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
- 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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- 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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Aceprometazine is combined with 1,2-Benzodiazepine. Acebutolol The serum concentration of Acebutolol can be increased when it is combined with Aceprometazine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Aceprometazine. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Aceprometazine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Aceprometazine. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Aceprometazine. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Aceprometazine. Agomelatine The risk or severity of CNS depression can be increased when Aceprometazine is combined with Agomelatine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Aceprometazine. Alfentanil The risk or severity of hypotension and CNS depression can be increased when Aceprometazine is combined with Alfentanil. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Antipsychotic Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Dopamine Agents
- Dopamine Antagonists
- Heterocyclic Compounds, Fused-Ring
- Histamine Antagonists
- Histamine H1 Antagonists
- Moderate Risk QTc-Prolonging Agents
- Neurotoxic agents
- Neurotransmitter Agents
- Phenothiazines
- Psychotropic Drugs
- QTc Prolonging Agents
- Sulfur Compounds
- Tranquilizing Agents
- 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
- External Links
- Human Metabolome Database
- HMDB0015553
- PubChem Compound
- 26035
- PubChem Substance
- 46506646
- ChemSpider
- 24249
- 161203
- ChEBI
- 53770
- ChEMBL
- CHEMBL2104054
- Therapeutic Targets Database
- DAP001075
- PharmGKB
- PA164743727
- Wikipedia
- Aceprometazine
Clinical Trials
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
Property Value Source Water Solubility 0.0122 mg/mL ALOGPS logP 4.35 ALOGPS logP 3.85 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 16.06 Chemaxon pKa (Strongest Basic) 8.92 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 23.55 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 98.91 m3·mol-1 Chemaxon Polarizability 36.79 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.992 Blood Brain Barrier + 0.9852 Caco-2 permeable + 0.8427 P-glycoprotein substrate Substrate 0.8358 P-glycoprotein inhibitor I Inhibitor 0.9139 P-glycoprotein inhibitor II Inhibitor 0.5926 Renal organic cation transporter Inhibitor 0.5135 CYP450 2C9 substrate Non-substrate 0.7768 CYP450 2D6 substrate Substrate 0.8188 CYP450 3A4 substrate Substrate 0.5876 CYP450 1A2 substrate Inhibitor 0.8793 CYP450 2C9 inhibitor Non-inhibitor 0.9009 CYP450 2D6 inhibitor Inhibitor 0.7954 CYP450 2C19 inhibitor Non-inhibitor 0.8674 CYP450 3A4 inhibitor Non-inhibitor 0.7954 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5333 Ames test Non AMES toxic 0.8613 Carcinogenicity Non-carcinogens 0.8886 Biodegradation Not ready biodegradable 0.9941 Rat acute toxicity 2.6833 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9729 hERG inhibition (predictor II) Inhibitor 0.7319
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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