NAV

Aceprometazine

Identification

Generic Name
Aceprometazine
DrugBank Accession Number
DB01615
Background

Aceprometazine is a is a drug with neuroleptic and anti-histamine properties. Although not widely prescribed, it is used in combination with meprobamate for the treatment of sleep disorders in France under the trade name Mepronizine.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 326.456
Monoisotopic: 326.145284026
Chemical Formula
C19H22N2OS
Synonyms
  • 10-(2-(Dimethylamino)propyl)phenothiazin-2-yl methyl ketone
  • Aceprometazina
  • Aceprometazine
  • Acéprométazine
  • Aceprometazinum
  • Acepromethazine

Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Aceprometazine is combined with 1,2-Benzodiazepine.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Aceprometazine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Aceprometazine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Aceprometazine.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Aceprometazine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Aceprometazine.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Aceprometazine.
AgomelatineThe risk or severity of CNS depression can be increased when Aceprometazine is combined with Agomelatine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Aceprometazine.
AlfentanilThe risk or severity of hypotension and CNS depression can be increased when Aceprometazine is combined with Alfentanil.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Acetophenone / Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Aryl thioether / Azacycle / Benzenoid / Diarylthioether
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines, tertiary amine, methyl ketone, aromatic ketone (CHEBI:53770)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
984N9YTM4Y
CAS number
13461-01-3
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

References

General References
Not Available
Human Metabolome Database
HMDB0015553
PubChem Compound
26035
PubChem Substance
46506646
ChemSpider
24249
RxNav
161203
ChEBI
53770
ChEMBL
CHEMBL2104054
Therapeutic Targets Database
DAP001075
PharmGKB
PA164743727
Wikipedia
Aceprometazine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)8.92Chemaxon
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

Targets

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Details1. Histamine H1 receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at August 29, 2007 20:13 / Updated at February 21, 2021 18:51