Citalopram Hydrobromide

HCID 77995

Basic information

CAS
59729-32-7
Standard SMILES
Br.CN(C)CCCC1(c2ccc(F)cc2)OCc2cc(C#N)ccc21
InChIKey
WIHMBLDNRMIGDW-UHFFFAOYSA-N
Molecular formula
C20H22BrFN2O
Average molar mass
405.3 g/mol
Monoisotopic mass
404.08995364

Overview

Citalopram Hydrobromide is the orally bioavailable hydrobromide salt of the racemic bicyclic phthalene derivative citalopram with antidepressant activity. As a selective serotonin reuptake inhibitor (SSRI), citalopram selectively inhibits the CNS neuronal reuptake of serotonin, thereby potentiating serotonergic activity in the central nervous system (CNS). This agent has minimal effects on the CNS neuronal reuptake of norepinephrine (NE) and dopamine (DA).

Names & identifiers

Preferred name
Citalopram Hydrobromide
IUPAC
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;hydrobromide
English name
Citalopram hydrobromide
Molecular formula
C20H22BrFN2O
Molecular weight
405.3

Names & synonyms

citalopram hydrobromide59729-32-7Citalopram HBrSeropramElopramLu 10-171-BCitalopram (as hydrobromide)NSC-758684I1E9D14F36LU-10-171-BDTXSID408723441-(3-(dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile monohydrobromide
Show more names
ERDOSTEINCitalopram hydrogen bromideCitalopram for system suitability CRSBonitrile HBrLu 10-171 HBrCitalopran HBrCitalopram-D4BrCitalopraM HBr APICitalopram HBr Salt
5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, monohydrobromidePerrigo citalopramPaxoranRefChem:548341-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile monohydrobromide3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl)-N,N-dimethylpropan-1-aminium bromideCHEBI:3724DTXCID60819993

Database identifiers

CAS
59729-32-7
PubChem CID
77995
DTXSID
DTXSID40872344
ChEMBL
CHEMBL1200781
UNII
I1E9D14F36
EC Number
261-890-6

Properties

Computed structural properties

Topological polar surface area
36.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
25

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physicochemical properties

Melting point
182 · 182-188°C
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: soluble (sparingly)
form
powder
color
White

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (96.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 115 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationCitalopram hydrobromide: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (96.5%)

Toxicology

Treatment · 1 item

Establish and maintain an airway to ensure adequate ventilation and oxygenation. Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are recommended, along with general symptomatic and supportive care. Due to the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. There are no specific antidotes for Celexa. (L1712)

Exposure RoutesRapidly and well absorbed from the GI tract. Peak plasma concentrations occur within 4 hours of a single orally administered dose. Bioavailability is 80% following oral administration. Food does not affect absorption.
Toxicity Summary · 1 item

The antidepressant, antiobsessive-compulsive, and antibulimic actions of citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Citalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT<sub>1A</sub> autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.

Signs and Symptoms · 1 item

Symptoms most often accompanying citalopram overdose, alone or in combination with other drugs and/or alcohol, included dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. In more rare cases, observed symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and very rare cases of torsade de pointes). Acute renal failure has been very rarely reported accompanying overdose. Withdrawal symptoms include flu-like symptoms, insomnia, nausea, imbalance, sensory changes and hyperactivity.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Citalopram hydrobromide

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
3
rtecs
NP6313500
ridadr
3249
hs_code
29329990
risk_code
11-23/24/25-39/23/24/25-22
Signal word
Warning

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Citalopram is metabolized mainly in the liver via <i>N</i>-demethylation to its principle metabolite, demethylcitalopram. Other metabolites include didemethylcitalopram, citalopram <i>N</i>-oxide, and a deaminated propionic acid derivative. However, the predominant entity in plasma is unchanged citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be principally involved in producing demethylcitalopram. Demethylcitalopram appears to be further <i>N</i>-demethylated by CYP2D6 to didemethylcitalopram. Citalopram metabolites possess little pharmacologic activity in comparison to their parent compound and do not likely contribute to the clinical effect of the drug. Route of Elimination: 12-23% of an oral dose of citalopram is recovered unchanged in the urine, while 10% of the dose is recovered in the feces. Half Life: 35 hours

FDA Pharmacological Classification · 2 items

CITALOPRAM HYDROBROMIDE

Serotonin Reuptake Inhibitor [EPC]; Serotonin Uptake Inhibitors [MoA]

MeSH Pharmacological Classification · 2 items

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.

Compounds that specifically inhibit the reuptake of serotonin in the brain.

Uses & manufacturing

Uses · 1 item

For the treatment of depression. Unlabeled indications include: treatment of mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy.

Applications · 6 items

DescriptionCitalopram (hydrobromide) (Item No. 23252) is an analytical reference material categorized as an antidepressant. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .

UsesAn inhibitor of serotonin (5-HT) uptake. Used as an antidepressant

UsesAntidepressant;5HT uptake inhibitor

UsesAnti-depressant/Anti-psychotic

UsesCitalopram hydrobromide has been used:to examine its effects onsirtmRNA and mammalian sirtuins (SIRT) expression in miceto monitor body temperature and antidepressant-like behavioral responses in the forced swim test for ratsfor 5-hydroxytryptamine (5-HT) competition uptake assays

General DescriptionCitalopram is an antidepressant sold under the trade names Celexa and Cipramil for the treatment of major depression. Citalopram is a selective serotonin reuptake inhibitor, a class of drugs that also includes fluoxetine, paroxetine, and sertraline. This Certified Snap-N-Spike Solution is suitable for use in LC/MS or GC/MS applications for clinical toxicology, forensic analysis, urine drug testing, or pharmaceutical research.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Related reactions

23 records

Compound notes

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