2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine

• ChemBase ID: 316
• Molecular Formular: C20H24ClN3S
• Molecular Mass: 373.94266
• Monoisotopic Mass: 373.13794646
• SMILES: Clc1cc2N(CCCN3CCN(CC3)C)c3c(Sc2cc1)cccc3
• Canonical SMILES: CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(Cl)cc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
• IUPAC Traditional name: prochlorperazine; compro
• Brand Name: Bayer A 173; Buccastem; Compazine; Capazine; Combid; Compro; Emelent; Emetiral; Eskatrol; Kronocin; Meterazin; Meterazin Maleate; Meterazine; Nipodal; Novamin; Pasotomin; Stemetil; Tementil; Temetid; Vertigon
• Synonyms: Prochloroperazine; Prochlorpromazine; Prochlorperazine maleate; Prochlorperazine edisylate; Prochlorperazin; Prochlorpemazine; Proclorperazine; Procloperazine; Chlorperazine; Chlormeprazine; Prochlorperazine; Prochlorperazine edisylate salt; Novamin; Tementil; Prochlorperazine DimesylateAlso See: P755805; Buccastem; Emetiral; Meterazin Maleate; Pasotomin; Prochlorperazine Hydrogen Maleate; Prochloroperazine Dimaleate; Stemetil; Stemetil Dimaleate; Vertigon; Prochlorperazine DimaleateAlso See: P755800; 2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine Dimethanesulfonate; 3-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine Dimesylate; 2-Chloro-10-[3-(4-methyl-1-piper-azinyl)propyl]-10H-pheno-thiazine dimaleate; Compazine

Database IDs

• CAS Number: 58-38-8; 1257-78-9; 51888-09-6; 84-02-6
• EC Number: 215-019-1; 200-379-4
• MDL Number: MFCD00056797
• PubChem SID: 160963779; 46509018
• PubChem CID: 4917
• CHEBI ID: 8435
• ATC CODE: N05AB04
• CHEMBL: 728
• Chemspider ID: 4748
• DrugBank ID: DB00433
• KEGG ID: D00493
• Unique Ingredient Identifier: YHP6YLT61T
• Wikipedia Title: Prochlorperazine
• Medline Plus: a682116

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.5868546
• LogD (pH = 7.4): 3.352362
• Log P: 4.3821197
• Molar Refractivity: 109.8064 cm^3
• Polarizability: 42.294575 Å^3
• Polar Surface Area: 9.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.67
• LOG S: -4.53
• Solubility (Water): 1.10e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Methanol (sparingly); Very slightly soluble
• Apperance: Off-White Solid; Off-White to Pale Yellow Solid
• Melting Point: 196-198°C; 238-240°C
• Hydrophobicity(logP): 4.6

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Protect from light
• RTECS: SO2700000; SO2975000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 22; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Admin Routes: Oral, buccal, rectal, IM
• Bioavailability: not exactly known, but substantial
• Excretion: Biliary, (colored) inactive metabolites in urine
• Half Life: 4–8 hoursS, differs with the method of administration
• Metabolism: Mainly hepatic (CYP2D6 and/or CYP3A4)
• Protein Bound: 91–99%
• Legal Status: OTC/POM (UK); Rx-only (US)
• Pregnancy Category: C (Au, U.S.)

DETAILS

MP Biomedicals - 02153565

Dimaleate

DrugBank - DB00433

• Drug Groups: approved
• Description: A phenothiazine antipsychotic used principally in the treatment of nausea; vomiting; and vertigo. It is more likely than chlorpromazine to cause extrapyramidal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612)
• Indication: For the symptomatic management of psychotic disorders, short term management of nonpsychotic anxiety in patients with generalized anxiety disorder, and for the control of severe nausea and vomiting of various causes.
• Pharmacology: Prochlorperazine is a piperazine phenothiazine related to high-potency neuroleptics such as perphenazine. It shares many of the actions and adverse effects of the antipsychotics.
• Toxicity: Symptoms of central nervous system depression to the point of somnolence or coma. Agitation and restlessness may also occur. Other possible manifestations include convulsions, EKG changes and cardiac arrhythmias, fever and autonomic reactions such as hypotension, dry mouth and ileus; LD₅₀=400mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Undergoes metabolism in the gastric mucosa and on first pass through the liver, CYP2D6 and/or CYP3A4.
• Absorption: Rapidly absorbed following oral administration
• Half Life: 6 to 8 hours
• Protein Binding: 91-99%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - P7152

Biochem/physiol Actions
Phenothiazine antipsychotic; D2 antagonist; antispasmodic

Toronto Research Chemicals - P755800

Antiemetic, antipsychotic; used in treatment of vertigo.

Toronto Research Chemicals - P755805

Antiemetic.

REFERENCES

• Taylor, W.B., et al.: Br. J. Clin. Pharmacol., 23, 137 (1987)
• Ward, A.E., Br. J. Clin. Pract., 42, 228 (1987)
• Taylor, W.B., et al.: Br. J. Clin. Pharmacol., 23, 137 (1987)
• Ward, A.E., Br. J. Clin. Pract., 42, 228 (1988).