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Aminolevulinic acid

Catalog No. DB00855 Name DrugBank
CAS Number 106-60-5 Website http://www.ualberta.ca/
M. F. C5H9NO3 Telephone (780) 492-3111
M. W. 131.12986 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 733

SYNONYMS

IUPAC name
5-amino-4-oxopentanoic acid
IUPAC Traditional name
aminolevulinic acid
Brand Name
Aladerm
Levulan
Levulan Kerastick
Kerastick
Synonyms
Aminolevulinate
ALA
delta-Aminolevulinic acid

DATABASE IDS

PubChem CID 137
CAS Number 106-60-5
PubChem SID 46506856

PROPERTIES

Hydrophobicity(logP) -1.5
Solubility Very soluble

DETAILS

Description (English)
Item Information
Drug Groups approved
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]
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.
Pharmacology 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.
Toxicity Solution overdose have not been reported.
Affected Organisms
Humans and other mammals
Biotransformation Following topical administration, synthesis into protoporphyrin IX takes place in situ in the skin.
Absorption Oral bioavailability is 50-60%.
Half Life Mean half-life is 0.70 ± 0.18 h after the oral dose and 0.83 ± 0.05 h after the intravenous dose.
References
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. [Pubmed]
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. [Pubmed]
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REFERENCES

  • 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. Pubmed
  • 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. Pubmed