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Details

Stereochemistry ACHIRAL
Molecular Formula C24H33N3O3S2
Molecular Weight 475.667
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPOTIAZINE

SMILES

CN(C)S(=O)(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN4CCC(CCO)CC4)C2=C1

InChI

InChIKey=JOMHSQGEWSNUKU-UHFFFAOYSA-N
InChI=1S/C24H33N3O3S2/c1-25(2)32(29,30)20-8-9-24-22(18-20)27(21-6-3-4-7-23(21)31-24)14-5-13-26-15-10-19(11-16-26)12-17-28/h3-4,6-9,18-19,28H,5,10-17H2,1-2H3

HIDE SMILES / InChI

Description

Pipotiazine (Piportil), also known as Pipothiazine, is a typical antipsychotic of the phenothiazine class used in the United Kingdom and other countries for the treatment of schizophrenia. Its properties are similar to those of chlorpromazine. Piportil® L4 (pipotiazine palmitate) is the palmitic ester of pipotiazine, a piperidine phenothiazine with antipsychotic properties and weak sedative activity. The esterification of pipotiazine is responsible for its prolonged duration of action. The onset of action appears usually within the first 2 to 3 days after injection and the effects of the drug on psychotic symptoms are significant within one week. Improvement in symptomatology lasts from 3 to 6 weeks, but adequate control may frequently be maintained with one injection every 4 weeks. However, in view of the variations in individual response, careful supervision is required throughout treatment. Piportil L4 has actions similar to those of other phenothiazines. Among the different phenothiazine derivatives, Piportil L4 appears to be less sedating and to have a weak propensity for causing hypotension or potentiating the effects of CNS depressants and anesthetics. However, it produces a high incidence of extrapyramidal reactions.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.2 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PIPORTIL L4
PubMed

PubMed

TitleDatePubMed
Localization and function of the D3 dopamine receptor.
1992 Feb
Efficacy of typical and atypical antipsychotics for primary and comorbid anxiety symptoms or disorders: a review.
2006 Sep
Imputation methods for missing outcome data in meta-analysis of clinical trials.
2008
The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913).
2008 Dec 22
Relationship between obesity and antipsychotic drug use in the adult population: a longitudinal, retrospective claim database study in Primary Care settings.
2008 Feb
[Priapism associated with antipsychotic medications: a series of four patients].
2008 Nov
Availability and use of essential medicines in China: manufacturing, supply, and prescribing in Shandong and Gansu provinces.
2010 Jul 17
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Oral: 5-20 mg daily. Severe: 30 mg daily for brief periods. Intramuscular: As pipotiazine palmitate: Initially, 25 mg as test dose followed by 25-50 mg after 4 to 7 days. Adjust in increments of 25-50 mg according to response every 4 wk.
Route of Administration: Oral, Intramuscular
In Vitro Use Guide
Rats brain striata were dissected out and put in ice-cold 0.25 M sucrose containing 3 mM imidazole, pH 7.4. The striata were then homogenized by 10 strokes of the right pestle of a Duncan homogenizer. The homogenate was fractionated at 0-4°C by differential centrifugation. The assays were performed in 50 mM Tris-HC1 buffer pH 7.1 containing (mM): 120 NaC1, 5 KC1, 2 CaC12, 1 MgC12, 0.1% ascorbic acid and 10 mkM pargyline. The final protein concentration was 0.29 mg/ml. After 5 rain preincubation at 37°C, [3H]N.propylnorapomorphine (final concentration 0.3 nM) and different concentrations of unlabeled drugs were added. After 24 rain incubation at 37°C, the samples were filtered through Whatman GF/B glass fibre filters. Radioactivity retained on the filters was measured by liquid scintillation counting.
Name Type Language
PIPOTIAZINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
PIPOTIAZINE [MI]
Common Name English
PIPOTHIAZINE
Common Name English
PIPOTIAZINE [WHO-DD]
Common Name English
PIPOTIAZINE [INN]
Common Name English
PIPORTIL
Brand Name English
10H-PHENOTHIAZINE-2-SULFONAMIDE,10-(3-(4-(2-HYDROXYETHYL)-1-PIPERIDINYL)PROPYL)-N,N-DIMETHYL-
Common Name English
PIPOTIAZINE [MART.]
Common Name English
10-(3-(4-(2-HYDROXYETHYL)PIPERIDINO)PROPYL)-N,N-DIMETHYLPHENOTHIAZINE-2-SULFONAMIDE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QN05AC04
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
WHO-ATC N05AC04
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
Code System Code Type Description
PUBCHEM
62867
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY SWITZERF
IUPHAR
7557
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
INN
3046
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
WIKIPEDIA
Pipotiazine
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
DRUG BANK
DB01621
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
CAS
39860-99-6
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
EVMPD
SUB09879MIG
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
RXCUI
8348
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY RxNorm
ChEMBL
CHEMBL2106439
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
MESH
C084783
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
NCI_THESAURUS
C87657
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
EPA CompTox
39860-99-6
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
ECHA (EC/EINECS)
254-659-6
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY
MERCK INDEX
M8865
Created by admin on Tue Mar 06 11:40:38 UTC 2018 , Edited by admin on Tue Mar 06 11:40:38 UTC 2018
PRIMARY Merck Index