Prochlorperazine Chemical Properties

Melting point:

228 °C

Boiling point:

260-275 °C(Press: 2 Torr)

Density 

1.1679 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

pKa 8.1(H2O,t =24±1,I undefined) (Uncertain)

form 

Solid

color 

White to Yellow

Water Solubility 

14.96mg/L(24 ºC)

BCS Class

2

CAS DataBase Reference

58-38-8(CAS DataBase Reference)

NIST Chemistry Reference

Prochlorperazine(58-38-8)

Safety Information

Hazardous Substances Data

58-38-8(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 1800mg/kg

MSDS

• Language:English Provider:2-Chloro-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine

Prochlorperazine Usage And Synthesis

Uses

antiemetic, antipsychotic, treatment of vertigo

Uses

Prochlorperazine is antiemetic, antipsychotic; used in treatment of vertigo.

Definition

ChEBI: A member of the class of phenothiazines that is 10H-phenothiazine having a chloro substituent at the 2-position and a 3-(4-methylpiperazin-1-yl)propyl group at the N-10 position.

brand name

Compazine (GlaxoSmithKline).

Clinical Use

Nausea and vomiting
Labyrinthine disorders
Psychoses
Severe anxiety

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. Human systemic effects by ingestion: headache, blood pressure elevation. Implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of SOx, NOx, and Cl-.

Veterinary Drugs and Treatments

Prochlorperazine as a single agent is used in dogs and cats as an antiemetic. The only approved products for animals are combination products containing prochlorperazine, isopropamide, with or without neomycin (Darbazine?, Neo-Darbazine?—SKB Labs) which are no longer marketed in the USA. The approved indications for these products include: vomiting, non-specific gastroenteritis, drug induced diarrhea, infectious diarrhea, spastic colitis, and motion sickness in dogs and cats (injectable product only).

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids; increased risk of ventricular arrhythmias with methadone.
Anti-arrhythmics increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval, e.g. procainamide, disopyramide, dronedarone and amiodarone - avoid with amiodarone and dronedarone.
Antibacterials: increased risk of ventricular arrhythmias with delamanid and moxifloxacin - avoid.
Antidepressants: increase concentrations and additive antimuscarinic effects, notably with tricyclics; increased risk of ventricular arrhythmias with citalopram and escitalopram - avoid; increased risk of convulsions with vortioxetine.
Antiepileptics: antagonised (convulsive threshold lowered).
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Antipsychotics: increased risk of ventricular arrhythmias with droperidol and pimozide - avoid; increased risk of ventricular arrhythmias with risperidone.
Antivirals: concentration possibly increased with ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid.
Anxiolytics and hypnotics: increased sedative effects.
Atomoxetine: increased risk of ventricular arrhythmias.
Beta-blockers: enhanced hypotensive effect; increased risk of ventricular arrhythmias with sotalol.
Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide.
Desferrioxamine: avoid concomitant use.
Diuretics: enhanced hypotensive effect.
Lithium: increased risk of extrapyramidal side effects and possibly neurotoxicity.
Pentamidine: increased risk of ventricular arrhythmias.

Metabolism

Prochlorperazine undergoes extensive first pass metabolism in the gut wall. It is also extensively metabolised in the liver and is excreted in the urine and bile. The metabolites are inactive.

Prochlorperazine(58-38-8)Related Product Information

• 2-Chlorophenothiazine
• Chlorpromazine hydrochloride
• Allyl chloride
• 3-Chloropropyltrimethoxysilane
• Chloromethyl isopropyl carbonate
• Chlorpromazine
• Phenothiazine
• 3-Methyl-2-butanone
• Cyclopropyl methyl ketone
• Xylazine
• 1-Methylpiperazine
• PROCHLORPERAZINE DIMALEATE,Prochlorperazine Dimaleate Also See: P755800,PROCHLORPERAZINE MALEATE,PROCHLORPERAZINE DIMALEATE SALT
• Imiclopazine
• FLUPHENAZINE
• Difluorochloromethane
• Fluphenazine decanoate
• PROCHLORPERAZINE MESYLATE
• Methophenazine