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

Stem definition	Drug id	CAS RN
sulpiride derivatives	179	71675-85-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: barhemsys amisulpride aminosultopride deniban solian	A benzamide derivative that is used as an antipsychotic agent for the treatment of schizophrenia. It is also used as an antidepressive agent. Molecular weight: 369.48 Formula: C17H27N3O4S CLOGP: 1.80 LIPINSKI: 0 HAC: 7 HDO: 2 TPSA: 101.73 ALOGS: -3.10 ROTB: 7 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

barhemsys
amisulpride
aminosultopride
deniban
solian

A benzamide derivative that is used as an antipsychotic agent for the treatment of schizophrenia. It is also used as an antidepressive agent.

Molecular weight: 369.48
Formula: C17H27N3O4S
CLOGP: 1.80
LIPINSKI: 0
HAC: 7
HDO: 2
TPSA: 101.73
ALOGS: -3.10
ROTB: 7

Status: ONP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.40	g	O
7.50	mg	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	46.40 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	48 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
Feb. 26, 2020	FDA	ACACIA PHARMA LTD
Jan. 1, 1986	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
Extrapyramidal disorder	233.17	24.18	82	7680	12320	53328984
Schizophrenia	174.40	24.18	63	7699	10216	53331088
Hyperprolactinaemia	150.68	24.18	43	7719	3272	53338032
Sopor	146.05	24.18	68	7694	21016	53320288
Drug abuse	138.06	24.18	97	7665	65429	53275875
Blood prolactin increased	125.00	24.18	37	7725	3202	53338102
Electrocardiogram QT prolonged	103.91	24.18	77	7685	56326	53284978
Neuroleptic malignant syndrome	102.97	24.18	45	7717	11988	53329316
Galactorrhoea	96.91	24.18	32	7730	3963	53337341
Akathisia	96.61	24.18	39	7723	8532	53332772
Metabolic syndrome	90.13	24.18	24	7738	1410	53339894
Psychotic disorder	88.63	24.18	51	7711	24334	53316970
Antipsychotic drug level increased	82.01	24.18	27	7735	3312	53337992
Hallucination, auditory	78.48	24.18	37	7725	11736	53329568
Parkinsonism	74.82	24.18	33	7729	8980	53332324
Mental impairment	71.23	24.18	36	7726	13273	53328031
Drug interaction	68.70	24.18	118	7644	219211	53122093
Myocarditis	67.06	24.18	30	7732	8438	53332866
Sedation	64.90	24.18	45	7717	29630	53311674
Differential white blood cell count abnormal	64.15	24.18	16	7746	724	53340580
Confusional state	62.79	24.18	106	7656	194115	53147189
Aggression	54.75	24.18	37	7725	23366	53317938
Mydriasis	53.01	24.18	28	7734	11298	53330006
Pain	52.40	24.18	11	7751	588387	52752917
Dystonia	52.06	24.18	29	7733	12992	53328312
Suicide attempt	50.99	24.18	52	7710	58116	53283188
Tremor	50.75	24.18	76	7686	125660	53215644
Tardive dyskinesia	49.63	24.18	24	7738	8046	53333258
Delusion	48.71	24.18	27	7735	11982	53329322
Neutrophil count increased	47.70	24.18	29	7733	15281	53326023
