| Identification | More | [Name]
Prochlorperazine | [CAS]
58-38-8 | [Synonyms]
PROCHLORPERAZINE
10H-Phenothiazine, 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-
2-Chloro-10-(3-(1-methyl-4-piperazinyl)-propyl)-phenothiazine
2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-10h-phenothiazin
2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-phenothiazin
2-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine
2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine
3-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazine
3-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine
6140 R.P.
6140 RP
6140rp
Bayer A 173
bayera173
Capazine
Chlormeprazine
Chloro-3 (N-methylpiperazinyl-3 propyl)-10 phenothiazine
chloro-3(n-methylpiperazinyl-3propyl)-10phenothiazine
chloro-3(n-methylpiperazinyl-3propyl)-10phenothiazine(french)
Chlorperazine | [EINECS(EC#)]
200-379-4 | [Molecular Formula]
C20H24ClN3S | [MDL Number]
MFCD00056797 | [Molecular Weight]
373.94 | [MOL File]
58-38-8.mol |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
pKa 8.1(H2O,t =24±1,I undefined) (Uncertain) | [color ]
White to Yellow | [Water Solubility ]
14.96mg/L(24 ºC) | [BCS Class]
2 | [InChI]
InChI=1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3 | [InChIKey]
WIKYUJGCLQQFNW-UHFFFAOYSA-N | [SMILES]
C1=C2C(SC3=C(N2CCCN2CCN(C)CC2)C=CC=C3)=CC=C1Cl | [CAS DataBase Reference]
58-38-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Prochlorperazine(58-38-8) |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Lact.
Repr. 2
STOT SE 3 | [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-. | [Hazardous Substances Data]
58-38-8(Hazardous Substances Data) | [Toxicity]
LD50 oral in rat: 1800mg/kg |
| Hazard Information | Back Directory | [Uses]
antiemetic, antipsychotic, 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 | [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. |
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