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Substance Name: Trazodone hydrochloride [USAN:USP:JAN]
RN: 25332-39-2
UNII: 6E8ZO8LRNM
InChIKey: OHHDIOKRWWOXMT-UHFFFAOYSA-N

Note

  • 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)

Molecular Formula

  • C19-H22-Cl-N5-O.Cl-H

Molecular Weight

  • 408.3307
 

Classification Codes

  • Antidepressant
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Trazodone hydrochloride [USAN:USP:JAN]

Synonyms

  • 1,2,4-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-, monohydrochloride
  • 2-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-s-triazolo(4,3-a)pyridin-3(2H)-one monohydrochloride
  • AF 1161
  • AF-1161
  • Apo-Trazodone
  • Azona
  • Bimaran
  • Desyrel
  • Desyrel Dividose
  • Devidon
  • EINECS 246-855-5
  • HSDB 7048
  • KB-831
  • Molipaxin
  • NSC 292811
  • Oleptro
  • Pragmazone
  • Thombran
  • Tombran
  • Trazodone HCl
  • Trazodone hydrochloride
  • Trialodine
  • Tritico
  • Triticum
  • Trittico
  • UNII-6E8ZO8LRNM

Systematic Names

  • 1,2,4-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-, monohydrochloride
  • 2-(3-(4-(3-Chlorophenyl)piperazin-1-y)propyl)-1,2,4-triazolo(4,3-a)pyridine-3(2H)-one hydrochloride
  • s-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-, monohydrochloride

Registry Numbers

CAS Registry Number

  • 25332-39-2

FDA UNII

  • 6E8ZO8LRNM

System Generated Number

  • 0025332392

Molecular Formulas

Molecular Formula

  • C19-H22-Cl-N5-O.Cl-H

Molecular Formula Fragments

  • C19-H22-Cl-N5-O
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C19H22ClN5O.ClH/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;1H

InChIKey

OHHDIOKRWWOXMT-UHFFFAOYSA-N

Smiles

c1ccn2c(c1)nn(c2=O)CCCN3CCN(CC3)c4cccc(c4)Cl.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 40mg/kg (40mg/kg)   Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
dog LD50 oral 500mg/kg (500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: AGGRESSION
Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
man TDLo oral 667ug/kg (0.667mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION American Journal of Psychiatry. Vol. 141, Pg. 1472, 1984.
man TDLo oral 5714ug/kg/4D- (5.714mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: EUPHORIA
British Journal of Psychiatry. Vol. 158, Pg. 275, 1991.
man TDLo oral 43mg/kg/30D-I (43mg/kg) BLOOD: OTHER CHANGES

BLOOD: AGRANULOCYTOSIS
American Journal of Psychiatry. Vol. 150, Pg. 1563, 1993.
man TDLo oral 46mg/kg/8D-I (46mg/kg) BEHAVIORAL: EXCITEMENT

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Journal of Clinical Pyschopharmacology. Vol. 6, Pg. 117, 1986.
monkey LD50 intravenous 25mg/kg (25mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 94, 1981.
mouse LD50 intraperitoneal 255mg/kg (255mg/kg)   Journal of Pharmaceutical Sciences. Vol. 81, Pg. 99, 1992.
mouse LD50 intravenous 91mg/kg (91mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
mouse LD50 oral 584mg/kg (584mg/kg)   Drug Development Research. Vol. 22, Pg. 385, 1991.
mouse LD50 subcutaneous > 1500mg/kg (1500mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
rabbit LD50 intravenous 52mg/kg (52mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
rabbit LD50 oral 560mg/kg (560mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
rat LD50 intraperitoneal 178mg/kg (178mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
rat LD50 intravenous 91mg/kg (91mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
rat LD50 oral 690mg/kg (690mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974.
rat LD50 subcutaneous 2729mg/kg (2729mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
women TDLo oral 750ug/kg (0.75mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" American Journal of Psychiatry. Vol. 141, Pg. 434, 1984.
women TDLo oral 80mg/kg (80mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Analytical Toxicology. Vol. 8, Pg. 91, 1984.
women TDLo oral 100mg/kg (100mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Clinical Pharmacy. Vol. 4, Pg. 97, 1985.
women TDLo oral 720mg/kg/34W- (720mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
Annals of Internal Medicine. Vol. 118, Pg. 791, 1993.