Levosulpiride (RV 12309; RV-12309; S-(-)-Sulpiride) is the S-enantiomer of sulpiride, which is a potent and selective antagonist for D2 dopamine receptors used as an antipsychotic and prokinetic agent. Levosulpiride is an antipsychotic that is a substituted benzamide and is known to selectively block dopamine D2 receptor activity in both the central and peripheral nervous systems. It functions as both a prokinetic and an atypical neuroleptic. There are also claims that levosulpiride improves mood.

Physicochemical Properties

Molecular Formula	C15H23N3O4S
Molecular Weight	341.4258
Exact Mass	341.14
Elemental Analysis	C, 52.77; H, 6.79; N, 12.31; O, 18.74; S, 9.39
CAS #	23672-07-3
Related CAS #	Levosulpiride-d3; 124020-27-5
PubChem CID	688272
Appearance	Solid powder
Density	1.2±0.1 g/cm3
Melting Point	183-186 °C(lit.)
Index of Refraction	1.552
LogP	0.45
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Heavy Atom Count	23
Complexity	505
Defined Atom Stereocenter Count	1
SMILES	S(C1C([H])=C([H])C(=C(C=1[H])C(N([H])C([H])([H])[C@]1([H])C([H])([H])C([H])([H])C([H])([H])N1C([H])([H])C([H])([H])[H])=O)OC([H])([H])[H])(N([H])[H])(=O)=O
InChi Key	BGRJTUBHPOOWDU-NSHDSACASA-N
InChi Code	InChI=1S/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)/t11-/m0/s1
Chemical Name	N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide
Synonyms	Nexipride; RV-12309; S-(-)-Sulpiride; RV 12309; RV12309; Levosulpiride
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

Targets	D2 receptor
References	Wikipedia
Additional Infomation	(S)-(-)-sulpiride is an optically active form of sulpiride having (S)-configuration. The active enantiomer of the racemic drug sulpiride. Selective D2-like dopamine antagonist (Ki values are ~ 0.015. ~ 0.013, 1, ~ 45 and ~ 77 muM at D2, D3, D4, D1 and D5 receptors respectively). It has a role as a dopaminergic antagonist, an antidepressant, an antiemetic and an antipsychotic agent. It is an enantiomer of a (R)-(+)-sulpiride.

Solubility Data

Solubility (In Vitro)

DMSO: 50~69 mg/mL (146.4~202.1 mM) Water: <1 mg/mL Ethanol: <1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.32 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 (7.32 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 (7.32 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	2.9289 mL	14.6443 mL	29.2886 mL
	5 mM	0.5858 mL	2.9289 mL	5.8577 mL
	10 mM	0.2929 mL	1.4644 mL	2.9289 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.