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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-07 02:51:46 UTC
HMDB IDHMDB0015553
Secondary Accession Numbers
  • HMDB15553
Metabolite Identification
Common NameAceprometazine
DescriptionAceprometazine (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
ValueSource
10-(2-(dimethylamino)Propyl)phenothiazin-2-yl methyl ketoneChEBI
AceprometazinaChEBI
AceprometazinumChEBI
AcepromethazineChEBI
Aceprometazine maleateMeSH
Chemical FormulaC19H22N2OS
Average Molecular Weight326.456
Monoisotopic Molecular Weight326.145284026
IUPAC Name1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethan-1-one
Traditional Nameaceprometazine
CAS Registry Number13461-01-3
SMILES
CC(CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C(C)=O)N(C)C
InChI Identifier
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
InChI KeyXLOQNFNTQIRSOX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Acetophenone
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Aryl alkyl ketone
  • Aryl ketone
  • Para-thiazine
  • Benzenoid
  • Ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.91 m³·mol⁻¹ChemAxon
Polarizability36.79 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9051000000-03f2a14685e017271abeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3029000000-5031893b9796ba742b55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-8092000000-99937216f3d814ad927dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-9120000000-6bc3dec46a8ae4d11937View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-d0c6815b614eef4cac6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016u-0393000000-e86277491f70157f4bb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-5790000000-1c9be76522bbb625e321View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01615 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01615 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01615
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24249
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAceprometazine
METLIN IDNot Available
PubChem Compound26035
PDB IDNot Available
ChEBI ID53770
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
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 ]