Human Metabolome Database Version 3.5

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 | PDB | 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
  • Membrane (predicted from logP)
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
  • Membrane (predicted from logP)
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
DrugBank Metabolite ID Not Available
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: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA2A
Uniprot ID: P08913 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2B adrenergic receptor
Reactions: Not Available
Gene Name: ADRA2B
Uniprot ID: P18089 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(2) dopamine receptor
Reactions: Not Available
Gene Name: DRD2
Uniprot ID: P14416 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 7
Reactions: Not Available
Gene Name: HTR7
Uniprot ID: P34969 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1B
Reactions: Not Available
Gene Name: HTR1B
Uniprot ID: P28222 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(4) dopamine receptor
Reactions: Not Available
Gene Name: DRD4
Uniprot ID: P21917 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1A
Reactions: Not Available
Gene Name: HTR1A
Uniprot ID: P08908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 2A
Reactions: Not Available
Gene Name: HTR2A
Uniprot ID: P28223 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 2C
Reactions: Not Available
Gene Name: HTR2C
Uniprot ID: P28335 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 6
Reactions: Not Available
Gene Name: HTR6
Uniprot ID: P50406 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Histamine H1 receptor
Reactions: Not Available
Gene Name: HRH1
Uniprot ID: P35367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 3A
Reactions: Not Available
Gene Name: HTR3A
Uniprot ID: P46098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1D
Reactions: Not Available
Gene Name: HTR1D
Uniprot ID: P28221 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-1A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1A
Uniprot ID: P35348 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-1B adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1B
Uniprot ID: P35368 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2C adrenergic receptor
Reactions: Not Available
Gene Name: ADRA2C
Uniprot ID: P18825 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(3) dopamine receptor
Reactions: Not Available
Gene Name: DRD3
Uniprot ID: P35462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M3
Reactions: Not Available
Gene Name: CHRM3
Uniprot ID: P20309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(1A) dopamine receptor
Reactions: Not Available
Gene Name: DRD1
Uniprot ID: P21728 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M1
Reactions: Not Available
Gene Name: CHRM1
Uniprot ID: P11229 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M2
Reactions: Not Available
Gene Name: CHRM2
Uniprot ID: P08172 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M4
Reactions: Not Available
Gene Name: CHRM4
Uniprot ID: P08173 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Muscarinic acetylcholine receptor M5
Reactions: Not Available
Gene Name: CHRM5
Uniprot ID: P08912 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: D(1B) dopamine receptor
Reactions: Not Available
Gene Name: DRD5
Uniprot ID: P21918 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1E
Reactions: Not Available
Gene Name: HTR1E
Uniprot ID: P28566 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA