MedKoo Biosciences

Aminolevulinic Acid HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 100054

CAS#: 5451-09-2 (HCl)

Description: Aminolevulinic acid, also known as ALA, is a topically administered metabolic precursor of protoporphyrin IX. After topical administration, aminolevulinic acid (ALA) is converted to protoporphyrin IX (PpIX) which is a photosensitizer. When the proper wavelength of light activates protoporphyrin IX, singlet oxygen is produced, resulting in a local cytotoxic effect. In 1999, FDA approved this drug for for actinic keratosis.

Chemical Structure

Aminolevulinic Acid HCl

CAS# 5451-09-2 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100054
Name: Aminolevulinic Acid HCl
CAS#: 5451-09-2 (HCl)
Chemical Formula: C5H10ClNO3
Exact Mass: 0.00
Molecular Weight: 167.590
Elemental Analysis: C, 35.83; H, 6.01; Cl, 21.15; N, 8.36; O, 28.64

Price and Availability

Size	Price	Availability
1g	USD 90	Ready to ship
5g	USD 150	Ready to ship
10g	USD 250	Ready to ship
25g	USD 550	Ready to ship
50g	USD 950	Ready to ship
100g	USD 1650	Ready to ship
200g	USD 2950	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 5-ALA; ALA; dALA; 5-aminolevulinic acid; aminolevulinic acid; Aminolevulinic Acid HCl; Aminolevulinic Acid hydrochloride; US brand name: Levulan.

IUPAC/Chemical Name: 5-amino-4-oxopentanoic acid hydrochloride

InChi Key: ZLHFONARZHCSET-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9;/h1-3,6H2,(H,8,9);1H

SMILES Code: O=C(O)CCC(CN)=O.[H]Cl

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in water

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot# TZC61205

QC Data:

View QC data: current batch, Lot#TZC61205

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	5-Aminolevulinic Acid HCl is an intermediate in the porphyrin synthesis pathway, used as a photosensitizing agent and a antineoplastic agent.
In vitro activity:	Expression of GPX4 and HMOX1 in pathologic specimens of 97 ESCC (esophageal squamous cell carcinoma) patients was examined and real-time polymerase chain reaction (RT-PCR), RNA microarray, and Western blotting analyses were used to evaluate the role of 5-ALA in ferroptosis in vitro. The results showed that upregulation of GPX4 and downregulation of HMOX1 were poor prognostic factors in ESCC. In an RNA microarray analysis of KYSE30, ferroptosis was one of the most frequently induced pathways, with GPX4 suppressed and HMOX1 overexpressed by 5-ALA treatment. Furthermore, 5-ALA led to an increase in lipid peroxidation and exerted an antitumor effect in various cancer cell lines. Reference: Ann Surg Oncol. 2021 Jul;28(7):3996-4006. https://link.springer.com/article/10.1245%2Fs10434-020-09334-4
In vivo activity:	The role of 5-ALA in ferroptosis was evaulated by its effect on an ESCC (esophageal squamous cell carcinoma) subcutaneous xenograft mouse model. In vivo, 5-ALA suppressed GPX4 and overexpressed HMOX1 in tumor tissues and led to a reduction in tumor size. Reference: Ann Surg Oncol. 2021 Jul;28(7):3996-4006. https://link.springer.com/article/10.1245%2Fs10434-020-09334-4

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	64.7	385.88
	Water	42.0	250.61
	Ethanol	10.0	59.67
	PBS (pH 7.2)	10.0	59.67
	DMF	5.0	29.83

