sulpiride Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
sulpiride derivatives	2537	15676-16-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: sulpiride sulpirid sulpitil sulpyrid sursumid	A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed) Molecular weight: 341.43 Formula: C15H23N3O4S CLOGP: 1.11 LIPINSKI: 0 HAC: 7 HDO: 2 TPSA: 101.73 ALOGS: -2.80 ROTB: 6

Drug dosage:

Dose	Unit	Route
0.80	g	O
0.80	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	2.28 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	70 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	133.89 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	27 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.94 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1.90 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	1 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	6.50 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 1, 1972	YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Torsade de pointes	97.06	21.28	38	4281	12116	46669627
Parkinsonism	89.59	21.28	32	4287	7916	46673827
Electrocardiogram QT prolonged	70.35	21.28	49	4270	51276	46630467
Ventricular fibrillation	64.73	21.28	28	4291	11468	46670275
Fall	58.62	21.28	107	4212	328990	46352753
Cerebellar syndrome	50.86	21.28	17	4302	3448	46678295
Hypomagnesaemia	49.91	21.28	29	4290	22181	46659562
Extrapyramidal disorder	49.26	21.28	23	4296	11245	46670498
Persecutory delusion	43.40	21.28	14	4305	2541	46679202
Serotonin syndrome	42.52	21.28	27	4292	24193	46657550
Psychomotor retardation	36.35	21.28	13	4306	3220	46678523
Drug interaction	35.97	21.28	66	4253	203028	46478715
Rhabdomyolysis	35.34	21.28	30	4289	41879	46639864
Tension	33.92	21.28	12	4307	2880	46678863
Hypokalaemia	33.54	21.28	41	4278	87983	46593760
Metabolic syndrome	30.08	21.28	9	4310	1275	46680468
Depression	29.74	21.28	55	4264	170049	46511694
Hyponatraemia	28.99	21.28	41	4278	101291	46580452
Altered state of consciousness	28.96	21.28	21	4298	23327	46658416
Suicide attempt	28.37	21.28	30	4289	55006	46626737
Infectious mononucleosis	28.15	21.28	9	4310	1587	46680156
Somnolence	27.85	21.28	51	4268	156470	46525273
Urticaria vesiculosa	27.61	21.28	4	4315	12	46681731
Acinetobacter test positive	27.11	21.28	5	4314	83	46681660
Neuroleptic malignant syndrome	26.25	21.28	15	4304	11107	46670636
Dystonia	26.08	21.28	15	4304	11242	46670501
Nikolsky's sign	25.78	21.28	5	4314	110	46681633
Mixed anxiety and depressive disorder	25.01	21.28	5	4314	129	46681614
Social anxiety disorder	24.74	21.28	6	4313	383	46681360
Treatment noncompliance	24.48	21.28	21	4298	29710	46652033
Depressed mood	24.36	21.28	22	4297	33297	46648446
Long QT syndrome	22.37	21.28	9	4310	3071	46678672
Hyperthermia	22.17	21.28	12	4307	8002	46673741
Loss of consciousness	21.46	21.28	37	4282	108201	46573542
Cardio-respiratory arrest	21.36	21.28	27	4292	59842	46621901

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Neuroleptic malignant syndrome	94.79	21.04	42	3073	16253	29933110
Parkinsonism	46.33	21.04	20	3095	7249	29942114
Schizophrenia	45.22	21.04	21	3094	9027	29940336
Psychotic disorder	37.66	21.04	25	3090	21490	29927873
Extrapyramidal disorder	36.09	21.04	19	3096	10674	29938689
Suicide attempt	31.71	21.04	28	3087	36669	29912694
Eosinophil count decreased	29.97	21.04	9	3106	1148	29948215
Abnormal behaviour	27.17	21.04	22	3093	25601	29923762
Norovirus test positive	26.82	21.04	5	3110	78	29949285
Mean cell haemoglobin concentration decreased	26.70	21.04	8	3107	1012	29948351
Cognitive disorder	24.39	21.04	20	3095	23670	29925693
Neutrophil count decreased	22.83	21.04	25	3090	42429	29906934
Abulia	22.67	21.04	6	3109	484	29948879
Red cell distribution width increased	22.01	21.04	10	3105	4084	29945279
Stupor	21.72	21.04	9	3106	2944	29946419

Pharmacologic Action:

Source	Code	Description
ATC	N05AL01	NERVOUS SYSTEM PSYCHOLEPTICS ANTIPSYCHOTICS Benzamides
MeSH PA	D000928	Antidepressive Agents
MeSH PA	D018687	Antidepressive Agents, Second-Generation
MeSH PA	D014150	Antipsychotic Agents
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D015259	Dopamine Agents
MeSH PA	D018492	Dopamine Antagonists
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D011619	Psychotropic Drugs
MeSH PA	D014149	Tranquilizing Agents
CHEBI has role	CHEBI:35469	thymoanaleptics
CHEBI has role	CHEBI:35476	grosser tranquilizer
CHEBI has role	CHEBI:48561	dopamine blocker
CHEBI has role	CHEBI:50919	antiemetico

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Schizophrenia	indication	58214004	DOID:5419

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.47	acidic
pKa2	12.66	acidic
pKa3	8.85	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN	ANTAGONIST	Ki	8.12		CHEMBL	IUPHAR
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN		IC50	7.40		WOMBAT-PK
Carbonic anhydrase 12	Enzyme	O43570	CAH12_HUMAN		Ki	8.41		CHEMBL
D(4) dopamine receptor	GPCR	P21917	DRD4_HUMAN		Ki	5.68		CHEMBL
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN		Ki	8.10		CHEMBL
Carbonic anhydrase 3	Enzyme	P07451	CAH3_HUMAN		Ki	4.97		CHEMBL
Carbonic anhydrase 5A, mitochondrial	Enzyme	P35218	CAH5A_HUMAN		Ki	6.76		CHEMBL
Carbonic anhydrase 7	Enzyme	P43166	CAH7_HUMAN		Ki	8.44		CHEMBL
Carbonic anhydrase 9	Enzyme	Q16790	CAH9_HUMAN		Ki	7.51		CHEMBL
Carbonic anhydrase 1	Enzyme	P00915	CAH1_HUMAN		Ki	5.92		CHEMBL
Carbonic anhydrase 5B, mitochondrial	Enzyme	Q9Y2D0	CAH5B_HUMAN		Ki	7.74		CHEMBL
Carbonic anhydrase 6	Enzyme	P23280	CAH6_HUMAN		Ki	9.10		CHEMBL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	6.12		DRUG MATRIX
Dopamine receptor	GPCR		DRD1_RAT DRD2_RAT DRD3_RAT DRD4_RAT DRD5_RAT		Ki	5.80		CHEMBL
Alpha carbonic anhydrase	Unclassified		B5SU02_9CNID		Ki	6.37		CHEMBL
Astrosclerin-3	Unclassified		A6YCJ1_9METZ		Ki	6.42		CHEMBL
Beta-carbonic anhydrase 1	Enzyme		MTCA1_MYCTU		Ki	5.64		CHEMBL
Carbonic anhydrase	Unclassified		C0IX24_9CNID		Ki	6.38		CHEMBL
Delta carbonic anhydrase	Unclassified		Q5U9J1_THAWE		Ki	6.59		CHEMBL
Carbonic anhydrase	Enzyme		CAN_YEAST		Ki	6.91		CHEMBL
D(2) dopamine receptor	GPCR		DRD2_CANFA		IC50	6.70		CHEMBL
D(2) dopamine receptor	GPCR		DRD2_RAT		Kd	8.82		CHEMBL
Carbonic anhydrase	Enzyme		CYNT_HELPY		Ki	6.75		CHEMBL
Carbonic anhydrase 15	Enzyme		CAH15_MOUSE		Ki	7.14		CHEMBL
Carbonic anhydrase	Enzyme		CAN_CANAL		Ki	7.40		CHEMBL
Carbonic anhydrase 2	Enzyme		MTCA2_MYCTU		Ki	6.58		CHEMBL
Carbonic anhydrase	Unclassified		Q5TU56_ANOGA		Ki	7.53		CHEMBL
Carbonic anhydrase	Enzyme		Q6FTL6_CANGA		Ki	6.95		CHEMBL

External reference:

ID	Source
N0000166882	NUI
D01226	KEGG_DRUG
C0038803	UMLSCUI
CHEBI:32168	CHEBI
CHEMBL26	ChEMBL_ID
D013469	MESH_DESCRIPTOR_UI
2359	INN_ID
DB00391	DRUGBANK_ID
7MNE9M8287	UNII
5355	PUBCHEM_CID
5501	IUPHAR_LIGAND_ID
10239	RXNORM
003764	NDDF
321506004	SNOMEDCT_US
395891007	SNOMEDCT_US

Pharmaceutical products:

None