CAS 59729-32-7|CAS 59729-33-8|Cipramil|1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide|Celexa|citalopram hydrobromide|Citalopram Hydrobromide|Cita...

General Information

Structure

Molecular Formula

C₂₀H₂₂BrFN₂O

Molecular Mass

405.3038832

Exact Mass

404.08995355

Charge

InChI

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

Canonic Smiles

N#Cc1ccc2c(c1)COC2(CCCN(C)C)c1ccc(cc1)F.Br

Isomeric Smiles

c1(ccc(cc1)C1(c2c(CO1)cc(cc2)C#N)CCCN(C)C)F.Br

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.3290631

LogD (pH = 7.4)

1.409549

Log P

3.7643042

Molar Refractivity

94.0202

Polarizability

35.7618

Polar Surface Area

36.26

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

CipramilCelexaCitalopram HydrobromideCitalopram hydrobromide1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile hydrobromide(S)-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile hydrobromideNitalapram, LU-10-171, 1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dizohydro-5-isobenzofurancarbonitrile Hydrobromide SaltCitalopram, Hydrobromide Salt

IUPAC name

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide

IUPAC Traditional name

citalopram hydrobromide recital hydrobromide 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem SID

EC Number

PubChem CID

Registration numbers

Properties

Pharmacology Properties

Target

SSR

Gene Information

human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363)

Mechanism of Action

5HT re-uptake inhibitor

Safety Information

-20°C

-20°C Freezer

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S1372

Research Area: Neurological Disease
Biological Activity:
Citalopram (Celexa, Cipramil) is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. Most often used to treat major depression, it is also used on occasion in the treatment of body dysmorphic disorder, anxiety, and panic disorder. [1]

Sigma Aldrich

C7861

Biochem/physiol Actions
Potent and selective serotonin uptake inhibitor (Ki = 5.4 nM); antidepressant

TRC

C505000

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

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Citalopram

• Keller, M.B., et al.: J. Clin. Psychiatry, 61, 896 (1977)

• Von Moltke, L.L., et al.: Drug Metab. Dispos., 29, 1102 (1977)

• Christensen, A.V., et al.: Eur. J. Pharmacol., 41, 153 (1977)

• Ger. Pat., 1977, 2 657 013; CA, 87, 135040e, (synth)

• Hyttel, J., Dev. Psychiatry, 1986, 7, 820, (rev, pharmacol)

• Eur. Pat., 1989, Lundbeck, 347 066; CA, 113, 78150v, (isomers, synth, pharmacol)

• Pat. Coop. Treaty (WIPO), 2000, Lundbeck, 00 23 431; CA, 132, 308238d, (synth)

• Kragh-Soerensen, P. et al., Acta Pharmacol. Toxicol., 1981, 48, 53, (metab)

• Bigler, A.J. et al., Eur. J. Med. Chem. (Chim. Ther.), 1977, 12, 289, (synth, pharmacol)

• Christensen, A.V. et al., Eur. J. Pharmacol., 1977, 41, 153, (pharmacol)

• Rochat, B. et al., Brain Res., 1999, 831, 229-236, (pharmacol)

• Koch, H., Pharm. Int., 1980, 1, 66, (rev, pharmacol)

• Boeck, V. et al., Acta Pharmacol. Toxicol., 1982, 50, 169, (tox)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 281

• Goa, K.L. et al., Drugs, 1991, 41, 450, (rev)

• Sidhu, J. et al., Chirality, 1997, 9, 686-692, (pharmacol, enantiomers)

• Popik, P., J. Clin. Psychopharmacol., Suppl. 1, 1999, 19, 4S-22S, (rev)

• Noble, S. et al., CNS Drugs, 1997, 8, 410-431, (rev)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide

IUPAC Traditional name

citalopram hydrobromide recital hydrobromide 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide

Registration numbers

CAS Number

MDL Number

PubChem SID

EC Number

PubChem CID

Molecule Details

S1372

C7861

Biochem/physiol Actions
Potent and selective serotonin uptake inhibitor (Ki = 5.4 nM); antidepressant

TRC

C505000

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

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Citalopram

• Keller, M.B., et al.: J. Clin. Psychiatry, 61, 896 (1977)

• Von Moltke, L.L., et al.: Drug Metab. Dispos., 29, 1102 (1977)

• Christensen, A.V., et al.: Eur. J. Pharmacol., 41, 153 (1977)

• Ger. Pat., 1977, 2 657 013; CA, 87, 135040e, (synth)

• Hyttel, J., Dev. Psychiatry, 1986, 7, 820, (rev, pharmacol)

• Eur. Pat., 1989, Lundbeck, 347 066; CA, 113, 78150v, (isomers, synth, pharmacol)

• Pat. Coop. Treaty (WIPO), 2000, Lundbeck, 00 23 431; CA, 132, 308238d, (synth)

• Kragh-Soerensen, P. et al., Acta Pharmacol. Toxicol., 1981, 48, 53, (metab)

• Bigler, A.J. et al., Eur. J. Med. Chem. (Chim. Ther.), 1977, 12, 289, (synth, pharmacol)

• Christensen, A.V. et al., Eur. J. Pharmacol., 1977, 41, 153, (pharmacol)

• Rochat, B. et al., Brain Res., 1999, 831, 229-236, (pharmacol)

• Koch, H., Pharm. Int., 1980, 1, 66, (rev, pharmacol)

• Boeck, V. et al., Acta Pharmacol. Toxicol., 1982, 50, 169, (tox)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 281

• Goa, K.L. et al., Drugs, 1991, 41, 450, (rev)

• Sidhu, J. et al., Chirality, 1997, 9, 686-692, (pharmacol, enantiomers)

• Popik, P., J. Clin. Psychopharmacol., Suppl. 1, 1999, 19, 4S-22S, (rev)

• Noble, S. et al., CNS Drugs, 1997, 8, 410-431, (rev)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Target

SSR

Gene Information

Mechanism of Action

5HT re-uptake inhibitor

Safety Information

-20°C

-20°C Freezer

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Molecule

ID:72645