Preparing Stock Solutions

The following data is based on the product molecular weight 167.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Shishido Y, Amisaki M, Matsumi Y, Yakura H, Nakayama Y, Miyauchi W, Miyatani K, Matsunaga T, Hanaki T, Kihara K, Yamamoto M, Tokuyasu N, Takano S, Sakamoto T, Honjo S, Hasegawa T, Fujiwara Y. Antitumor Effect of 5-Aminolevulinic Acid Through Ferroptosis in Esophageal Squamous Cell Carcinoma. Ann Surg Oncol. 2021 Jul;28(7):3996-4006. doi: 10.1245/s10434-020-09334-4. Epub 2020 Nov 18. PMID: 33210267.
In vitro protocol:	1. Shishido Y, Amisaki M, Matsumi Y, Yakura H, Nakayama Y, Miyauchi W, Miyatani K, Matsunaga T, Hanaki T, Kihara K, Yamamoto M, Tokuyasu N, Takano S, Sakamoto T, Honjo S, Hasegawa T, Fujiwara Y. Antitumor Effect of 5-Aminolevulinic Acid Through Ferroptosis in Esophageal Squamous Cell Carcinoma. Ann Surg Oncol. 2021 Jul;28(7):3996-4006. doi: 10.1245/s10434-020-09334-4. Epub 2020 Nov 18. PMID: 33210267.
In vivo protocol:	1. Shishido Y, Amisaki M, Matsumi Y, Yakura H, Nakayama Y, Miyauchi W, Miyatani K, Matsunaga T, Hanaki T, Kihara K, Yamamoto M, Tokuyasu N, Takano S, Sakamoto T, Honjo S, Hasegawa T, Fujiwara Y. Antitumor Effect of 5-Aminolevulinic Acid Through Ferroptosis in Esophageal Squamous Cell Carcinoma. Ann Surg Oncol. 2021 Jul;28(7):3996-4006. doi: 10.1245/s10434-020-09334-4. Epub 2020 Nov 18. PMID: 33210267.

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1: Inoue K. 5-Aminolevulinic acid-mediated photodynamic therapy for bladder cancer. Int J Urol. 2017 Feb;24(2):97-101. doi: 10.1111/iju.13291. Review. PubMed PMID: 28191719.

2: Kumar N, Warren CB. Photodynamic Therapy for Dermatologic Conditions in the Pediatric Population: A Literature Review. Photodermatol Photoimmunol Photomed. 2017 Jan 28. doi: 10.1111/phpp.12296. [Epub ahead of print] Review. PubMed PMID: 28130791.

3: Huang Z, Shi S, Qiu H, Li D, Zou J, Hu S. Fluorescence-guided resection of brain tumor: review of the significance of intraoperative quantification of protoporphyrin IX fluorescence. Neurophotonics. 2017 Jan;4(1):011011. doi: 10.1117/1.NPh.4.1.011011. Review. PubMed PMID: 28097209; PubMed Central PMCID: PMC5227178.

4: Zhang Y, Avalos JL. Traditional and novel tools to probe the mitochondrial metabolism in health and disease. Wiley Interdiscip Rev Syst Biol Med. 2017 Jan 9. doi: 10.1002/wsbm.1373. [Epub ahead of print] Review. PubMed PMID: 28067471.

5: Lane AM, McKay JT, Bonkovsky HL. Advances in the management of erythropoietic protoporphyria - role of afamelanotide. Appl Clin Genet. 2016 Dec 12;9:179-189. doi: 10.2147/TACG.S122030. Review. PubMed PMID: 28003770; PubMed Central PMCID: PMC5161401.

6: Ameluz for actinic keratoses. Med Lett Drugs Ther. 2016 Dec 5;58(1509):155-156. Review. PubMed PMID: 27906150.

7: Xue J, Liu C, Liu Y. Photodynamic therapy as an alternative treatment for relapsed or refractory mycosis fungoides: a systemic review. Photodiagnosis Photodyn Ther. 2016 Nov 22. pii: S1572-1000(16)30184-3. doi: 10.1016/j.pdpdt.2016.11.010. [Epub ahead of print] Review. PubMed PMID: 27888162.

8: Senders JT, Muskens IS, Schnoor R, Karhade AV, Cote DJ, Smith TR, Broekman ML. Agents for fluorescence-guided glioma surgery: a systematic review of preclinical and clinical results. Acta Neurochir (Wien). 2017 Jan;159(1):151-167. doi: 10.1007/s00701-016-3028-5. Review. PubMed PMID: 27878374; PubMed Central PMCID: PMC5177668.

9: Belykh E, Martirosyan NL, Yagmurlu K, Miller EJ, Eschbacher JM, Izadyyazdanabadi M, Bardonova LA, Byvaltsev VA, Nakaji P, Preul MC. Intraoperative Fluorescence Imaging for Personalized Brain Tumor Resection: Current State and Future Directions. Front Surg. 2016 Oct 17;3:55. Review. PubMed PMID: 27800481; PubMed Central PMCID: PMC5066076.

