Acetophenazine
Identification
- Name
- Acetophenazine
- Accession Number
- DB01063
- Description
Acetophenazine is an antipsychotic drug of moderate-potency. It is used in the treatment of disorganized and psychotic thinking. It is also used to help treat false perceptions (e.g. hallucinations or delusions). It primarily targets the dopamine D2 receptor.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Acetophenazine (DB01063)
- Weight
- Average: 411.56
Monoisotopic: 411.198047877 - Chemical Formula
- C23H29N3O2S
- Synonyms
- Acetophenazina
- Acetophenazine
- Acetophenazinum
Pharmacology
- Indication
For the treatment of disorganized and psychotic thinking. Also used to help treat false perceptions (e.g. hallucinations or delusions.)
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Acetophenzine is a phenothiazine antipsychotic intended for the management of schizophrenia and other psychotic disorders.
- Mechanism of action
Acetophenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
Target Actions Organism ADopamine D2 receptor antagonistHumans UAndrogen receptor Not Available Humans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAcebutolol The serum concentration of Acebutolol can be increased when it is combined with Acetophenazine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Acetophenazine. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Acetophenazine. Aclidinium Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Agomelatine. Alfentanil The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Alfentanil. Alimemazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Alimemazine. Almasilate Almasilate can cause a decrease in the absorption of Acetophenazine resulting in a reduced serum concentration and potentially a decrease in efficacy. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Acetophenazine. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Acetophenazine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Acetophenazine maleate 3P5HNU5JTC 5714-00-1 NUKVZKPNSKJGBK-SPIKMXEPSA-N - International/Other Brands
- Tindal (Schering)
Categories
- ATC Codes
- N05AB07 — Acetophenazine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazines
- Sub Class
- Phenothiazines
- Direct Parent
- Phenothiazines
- Alternative Parents
- Alkyldiarylamines / Diarylthioethers / Acetophenones / Aryl alkyl ketones / N-alkylpiperazines / 1,4-thiazines / Trialkylamines / 1,2-aminoalcohols / Azacyclic compounds / Primary alcohols show 3 more
- Substituents
- 1,2-aminoalcohol / 1,4-diazinane / Acetophenone / Alcohol / Alkanolamine / Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- phenothiazines, N-(2-hydroxyethyl)piperazine, N-alkylpiperazine (CHEBI:2401)
Chemical Identifiers
- UNII
- 8620H6K4QH
- CAS number
- 2751-68-0
- InChI Key
- WNTYBHLDCKXEOT-UHFFFAOYSA-N
- InChI
- InChI=1S/C23H29N3O2S/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27/h2-3,5-8,17,27H,4,9-16H2,1H3
- IUPAC Name
- 1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)ethan-1-one
- SMILES
- CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1
References
- Synthesis Reference
- US2985654
- General References
- Jones GL, Woodbury DM: Spin-label study of phenothiazine interactions with erythrocyte ghost membranes: a possible membrane-mediated antisickling action. J Pharmacol Exp Ther. 1978 Oct;207(1):203-11. [PubMed:702341]
- Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851]
- External Links
- Human Metabolome Database
- HMDB0015196
- KEGG Compound
- C06807
- PubChem Compound
- 17676
- PubChem Substance
- 46507036
- ChemSpider
- 16708
- BindingDB
- 82475
- 16735
- ChEBI
- 2401
- ChEMBL
- CHEMBL1085
- ZINC
- ZINC000022446634
- Therapeutic Targets Database
- DAP000844
- PharmGKB
- PA164781360
- Wikipedia
- Acetophenazine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 167-168.5 Sherlock, M.H. and Sperber, N.;U .S. Patent 2,985,654; May 23,1961; assigned to Schering Corporation logP 2.62 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0601 mg/mL ALOGPS logP 3.48 ALOGPS logP 2.65 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 15.46 ChemAxon pKa (Strongest Basic) 8.07 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 47.02 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 121.7 m3·mol-1 ChemAxon Polarizability 46.68 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9893 Blood Brain Barrier + 0.9469 Caco-2 permeable - 0.5303 P-glycoprotein substrate Substrate 0.846 P-glycoprotein inhibitor I Inhibitor 0.8809 P-glycoprotein inhibitor II Inhibitor 0.6834 Renal organic cation transporter Inhibitor 0.5248 CYP450 2C9 substrate Non-substrate 0.6788 CYP450 2D6 substrate Substrate 0.7697 CYP450 3A4 substrate Non-substrate 0.644 CYP450 1A2 substrate Inhibitor 0.8354 CYP450 2C9 inhibitor Non-inhibitor 0.9186 CYP450 2D6 inhibitor Inhibitor 0.8979 CYP450 2C19 inhibitor Non-inhibitor 0.8746 CYP450 3A4 inhibitor Non-inhibitor 0.7426 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5 Ames test Non AMES toxic 0.817 Carcinogenicity Non-carcinogens 0.891 Biodegradation Not ready biodegradable 0.9893 Rat acute toxicity 2.7720 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8509 hERG inhibition (predictor II) Inhibitor 0.7117
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-0h2f-7962200000-29f2e9055979e0add70b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706]
- Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
References
- Bisson WH, Cheltsov AV, Bruey-Sedano N, Lin B, Chen J, