 2A00.0 Approved [5]
Oral mucosa leukoplakia N.A. Approved [6]
Adult glioblastoma N.A. Investigative [7]
Cervical Intraepithelial neoplasia 2E66.1 Investigative [8]
⏷ Show the Full List of Indication(s)
Affected Organisms
Humans and other mammals
ATC Code
L01XD04: Aminolevulinic acid hci
L01XD: Sensitizers used in photodynamic/radiation therapy
L01X: OTHER ANTINEOPLASTIC AGENTS
L01: ANTINEOPLASTIC AGENTS
L: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 131.13
Logarithm of the Partition Coefficient (xlogp) -3.8
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Bioavailability
The bioavailability of drug is 50-60% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.88 mL/min/kg [9]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.70 +/-0.18 hours [9]
Metabolism
The drug is metabolized via skin []
Unbound Fraction
The unbound fraction of drug in plasma is 0.88% [9]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.12 L/kg [9]
Chemical Identifiers
Formula
C5H9NO3
IUPAC Name
5-amino-4-oxopentanoic acid
Canonical SMILES
C(CC(=O)O)C(=O)CN
InChI
InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
InChIKey
ZGXJTSGNIOSYLO-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
137
ChEBI ID
CHEMBL601
CAS Number
106-60-5
UNII
88755TAZ87
DrugBank ID
DB00855
TTD ID
D0Y7ZD
VARIDT ID
DR00057
INTEDE ID
DR0088
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Delta-aminolevulinic acid dehydratase (ALAD) TTJHKYD HEM2_HUMAN Inhibitor [10]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 2 (SLC15A2) DT8QKNP S15A2_HUMAN Substrate [11]
Proton-coupled amino acid transporter 1 (SLC36A1) DT48WEM S36A1_HUMAN Substrate [12]
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [13]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Porphobilinogen synthase (ALAD)
Main DME 		DETBNY4 HEM2_HUMAN Substrate [14]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
FAS-associated death domain protein (FADD) OTV7GFHH FADD_HUMAN Post-Translational Modifications [15]
Interstitial collagenase (MMP1) OTI4I2V1 MMP1_HUMAN Gene/Protein Processing [16]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [15]
Stromelysin-1 (MMP3) OTGBI74Z MMP3_HUMAN Gene/Protein Processing [16]
Transcription factor p65 (RELA) OTUJP9CN TF65_HUMAN Protein Interaction/Cellular Processes [15]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4784).
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Physical approaches to treat glioblastoma. Curr Opin Oncol. 2020 Nov;32(6):640-649.
4 Comparison of commercial 5-aminolevulinic acid (Gliolan?) and the pharmacy-compounded solution fluorescence in glioblastoma. Acta Neurochir (Wien). 2019 Aug;161(8):1733-1741.
5 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.
6 Vascular alterations after photodynamic therapy mediated by 5-aminolevulinic acid in oral leukoplakia. Lasers Med Sci. 2017 Feb;32(2):379-387.
7 5-Aminolevulinic acid-guided resection improves the overall survival of patients with glioblastoma-a comparative cohort study of 343 patients. Neurooncol Adv. 2021 Mar 26;3(1):vdab047.
8 Photodetection and Safety of 5-Aminolevulinic Acid-Induced Porphyrin in Patients With Cervical Intraepithelial Neoplasia. Lasers Surg Med. 2021 Jul;53(5):654-663.
9 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
10 Exploring proteomes and analyzing protein processing by mass spectrometric identification of sorted N-terminal peptides. Nat Biotechnol. 2003 May;21(5):566-9.
11 PEPT2-mediated transport of 5-aminolevulinic acid and carnosine in astrocytes. Brain Res. 2006 Nov 29;1122(1):18-23.
12 Delta-aminolevulinic acid is a substrate for the amino acid transporter SLC36A1 (hPAT1). Br J Pharmacol. 2010 Mar;159(6):1339-53.
13 Transport of the photodynamic therapy agent 5-aminolevulinic acid by distinct H+-coupled nutrient carriers coexpressed in the small intestine. J Pharmacol Exp Ther. 2010 Jan;332(1):220-8.
14 Modifying effects of delta-Aminolevulinate dehydratase polymorphism on blood lead levels and ALAD activity. Toxicol Lett. 2018 Oct 1;295:351-356.
15 5-aminolevulinic acid induce apoptosis via NF-B/JNK pathway in human oral cancer Ca9-22 cells. J Oral Pathol Med. 2011 Jul;40(6):483-9. doi: 10.1111/j.1600-0714.2010.00973.x. Epub 2010 Dec 8.
16 Influence of 5-aminolevulinic acid and red light on collagen metabolism of human dermal fibroblasts. J Invest Dermatol. 2003 Feb;120(2):325-31. doi: 10.1046/j.1523-1747.2003.12037.x.