D-Aminolevulinic acid
Clinical data | |
---|---|
ATC code | |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
DrugBank | |
E number | {{#property:P628}} |
ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
Chemical and physical data | |
Formula | C5H9NO3 |
Molar mass | 131.13 g/mol |
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
D-Aminolevulinic acid (dALA or δ-ALA or 5-aminolevulinic acid) is the first compound in the porphyrin synthesis pathway, the pathway that leads to hemoglobin in mammals.
- The presence of δ-aminolevulinic acid in the urine is a key guideline for patients suspected of having porhyria use
- Normal values: <7.5 mg/24h urine in a 20ml urine sample. [1]
In non-photosynthetic eukaryotes such as animals, insects, fungi, and protozoa as well as the α-proteobacteria group of bacteria it is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway.
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 aminotransferase. This pathway is known as the C5 or Beale pathway.[2][3]
Test Indications
- Acute intermittent porphyria
- Chronic hepatic porphyria
- Drug damage to the liver
- Hereditary coproporphyria
- Porphyria variegata
Clinical significance
It elicits synthesis and accumulation of fluorescent porphyrins (protoporphyrin IX) in epithelia and neoplastic tissues, among them malignant gliomas. It is used to visualise tumorous tissue in neurosurgical procedures. Studies [4] have shown that the intraoperative use of this guiding method may reduce the tumour residual volume and prolong progression-free survival in patients suffering from this disease.
dALA is also a photosensitizer for photodynamic therapy.
References
- ↑ Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:77 ISBN 1591032016
- ↑ Beale, Samuel I. (1990) Biosynthesis of the tetrapyrrole pigment precursor, d-aminolevulinic acid, from glutamate. Plant Physiology, 93(4), 1273-1279
- ↑ Willows R.D. (2004) Chlorophylls In: Encylopaedia of Plant and Crop Science. pp 258-262, Ed: Robert M. Goodman. Marcel Dekker Inc, ISBN 0-8247-4268-0
- ↑ Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ (2006). "Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial". Lancet Oncol. 7 (5): 392–401. doi:10.1016/S1470-2045(06)70665-9. PMID 16648043.
See also
- Pages with script errors
- CS1 maint: Multiple names: authors list
- E number from Wikidata
- ECHA InfoCard ID from Wikidata
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Drugs with no legal status
- Articles containing unverified chemical infoboxes
- Biomolecules
- Amines
- Carboxylic acids