Chlorpromazine
- CAS NO.:50-53-3
- Empirical Formula: C17H19ClN2S
- Molecular Weight: 318.86
- MDL number: MFCD00133295
- EINECS: 200-045-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-07-21 14:17:16
What is Chlorpromazine?
Absorption
Readily absorbed from the GI tract. Bioavailability varies due to first-pass metabolism by the liver.
Toxicity
Agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, restlessness
Description
This phenothiazine with sedative properties is used in human medicines and has induced contact dermatitis in nurses or in those working in the pharmaceutical industry. It is also used in veterinary medicine to avoid mortality of pigs during transportation. It is a sensitizer and a photosensitizer.
Chemical properties
Oily liquid; amine odor.
The Uses of Chlorpromazine
In psychiatric practice, chlorpromazine is used in various conditions of psychomotor excitement in patients with schizophrenia, chronic paranoid and also manic-depressive conditions, neurosis, alcohol psychosis and neurosis accompanied by excitement, fear, stress, and insomnia. In comparison with other neuroleptics, chlorpromazine is unique in that it has an expressed sedative effect. It is sometimes used in anesthesiological practice for potentiating narcosis. It also has moderate anticonvulsant action.
The Uses of Chlorpromazine
antiemetic, antipsychotic
The Uses of Chlorpromazine
Chlorpromazine is approved by FDA for use in humans for the
management of psychotic disorders (i.e., control of mania,
treatment of schizophrenia); control of nausea and vomiting;
relief of apprehension before surgery; acute intermittent
porphyria; adjunctive treatment of tetanus; intractable hiccups;
combativeness or explosive hyperexcitable behavior in children
aged 1–12 years; and short-term treatment of hyperactivity in
children with symptoms of impulsivity, difficulty sustaining
attention, aggressiveness, mood lability, and poor frustration
tolerance. Chlorpromazine is commonly used off-label for
treatment of behavioral symptoms associated with dementia in
the elderly and psychosis and agitation related to Alzheimer’s
dementia; however, it carries a boxed warning regarding increased risk of death in patients with dementia-related
psychosis. Chlorpromazine is also used off-label for managing
agitation in terminal cancer patients, autonomic dysreflexia,
cancer pain, adjunctive treatment of cholera, migraine headaches,
opioid withdrawal, ocular pain, paralytic ileus, and
phantom limb syndrome.
In veterinary medicine, the use of chlorpromazine has been
largely replaced by the phenothiazine acepromazine due to its
more favorable pharmacokinetic profile. Chlorpromazine may
be used as an antiemetic for small animals or for preoperative
sedation. Chlorpromazine may also be used for management
of hypertension in dogs and cats.
Background
The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class, chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking dopamine receptors. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.
What are the applications of Application
Chlorpromazine is a anticholinergic, antidopaminergic and antihistaminic agent
Indications
For the treatment of schizophrenia; to control nausea and vomiting; for relief of restlessness and apprehension before surgery; for acute intermittent porphyria; as an adjunct in the treatment of tetanus; to control the manifestations of the manic type of manic-depressive illness; for relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability, and poor frustration tolerance.
Definition
ChEBI: A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.
brand name
Thorazine (GlaxoSmithKline).
Hazard
Toxic by ingestion.
Contact allergens
This phenothiazine with sedative properties is used in human medicine and induced contact dermatitis in nurses or those working in the pharmaceutical industry. It is also used in veterinary medicine to avoid mortality of pigs during transportation. It is a sensitizer and a photosensitizer.
Pharmacokinetics
Chlorpromazine is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Chlorpromazine has actions at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Chlorpromazine has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity.
Synthesis
Chlorpromazine, 2-chloro-10-(3-dimethylaminopropyl)phenothiazine, is synthesized in an analogous manner, except by alkylation of 2-chlorophenothiazine with 3-dimethylaminopropylchloride.
