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19794-93-5 molecular structure
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2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

ChemBase ID: 538
Molecular Formular: C19H22ClN5O
Molecular Mass: 371.86388
Monoisotopic Mass: 371.15128803
SMILES and InChIs

SMILES:
Clc1cc(N2CCN(CC2)CCCn2nc3n(c2=O)cccc3)ccc1
Canonical SMILES:
Clc1cccc(c1)N1CCN(CC1)CCCn1nc2n(c1=O)cccc2
InChI:
InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2
InChIKey:
PHLBKPHSAVXXEF-UHFFFAOYSA-N

Cite this record

CBID:538 http://www.chembase.cn/molecule-538.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one
IUPAC Traditional name
trazodone
Brand Name
Beneficat
Bimaran
Desirel
Desyrel
Molipaxin
Pragmazone
Sideril
Thombran
Tombran
Trazalon
Trazodil
Trazodon
Trazolan
Trazonil
Trialodine
Trittico
Desyrel Dividose
Synonyms
Trazodonum [INN-Latin]
Trazodona [INN-Spanish]
Trazodone Hcl
Trazodone Hydrochloride
trazodone
Trazodone
CAS Number
19794-93-5
PubChem SID
46506648
160964001
PubChem CID
5533
CHEBI ID
9654
ATC CODE
N06AX05
CHEMBL
621
Chemspider ID
5332
DrugBank ID
DB00656
IUPHAR ligand ID
213
KEGG ID
D08626
Unique Ingredient Identifier
YBK48BXK30
Wikipedia Title
Trazodone
Medline Plus
a681038

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.5380111  LogD (pH = 7.4) 2.9594436 
Log P 3.1318567  Molar Refractivity 105.8796 cm3
Polarizability 39.210217 Å3 Polar Surface Area 42.39 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.68  LOG S -3.11 
Solubility (Water) 2.90e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
Sparigly soluble expand Show data source
Hydrophobicity(logP)
2.9 expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
High expand Show data source
Excretion
20% feces,
80% urine
expand Show data source
Half Life
3-6 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Pharmacist only (Australia) expand Show data source
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
C (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00656 external link
Item Information
Drug Groups approved; investigational
Description A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309)
Indication For the treatment of depression.
Pharmacology Trazodone is an antidepressant and hypnotic chemically unrelated to tricyclic, tetracyclic, or other known antidepressant agents. The mechanism of trazodone's antidepressant action in man is not fully understood. In animals, trazodone selectively inhibits serotonin uptake by brain synaptosomes and potentiates the behavioral changes induced by the serotonin precursor, 5-hydroxytryptophan. Cardiac conduction effects of trazodone in the anesthetized dog are qualitatively dissimilar and quantitatively less pronounced than those seen with tricyclic antidepressants. Trazodone is not a monoamine oxidase inhibitor and, unlike amphetamine-type drugs, does not stimulate the central nervous system. In man, trazodone is well absorbed after oral administration without selective localization in any tissue. Since the clearance of trazodone from the body is sufficiently variable, in some patients trazodone may accumulate in the plasma.
Toxicity LD50=96mg/kg (i.v. in mice)
Affected Organisms
Humans and other mammals
Biotransformation Undergoes extensive hepatic metabolism via hydroxylation, N-dealkylation, N-oxidation and splitting of the pyridine ring. Cytochrome P450 (CYP) 3A4 catalyzes the formation of the major active metabolite, m-chlorophenylpiperazine (m-CPP). Metabolites may be further conjugated to glucuonic acid or glutathione. CYP2D6 is responsible for 4'-hydroxylation of m-CPP and the formation of at least one glutathione conjugates of m-CPP, a quinone imine-sulhydryl adduct. Oxotriazolopyridinpropionic acid, an inactive metabolite, and its conjugates account for about 20% of the total excreted oral dose. Less than 1% of the oral dose is excreted unchanged. Approximately 70-75% of the dose is eliminated in urine with the remainder being excreted in feces via biliary elimination.
Absorption Rapidly and almost completely absorbed following oral administration. Food may decrease the rate and extent of absorption.
Half Life Undergoes biphasic elimination with an initial phase t1/2 α of 3-6 hours and a terminal phase t1/2 β of 5-9 hours.
Protein Binding 89-95% bound to plasma proteins in vitro
References
Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [Pubmed]
Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)] Arzneimittelforschung. 1976;26(11):2084-9. [Pubmed]
Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. [Pubmed]
Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. [Pubmed]
Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7. [Pubmed]
Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60. [Pubmed]
Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)] Arzneimittelforschung. 1976;26(11):2084-9. Pubmed
  • • Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. Pubmed
  • • Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. Pubmed
  • • Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7. Pubmed
  • • Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. Pubmed
  • • Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60. Pubmed
  • • Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6. Pubmed
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