aripiprazole (CHEBI:31236)

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CHEBI:31236 - aripiprazole

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ChEBI Name	aripiprazole

ChEBI ID	CHEBI:31236

Definition	An N-arylpiperazine that is piperazine substituted by a 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl group at position 1 and by a 2,3-dichlorophenyl group at position 4. It is an antipsychotic drug used for the treatment of Schizophrenia, and other mood disorders.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000328578076

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

9SC - Ideal conformer

RDKit 3D

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Time for openFile(9SC - Ideal conformer

RDKit 3D

57 60 0 0 0 0 0 0 0 0999 V2000

-4.5990 -0.9360 -0.1600 N 0 0 0 0 0 0 0 0 0 0 0 0

8.9650 -0.1550 -0.7480 N 0 0 0 0 0 0 0 0 0 0 0 0

-6.4150 -1.2910 1.3900 C 0 0 0 0 0 0 0 0 0 0 0 0

-7.6420 -0.9150 1.9020 C 0 0 0 0 0 0 0 0 0 0 0 0

-8.3010 0.1860 1.3870 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.2000 -2.2600 0.3390 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8780 -2.6700 -0.3140 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.5720 0.0700 0.1440 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8970 -1.5430 -0.5830 C 0 0 0 0 0 0 0 0 0 0 0 0

5.3300 -0.2660 -0.1870 C 0 0 0 0 0 0 0 0 0 0 0 0

6.2660 1.5500 1.0750 C 0 0 0 0 0 0 0 0 0 0 0 0

6.5910 -0.5860 -0.6650 C 0 0 0 0 0 0 0 0 0 0 0 0

8.7210 2.0510 1.0200 C 0 0 0 0 0 0 0 0 0 0 0 0

9.9440 1.1390 1.1260 C 0 0 0 0 0 0 0 0 0 0 0 0

-7.7340 0.9160 0.3570 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5470 -2.0620 -0.5560 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5390 -1.1300 -0.0140 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9830 -0.6110 -0.0410 C 0 0 0 0 0 0 0 0 0 0 0 0

5.1700 0.8020 0.6840 C 0 0 0 0 0 0 0 0 0 0 0 0

7.5240 1.2310 0.6020 C 0 0 0 0 0 0 0 0 0 0 0 0

7.6900 0.1630 -0.2700 C 0 0 0 0 0 0 0 0 0 0 0 0

-6.5060 0.5450 -0.1610 C 0 0 0 0 0 0 0 0 0 0 0 0

10.0640 0.2950 -0.1140 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.8400 -0.5580 0.3600 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2500 -0.3410 -0.5080 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8510 -1.6640 -0.0090 N 0 0 0 0 0 0 0 0 0 0 0 0

4.2510 -0.9980 -0.5720 O 0 0 0 0 0 0 0 0 0 0 0 0

11.1620 0.0180 -0.5470 O 0 0 0 0 0 0 0 0 0 0 0 0

-8.5650 2.2980 -0.2870 Cl 0 0 0 0 0 0 0 0 0 0 0 0

-5.7960 1.4600 -1.4540 Cl 0 0 0 0 0 0 0 0 0 0 0 0

9.0590 -0.7080 -1.5400 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.9020 -2.1510 1.7930 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.0870 -1.4820 2.7060 H 0 0 0 0 0 0 0 0 0 0 0 0

-9.2600 0.4770 1.7900 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0740 -2.2170 1.4210 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.9710 -2.9890 0.0900 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5660 -3.6390 0.0770 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0110 -2.7390 -1.3930 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8850 1.0380 -0.2460 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4390 0.1390 1.2240 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1180 -2.5690 -0.2870 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8710 -1.4770 -1.6700 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1380 2.3880 1.7450 H 0 0 0 0 0 0 0 0 0 0 0 0

6.7180 -1.4180 -1.3430 H 0 0 0 0 0 0 0 0 0 0 0 0

8.5230 2.5080 1.9890 H 0 0 0 0 0 0 0 0 0 0 0 0

8.9130 2.8310 0.2830 H 0 0 0 0 0 0 0 0 0 0 0 0

10.8420 1.7490 1.2310 H 0 0 0 0 0 0 0 0 0 0 0 0

9.8420 0.4960 2.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5730 -1.9950 -1.6430 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3260 -3.0870 -0.2600 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5650 -1.1960 1.0740 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3180 -0.1040 -0.3100 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7620 0.4140 -0.3360 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0090 -0.6780 1.0470 H 0 0 0 0 0 0 0 0 0 0 0 0

4.1860 1.0520 1.0540 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3760 -0.3830 -1.5900 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4800 0.3890 -0.2600 H 0 0 0 0 0 0 0 0 0 0 0 0

