Cariporide (HOE-642) is a selective Na+/H+ exchange inhibitor.

Physicochemical Properties

Molecular Formula	C12H17N3O3S
Molecular Weight	283.34
Exact Mass	283.099
CAS #	159138-80-4
Related CAS #	Cariporide (mesilate);159138-81-5
PubChem CID	151172
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	542.8±60.0 °C at 760 mmHg
Flash Point	282.1±32.9 °C
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.602
LogP	0.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Heavy Atom Count	19
Complexity	461
Defined Atom Stereocenter Count	0
InChi Key	IWXNYAIICFKCTM-UHFFFAOYSA-N
InChi Code	InChI=1S/C12H17N3O3S/c1-7(2)9-5-4-8(11(16)15-12(13)14)6-10(9)19(3,17)18/h4-7H,1-3H3,(H4,13,14,15,16)
Chemical Name	N-(Diaminomethylidene)-3-methylsulfonyl-4-propan-2-ylbenzamide
Synonyms	Cariporide HOE642 HOE-642 HOE 642
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
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

ln Vitro	At 8 or 16 hours, ciprofloxacin dramatically reduced cell death indicators such TUNEL positivity and caspase-3 cleavage. The buildup of Na+ and Ca2+ in the cytoplasm is strongly inhibited by carboride. Cariporide inhibits H2+O2+-induced decrease of mitochondrial membrane potential [1]. By blocking Na+/H+ exchange, ciporide (HOE-642) lowers cytosolic Ca2+ in cardiomyocytes, reducing cardiac ischemia/reperfusion injury [2]. Human platelet degranulation, platelet leukocyte aggregation formation, and GPIIb/IIIa receptor (PAC-1) activation are all inhibited by carbariporide (HOE-642) [3].
ln Vivo	Caripoli injection intravenously dramatically lowers cerebral edema, brain swelling, and infarct volume in addition to brain Na+ uptake [4].
References	[1]. Cariporide (HOE642), a selective Na+-H+ exchange inhibitor, inhibits the mitochondrial death pathway. Circulation. 2003 Nov 4;108(18):2275-81. [2]. Na(+)/H(+) exchanger in the regulation of platelet activation and paradoxical effects of cariporide. Exp Neurol. 2015 Oct;272:11-6. [3]. Intravenous HOE-642 reduces brain edema and Na uptake in the rat permanent middle cerebral artery occlusion model of stroke: evidence for participation of the blood-brain barrier Na/H exchanger. J Cereb Blood Flow Metab. 2013 Feb;33(2):225-34.
Additional Infomation	See also: Cariporide Mesylate (annotation moved to). Drug Indication Investigated for use/treatment in cardiac surgery. Mechanism of Action Cariporide is a selective sodium-hydrogen antiporter inhibitor. The sodium-hydrogen exchanger is an importatn player in the pathophysiology of myocardial ischemia-referfusion injury. The accumulation of hydrogen ions in the myocyte cytoso; during ischemia creates a proton gradiant that promote the efflux of hydrogen ions in exchange for the influx of sodium ions. This sodium buildup can secondary activates the sodium-calcium exchanger to operate in the reverse mode, resulting in a net calcium accumulation in myocyte cytosol, which leads to dysfunction and cell death. By inhibiting sodium-hydrogen exchange, Cariporide can prevent the accumulation of calcium in cytosol, therefore reduce the infarct size.

Solubility Data

Solubility (In Vitro)

DMSO : ≥ 100 mg/mL (~352.92 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.82 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 (8.82 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 (8.82 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	3.5293 mL	17.6466 mL	35.2933 mL
	5 mM	0.7059 mL	3.5293 mL	7.0587 mL
	10 mM	0.3529 mL	1.7647 mL	3.5293 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.