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
Show more names
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
- Formal charge
- 0
- Complexity
- 466
Experimental & physicochemical properties
Human Drugs
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
- Water Solubility
- 50 mM · Soluble to 50 mM in ethanol and to 10 mM in water
- Merck
- 14 · 14,2318
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- clinical testing
- InChI
- 1S/C20H21FN2O.BrH/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;/h4-9,12H,3,10-11,14H2,1-2H3;1H
- InChIKey
- WIHMBLDNRMIGDW-UHFFFAOYSA-N
- SMILES
- Br.CN(C)CCCC1(OCc2cc(ccc12)C#N)c3ccc(F)cc3
- CAS DataBase Reference
- 59729 · 59729-32-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 E9D14F36 · I1E9D14F36
- NCI Drug Dictionary
- citalopram hydrobromide
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 302 · H302-H336-H361d-H412
- Precautionary statements
- 201 · P201-P273-P301+P312+P330-P308+P313
- target organs
- Eyes
- Hazard Codes
- F,T
- Risk Statements
- 11 · 11-23/24/25-39/23/24/25-22
- Safety Statements
- 7 · 7-16-36/37-45-24/25
- RIDADR
- 3249 · 3249
- WGK Germany
- 3 · 3
- RTECS
- 6313500 · NP6313500
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29329990 · 29329990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Treatment
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)
Toxicity Summary
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
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.
Drug Induced Liver Injury
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
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- F,T
- safety_code
- 7-16-36/37-45-24/25
- hazard_class
- 6.1(b)
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- target organs
- Eyes
- Hazard statements
- H302-H336-H361d-H412
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Precautionary statements
- P201-P273-P301+P312+P330-P308+P313
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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
CITALOPRAM HYDROBROMIDE
Serotonin Reuptake Inhibitor [EPC]; Serotonin Uptake Inhibitors [MoA]
MeSH Pharmacological Classification
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
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
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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
Compound notes
Loading…