Environmental Fate
Acute and chronic toxicity due to chlorpromazine generally
manifests as an extension of normal pharmacological activity.
The precise mechanism of action of chlorpromazine, and other
phenothiazines, is unknown; however, it is thought to primarily
involve antagonism of dopaminergic (D2) neurotransmission
at synaptic sites and blockade of postsynaptic dopamine
receptor sites at the subcortical levels of the reticular formation,
limbic system, and hypothalamus. This activity contributes to
chlorpromazine’s extrapyramidal reactions. Chlorpromazine
also has strong central and peripheral activity directed against
adrenergic receptors and weak activity against serotonergic,
histaminic (H1), and muscarinic receptors. Chlorpromazine
has slight ganglionic blocking action. Chlorpromazine is
known to depress vasomotor reflexes medicated by the hypothalamus
and/or brain stem; inhibit release of growth hormone;
antagonize secretion of prolactin release-inhibiting hormone;
and reduce secretion of corticotropin-regulatory hormone.
Chlorpromazine also has direct effects on cardiac myocytes;
it can induce early after-depolarizations, block depolarizing
sodium channels, and cause significant prolongation of the
QTc interval.
Chlorpromazine may be irritating to eyes, mucous
membranes, and skin. Contact and inhalation should be
avoided.
Metabolic pathway
The in vivo photodegradation of chlorpromazine in rat skin exposed to UV-A results in the formation of promazine and 2-hydroxypromazine in irradiated rats, but not in the skin of rats kept in the dark. Chlorpromazine sulfoxide is a major metabolite of chlorpromazine, found in smaller quantity in the skin of irradiated rats compared with those kept in the dark. Chlorpromazine sulfoxide is not a photoproduct of chlorpromazine under the experimental conditions.
Metabolism
Extensively metabolized in the liver and kidneys. It is extensively metabolized by cytochrome P450 isozymes CYP2D6 (major pathway), CYP1A2 and CYP3A4. Approximately 10 to 12 major metabolite have been identified. Hydroxylation at positions 3 and 7 of the phenothiazine nucleus and the N-dimethylaminopropyl side chain undergoes demethylation and is also metabolized to an N-oxide. In urine, 20% of chlopromazine and its metabolites are excreted unconjugated in the urine as unchanged drug, demonomethylchlorpromazine, dedimethylchlorpromazine, their sulfoxide metabolites, and chlorpromazine-N-oxide. The remaining 80% consists of conjugated metabolites, principally O-glucuronides and small amounts of ethereal sulfates of the mono- and dihydroxy-derivatives of chlorpromazine and their sulfoxide metabolites. The major metabolites are the monoglucuronide of N-dedimethylchlorpromazine and 7-hydroxychlorpromazine. Approximately 37% of the administered dose of chlorpromazine is excreted in urine.
Toxicity evaluation
Chlorpromazine exists as both a vapor and particulate at ambient atmospheric conditions. Chlorpromazine vapor is degraded by photochemically produced hydroxyl radicals with an estimated half-life of 1.6 h. Chlorpromazine particulate is removed by wet or dry deposition. Chlorpromazine is likely to be immobile in soil (Koc 9900, pKa 9.3) and to adsorb to sediment if released into water. It is not expected to volatilize from soil or water. There is high potential for bioconcentration.
Properties of Chlorpromazine
Melting point: | 56.5°C |
Boiling point: | bp0.8 200-205° |
Density | 1.1644 (rough estimate) |
refractive index | 1.6230 (estimate) |
solubility | Chloroform (Slightly), Methanol (Slightly) |
pka | pKa 9.3(H2O,t =24±1) (Uncertain) |
form | Solid |
color | White to Off-White |
NIST Chemistry Reference | Chlorpromazine(50-53-3) |
EPA Substance Registry System | Chlorpromazine (50-53-3) |
Safety information for Chlorpromazine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Chlorpromazine
Abamectin manufacturer
Sibram Pharmaceutical
Amoli Organics Pvt Ltd
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