Hexaminolevulinate HCl (also known as hexyl 5-aminolevulinate) is the hexyl ester of 5-aminolevulinic acid (ALA) with photodynamic properties, and has been approved as a fluorescent agent for cystoscopic detection of papillary bladder cancer. As a precursor of photoactive porphorins, hexyl 5-aminolevulinate induces the endogenous production of the photosensitizer protoporphyrin IX (PPIX) which accumulates selectively in tumor tissue. When exposed to specific wavelengths of light, PPIX is activated and, depending on the wavelength and/or intensity of light, either fluoresces, thereby allowing tumor imaging, or induces tumor cell apoptosis.

Physicochemical Properties

Molecular Formula	C11H22CLNO3
Molecular Weight	251.7503
Exact Mass	251.128
CAS #	140898-91-5
Related CAS #	140898-91-5 (HCl);140898-97-1 (free);
PubChem CID	6433082
Appearance	White to off-white solid powder
Boiling Point	313.2ºC at 760mmHg
Melting Point	145 - 147 °C
Flash Point	112.6ºC
Vapour Pressure	0.000504mmHg at 25°C
LogP	2.92
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	10
Heavy Atom Count	16
Complexity	192
Defined Atom Stereocenter Count	0
InChi Key	LZYXPFZBAZTOCH-UHFFFAOYSA-N
InChi Code	InChI=1S/C11H21NO3.ClH/c1-2-3-4-5-8-15-11(14)7-6-10(13)9-12;/h2-9,12H2,1H3;1H
Chemical Name	hexyl 5-amino-4-oxopentanoate hydrochloride.
Synonyms	P-1206; P1206; P1206. HAL. hexaminolevulinate; 5-Aminolevulinic acid hexyl ester; 5-ALA hexylester; Hexyl 5-aminolevulinate hydrochloride; 5-Aminolevulinic acid hexyl ester hydrochloride; US trade names: Hexvix; Cysview
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

BJU Int.2016 Jun;117(6B):E102-13.

Additional Infomation

Hexaminolevulinate Hydrochloride is the hydrochloride salt form of hexaminolevulinate, a hexyl ester of the heme precursor 5-aminolevulinic acid (ALA) with potential photosensitizing activity. Hexaminolevulinate serves as a precursor of photoactive porphyrins (PAPs), particularly protoporphyrin IX (PpIX), which selectively accumulate in rapidly proliferating cells, such as those seen in tumor tissue. When exposed to blue light, PAPs are activated and emit red light thereby allowing tumor imaging. See also: Hexaminolevulinate (has active moiety).

Solubility Data

Solubility (In Vitro)

DMSO : ≥ 100 mg/mL (~397.22 mM) H2O : ~100 mg/mL (~397.22 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (9.93 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 (9.93 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 (9.93 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. Solubility in Formulation 4: 100 mg/mL (397.22 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.9722 mL	19.8610 mL	39.7219 mL
	5 mM	0.7944 mL	3.9722 mL	7.9444 mL
	10 mM	0.3972 mL	1.9861 mL	3.9722 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.