Salivary hypersecretion	46.82	24.18	22	7740	6921	53334383
Overdose	46.17	24.18	67	7695	107669	53233635
CSF measles antibody positive	45.94	24.18	8	7754	57	53341247
Rubella antibody positive	45.12	24.18	8	7754	64	53341240
Hallucination	43.36	24.18	46	7716	53792	53287512
Intentional self-injury	43.14	24.18	33	7729	25251	53316053
Neutropenia	42.54	24.18	80	7682	159105	53182199
Blood brain barrier defect	42.03	24.18	8	7754	98	53341206
Mental disorder	41.99	24.18	32	7730	24344	53316960
White blood cell count increased	41.73	24.18	42	7720	46203	53295101
Catatonia	40.80	24.18	17	7745	4023	53337281
Treatment noncompliance	37.38	24.18	34	7728	33001	53308303
Thunderclap headache	37.25	24.18	8	7754	185	53341119
Antipsychotic drug level decreased	36.69	24.18	8	7754	199	53341105
Accommodation disorder	36.52	24.18	9	7753	387	53340917
Organic brain syndrome	35.92	24.18	8	7754	220	53341084
Grandiosity	35.82	24.18	8	7754	223	53341081
Euphoric mood	35.71	24.18	16	7746	4513	53336791
CSF protein increased	34.07	24.18	9	7753	512	53340792
Loss of consciousness	33.77	24.18	60	7702	114152	53227152
Leukopenia	33.38	24.18	47	7715	73416	53267888
Coma	33.37	24.18	43	7719	61740	53279564
Negative thoughts	33.18	24.18	10	7752	919	53340385
Ventricular dyskinesia	32.80	24.18	7	7755	157	53341147
Type 2 diabetes mellitus	32.75	24.18	31	7731	31639	53309665
Bladder trabeculation	32.73	24.18	6	7756	59	53341245
Amenorrhoea	32.48	24.18	19	7743	9330	53331974
Blood folate decreased	32.44	24.18	9	7753	617	53340687
Antipsychotic drug level above therapeutic	32.11	24.18	10	7752	1026	53340278
Agitation	31.97	24.18	41	7721	58585	53282719
Binge eating	30.75	24.18	8	7754	429	53340875
Cerebral artery stenosis	30.46	24.18	8	7754	445	53340859
Arthralgia	30.44	24.18	13	7749	439770	52901534
Rash	29.61	24.18	14	7748	446177	52895127
Serotonin syndrome	29.52	24.18	27	7735	26379	53314925
Pruritus	29.37	24.18	4	7758	293828	53047476
Intentional overdose	29.06	24.18	42	7720	67163	53274141
Waxy flexibility	28.77	24.18	6	7756	120	53341184
Morose	28.66	24.18	5	7757	36	53341268
Hemianopia	28.60	24.18	9	7753	955	53340349
Pain in extremity	28.21	24.18	4	7758	285046	53056258
Pleocytosis	28.17	24.18	8	7754	597	53340707
Muscle rigidity	27.42	24.18	18	7744	10823	53330481
Vertigo	27.15	24.18	37	7725	56044	53285260
Weight increased	27.06	24.18	78	7684	204489	53136815
Electrocardiogram T wave abnormal	26.98	24.18	11	7751	2465	53338839
Cor pulmonale acute	26.86	24.18	7	7755	378	53340926
Hypochromic anaemia	26.22	24.18	10	7752	1879	53339425
Cardiogenic shock	25.90	24.18	21	7741	17461	53323843
Psychiatric decompensation	25.55	24.18	9	7753	1353	53339951
Toxicity to various agents	25.53	24.18	80	7682	219518	53121786
Cognitive disorder	25.49	24.18	32	7730	44746	53296558
Hallucination, olfactory	24.84	24.18	6	7756	237	53341067

