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

Stem definition	Drug id	CAS RN
	1211	2709-56-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: flupentixol hydrochloride flupenthixol fluanxol flupentixol fluxanxol flupentixol dihydrochloride N-7009 flupentixol HCl	A thioxanthene neuroleptic that, unlike CHLORPROMAZINE, is claimed to have CNS-activating properties. It is used in the treatment of psychoses although not in excited or manic patients. (From Martindale, The Extra Pharmacopoeia, 30th ed, p595) Molecular weight: 434.52 Formula: C23H25F3N2OS CLOGP: 4.34 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 26.71 ALOGS: -5.04 ROTB: 6

Molecule

Description

Molfile Inchi Smiles

Synonyms:

flupentixol hydrochloride
flupenthixol
fluanxol
flupentixol
fluxanxol
flupentixol dihydrochloride
N-7009
flupentixol HCl

A thioxanthene neuroleptic that, unlike CHLORPROMAZINE, is claimed to have CNS-activating properties. It is used in the treatment of psychoses although not in excited or manic patients. (From Martindale, The Extra Pharmacopoeia, 30th ed, p595)

Molecular weight: 434.52
Formula: C23H25F3N2OS
CLOGP: 4.34
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 26.71
ALOGS: -5.04
ROTB: 6

Drug dosage:

Dose	Unit	Route
6	mg	O
4	mg	P

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.10 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	50 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
CL (Clearance)	4.14 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	34.20 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 1, 1964	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
Blood prolactin abnormal	483.15	38.66	82	2979	1207	46681794
Anosognosia	482.92	38.66	83	2978	1322	46681679
Disturbance in social behaviour	459.00	38.66	82	2979	1649	46681352
Sexual dysfunction	432.15	38.66	82	2979	2321	46680680
Metabolic disorder	382.08	38.66	82	2979	4350	46678651
Personality change	373.63	38.66	83	2978	5175	46677826
Dystonia	296.63	38.66	80	2981	11177	46671824
Suicide attempt	281.77	38.66	113	2948	54923	46628078
Dyskinesia	264.46	38.66	91	2970	28834	46654167
Sedation	256.64	38.66	84	2977	22826	46660175
Schizophrenia	166.43	38.66	48	3013	8520	46674481
Blood glucose increased	163.57	38.66	84	2977	71929	46611072
Insurance issue	93.48	38.66	22	3039	1756	46681245
Extrapyramidal disorder	67.43	38.66	26	3035	11242	46671759
Condition aggravated	60.34	38.66	77	2984	244975	46438026
Drug ineffective	54.10	38.66	129	2932	677709	46005292
Suicidal ideation	52.11	38.66	37	3024	56345	46626656
Hallucination, auditory	44.34	38.66	19	3042	10737	46672264

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
Akathisia	172.31	45.77	48	2474	5856	29944100
Suicide attempt	168.33	45.77	75	2447	36622	29913334
Antipsychotic drug level below therapeutic	165.34	45.77	35	2487	1337	29948619
Therapeutic product effect variable	164.91	45.77	35	2487	1354	29948602
Anosognosia	163.74	45.77	31	2491	663	29949293
Blood prolactin abnormal	161.71	45.77	31	2491	710	29949246
Obsessive-compulsive disorder	159.93	45.77	42	2480	4099	29945857
Disinhibition	152.95	45.77	35	2487	1922	29948034
Disturbance in social behaviour	140.51	45.77	31	2491	1440	29948516
Euphoric mood	130.28	45.77	36	2486	4254	29945702
Increased appetite	125.05	45.77	37	2485	5580	29944376
Metabolic disorder	112.85	45.77	31	2491	3580	29946376
Sexual dysfunction	109.84	45.77	34	2488	5967	29943989
Dyskinesia	104.34	45.77	46	2476	21788	29928168
Dystonia	97.48	45.77	35	2487	9692	29940264
Personality change	88.13	45.77	27	2495	4573	29945383
Weight increased	84.32	45.77	61	2461	74852	29875104
Sedation	83.07	45.77	36	2486	16337	29933619
Hangover	77.37	45.77	18	2504	1060	29948896
Schizophrenia	73.83	45.77	28	2494	9020	29940936
Obesity	64.51	45.77	25	2497	8530	29941426
Drug ineffective	63.86	45.77	107	2415	340280	29609676
Leukopenia	63.72	45.77	46	2476	56113	29893843
Dyslipidaemia	62.62	45.77	22	2500	5705	29944251
Therapeutic product effect incomplete	55.85	45.77	35	2487	33799	29916157
Aggression	50.64	45.77	34	2488	36873	29913083

Pharmacologic Action:

Source	Code	Description
ATC	N05AF01	NERVOUS SYSTEM PSYCHOLEPTICS ANTIPSYCHOTICS Thioxanthene derivatives
CHEBI has role	CHEBI:35469	thymoanaleptics
CHEBI has role	CHEBI:35474	minor tranquilisers
CHEBI has role	CHEBI:37890	alpha-adrenoceptor antagonists
CHEBI has role	CHEBI:48561	dopamine blocker
CHEBI has role	CHEBI:65190	typical antipsychotic drug
CHEBI has role	CHEBI:76779	prolyl oligopeptidase (ec 3.4.21.26) inhibitor
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

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	8.19	Basic
pKa2	4.19	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])	Bioact source	MoA source
D(1A) dopamine receptor	GPCR	P21728	DRD1_HUMAN	ANTAGONIST	Ki	8.40	IUPHAR	IUPHAR
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN	ANTAGONIST	Ki	8.82	IUPHAR	IUPHAR
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN	ANTAGONIST	Ki	8.96	IUPHAR
D(1B) dopamine receptor	GPCR	P21918	DRD5_HUMAN	ANTAGONIST	Ki	8.10	IUPHAR
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN				WOMBAT-PK
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	7.06	PDSP
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	5.10	PDSP
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.05	CHEMBL
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		IC50	8.65	CHEMBL
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN		Ki	9.07	PDSP
D(4) dopamine receptor	GPCR	P21917	DRD4_HUMAN		Ki	8.80	PDSP
Dopamine receptor	GPCR		DRD1_RAT DRD2_RAT DRD3_RAT DRD4_RAT DRD5_RAT		IC50	8.52	CHEMBL
D(1A) dopamine receptor	GPCR		DRD1_RAT		IC50	9.52	CHEMBL
D(1A) dopamine receptor	GPCR		DRD1_BOVIN		Ki	7.75	CHEMBL

External reference:

ID	Source
D01044	KEGG_DRUG
2413-38-9	SECONDARY_CAS_RN
C0016272	UMLSCUI
CHEBI:93235	CHEBI
CHEMBL42055	ChEMBL_ID
CHEMBL54661	ChEMBL_ID
DB00875	DRUGBANK_ID
D005475	MESH_DESCRIPTOR_UI
948	IUPHAR_LIGAND_ID
1745	INN_ID
21HMQ851IS	UNII
5281881	PUBCHEM_CID
235742	RXNORM
003477	NDDF
003479	NDDF
387567006	SNOMEDCT_US
442075003	SNOMEDCT_US
96220002	SNOMEDCT_US

Pharmaceutical products:

None