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citalopram 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	663	59729-33-8

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: citalopram nitalapram bonitrile citalopram hydrobromide	A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia. Molecular weight: 324.40 Formula: C20H21FN2O CLOGP: 3.13 LIPINSKI: 0 HAC: 3 HDO: 0 TPSA: 36.26 ALOGS: -4.74 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

citalopram
nitalapram
bonitrile
citalopram hydrobromide

A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.

Molecular weight: 324.40
Formula: C20H21FN2O
CLOGP: 3.13
LIPINSKI: 0
HAC: 3
HDO: 0
TPSA: 36.26
ALOGS: -4.74
ROTB: 5

Status: OFP

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

Drug dosage:

Dose	Unit	Route
20	mg	O
20	mg	P

ADMET properties:

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Property	Value	Reference
CL (Clearance)	4.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	33 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	2.64 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	12 L/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	12 %	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.20 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.03 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
July 17, 1998	FDA	FOREST LABS

FDA Adverse Event Reporting System (Female)

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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
Completed suicide	1408.42	9.54	1977	193726	143696	63149623
Toxicity to various agents	1232.52	9.54	2494	193209	244756	63048563
Drug abuse	1066.27	9.54	1214	194489	71304	63222015
Electrocardiogram QT prolonged	687.47	9.54	882	194821	58648	63234671
Serotonin syndrome	598.14	9.54	579	195124	28103	63265216
Overdose	523.94	9.54	1120	194583	113958	63179361
Drug interaction	523.41	9.54	1724	193979	227407	63065912
Pemphigus	508.87	9.54	12	195691	183714	63109605
Systemic lupus erythematosus	464.56	9.54	51	195652	208867	63084452
Intentional overdose	460.83	9.54	823	194880	73329	63219990

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FDA Adverse Event Reporting System (Male)

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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
Completed suicide	1016.16	10.74	1273	91177	96895	34767586
Toxicity to various agents	893.28	10.74	1762	90688	198600	34665881
Serotonin syndrome	526.00	10.74	430	92020	19503	34844978
Drug abuse	459.86	10.74	888	91562	98208	34766273
Suicidal ideation	452.68	10.74	546	91904	39842	34824639
Intentional overdose	297.39	10.74	464	91986	43210	34821271
Overdose	289.96	10.74	701	91749	90358	34774123
Suicide attempt	276.71	10.74	423	92027	38693	34825788
Paranoia	248.50	10.74	226	92224	11842	34852639
Foetal exposure during pregnancy	233.62	10.74	386	92064	37715	34826766

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FDA Adverse Event Reporting System (Geriatric)

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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
Completed suicide	2255.12	9.72	3183	232892	242584	79265729
Toxicity to various agents	1944.58	9.72	4018	232057	417522	79090791
Drug abuse	1382.90	9.72	2034	234041	160657	79347656
Serotonin syndrome	1019.05	9.72	934	235141	44093	79464220
Electrocardiogram QT prolonged	741.14	9.72	1112	234963	89274	79419039
Overdose	715.84	9.72	1642	234433	182564	79325749
Drug interaction	629.43	9.72	2663	233412	412520	79095793
Intentional overdose	625.60	9.72	1124	234951	104836	79403477
Suicidal ideation	616.94	9.72	933	235142	75407	79432906
Suicide attempt	478.29	9.72	871	235204	82061	79426252

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FDA Adverse Event Reporting System (Pediatric)

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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
Cryptorchism	34.98	29.56	38	1433	371	87950
Respiratory disorder neonatal	34.30	29.56	80	1391	1586	86735

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Pharmacologic Action:

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Source	Code	Description
ATC	N06AB04	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Selective serotonin reuptake inhibitors
CHEBI has role	CHEBI:35469	antidepressants
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:50949	SSRI
CHEBI has role	CHEBI:76779	post-proline endopeptidase inhibitors
CHEBI has role	CHEBI:77402	EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitors
CHEBI has role	CHEBI:78298	environmental contaminants
FDA EPC	N0000175696	Serotonin Reuptake Inhibitor
FDA MoA	N0000000109	Serotonin Uptake Inhibitors
MeSH PA	D000928	Antidepressive Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Generalized anxiety disorder	indication	21897009	DOID:14320
Depressive disorder	indication	35489007
Major depressive disorder	indication	370143000
Posttraumatic stress disorder	off-label use	47505003	DOID:2055
Bipolar affective disorder, current episode depression	off-label use	191627008	DOID:3312
Obsessive-compulsive disorder	off-label use	191736004	DOID:10933
Menopausal flushing	off-label use	198436008
Panic disorder	off-label use	371631005	DOID:594
Suicidal thoughts	contraindication	6471006
Bipolar disorder	contraindication	13746004	DOID:3312

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.33	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN	INHIBITOR	Kd	8.94	WOMBAT-PK	CHEMBL
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	5.40	WOMBAT-PK
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	5.21	CHEMBL
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	5.19	PDSP
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	5.93	DRUG MATRIX
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		Ki	6.21	WOMBAT-PK
Histamine H1 receptor	GPCR	P35367	HRH1_HUMAN		Ki	6.46	WOMBAT-PK
Muscarinic acetylcholine receptor M1	GPCR	P11229	ACM1_HUMAN		Ki	5.88	PDSP
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN		Ki	4.78	CHEMBL
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN		Ki	6.15	DRUG MATRIX

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External reference:

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ID	Source
005106	NDDF
005107	NDDF
0DHU5B8D6V	UNII
116521005	SNOMEDCT_US
21814	MMSL
221078	RXNORM
2771	PUBCHEM_CID
321986007	SNOMEDCT_US
372596005	SNOMEDCT_US
4021129	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4010	TABLET, FILM COATED	10 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4010	TABLET, FILM COATED	10 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4010	TABLET, FILM COATED	10 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4020	TABLET, FILM COATED	20 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4020	TABLET, FILM COATED	20 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4020	TABLET, FILM COATED	20 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4040	TABLET, FILM COATED	40 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4040	TABLET, FILM COATED	40 mg	ORAL	NDA	35 sections
Celexa	HUMAN PRESCRIPTION DRUG LABEL	1	0456-4040	TABLET, FILM COATED	40 mg	ORAL	NDA	35 sections
Citalopram	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0062	SOLUTION	10 mg	ORAL	ANDA	27 sections

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