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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-17 11:54:18 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005042
Secondary Accession Numbers
  • HMDB05042
Metabolite Identification
Common NameAripiprazole
DescriptionAripiprazole 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
Data?1582752342
Synonyms
ValueSource
AbilifyChEBI
AbilitatChEBI
AripiprazolChEBI
AripiprazolumChEBI
7-(4-(4-(2,3-Dichlorophenyl)-1-piperazinyl)butyloxy)-3,4-dihydro-2(1H)-quinolinoneHMDB
Chemical FormulaC23H27Cl2N3O2
Average Molecular Weight448.385
Monoisotopic Molecular Weight447.148032537
IUPAC Name7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one
Traditional Namearipiprazole
CAS Registry Number129722-12-9
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 KeyCEUORZQYGODEFX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Tetrahydroquinolone
  • Quinolone
  • Tetrahydroquinoline
  • 1,2-dichlorobenzene
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Alkyl aryl ether
  • Halobenzene
  • Chlorobenzene
  • N-alkylpiperazine
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM205.830932474
[M+H]+Not Available203.476http://allccs.zhulab.cn/database/detail?ID=AllCCS00001078
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0078 g/LALOGPS
logP5.21ALOGPS
logP4.9ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)7.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.81 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.34 m³·mol⁻¹ChemAxon
Polarizability49.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+203.18530932474
DeepCCS[M-H]-200.73230932474
DeepCCS[M-2H]-235.04730932474
DeepCCS[M+Na]+210.92830932474
AllCCS[M+H]+203.032859911
AllCCS[M+H-H2O]+200.932859911
AllCCS[M+NH4]+204.932859911
AllCCS[M+Na]+205.532859911
AllCCS[M-H]-199.132859911
AllCCS[M+Na-2H]-199.432859911
AllCCS[M+HCOO]-199.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AripiprazoleClC1=CC=CC(N2CCN(CCCCOC3=CC4=C(CCC(=O)N4)C=C3)CC2)=C1Cl4811.7Standard polar33892256
AripiprazoleClC1=CC=CC(N2CCN(CCCCOC3=CC4=C(CCC(=O)N4)C=C3)CC2)=C1Cl3584.7Standard non polar33892256
AripiprazoleClC1=CC=CC(N2CCN(CCCCOC3=CC4=C(CCC(=O)N4)C=C3)CC2)=C1Cl4083.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aripiprazole,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCC2=CC=C(OCCCCN3CCN(C4=CC=CC(Cl)=C4Cl)CC3)C=C213727.4Semi standard non polar33892256
Aripiprazole,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCC2=CC=C(OCCCCN3CCN(C4=CC=CC(Cl)=C4Cl)CC3)C=C213717.3Standard non polar33892256
Aripiprazole,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCC2=CC=C(OCCCCN3CCN(C4=CC=CC(Cl)=C4Cl)CC3)C=C214628.5Standard polar33892256
Aripiprazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCC2=CC=C(OCCCCN3CCN(C4=CC=CC(Cl)=C4Cl)CC3)C=C213947.9Semi standard non polar33892256
Aripiprazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCC2=CC=C(OCCCCN3CCN(C4=CC=CC(Cl)=C4Cl)CC3)C=C213947.8Standard non polar33892256
Aripiprazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCC2=CC=C(OCCCCN3CCN(C4=CC=CC(Cl)=C4Cl)CC3)C=C214655.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aripiprazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w4i-1490100000-261de3e19904b78dcdc22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aripiprazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aripiprazole LC-ESI-qTof , Positive-QTOFsplash10-000i-3970100000-6b98b53e8175df39986e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aripiprazole , positive-QTOFsplash10-0f72-0340900000-34d93478ad0d9f5cf2b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aripiprazole , positive-QTOFsplash10-000i-3970100000-6b98b53e8175df39986e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aripiprazole 35V, Positive-QTOFsplash10-000b-0280900000-b9247c5494e58e66124c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aripiprazole 