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 |
MOL RATIO
1 MOL RATIO (average) |
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
Originator
Approval Year
Cmax
AUC
T1/2
Doses
AEs
Sourcing
PubMed
Patents
Sample Use Guides
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