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Identification
NameAceprometazine
Accession NumberDB01615
TypeSmall Molecule
GroupsApproved
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
SynonymLanguageCode
10-(2-(Dimethylamino)propyl)phenothiazin-2-yl methyl ketoneNot AvailableNot Available
AceprometazinaSpanishINN
AceprometazinumLatinINN
AcepromethazineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
MepronizineNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number13461-01-3
WeightAverage: 326.456
Monoisotopic: 326.145284026
Chemical FormulaC19H22N2OS
InChI KeyXLOQNFNTQIRSOX-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Benzenoid
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Azacycle
  • Thioether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationAceprometazine is often used in combination with meprobamate for the treatment of sleep disorders.
PharmacodynamicsAceprometazine is a drug with neuroleptic and anti-histamine properties. It is not widely prescribed.
Mechanism of actionAceprometazine, 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.
AbsorptionRapidly absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9009
CYP450 2D6 substrateInhibitor0.7954
CYP450 2C19 substrateNon-inhibitor0.8674
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

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
  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
  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
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on August 29, 2007 14:13 / Updated on September 16, 2013 17:15