Oxazepam hemisuccinate

Oxazepam hemisuccinate

Clinical data
Trade names	Empracil
Identifiers
IUPAC name 4-[(7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)oxy]-4-oxobutanoic acid
CAS Number	4700-56-5
PubChem CID	36754
Chemical and physical data
Formula	C19H15ClN2O5
Molar mass	386.79 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)OC(=O)CCC(=O)O
InChI InChI=1S/C19H15ClN2O5/c20-12-6-7-14-13(10-12)17(11-4-2-1-3-5-11)22-19(18(26)21-14)27-16(25)9-8-15(23)24/h1-7,10,19H,8-9H2,(H,21,26)(H,23,24) Key:UCUOKZUJHTYPJT-UHFFFAOYSA-N

Oxazepam hemisuccinate (Empracil), is a benzodiazepine derivative which is an ester substituted prodrug of oxazepam. It was developed as a water-soluble benzodiazepine suitable for administration by injection, for use as an anxiolytic and for procedural sedation. It was used medically to a limited extent during the 1970s and 1980s under the brand name Empracil, but fell into disuse following the introduction of midazolam, which is similarly water-soluble and is more potent and effective than oxazepam hemisuccinate for the same medical applications. It has two isomers, with the R enantiomer being more effective due to more efficient cleavage of the ester link. ^{[1] [2] [3] [4] [5] [6]}

See also

• Luvesilocin
• THC hemisuccinate
• Propofol hemisuccinate

References

1. Zafiri O, Alessio-Vernì A, Mastroianni A, Marin LA (November 1968). "[A new benzodiazepine derivative, oxazepam hemisuccinate ester, in anesthesilogy and resuscitation]". Minerva Anestesiologica. 34 (11): 1285–1294. PMID   5715826.
2. de Angelis L, Predominato M, Vertua R (August 1972). "Stereostructure-activity relationships for oxazepam hemisuccinate. Effects on central nervous system". Arzneimittel-Forschung. 22 (8): 1328–1333. PMID   4678394.
3. Babbini M, Torrielli MV (June 1972). "Investigation on pharmacological properties of hexadiphane, oxazepam hemisuccinate and of their combination". Current Therapeutic Research, Clinical and Experimental. 14 (6): 311–323. PMID   4403034.
4. Lescovelli M, Castellani A, Perbellini D (1976). "A double-blind cross-over evaluation of the activity of d-oxazepam hemisuccinate sodium salt (D-7-chloro-1,3-dihydro-3-hemisuccinyloxy-5-phenyl-2H-1,4-benzodiazepine-2-one) compared to its racemic form". Arzneimittel-Forschung. 26 (8): 1623–1626. PMID   795440.
5. Maksay G, Kardos J, Simonyi M, Tegyey Z, Otvös L (1981). "Specific binding of racemic oxazepam esters to rat brain synaptosomes and the influence of bioactivation by esterases". Arzneimittel-Forschung. 31 (6): 979–981. PMID   7196245.
6. Cesari A, Balzano F, Uccello Barretta G, Recchimurzo A (October 2021). "Hydrolysis and Enantiodiscrimination of (R)- and (S)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation". Molecules. 26 (21). doi: 10.3390/molecules26216347 . PMC   8587842 . PMID   34770758.