Methyl-5-aminolevulinate HCl, a prodrug that is metabolised to Protoporphyrin IX (sensitizer) used in photodynamic therapy, is a used as a topical cream formulation which contains the hydrochloride salt of methyl-5-aminolevulinate, a lipophilic methyl ester of 5-aminolevulinic acid, with photosensitizer prodrug activity. Methyl-5-aminolevulinate in the cream is selectively absorbed by tumor cells upon topical administration, where it is converted to the photosensitizer protoporphyrin IX (PpIX). After photoirradiation, PpIX is activated and transfers energy to oxygen, generating singlet oxygen and superoxide and hydroxyl radicals, which may result in free-radical-mediated DNA damage and cell death.

Physicochemical Properties

Molecular Formula	C6H12CLNO3
Molecular Weight	181.6174
Exact Mass	181.05
CAS #	79416-27-6
Related CAS #	Methyl aminolevulinate;33320-16-0
PubChem CID	157921
Appearance	White to off-white solid powder
Boiling Point	228ºC at 760 mmHg
Melting Point	122 °C
Flash Point	99.5ºC
LogP	0.969
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Heavy Atom Count	11
Complexity	133
Defined Atom Stereocenter Count	0
InChi Key	UJYSYPVQHFNBML-UHFFFAOYSA-N
InChi Code	InChI=1S/C6H11NO3.ClH/c1-10-6(9)3-2-5(8)4-7;/h2-4,7H2,1H3;1H
Chemical Name	methyl 5-amino-4-oxo-pentanoate hydrochloride
Synonyms	5-Aminolevulinic acid methyl ester; LS-187769; LS 187769; LS187769; MAL; Aminolevulinic acid methyl ester; methyl 5-amino-4-oxopentanoate; methyl 5-aminolevulinate; Methyl aminolevulinate hydrochloride. brand name: Metvix.
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References	Int J Immunopathol Pharmacol. 2011 Jul-Sep;24(3):793-5.
Additional Infomation	See also: Methyl Aminolevulinate (has active moiety). Drug Indication Treatment of acne vulgaris

Solubility Data

Solubility (In Vitro)

H2O : ~100 mg/mL (~550.60 mM) DMSO : ~100 mg/mL (~550.60 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.77 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.77 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (13.77 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.5060 mL	27.5300 mL	55.0600 mL
	5 mM	1.1012 mL	5.5060 mL	11.0120 mL
	10 mM	0.5506 mL	2.7530 mL	5.5060 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.