Banner
Identification
Name Citalopram
Accession Number DB00215 (APRD00147)
Type small molecule
Groups approved
Description

Citalopram hydrobromide belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Citalopram is approved for treatment of depression. Unlabeled indications include mild dementia-associated agitation in nonpsychotic patients, smoking cessation, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy. Citalopram has the fewest drug-drug interactions of the SSRIs.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Citalopram Hydrobromide
Citalopramum [INN-Latin]
Salts Not Available
Brand names
Name Company
Akarin
Celapram
Celexa Forest Laboratories
Celius
Ciazil
Cilift
Cipram
Cipramil
Ciprapine
Citabax
Citalec
Citol
Citopam
Citox
Citrol
Dalsan
Elopram
Humorup
Nitalapram
Oropram
Pramcit
Recital
Seropram
Talam
Talohexal
Temperax
Vodelax
Zentius
Zetalo
First Prev Next Last
Brand mixtures Not Available
Categories
  • Antidepressants
  • Selective Serotonin Reuptake Inhibitors (SSRIs)
  • Serotonin Uptake Inhibitors
  • Antidepressive Agents, Second-Generation
CAS number 59729-33-8
Weight Average: 324.3919
Monoisotopic: 324.163791509
Chemical Formula C20H21FN2O
InChI Key InChIKey=WSEQXVZVJXJVFP-UHFFFAOYSA-N
InChI
InChI=1S/C20H21FN2O/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
Plain Text
IUPAC Name
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
SMILES
CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzofurans
  • Benzyl Alcohols and Derivatives
  • Nitriles and Derivatives
Substructures
  • Benzofurans
  • Benzyl Alcohols and Derivatives
  • Nitriles and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Cyanides
  • Aliphatic and Aryl Amines
  • Halobenzenes
  • Heterocyclic compounds
  • Aromatic compounds
  • Aryl Halides
Pharmacology
Indication 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.
Pharmacodynamics Citalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that citalopram is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Citalopram has no significant affinity for adrenergic (α1, α2, β), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of citalopram was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase.
Mechanism of action 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 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
Absorption Rapidly 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.
Volume of distribution
  • 12 L/kg
    Citalopram is highly lipophilic and likely widely distributed throughout the body.
Protein binding 80% based on in vitro studies.
Metabolism Citalopram is metabolized mainly in the liver via N-demethylation to its principle metabolite, demethylcitalopram. Other metabolites include didemethylcitalopram, citalopram N-oxide, and a deaminated propionic acid derivative. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be principally involved in producing demethylcitalopram. Demethylcitalopram appears to be further N-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 The systemic clearance of citalopram was 330 mL/min, with approximately 20% of that due to renal clearance. Citalopram is metabolized to demethylcitalopram (DCT), didemethylcitalopram (DDCT), citalopram-N-oxide, and a deaminated propionic acid derivative.
Half life 35 hours
Clearance Not Available
Toxicity 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.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00424 Citalopram Pathway SMP00424
Pharmacoeconomics
Manufacturers
  • Alphapharm party ltd
  • Forest laboratories inc
  • Apotex inc richmond hill
  • Aurobindo pharma ltd inc
  • Roxane laboratories inc
  • Silarx pharmaceuticals inc
  • Biovail laboratories international srl
  • Actavis elizabeth llc
  • Amneal pharmaceuticals ny llc
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Corepharma llc
  • Dr reddys laboratories ltd
  • Epic pharma llc
  • Glenmark generics ltd
  • Invagen pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Matrix laboratories inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Natco pharma ltd
  • Pliva inc
  • Sandoz inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Torrent pharmaceuticals ltd
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Solution Oral 10 mg/5 ml
Tablet, film coated Oral 10 mg
Tablet, film coated Oral 20 mg
Tablet, film coated Oral 40 mg
Prices
Unit description Cost Unit
Citalopram Hydrobromide 10 mg/5ml Solution 240ml Bottle 122.28 USD bottle
Celexa 40 mg tablet 3.88 USD tablet
Celexa 20 mg tablet 3.72 USD tablet
Celexa 10 mg tablet 3.57 USD tablet
Citalopram Hydrobromide 40 mg tablet 2.89 USD tablet
Citalopram Hydrobromide 20 mg tablet 2.8 USD tablet
Citalopram Hydrobromide 10 mg tablet 2.68 USD tablet
Citalopram hbr 40 mg tablet 2.53 USD tablet
Citalopram hbr 20 mg tablet 2.43 USD tablet
Citalopram hbr 10 mg tablet 2.33 USD tablet
Celexa 20 mg Tablet 1.47 USD tablet
Celexa 40 mg Tablet 1.47 USD tablet
Ctp 30 30 mg Tablet 0.99 USD tablet
Apo-Citalopram 20 mg Tablet 0.82 USD tablet
Apo-Citalopram 40 mg Tablet 0.82 USD tablet
Citalopram 20 mg Tablet 0.82 USD tablet
Citalopram 40 mg Tablet 0.82 USD tablet
Citalopram-Odan 20 mg Tablet 0.82 USD tablet
Citalopram-Odan 40 mg Tablet 0.82 USD tablet
Co Citalopram 20 mg Tablet 0.82 USD tablet
Co Citalopram 40 mg Tablet 0.82 USD tablet
Jamp-Citalopram 20 mg Tablet 0.82 USD tablet
Jamp-Citalopram 40 mg Tablet 0.82 USD tablet
Mint-Citalopram 20 mg Tablet 0.82 USD tablet
Mint-Citalopram 40 mg Tablet 0.82 USD tablet
Mylan-Citalopram 20 mg Tablet 0.82 USD tablet
Mylan-Citalopram 40 mg Tablet 0.82 USD tablet
Ng Citalopram 20 mg Tablet 0.82 USD tablet
Ng Citalopram 40 mg Tablet 0.82 USD tablet
Novo-Citalopram 20 mg Tablet 0.82 USD tablet
Novo-Citalopram 40 mg Tablet 0.82 USD tablet
Phl-Citalopram 20 mg Tablet 0.82 USD tablet
Phl-Citalopram 40 mg Tablet 0.82 USD tablet
Pms-Citalopram 20 mg Tablet 0.82 USD tablet
Pms-Citalopram 40 mg Tablet 0.82 USD tablet
Ran-Citalo 20 mg Tablet 0.82 USD tablet
Ran-Citalo 40 mg Tablet 0.82 USD tablet
Ran-Citalopram 20 mg Tablet 0.82 USD tablet
Ran-Citalopram 40 mg Tablet 0.82 USD tablet
Ratio-Citalopram 20 mg Tablet 0.82 USD tablet
