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Human Metabolome Database Version 3.5

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Showing metabocard for Aripiprazole (HMDB05042)

Record Information
Version 3.5
Creation Date 2006-10-17 05:54:18 -0600
Update Date 2013-02-08 17:13:50 -0700
HMDB ID HMDB05042
Secondary Accession Numbers None
Metabolite Identification
Common Name Aripiprazole
Description Aripiprazole is a warning has gone out recently because of this drug's name. The '-prazole' ending of this drug name makes this drug sound like it is one of the proton pump inhibitors (such as omeprazole, pantoprazole, lansoprazole) which are used in treating peptic ulcer disease. However, aripiprazole and these drugs are in an entirely different class of drugs altogether and confusing the two can lead to some unnecessary side effects. Aripiprazole is the sixth and most recent of the atypical antipsychotic medications to be approved by the Food and Drug Administration (FDA) for the treatment of schizophrenia. It has also recently received FDA approval for the treatment of acute manic and mixed episodes associated with bipolar disorder. Aripiprazole appears to mediate its antipsychotic effects primarily by partial agonism at the Dopamine 2 (D2)receptor.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Abilify
  2. Abilitat
  3. Aripiprazole
Chemical Formula C23H27Cl2N3O2
Average Molecular Weight 448.385
Monoisotopic Molecular Weight 447.148032537
IUPAC Name 7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one
Traditional IUPAC Name aripiprazole
CAS Registry Number 129722-12-9
SMILES ClC1=CC=CC(N2CCN(CCCCOC3=CC4=C(CCC(=O)N4)C=C3)CC2)=C1Cl
InChI Identifier InChI=1S/C23H27Cl2N3O2/c24-19-4-3-5-21(23(19)25)28-13-11-27(12-14-28)10-1-2-15-30-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)
InChI Key CEUORZQYGODEFX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Phenylpiperazines
Sub Class N/A
Other Descriptors
  • Hydroquinolones
  • N-alkylpiperazine(ChEBI)
  • N-arylpiperazine(ChEBI)
  • Organic Compounds
  • quinolone(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Aryl Chloride
  • Carboxamide Group
  • Chlorobenzene
  • Lactam
  • Organochloride
  • Piperazine
  • Secondary Carboxylic Acid Amide
  • Tertiary Aliphatic Amine (Trialkylamine)
  • Tetrahydroquinoline
Direct Parent Phenylpiperazines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0078 g/L ALOGPS
LogP 5.21 ALOGPS
LogP 4.9 ChemAxon
LogS -4.76 ALOGPS
pKa (strongest acidic) 13.51 ChemAxon
pKa (strongest basic) 7.46 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 44.81 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 124.34 ChemAxon
Polarizability 49.24 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01238 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB004879
KNApSAcK ID Not Available
Chemspider ID 54790 Link_out
KEGG Compound ID C12564 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Aripiprazole Link_out
NuGOwiki Link HMDB05042 Link_out
Metagene Link HMDB05042 Link_out
METLIN ID Not Available
PubChem Compound 60795 Link_out
PDB ID Not Available
ChEBI ID 31236 Link_out
References
Synthesis Reference Tsujimori, Hisayuki; Yamaguchi, Tatsuya. Process for preparing aripiprazole. PCT Int. Appl. (2004), 20 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available
Enzymes
Name: Cytochrome P450 3A4
Reactions:
  • (1) taurochenodeoxycholate + NADPH + H+ + O2 = taurohyocholate + NADP+ + H2O [RN:R07205]
  • (2) lithocholate + NADPH + H+ + O2 = hyodeoxycholate + NADP+ + H2O [RN:R07206]
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions:
  • RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2A adrenergic receptor
Reactions:
    Gene Name: ADRA2A
    Uniprot ID: P08913 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alpha-2B adrenergic receptor
    Reactions:
      Gene Name: ADRA2B
      Uniprot ID: P18089 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: D(2) dopamine receptor
      Reactions:
        Gene Name: DRD2
        Uniprot ID: P14416 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 5-hydroxytryptamine receptor 7
        Reactions:
          Gene Name: HTR7
          Uniprot ID: P34969 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: 5-hydroxytryptamine receptor 1B
          Reactions:
            Gene Name: HTR1B
            Uniprot ID: P28222 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: D(4) dopamine receptor
            Reactions:
              Gene Name: DRD4
              Uniprot ID: P21917 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: 5-hydroxytryptamine receptor 1A
              Reactions:
                Gene Name: HTR1A
                Uniprot ID: P08908 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: 5-hydroxytryptamine receptor 2A
                Reactions:
                  Gene Name: HTR2A
                  Uniprot ID: P28223 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: 5-hydroxytryptamine receptor 2C
                  Reactions:
                    Gene Name: HTR2C
