Aminolevulinic Acid HCl
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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

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Aminolevulinic Acid HCl
CAS# 5451-09-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 100054
Name: Aminolevulinic Acid HCl
CAS#: 5451-09-2 (HCl)
Chemical Formula: C5H10ClNO3
Exact Mass:
Molecular Weight: 167.59
Elemental Analysis: C, 35.83; H, 6.01; Cl, 21.15; N, 8.36; O, 28.64

Price and Availability

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1.0g USD 90.0 Ready to ship
5.0g USD 150.0 Ready to ship
10.0g USD 250.0 Ready to ship
25.0g USD 550.0 Ready to ship
50.0g USD 950.0 Ready to ship
100.0g USD 1650.0 Ready to ship
200.0g USD 2550.0 2 Weeks
500.0g USD 3950.0 2 Weeks
1.0kg USD 7650.0 2 Weeks
2.0kg USD 12450.0 2 Weeks
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Related CAS #: 5451-09-2 (HCl)   106-60-5 (free)   868074-65-1 (phosphate)    

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

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 64.67 385.88
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.

Recalculate based on batch purity %
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.

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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.

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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.

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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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