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
Schizophrenia	371.85	23.69	134	10179	9850	32493363
Antipsychotic drug level below therapeutic	318.90	23.69	82	10231	1887	32501326
Akathisia	252.91	23.69	92	10221	6933	32496280
Disinhibition	225.68	23.69	67	10246	2653	32500560
Obsessive-compulsive disorder	217.05	23.69	75	10238	4859	32498354
Therapeutic product effect variable	215.51	23.69	61	10252	2035	32501178
Neuroleptic malignant syndrome	189.35	23.69	98	10215	17397	32485816
Euphoric mood	186.42	23.69	68	10245	5159	32498054
Increased appetite	172.24	23.69	68	10245	6408	32496805
Neutrophil count increased	167.89	23.69	88	10225	16026	32487187
Psychotic disorder	156.42	23.69	95	10218	22925	32480288
Electrocardiogram QT prolonged	154.84	23.69	116	10197	39525	32463688
Antipsychotic drug level increased	148.60	23.69	52	10261	3494	32499719
Extrapyramidal disorder	138.43	23.69	70	10243	11825	32491388
Salivary hypersecretion	135.03	23.69	61	10252	8027	32495186
Suicide attempt	127.71	23.69	102	10211	38142	32465071
Blood prolactin increased	126.46	23.69	38	10275	1567	32501646
White blood cell count increased	120.61	23.69	102	10211	41300	32461913
Mental impairment	116.73	23.69	59	10254	9953	32493260
Blood creatine phosphokinase increased	104.54	23.69	98	10215	45378	32457835
Obesity	104.28	23.69	55	10258	10127	32493086
Leukopenia	102.23	23.69	110	10203	60012	32443201
Weight increased	95.73	23.69	125	10188	83538	32419675
Antipsychotic drug level decreased	95.34	23.69	27	10286	901	32502312
Antipsychotic drug level above therapeutic	93.56	23.69	28	10285	1138	32502075
Delusion	88.74	23.69	54	10259	13054	32490159
Hallucination, auditory	81.46	23.69	47	10266	10303	32492910
Dyslipidaemia	78.58	23.69	40	10273	6843	32496370
Therapeutic product effect incomplete	70.85	23.69	76	10237	41265	32461948
Aggression	68.53	23.69	73	10240	39316	32463897
Tachycardia	67.86	23.69	103	10210	78985	32424228
Prescribed overdose	61.32	23.69	38	10275	9481	32493732
Hyperprolactinaemia	57.79	23.69	20	10293	1298	32501915
Dystonia	57.50	23.69	38	10275	10585	32492628
Sedation	56.68	23.69	47	10266	18479	32484734
Leukaemia	53.91	23.69	26	10287	3960	32499253
Neutropenia	52.02	23.69	129	10184	142046	32361167
Nausea	49.56	23.69	20	10293	320829	32182384
Agitation	46.88	23.69	73	10240	57163	32446050
Diarrhoea	44.23	23.69	31	10282	364771	32138442
Breast engorgement	43.61	23.69	7	10306	9	32503204
Lower respiratory tract infection	43.59	23.69	50	10263	29193	32474020
White blood cell count decreased	43.57	23.69	92	10221	91106	32412107
Neutrophil count decreased	42.68	23.69	63	10250	47076	32456137
Drug interaction	39.55	23.69	155	10158	218030	32285183
Schizoaffective disorder	39.24	23.69	15	10298	1293	32501920
Psychotic symptom	37.55	23.69	15	10298	1454	32501759
Parkinsonism	37.45	23.69	26	10287	7843	32495370
Persecutory delusion	36.99	23.69	17	10296	2322	32500891
Sopor	36.33	23.69	30	10283	11719	32491494
Pleurothotonus	34.61	23.69	13	10300	1068	32502145
Suicidal ideation	34.61	23.69	51	10262	38032	32465181
Blepharospasm	34.30	23.69	13	10300	1095	32502118
Paranoia	34.28	23.69	28	10285	10771	32492442
Hypoventilation	34.04	23.69	18	10295	3326	32499887
Conduction disorder	33.16	23.69	15	10298	1975	32501238
Thinking abnormal	32.55	23.69	21	10292	5614	32497599
Somnolence	31.59	23.69	88	10225	103709	32399504
Drug ineffective	31.29	23.69	218	10095	383259	32119954
Disturbance in attention	31.07	23.69	38	10275	23715	32479498
Arthralgia	30.96	23.69	5	10308	148443	32354770
Left ventricular dysfunction	30.49	23.69	25	10288	9670	32493543
Platelet count increased	29.51	23.69	24	10289	9177	32494036
Drug level increased	29.35	23.69	34	10279	20046	32483167
Abnormal behaviour	29.34	23.69	39	10274	26427	32476786
Subacute endocarditis	28.64	23.69	6	10307	53	32503160
Diffuse large B-cell lymphoma stage II	28.54	23.69	6	10307	54	32503159
Pain	28.39	23.69	12	10301	187544	32315669
Treatment noncompliance	27.01	23.69	38	10275	27164	32476049
Overdose	26.65	23.69	74	10239	87003	32416210
Myocarditis	26.62	23.69	25	10288	11565	32491648
Intentional self-injury	26.36	23.69	27	10286	13873	32489340
Toxicity to various agents	26.36	23.69	119	10194	177922	32325291
Eosinophil count decreased	25.68	23.69	11	10302	1272	32501941
Sarcoma metastatic	25.49	23.69	6	10307	94	32503119
Pain in extremity	24.80	23.69	4	10309	118897	32384316
Hangover	23.92	23.69	10	10303	1089	32502124
Impaired self-care	23.78	23.69	10	10303	1105	32502108