10: Arora S, Young S, Kodali S, Singal AK. Hepatic porphyria: A narrative review. Indian J Gastroenterol. 2016 Nov;35(6):405-418. Review. PubMed PMID: 27796941.

11: Cohen DK, Lee PK. Photodynamic Therapy for Non-Melanoma Skin Cancers. Cancers (Basel). 2016 Oct 4;8(10). pii: E90. Review. PubMed PMID: 27782043; PubMed Central PMCID: PMC5082380.

12: Chou R, Selph S, Buckley DI, Fu R, Griffin JC, Grusing S, Gore JL. Comparative Effectiveness of Fluorescent Versus White Light Cystoscopy for Initial Diagnosis or Surveillance of Bladder Cancer on Clinical Outcomes: Systematic Review and Meta-Analysis. J Urol. 2016 Oct 22. pii: S0022-5347(16)31585-3. doi: 10.1016/j.juro.2016.10.061. [Epub ahead of print] Review. PubMed PMID: 27780784.

13: Girotti AW, Fahey JM, Korytowski W. Multiple Means by Which Nitric Oxide can Antagonize Photodynamic Therapy. Curr Med Chem. 2016;23(24):2754-2769. Review. PubMed PMID: 27776475.

14: Fonda-Pascual P, Moreno-Arrones OM, Alegre-Sanchez A, Saceda-Corralo D, Buendia-Castaño D, Pindado-Ortega C, Fernandez-Gonzalez P, Velazquez-Kennedy K, Calvo-Sánchez MI, Harto-Castaño A, Perez-Garcia B, Bagazgoitia L, Vaño-Galvan S, Espada J, Jaen-Olasolo P. In situ production of ROS in the skin by photodynamic therapy as a powerful tool in clinical dermatology. Methods. 2016 Oct 15;109:190-202. doi: 10.1016/j.ymeth.2016.07.008. Review. PubMed PMID: 27422482.

15: Halani SH, Adamson DC. Clinical utility of 5-aminolevulinic acid HCl to better visualize and more completely remove gliomas. Onco Targets Ther. 2016 Sep 12;9:5629-42. doi: 10.2147/OTT.S97030. Review. PubMed PMID: 27672334; PubMed Central PMCID: PMC5026178.

16: Barbaric J, Abbott R, Posadzki P, Car M, Gunn LH, Layton AM, Majeed A, Car J. Light therapies for acne. Cochrane Database Syst Rev. 2016 Sep 27;9:CD007917. [Epub ahead of print] Review. PubMed PMID: 27670126.

17: Andrew H, Gossedge G, Croft J, Corrigan N, Brown JM, West N, Quirke P, Tolan D, Cahill R, Jayne DG. Next Generation intraoperative Lymph node staging for Stratified colon cancer surgery (GLiSten): a multicentre, multinational feasibility study of fluorescence in predicting lymph node-positive disease. Southampton (UK): NIHR Journals Library; 2016 Aug. PubMed PMID: 27536753.

18: Maranda EL, Nguyen AH, Lim VM, Shah VV, Jimenez JJ. Erythroplasia of Queyrat treated by laser and light modalities: a systematic review. Lasers Med Sci. 2016 Dec;31(9):1971-1976. Review. PubMed PMID: 27324019.

19: Fujita AK, Rodrigues PG, Requena MB, Escobar A, da Rocha RW, Nardi AB, Kurachi C, de Menezes PF, Bagnato VS. Fluorescence evaluations for porphyrin formation during topical PDT using ALA and methyl-ALA mixtures in pig skin models. Photodiagnosis Photodyn Ther. 2016 Sep;15:236-44. doi: 10.1016/j.pdpdt.2016.05.008. Review. PubMed PMID: 27288253.

20: Kamp MA, Krause Molle Z, Munoz-Bendix C, Rapp M, Sabel M, Steiger HJ, Cornelius JF. Various shades of red-a systematic analysis of qualitative estimation of ALA-derived fluorescence in neurosurgery. Neurosurg Rev. 2016 May 25. [Epub ahead of print] Review. PubMed PMID: 27225452.

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Aminolevulinic Acid HCl featured