19 11 1 0

19 10 2 0

11 20 2 0

27 10 1 0

27 18 1 0

10 12 1 0

9 17 1 0

9 18 1 0

6 7 1 0

6 1 1 0

7 26 1 0

17 16 1 0

20 13 1 0

20 21 1 0

13 14 1 0

16 26 1 0

12 21 2 0

26 25 1 0

21 2 1 0

1 24 1 0

1 8 1 0

24 3 2 0

24 22 1 0

30 22 1 0

3 4 1 0

14 23 1 0

25 8 1 0

22 15 2 0

2 23 1 0

4 5 2 0

15 5 1 0

15 29 1 0

23 28 2 0

2 31 1 0

3 32 1 0

4 33 1 0

5 34 1 0

6 35 1 0

6 36 1 0

7 37 1 0

7 38 1 0

8 39 1 0

8 40 1 0

9 41 1 0

9 42 1 0

11 43 1 0

12 44 1 0

13 45 1 0

13 46 1 0

14 47 1 0

14 48 1 0

16 49 1 0

16 50 1 0

17 51 1 0

17 52 1 0

18 53 1 0

18 54 1 0

19 55 1 0

25 56 1 0

25 57 1 0

M END): 36 ms

reading 57 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

57 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
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Read full article at Wikipedia

Formula

C23H27Cl2N3O2

Net Charge

Average Mass

448.390

Monoisotopic Mass

447.14803

InChI

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)

InChIKey

CEUORZQYGODEFX-UHFFFAOYSA-N

SMILES

ClC1=C(Cl)C(=CC=C1)N1CCN(CCCCOC2=CC=C3CCC(=O)NC3=C2)CC1

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	drug metabolite H1-receptor antagonist H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. serotonergic agonist An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.

Application(s):	second generation antipsychotic Antipsychotic drugs which can have different modes of action but which tend to be less likely than first generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements. H1-receptor antagonist H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. serotonergic agonist An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	aripiprazole (CHEBI:31236) has role drug metabolite (CHEBI:49103) aripiprazole (CHEBI:31236) has role H₁-receptor antagonist (CHEBI:37955) aripiprazole (CHEBI:31236) has role second generation antipsychotic (CHEBI:65191) aripiprazole (CHEBI:31236) has role serotonergic agonist (CHEBI:35941) aripiprazole (CHEBI:31236) is a δ-lactam (CHEBI:77727) aripiprazole (CHEBI:31236) is a N-alkylpiperazine (CHEBI:46845) aripiprazole (CHEBI:31236) is a N-arylpiperazine (CHEBI:46848) aripiprazole (CHEBI:31236) is a aromatic ether (CHEBI:35618) aripiprazole (CHEBI:31236) is a dichlorobenzene (CHEBI:23697) aripiprazole (CHEBI:31236) is a quinolone (CHEBI:23765)

IUPAC Name

7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-3,4-dihydroquinolin-2(1H)-one

INNs	Sources
aripiprazol	WHO MedNet
aripiprazole	WHO MedNet
aripiprazole	WHO MedNet
aripiprazolum	WHO MedNet

Synonyms	Sources
7-(4-(4-(2,3-dichlorophenyl)-1-piperazinyl)butyloxy)-3,4-dihydro-2(1H)-quinolinone	ChemIDplus
7-[4-[4-[2,3-bis(chloranyl)phenyl]piperazin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one	PDBeChem
7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one	ChEBI
OPC 14597	ChemIDplus
OPC 31	ChemIDplus
OPC-14597	ChemIDplus
OPC-31	ChemIDplus

Brand Names	Sources
Abilify	DrugBank
Abilify Discmelt	ChemIDplus
Abilify Maintena	ChemIDplus
Abilify MyCite	ChemIDplus
Abilitat	DrugBank
Arpizol	DrugCentral
Asprito	ChEBI
Discmelt	ChemIDplus
Pripiprazole	DrugCentral

Manual Xrefs	Databases
242	DrugCentral
54790	ChemSpider
9SC	PDBeChem
Aripiprazole	Wikipedia
C12564	KEGG COMPOUND
D01164	KEGG DRUG
DB01238	DrugBank
EP367141	Patent
FDB004879	FooDB
HMDB0005042	HMDB
LSM-5776	LINCS
US5006528	Patent
View more database links

Registry Number	Type	Source
129722-12-9	CAS Registry Number	ChemIDplus

Citations	Types	Sources
12063084	PubMed citation	Europe PMC
12784105	PubMed citation	Europe PMC
14998222	PubMed citation	Europe PMC
15019558	PubMed citation	Europe PMC
15189766	PubMed citation	Europe PMC
15257633	PubMed citation	Europe PMC
15825673	PubMed citation	Europe PMC
16401666	PubMed citation	Europe PMC
16508892	PubMed citation	Europe PMC
16554739	PubMed citation	Europe PMC
16648324	PubMed citation	Europe PMC
16880478	PubMed citation	Europe PMC
17115868	PubMed citation	Europe PMC
17472545	PubMed citation	Europe PMC
17501690	PubMed citation	Europe PMC
18021764	PubMed citation	Europe PMC
18646161	PubMed citation	Europe PMC
18720421	PubMed citation	Europe PMC
18765484	PubMed citation	Europe PMC
18788833	PubMed citation	Europe PMC
19412463	PubMed citation	Europe PMC
19956463	PubMed citation	Europe PMC
20201815	PubMed citation	Europe PMC
30292748	PubMed citation	Europe PMC
30411049	PubMed citation	Europe PMC
30856161	PubMed citation	Europe PMC
31152368	PubMed citation	Europe PMC
31320322	PubMed citation	Europe PMC
32891516	PubMed citation	Europe PMC
33064050	PubMed citation	Europe PMC
33347031	PubMed citation	Europe PMC

Last Modified

05 January 2021

CHEBI:31236 - aripiprazole

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