Pharmacologic Action:

Source	Code	Description
ATC	N05AL05	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
FDA MoA	N0000175799	Dopamine D2 Antagonists
FDA EPC	N0000175800	Dopamine-2 Receptor Antagonist
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:65191	atypical antipsychotics
CHEBI has role	CHEBI:78298	environmental contaminants

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Postoperative nausea and vomiting	indication	1488000
Chronic schizophrenia	indication	83746006
Dysthymia	off-label use	78667006	DOID:12139

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.78	acidic
pKa2	9.09	Basic
pKa3	0.54	Basic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
10MG/4ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Sept. 1, 2020	RX	SOLUTION	INTRAVENOUS	9084765	March 10, 2031	PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Sept. 1, 2020	RX	SOLUTION	INTRAVENOUS	9084765	March 10, 2031	TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Sept. 1, 2020	RX	SOLUTION	INTRAVENOUS	9545426	March 10, 2031	PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Sept. 1, 2020	RX	SOLUTION	INTRAVENOUS	9545426	March 10, 2031	TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Sept. 1, 2020	RX	SOLUTION	INTRAVENOUS	9889118	March 10, 2031	PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
10MG/4ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Sept. 1, 2020	RX	SOLUTION	INTRAVENOUS	9889118	March 10, 2031	TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Feb. 26, 2020	RX	SOLUTION	INTRAVENOUS	9084765	March 10, 2031	PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Feb. 26, 2020	RX	SOLUTION	INTRAVENOUS	9084765	March 10, 2031	TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Feb. 26, 2020	RX	SOLUTION	INTRAVENOUS	9545426	March 10, 2031	PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Feb. 26, 2020	RX	SOLUTION	INTRAVENOUS	9545426	March 10, 2031	TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Feb. 26, 2020	RX	SOLUTION	INTRAVENOUS	9889118	March 10, 2031	PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
5MG/2ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Feb. 26, 2020	RX	SOLUTION	INTRAVENOUS	9889118	March 10, 2031	TREATMENT OF POST-OPERATIVE NAUSEA AND VOMITING

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
10MG/4ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Sept. 1, 2020	RX	SOLUTION	INTRAVENOUS	Feb. 26, 2025	NEW CHEMICAL ENTITY
5MG/2ML (2.5MG/ML)	BARHEMSYS	ACACIA	N209510	Feb. 26, 2020	RX	SOLUTION	INTRAVENOUS	Feb. 26, 2025	NEW CHEMICAL ENTITY

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN	ANTAGONIST	Ki	8.55	WOMBAT-PK	SCIENTIFIC LITERATURE
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN	ANTAGONIST	Ki	8.50	WOMBAT-PK	SCIENTIFIC LITERATURE
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	7.89	PDSP
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	5.38	PDSP
5-hydroxytryptamine receptor 7	GPCR	P34969	5HT7R_HUMAN		Ki	7.94	PDSP
5-hydroxytryptamine receptor 1B	GPCR	P28222	5HT1B_HUMAN		Ki	5.76	PDSP
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	5.95	PDSP
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN		Ki	5.81	PDSP
D(4) dopamine receptor	GPCR	P21917	DRD4_HUMAN		Ki	5.63	PDSP
5-hydroxytryptamine receptor 1D	GPCR	P28221	5HT1D_HUMAN		Ki	5.87	PDSP
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	5.08	PDSP
D(3) dopamine receptor	GPCR		DRD3_RAT	ANTAGONIST	Ki	7.40	IUPHAR

External reference:

ID	Source
D07310	KEGG_DRUG
2284233	RXNORM
C0103045	UMLSCUI
CHEBI:64045	CHEBI
CHEMBL243712	ChEMBL_ID
DB06288	DRUGBANK_ID
D000077582	MESH_DESCRIPTOR_UI
2159	PUBCHEM_CID
963	IUPHAR_LIGAND_ID
4960	INN_ID
8110R61I4U	UNII
17788	MMSL
331491	MMSL
d04990	MMSL
005229	NDDF
321636003	SNOMEDCT_US
391761004	SNOMEDCT_US
4039609	VANDF

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Barhemsys	HUMAN PRESCRIPTION DRUG LABEL	1	71390-125	INJECTION, SOLUTION	2.50 mg	INTRAVENOUS	NDA	30 sections