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Product Details:

  • CAS No: 50-53-3
  • AHFC code: 28:16.08.24
  • Synonyms: 2-Chloro-10-(3-(dimethylamino)propyl)phenothiazine, 2-Chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine, 2-Chloropromazine, 2-Cloro-10 (3-dimetilaminopropil)fenotiazina, 2-Cloro-10 (3-dimetilaminopropil)fenotiazina [Italian], 4560 R.P., Aminazin, Aminazine, Ampliactil, BC 135, CCRIS 3711, Chlor-Promanyl, Chlorderazin, Chloro-3 (dimethylamino-3 propyl)-10 phenothiazine, Chloro-3 (dimethylamino-3 propyl)-10 phenothiazine [French], Chloropromazine, Chlorpromados, Chlorpromazin, Chlorpromazine, Chlorpromazinum, Chlorpromazinum [INN-Latin], Clorpromazina, Clorpromazina [INN-Spanish], Clorpromazina [Italian], Contomin, CPZ, EINECS 200-045-8, Elmarin, Esmind, Fenactil, Fenaktyl, Fraction AB, GG 407, HL 5746, HSDB 3033, Largactil, Largactilothiazine, Largactyl, Megaphen, N-(3-Dimethylaminopropyl)-3-chlorophenothiazine, Novomazina, NSC 167745, Phenactyl, Proma, Promactil, Promazil, Propaphenin, Prozil, Psychozine, Sanopron, SKF 2601-A, Thorazine, Thorazine Suppositories, Torazina, UNII-U42B7VYA4P, Wintermin
  • ATC Code: N05AA01
  • Chemical Formula: C17-H19-Cl-N2-S
  • Molecular Weight: 318.8701
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00477 (APRD00482)
  • SMILES: CN(C)CCCN1c2ccccc2Sc3c1cc(cc3)Cl
  • InChl: 1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3
  • PubChem: http://www.ncbi.nlm.nih.gov/pcsubstance?term=50-53-3~%5Bsynonym%5D
  • IUPAC: [3-(2-chloro-10H-phenothiazin-10-yl)propyl]dimethylamine

Additional Details

Indication:
For the treatment of schizophrenia, control nausea and vomiting, For relief of restlessness and apprehension before surgery, adjunct in the treatment of tetanus, control the manifestations of the manic type of manic-depressive illness.
Pharmacodynamics:
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.
Mode of Action:
Chlorpromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 – different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism – controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Additionally, Chlorpromazine is a weak presynaptic inhibitor of Dopamine reuptake, which may lead to (mild) antidepressive and antiparkinsonian effects. This action could also account for psychomotor agitation and amplification of psychosis (very rarely noted in clinical use).
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:
Agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, restlessness
General Reference:
Leucht S, Wahlbeck K, Hamann J, Kissling W: New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. Lancet. 2003 May 10;361(9369):1581-9. Pubmed
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