Lorazepam acetate, (S)-

• CAT Number: I030996
• CAS Number: 84799-34-8
• Molecular Formula: C17H12Cl2N2O3
• Molecular Weight: 363.19
• Purity: 98%
• Synonyms: Lorazepam acetate, (S)-; (-)-Lorazepam acetate; (S)-Lorazepam acetate; L-Lorazepam acetate
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (S)-7-chloro-5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl acetate
• InChI: InChI=1S/C17H12Cl2N2O3/c1-9(22)24-17-16(23)20-14-7-6-10(18)8-12(14)15(21-17)11-4-2-3-5-13(11)19/h2-8,17H,1H3,(H,20,23)/t17-/m0/s1
• InChIKey: CYDZMDOLVUBPNL-KRWDZBQOSA-N
• SMILES: O=C1NC2=CC=C(Cl)C=C2C(C3=CC=CC=C3Cl)=N[C@H]1OC(C)=O

Lorazepam acetate, (S)- is used to treat anxiety disorders, trouble sleeping, active seizures including status epilepticus, alcohol withdrawal, and chemotherapy induced nausea and vomiting, as well as for surgery to interfere with memory formation and to sedate those who are being mechanically ventilated. Lorazepam acetate, (S)- is discontinued (DEA controlled substance).

Reference

1: Liu K, Guengerich FP, Yang SK. Enantioselective hydrolysis of lorazepam 3-acetate by esterases in human and rat liver microsomes and rat brain S9 fraction. Drug Metab Dispos. 1991 May-Jun;19(3):609-13. PubMed PMID: 1680626.
2: Fitos I, Visy J, Simonyi M, Hermansson J. Stereoselective allosteric binding interaction on human serum albumin between ibuprofen and lorazepam acetate. Chirality. 1999;11(2):115-20. PubMed PMID: 9951402.
3: Fitos I, Tegyey Z, Simonyi M, Sjöholm I, Larsson T, Lagercrantz C. Stereoselective binding of 3-acetoxy-, and 3-hydroxy-1,4-benzodiazepine-2-ones to human serum albumin. Selective allosteric interaction with warfarin enantiomers. Biochem Pharmacol. 1986 Jan 15;35(2):263-9. PubMed PMID: 3942599.
4: Fitos I, Visy J, Kardos J. Stereoselective kinetics of warfarin binding to human serum albumin: effect of an allosteric interaction. Chirality. 2002 May 15;14(5):442-8. PubMed PMID: 11984760.
5: Simonyi M, Fitos I, Tegyey Z, Otvös L. Stationary ultrafiltration: a radio-tracer technique for studying stereoselective binding of racemic ligands. Biochem Biophys Res Commun. 1980 Nov 17;97(1):1-7. PubMed PMID: 7458928.
6: Simonyi M, Fitos I, Kajtár J, Kajtár M. Application of ultrafiltration and CD spectroscopy for studying stereoselective binding of racemic ligands. Biochem Biophys Res Commun. 1982 Dec 15;109(3):851-7. PubMed PMID: 6130765.