Basic information
- CAS
316-81-4- Standard SMILES
CN1CCN(CCCN2c3ccccc3Sc3ccc(S(=O)(=O)N(C)C)cc32)CC1- InChIKey
VZYCZNZBPPHOFY-UHFFFAOYSA-N- Molecular formula
- C22H30N4O2S2
- Average molar mass
- 446.6 g/mol
- Monoisotopic mass
- 446.18101856
Overview
Thioproperazine is a phenothiazine derivative in which the phenothiazine tricycle has a dimethylaminosulfonyl substituent at the 2-position and a 3-(4-methylpiperazin-1-yl)propyl group at N-10. It has a role as a phenothiazine antipsychotic drug. It is a sulfonamide, a member of phenothiazines, a N-alkylpiperazine and a N-methylpiperazine.
Names & identifiers
- Preferred name
- Thioproperazine
- IUPAC
- N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine-2-sulfonamide
- English name
- Thioproperazine
- Molecular formula
- C22H30N4O2S2
- Molecular weight
- 446.63
Names & synonyms
Thioproperazine316-81-4ThioperazineThioproperazinVontilTioproperazinaTioproferazinaThioproperazinumSKF 5883RP 7843YJ050AQ56X(Thioproperazine)-2-dimethylsulfamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazine
Show more names
MegeptilMazeptylMajeptylCephalminSulfenazinhioproperazineN'-(4-chlorophenyl)-N,N-dimethylcarbamimidic acid methyl esterN,N-Dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine-2-sulfonamide
DTXSID1023655CHEBI:591202-dimethylsulfamido-(10-(3-1-methylpiperazinyl-4)propyl)-phenothiazineN,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine-2-sulfonamide10H-Phenothiazine-2-sulfonamide, N,N-dimethyl-10-(3-(4-methyl-1-piperazinyl)propyl)-N,N-Dimethyl-10-(3-(4-methylpiperazin-1-yl)propyl)-10H-phenothiazine-2-sulfonamideN,N-Dimethyl-10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine-2-sulfonamideN,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-sulfonamide
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 80.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 6
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 661
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility5.69e-02 g/L
Human DrugsPharmaceuticals
Melting Point140 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 140 ° · 140°
- Boiling point
- 612.2 · 612.2±65.0 °C(Predicted)
- Density
- 1.1476 · 1.1476 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- form
- Solid
- pka
- 7.65 · 7.65±0.10(Predicted)
- color
- Light yellow to yellow
- FDA UNII
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 oral in mouse: 830mg/kg
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Thioproperazine is a potent neuroleptic with antipsychotic properties. Thioproperazine has a marked cataleptic and antiapomorphine activity associated with relatively slight sedative, hypothermic and spasmolytic effects. It is virtually without antiserotonin and hypotensive action and has no antihistaminic property.
Mechanism of Action
Thioproperazine 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
Uses & manufacturing
Use ClassificationPharmaceuticals
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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