35V, Negative-QTOFsplash10-0006-0190000000-f292c098f875dc5bf1032021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 10V, Positive-QTOFsplash10-0002-0130900000-09f4b35bcf7ec5b72e812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 20V, Positive-QTOFsplash10-000j-0691700000-856146a0ee910fc8c54b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 40V, Positive-QTOFsplash10-000b-3950000000-13c06e4b3b715a51d3e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 10V, Negative-QTOFsplash10-0002-0400900000-00ad2c66f6eb650acc112016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 20V, Negative-QTOFsplash10-03dl-2900400000-2f2ae13359ce2017c9792016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 40V, Negative-QTOFsplash10-0006-5900000000-0638ccc974f117bcfc432016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 10V, Positive-QTOFsplash10-0002-0000900000-80596c933df60e9bbd282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 20V, Positive-QTOFsplash10-0002-0011900000-850b35a9d8f2a8e5dbe62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 40V, Positive-QTOFsplash10-006t-3920200000-00b90fd36a9ef68756de2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 10V, Negative-QTOFsplash10-0002-0000900000-ac7e0802ed0bc5c520a72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 20V, Negative-QTOFsplash10-0002-2000900000-2fd89cebd272760b74452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aripiprazole 40V, Negative-QTOFsplash10-03e9-6920100000-943ee90010dfdaceadee2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01238
Phenol Explorer Compound IDNot Available
FooDB IDFDB004879
KNApSAcK IDNot Available
Chemspider ID54790
KEGG Compound IDC12564
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAripiprazole
METLIN IDNot Available
PubChem Compound60795
PDB IDNot Available
ChEBI ID31236
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTsujimori, Hisayuki; Yamaguchi, Tatsuya. Process for preparing aripiprazole. PCT Int. Appl. (2004), 20 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Only showing the first 10 proteins. There are 29 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Hirose T, Kikuchi T: Aripiprazole, a novel antipsychotic agent: dopamine D2 receptor partial agonist. J Med Invest. 2005 Nov;52 Suppl:284-90. [PubMed:16366516 ]
  2. Inoue A, Miki S, Seto M, Kikuchi T, Morita S, Ueda H, Misu Y, Nakata Y: Aripiprazole, a novel antipsychotic drug, inhibits quinpirole-evoked GTPase activity but does not up-regulate dopamine D2 receptor following repeated treatment in the rat striatum. Eur J Pharmacol. 1997 Feb 19;321(1):105-11. [PubMed:9083792 ]
  3. Wood MD, Scott C, Clarke K, Westaway J, Davies CH, Reavill C, Hill M, Rourke C, Newson M, Jones DN, Forbes IT, Gribble A: Aripiprazole and its human metabolite are partial agonists at the human dopamine D2 receptor, but the rodent metabolite displays antagonist properties. Eur J Pharmacol. 2006 Sep 28;546(1-3):88-94. Epub 2006 Jul 21. [PubMed:16925992 ]
  4. Kim E, Yu KS, Cho JY, Shin YW, Yoo SY, Kim YY, Jang IJ, Shin SG, Kwon JS: Effects of DRD2 and CYP2D6 genotypes on delta EEG power response to aripiprazole in healthy male volunteers: a preliminary study. Hum Psychopharmacol. 2006 Dec;21(8):519-28. [PubMed:16981227 ]
  5. Wood M, Reavill C: Aripiprazole acts as a selective dopamine D2 receptor partial agonist. Expert Opin Investig Drugs. 2007 Jun;16(6):771-5. [PubMed:17501690 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular weight:
53554.4
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular weight:
48359.9
References
  1. Nasrallah HA: Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol Psychiatry. 2008 Jan;13(1):27-35. Epub 2007 Sep 11. [PubMed:17848919 ]

Only showing the first 10 proteins. There are 29 proteins in total.