Aminolevulinic acid

δ-Aminolevulinic acid
Clinical data
Trade names	Levulan, NatuALA, Ameluz, others
Other names	5-aminolevulinic acid
AHFS/Drugs.com	Monograph
MedlinePlus	a607062
License data	US DailyMed: Aminolevulinic acid;
Routes of; administration	Topical, By mouth
ATC code	L01XD04 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Identifiers
	IUPAC name 5-Amino-4-oxo-pentanoic acid;
CAS Number	106-60-5 ;
PubChem CID	137;
IUPHAR/BPS	4784;
DrugBank	DB00855 ;
ChemSpider	134 ;
UNII	88755TAZ87;
KEGG	D07567 ;
ChEBI	CHEBI:356416 ;
ChEMBL	ChEMBL601 ;
CompTox Dashboard (EPA)	DTXSID8048490 ;
ECHA InfoCard	100.003.105
Chemical and physical data
Formula	C5H9NO3
Molar mass	131.131 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	118 °C (244 °F)
	SMILES O=C(CN)CCC(=O)O;
	InChI InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9) ; Key:ZGXJTSGNIOSYLO-UHFFFAOYSA-N ;
	(verify)

δ-Aminolevulinic acid (also dALA, δ-ALA, 5ALA or 5-aminolevulinic acid), an endogenous non-proteinogenic amino acid, is the first compound in the porphyrin synthesis pathway, the pathway that leads to heme^[3] in mammals, as well as chlorophyll^[4] in plants.

5ALA is used in photodynamic detection and surgery of cancer.^[5]^[6]^[7]^[8]

^ "Levulan Kerastick Product information". Health Canada. 25 April 2012. Retrieved 4 June 2022.
^ "Gleolan Product information". Health Canada. 25 April 2012. Retrieved 4 June 2022.
^ Gardener LC, Cox TM (1988). "Biosynthesis of heme in immature erythroid cells". The Journal of Biological Chemistry. 263: 6676–6682. doi:10.1016/S0021-9258(18)68695-8.
^ Von Wettstein D, Gough S, Kannangara CG (July 1995). "Chlorophyll Biosynthesis". The Plant Cell. 7 (7): 1039–1057. doi:10.1105/tpc.7.7.1039. PMC 160907. PMID 12242396.
^ Wagnières, G.., Jichlinski, P., Lange, N., Kucera, P., Van den Bergh, H. (2014). Detection of Bladder Cancer by Fluorescence Cystoscopy: From Bench to Bedside - the Hexvix Story. Handbook of Photomedicine, 411-426.
^ Eyüpoglu IY, Buchfelder M, Savaskan NE (March 2013). "Surgical resection of malignant gliomas-role in optimizing patient outcome". Nature Reviews. Neurology. 9 (3): 141–151. doi:10.1038/nrneurol.2012.279. PMID 23358480. S2CID 20352840.
^ Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ (May 2006). "Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial". The Lancet. Oncology. 7 (5): 392–401. doi:10.1016/s1470-2045(06)70665-9. PMID 16648043.
^ Eyüpoglu IY, Hore N, Savaskan NE, Grummich P, Roessler K, Buchfelder M, et al. (2012). "Improving the extent of malignant glioma resection by dual intraoperative visualization approach". PLOS ONE. 7 (9): e44885. Bibcode:2012PLoSO...744885E. doi:10.1371/journal.pone.0044885. PMC 3458892. PMID 23049761.

[1] "Levulan Kerastick Product information". Health Canada. 25 April 2012. Retrieved 4 June 2022.

[2] "Gleolan Product information". Health Canada. 25 April 2012. Retrieved 4 June 2022.

[Gardener1988-3] Gardener LC, Cox TM (1988). "Biosynthesis of heme in immature erythroid cells". The Journal of Biological Chemistry. 263: 6676–6682. doi:10.1016/S0021-9258(18)68695-8.

[Wettstein1995-4] Von Wettstein D, Gough S, Kannangara CG (July 1995). "Chlorophyll Biosynthesis". The Plant Cell. 7 (7): 1039–1057. doi:10.1105/tpc.7.7.1039. PMC 160907. PMID 12242396.

[Wagnières2014-5] Wagnières, G.., Jichlinski, P., Lange, N., Kucera, P., Van den Bergh, H. (2014). Detection of Bladder Cancer by Fluorescence Cystoscopy: From Bench to Bedside - the Hexvix Story. Handbook of Photomedicine, 411-426.

[Eyüpoglu2013-6] Eyüpoglu IY, Buchfelder M, Savaskan NE (March 2013). "Surgical resection of malignant gliomas-role in optimizing patient outcome". Nature Reviews. Neurology. 9 (3): 141–151. doi:10.1038/nrneurol.2012.279. PMID 23358480. S2CID 20352840.

[StummerW2006-7] Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ (May 2006). "Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial". The Lancet. Oncology. 7 (5): 392–401. doi:10.1016/s1470-2045(06)70665-9. PMID 16648043.

[Eyüpoglu2012-8] Eyüpoglu IY, Hore N, Savaskan NE, Grummich P, Roessler K, Buchfelder M, et al. (2012). "Improving the extent of malignant glioma resection by dual intraoperative visualization approach". PLOS ONE. 7 (9): e44885. Bibcode:2012PLoSO...744885E. doi:10.1371/journal.pone.0044885. PMC 3458892. PMID 23049761.

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