Ratio-Citalopram 40 mg Tablet 0.82 USD tablet
Sandoz Citalopram 20 mg Tablet 0.82 USD tablet
Sandoz Citalopram 40 mg Tablet 0.82 USD tablet
Pms-Citalopram 10 mg Tablet 0.47 USD tablet
First Prev Next Last
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
Canada 2353693 2003-07-22 2021-07-24
Canada 2049368 2001-10-23 2011-08-16
Properties
State solid
Experimental Properties
Property Value Source
melting point 182-183 °C Not Available
water solubility 31 mg/L Not Available
logP 3.5 Not Available
Predicted Properties
Property Value Source
water solubility 5.88e-03 g/l ALOGPS
logP 3.58 ALOGPS
logP 3.76 ChemAxon
logS -4.7 ALOGPS
pKa (strongest basic) 9.78 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 36.26 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 94.02 ChemAxon
polarizability 35.4 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Sindrup SH, Bjerre U, Dejgaard A, Brosen K, Aaes-Jorgensen T, Gram LF: The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy. Clin Pharmacol Ther. 1992 Nov;52(5):547-52. Pubmed
  2. Atmaca M, Kuloglu M, Tezcan E, Semercioz A: The efficacy of citalopram in the treatment of premature ejaculation: a placebo-controlled study. Int J Impot Res. 2002 Dec;14(6):502-5. Pubmed
  3. Andersen G, Vestergaard K, Riis JO: Citalopram for post-stroke pathological crying. Lancet. 1993 Oct 2;342(8875):837-9. Pubmed
  4. Clayton A, Keller A, McGarvey EL: Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord. 2006 Mar;91(1):27-32. Epub 2006 Jan 20. Pubmed
External Links
Resource Link
KEGG Drug D07704 Link_out
KEGG Compound C07572 Link_out
PubChem Compound 2771 Link_out
PubChem Substance 46508746 Link_out
ChemSpider 2669 Link_out
BindingDB 25870 Link_out
ChEBI 3723 Link_out
ChEMBL 3723 Link_out
Therapeutic Targets Database DAP000118 Link_out
PharmGKB PA449015 Link_out
Drug Product Database 2248051 Link_out
RxList http://www.rxlist.com/cgi/generic/citalo.htm Link_out
Drugs.com http://www.drugs.com/citalopram.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Citalopram Link_out
ATC Codes
  • N06AB04
  • N06AB10
AHFS Codes
  • 28:16.04.20
PDB Entries Not Available
FDA label show (148 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Acenocoumarol The SSRI, citalopram, increases the effect of anticoagulant, acenocoumarol.
Almotriptan Increased risk of CNS adverse effects
Anisindione The SSRI, citalopram, increases the effect of anticoagulant, anisindione.
Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Carvedilol The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
Clarithromycin Possible serotoninergic syndrome with this combination
Clozapine The antidepressant increases the effect of clozapine
Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dicumarol The SSRI, citalopram, increases the effect of anticoagulant, dicumarol.
Eletriptan Increased risk of CNS adverse effects
Erythromycin Possible serotoninergic syndrome with this combination
Frovatriptan Increased risk of CNS adverse effects
Ginkgo biloba Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Isocarboxazid Possible severe adverse reaction with this combination
Josamycin Possible serotoninergic sydrome with this combination
Ketoprofen Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Linezolid Combination associated with possible serotoninergic syndrome
Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Metoprolol The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
Moclobemide Possible serotoninergic syndrome
Naratriptan Increased risk of CNS adverse effects
Oxycodone Increased risk of serotonin syndrome
Phenelzine Possible severe adverse reaction with this combination
Pimozide The SSRI, citalopram, may increase the effect and toxicity of pimozide.
Propranolol The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
Rasagiline Possible severe adverse reaction with this combination
Rizatriptan Increased risk of CNS adverse effects
Selegiline Possible severe adverse reaction with this combination
Sibutramine Risk of serotoninergic syndrome
St. John's Wort St. John's Wort increases the effect and toxicity of the SSRI, citalopram.
Sumatriptan Increased risk of CNS adverse effects
Telithromycin Telithromycin may reduce clearance of Citalopram. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Citalopram if Telithromycin is initiated, discontinued or dose changed.
Tiaprofenic acid Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Ticlopidine Ticlopidine may decrease the metabolism and clearance of Citalopram. Consider alternate therapy or monitor for adverse/toxic effects of Citalopram if Ticlopidine is initiated, discontinued or dose changed.
Tolmetin Increased antiplatelet effects may enhance the risk of bleeding. Alternate therapy may be considered or monitor for inreased bleeding during concomitant therapy.
Tramadol The use of two serotonin modulators, such as citalopram and tramadol, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Tranylcypromine Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Treprostinil The prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Citalopram. Monitor for increased bleeding during concomitant thearpy.
Trimipramine The SSRI, Citalopram, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Citalopram is initiated, discontinued or dose changed.
Triprolidine The CNS depressants, Triprolidine and Citalopram, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Troleandomycin Possible serotoninergic syndrome with this combination
Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of citalopram by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of citalopram if voriconazole is initiated, discontinued or dose changed.
Warfarin The SSRI, citalopram, increases the effect of anticoagulant, warfarin.
Ziprasidone Additive QTc-prolongation may occur increasing the risk of life-threatening ventricular arrhythmias and torsade de pointes. Concomitant therapy should be avoided.
Zolmitriptan The use of two serotonin modulators, such as zolmitriptan and citalopram, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Food Interactions
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Take without regard to meals.
Targets

