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.
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
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 |
| 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 |
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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