Identification

Name
Aceprometazine
Accession Number
DB01615
Type
Small Molecule
Groups
Experimental
Description

Aceprometazine (INN) is a prescription drug with neuroleptic and anti-histamine properties. It is not widely prescribed. It may be used in combination with meprobamate for the treatment of sleep disorders. This combination is available in France under the trade name Mepronizine. [Wikipedia]

Structure
Thumb
Synonyms
  • 10-(2-(Dimethylamino)propyl)phenothiazin-2-yl methyl ketone
  • Aceprometazina
  • Aceprometazinum
  • Acepromethazine
International/Other Brands
Mepronizine
Categories
UNII
984N9YTM4Y
CAS number
13461-01-3
Weight
Average: 326.456
Monoisotopic: 326.145284026
Chemical Formula
C19H22N2OS
InChI Key
XLOQNFNTQIRSOX-UHFFFAOYSA-N
InChI
InChI=1S/C19H22N2OS/c1-13(20(3)4)12-21-16-7-5-6-8-18(16)23-19-10-9-15(14(2)22)11-17(19)21/h5-11,13H,12H2,1-4H3
IUPAC Name
1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethan-1-one
SMILES
CC(CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C(C)=O)N(C)C

Pharmacology

Indication

Aceprometazine is often used in combination with meprobamate for the treatment of sleep disorders.

Pharmacodynamics

Aceprometazine is a drug with neuroleptic and anti-histamine properties. It is not widely prescribed.

Mechanism of action

Aceprometazine, acting as an H1-receptor antagonist can induce sedation by being able to cross the blood-brain-barrier and binding to H1-receptors in the central nervous system.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption

Rapidly absorbed following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineAceprometazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineAceprometazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineAceprometazine may decrease the stimulatory activities of 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineAceprometazine may decrease the stimulatory activities of 4-Bromo-2,5-dimethoxyamphetamine.
5'-Deoxy-5'-MethylthioadenosineThe serum concentration of Aceprometazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Aceprometazine is combined with 7-Nitroindazole.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Aceprometazine.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Aceprometazine.
AcetazolamideThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Acetazolamide.
AdipiplonThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Adipiplon.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015553
PubChem Compound
26035
PubChem Substance
46506646
ChemSpider
24249
ChEBI
53770
ChEMBL
CHEMBL2104054
Therapeutic Targets Database
DAP001075
PharmGKB
PA164743727
Wikipedia
Aceprometazine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0122 mg/mLALOGPS
logP4.35ALOGPS
logP3.85ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)16.06ChemAxon
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.91 m3·mol-1ChemAxon
Polarizability36.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.992
Blood Brain Barrier+0.9852
Caco-2 permeable+0.8427
P-glycoprotein substrateSubstrate0.8358
P-glycoprotein inhibitor IInhibitor0.9139
P-glycoprotein inhibitor IIInhibitor0.5926
Renal organic cation transporterInhibitor0.5135
CYP450 2C9 substrateNon-substrate0.7768
CYP450 2D6 substrateSubstrate0.8188
CYP450 3A4 substrateSubstrate0.5876
CYP450 1A2 substrateInhibitor0.8793
CYP450 2C9 inhibitorNon-inhibitor0.9009
CYP450 2D6 inhibitorInhibitor0.7954
CYP450 2C19 inhibitorNon-inhibitor0.8674
CYP450 3A4 inhibitorNon-inhibitor0.7954
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5333
Ames testNon AMES toxic0.8613
CarcinogenicityNon-carcinogens0.8886
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.6833 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9729
hERG inhibition (predictor II)Inhibitor0.7319
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / Acetophenones / Aryl alkyl ketones / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Phenothiazine / Alkyldiarylamine / Diarylthioether / Acetophenone / Aryl thioether / Tertiary aliphatic/aromatic amine / Aryl alkyl ketone / Aryl ketone / Para-thiazine / Benzenoid
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines, tertiary amine, methyl ketone, aromatic ketone (CHEBI:53770)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Mercier J, Dessaigne S, Menguy A, Manez J: Electro-encephalographic study on the action of the combination meprobamate-aceprometazine on various cerebral systems. Arzneimittelforschung. 1974 Feb;24(2):163-6. [PubMed:4406367]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on August 29, 2007 14:13 / Updated on October 01, 2018 13:06