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Pipotiazine

HCID 62867
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
39860-99-6
Standard SMILES
CN(C)S(=O)(=O)c1ccc2c(c1)N(CCCN1CCC(CCO)CC1)c1ccccc1S2
InChIKey
JOMHSQGEWSNUKU-UHFFFAOYSA-N
Molecular formula
C24H33N3O3S2
Average molar mass
475.7 g/mol
Monoisotopic mass
475.19633427

Overview

Pipotiazine has actions similar to those of other phenothiazines. Among the different phenothiazine derivatives, it 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 extra pyramidal reactions. It is used for the maintenance treatment of chronic non-agitated schizophrenic patients. Symptoms of overdose include severe extrapyramidal manifestations, hypotension, lethargy and sedation.

Names & identifiers

Preferred name
Pipotiazine
IUPAC
10-[3-[4-(2-hydroxyethyl)piperidin-1-yl]propyl]-N,N-dimethylphenothiazine-2-sulfonamide
English name
Pipotiazine
Molecular formula
C24H33N3O3S2
Molecular weight
475.67

Names & synonyms

Pipotiazine39860-99-6PipothiazinePiportilPipotiazinumPipotiazina10-[3-[4-(2-hydroxyethyl)piperidin-1-yl]propyl]-N,N-dimethylphenothiazine-2-sulfonamideL903J9JPYVDTXSID4019291310-(3-(4-(2-hydroxyethyl)piperidin-1-yl)propyl)-N,N-dimethyl-10H-phenothiazine-2-sulfonamide10-{3-[4-(2-HYDROXYETHYL)PIPERIDIN-1-YL]PROPYL}-N,N-DIMETHYL-10H-PHENOTHIAZINE-2-SULFONAMIDE10H-Phenothiazine-2-sulfonamide,10-(3-(4-(2-hydroxyethyl)-1-piperidinyl)propyl)-N,N-dimethyl-
Show more names
19366 RPPipothizainePipotiazine USP/EP/BPPipotiazine (base and/or unspecified esters)10-[3-[4-(2-Hydroxyethyl)piperidino]propyl]-N,N-dimethyl-10H-phenothiazine-2-sulfonamide10H-Phenothiazine-2-sulfonamide, 10-[3-[4-(2-hydroxyethyl)-1-piperidinyl]propyl]-N,N-dimethyl-
10-(3-(4-(2-HYDROXYETHYL)PIPERIDINO)PROPYL)-N,N-DIMETHYLPHENOTHIAZINE-2-SULFONAMIDEpipotiazin10-(3-(4-(2-hydroxyethyl)piperidin-1-yl)propyl)-N,N-dimethylphenothiazine-2-sulfonamideRP 19366RefChem:863632DTXCID80115404N05AC0419366-RP

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
97.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
8
Heavy atoms
32
Formal charge
0
Complexity
691

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Solubility1.27e-02 g/L
Physical DescriptionSolid

Physicochemical properties

Boiling point
650.4 · 650.4±65.0 °C(Predicted)
Density
1.236 · 1.236±0.06 g/cm3(Predicted)
solubility
Chloroform (Slightly), Methanol (Sparingly)
pka
15.1 · 15.10±0.10(Predicted)
form
Solid
color
Pale Yellow to Light Yellow
FDA UNII
903 J9JPYV · L903J9JPYV
ATC code
5 AC04 · N05AC04
Toxicity
50 in · LD50 in mice (mg/kg): 108 i.p.; 360 s.c.; 440 orally (Julou)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

Toxicity
LD50 in mice (mg/kg): 108 i.p.; 360 s.c.; 440 orally (Julou)

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1 item

Pipotiazine has actions similar to those of other phenothiazines. Among the different phenothiazine derivatives, it 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 extra pyramidal reactions. It reduces activity of dopamine receptors in the limbic system. Its 5-HT antagonism helps normalize dopamine activity in the cortical regions.

Mechanism of Action · 1 item

Pipotiazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects).

Cellular LocationsExtracellular

Applications

UsesPipotiazine is drug repurposing for Covid-19: discovery of potential small-molecule inhibitors of spike protein-ACE2 receptor interaction through virtual screening and consensus scoring.

UsesAntipsychotic.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
39860-99-6
PubChem CID
62867
DTXSID
DTXSID40192913
ChEMBL
CHEMBL398880
UNII
L903J9JPYV
EC Number
254-659-6
Nikkaji
J16.029F

Upstream & downstream products

Upstream raw materials

Sodium amideSodium hydroxideHydrochloric acidMethanesulfonyl chloride

Suppliers10 total

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
BOC Sciences16314854226 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
陕西缔都医药化工有限公司029-81154043 17391733319 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]
Dideu Industries Group Limited+86-29-81148696 +86-15129568250 · [email protected]