1. Sodium-dependent serotonin transporter

Pharmacological action: yes
Actions: inhibitor

Terminates the action of serotonine by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: P31645 Link_out
Gene: SLC6A4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Eriksson E, Engberg G, Bing O, Nissbrandt H: Effects of mCPP on the extracellular concentrations of serotonin and dopamine in rat brain. Neuropsychopharmacology. 1999 Mar;20(3):287-96. Pubmed
  2. Maines LW, Keck BJ, Smith JE, Lakoski JM: Corticosterone regulation of serotonin transporter and 5-HT1A receptor expression in the aging brain. Synapse. 1999 Apr;32(1):58-66. Pubmed
  3. Vicentic A, Battaglia G, Carroll FI, Kuhar MJ: Serotonin transporter production and degradation rates: studies with RTI-76. Brain Res. 1999 Sep 11;841(1-2):1-10. Pubmed
  4. Dugar A, Keck BJ, Maines LW, Miller S, Njai R, Lakoski JM: Compensatory responses in the aging hippocampal serotonergic system following neurodegenerative injury with 5,7-dihydroxytryptamine. Synapse. 2001 Feb;39(2):109-21. Pubmed
  5. Dutta AK, Fei XS, Beardsley PM, Newman JL, Reith ME: Structure-activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: evaluation of O-and N-analogues and their binding to monoamine transporters. J Med Chem. 2001 Mar 15;44(6):937-48. Pubmed
  6. Plenge P, Wiborg O: High- and low-affinity binding of S-citalopram to the human serotonin transporter mutated at 20 putatively important amino acid positions. Neurosci Lett. 2005 Aug 5;383(3):203-8. Epub 2005 Apr 25. Pubmed
  7. Schloss P, Betz H: Heterogeneity of antidepressant binding sites on the recombinant rat serotonin transporter SERT1. Biochemistry. 1995 Oct 3;34(39):12590-5. Pubmed
  8. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
  9. Zhong H, Hansen KB, Boyle NJ, Han K, Muske G, Huang X, Egebjerg J, Sanchez C: An allosteric binding site at the human serotonin transporter mediates the inhibition of escitalopram by R-citalopram: kinetic binding studies with the ALI/VFL-SI/TT mutant. Neurosci Lett. 2009 Oct 25;462(3):207-12. Epub 2009 Jul 16. Pubmed
  10. Rasmussen TN, Plenge P, Bay T, Egebjerg J, Gether U: A single nucleotide polymorphism in the human serotonin transporter introduces a new site for N-linked glycosylation. Neuropharmacology. 2009 Sep;57(3):287-94. Epub 2009 Jun 3. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. Pubmed
  2. Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. Pubmed
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  4. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. Pubmed
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C19

Actions: substrate, inhibitor

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. Pubmed
  2. Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. Pubmed
  3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  5. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. Pubmed
  6. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Actions: substrate, inhibitor

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

4. Cytochrome P450 2E1

Actions: substrate

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 1A2

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2B6

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P20813 Link_out
Gene: CYP2B6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Multidrug resistance protein 1

Actions: inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19