                    Uniprot ID: P28335 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: 5-hydroxytryptamine receptor 6
                    Reactions:
                      Gene Name: HTR6
                      Uniprot ID: P50406 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Histamine H1 receptor
                      Reactions:
                        Gene Name: HRH1
                        Uniprot ID: P35367 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: 5-hydroxytryptamine receptor 3A
                        Reactions:
                          Gene Name: HTR3A
                          Uniprot ID: P46098 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: 5-hydroxytryptamine receptor 1D
                          Reactions:
                            Gene Name: HTR1D
                            Uniprot ID: P28221 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Alpha-1A adrenergic receptor
                            Reactions:
                              Gene Name: ADRA1A
                              Uniprot ID: P35348 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: Alpha-1B adrenergic receptor
                              Reactions:
                                Gene Name: ADRA1B
                                Uniprot ID: P35368 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA
                                Name: Alpha-2C adrenergic receptor
                                Reactions:
                                  Gene Name: ADRA2C
                                  Uniprot ID: P18825 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: D(3) dopamine receptor
                                  Reactions:
                                    Gene Name: DRD3
                                    Uniprot ID: P35462 Link_out
                                    Protein Sequence: FASTA
                                    Gene Sequence: FASTA
                                    Name: Muscarinic acetylcholine receptor M3
                                    Reactions:
                                      Gene Name: CHRM3
                                      Uniprot ID: P20309 Link_out
                                      Protein Sequence: FASTA
                                      Gene Sequence: FASTA
                                      Name: D(1A) dopamine receptor
                                      Reactions:
                                        Gene Name: DRD1
                                        Uniprot ID: P21728 Link_out
                                        Protein Sequence: FASTA
                                        Gene Sequence: FASTA
                                        Name: Muscarinic acetylcholine receptor M1
                                        Reactions:
                                          Gene Name: CHRM1
                                          Uniprot ID: P11229 Link_out
                                          Protein Sequence: FASTA
                                          Gene Sequence: FASTA
                                          Name: Muscarinic acetylcholine receptor M2
                                          Reactions:
                                            Gene Name: CHRM2
                                            Uniprot ID: P08172 Link_out
                                            Protein Sequence: FASTA
                                            Gene Sequence: FASTA
                                            Name: Muscarinic acetylcholine receptor M4
                                            Reactions:
                                              Gene Name: CHRM4
                                              Uniprot ID: P08173 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Muscarinic acetylcholine receptor M5
                                              Reactions:
                                                Gene Name: CHRM5
                                                Uniprot ID: P08912 Link_out
                                                Protein Sequence: FASTA
                                                Gene Sequence: FASTA
                                                Name: D(1B) dopamine receptor
                                                Reactions:
                                                  Gene Name: DRD5
                                                  Uniprot ID: P21918 Link_out
                                                  Protein Sequence: FASTA
                                                  Gene Sequence: FASTA
                                                  Name: 5-hydroxytryptamine receptor 1E
                                                  Reactions:
                                                    Gene Name: HTR1E
                                                    Uniprot ID: P28566 Link_out
                                                    Protein Sequence: FASTA
                                                    Gene Sequence: FASTA