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Details

Stereochemistry RACEMIC
Molecular Formula C21H26N2O2S2.C6H6O3S
Molecular Weight 560.748
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFORIDAZINE BESYLATE

SMILES

OS(=O)(=O)C1=CC=CC=C1.CN2CCCCC2CCN3C4=CC(=CC=C4SC5=C3C=CC=C5)S(C)(=O)=O

InChI

InChIKey=POTAUFBGHYTSIE-UHFFFAOYSA-N
InChI=1S/C21H26N2O2S2.C6H6O3S/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)26-21-11-10-17(15-19(21)23)27(2,24)25;7-10(8,9)6-4-2-1-3-5-6/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3;1-5H,(H,7,8,9)

HIDE SMILES / InChI

Molecular Formula C6H6O3S
Molecular Weight 158.175
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H26N2O2S2
Molecular Weight 402.573
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Sulforidazine (Imagotan (Sandoz); Inofal (Sandoz)) is a typical piperidine-type phenothiazine antipsychotic agent. It is dopamine receptor blocker. Being the second active metabolite of thioridazine (converted from mesoridazine), Sulforidazine is significantly more potent than the parent drug.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effect of thioridazine dosage on the debrisoquine hydroxylation phenotype in psychiatric patients with different CYP2D6 genotypes.
2001 Dec
Thioridazine steady-state plasma concentrations are influenced by tobacco smoking and CYP2D6, but not by the CYP2C9 genotype.
2003 May
Using absolute and relative reasoning in the prediction of the potential metabolism of xenobiotics.
2003 Sep-Oct
No effect of the CYP1A2*1F genotype on thioridazine, mesoridazine, sulforidazine plasma concentrations in psychiatric patients.
2007 May
Factors affecting drug concentrations and QT interval during thioridazine therapy.
2007 Nov

Sample Use Guides

The metabolism of sulforidazine was studied in female dogs and adult male humans after oral administration of 37.5 mg and 25.0 mg, respectively.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The electrically evoked overflow of dopamine (DA) from perfused rabbit striatal slices was used to assess the relative functional potencies of thioridazine, a phenothiazine antipsychotic agent, and two of its major metabolites, mesoridazine (thioridazine-2-sulfoxide) and sulforidazine (thioridazine-2-sulfone).
Mesoridazine and sulforidazine likewise produced only small increases (5-20%) in evoked overflow of DA from slices stimulated at 0.3 Hz. At this frequency of stimulation, apomorphine (30 nM) inhibited the overflow of DA by 71.4 +/- 8.43% (n = 40). All three drugs antagonized, in a concentration-dependent fashion, the inhibitory effect of apomorphine (30 nM) on electrically evoked DA release at 0.3 Hz. The IC50 for thioridazine for antagonizing the effect of apomorphine was 130 nM, whereas that for mesoridazine was 14.4 nM and for sulforidazine was 6.1 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:51:58 GMT 2023
Edited
by admin
on Fri Dec 15 18:51:58 GMT 2023
Record UNII
7L0AV9G67Z
Record Status Validated (UNII)
Record Version
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Name Type Language
SULFORIDAZINE BESYLATE
Common Name English
Sulforidazine besylate [WHO-DD]
Common Name English
Code System Code Type Description
CAS
23255-94-9
Created by admin on Fri Dec 15 18:51:58 GMT 2023 , Edited by admin on Fri Dec 15 18:51:58 GMT 2023
PRIMARY
FDA UNII
7L0AV9G67Z
Created by admin on Fri Dec 15 18:51:58 GMT 2023 , Edited by admin on Fri Dec 15 18:51:58 GMT 2023
PRIMARY
PUBCHEM
23619868
Created by admin on Fri Dec 15 18:51:58 GMT 2023 , Edited by admin on Fri Dec 15 18:51:58 GMT 2023
PRIMARY
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ACTIVE MOIETY