Aminolevulinic acid
 |
|
| Clinical data | |
|---|---|
| Trade names | Levulan, NatuALA, others |
| License data | |
| Pregnancy category |
|
| ATC code | |
| Legal status | |
| Legal status |
|
| Identifiers | |
|
|
| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| ECHA InfoCard | 100.003.105 |
| Chemical and physical data | |
| Formula | C5H9NO3 |
| Molar mass | 131.13 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 118 °C (244 °F) |
|
|
|
|
δ-Aminolevulinic acid (also dALA, δ-ALA, 5ALA or 5-aminolevulinic acid), an endogenous non-protein amino acid, is the first compound in the porphyrin synthesis pathway, the pathway that leads to heme in mammals and chlorophyll in plants.
5ALA is used in photo dynamic detection and photo dynamic surgery of cancer.
Being a precursor of a photosensitizer, 5ALA is also used as an add on agent for photodynamic therapy.
Photodynamic detection is the use of photosensitive drugs with a light source of the right wavelength for the detection of cancer, using fluorescence of the drug. 5ALA, or derivatives thereof, can be used to visualize bladder cancer by fluorescence imaging.
Aminolevulinic acid is being studied for photodynamic therapy (PDT) in a number of types of cancer. It is not currently a first line treatment for Barrett's esophagus. It use in brain cancer is currently experimental. It has been studied in a number of gynecological cancers.
It is used to visualise tumorous tissue in neurosurgical procedures. Studies since 2006 have shown that the intraoperative use of this guiding method may reduce the tumour residual volume and prolong progression-free survival in people with malignant gliomas. The US FDA approved aminolevulinic acid hydrochloride (ALA HCL) for this use in 2017.
Side effects may include liver damage and nerve problems.Hyperthermia may also occur. Deaths have also resulted.
In non-photosynthetic eukaryotes such as animals, fungi, and protozoa, as well as the Alphaproteobacteria class of bacteria, it is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway, which occurs in mitochondria.
In plants, algae, bacteria (except for the α-proteobacteria group) and archaea, it is produced from glutamic acid via glutamyl-tRNA and glutamate-1-semialdehyde. The enzymes involved in this pathway are glutamyl-tRNA synthetase, glutamyl-tRNA reductase, and glutamate-1-semialdehyde 2,1-aminomutase. This pathway is known as the C5 or Beale pathway. In most plastid-containing species, glutamyl-tRNA is encoded by a plastid gene, and the transcription, as well as the following steps of C5 pathway, take place in plastids.
...
Wikipedia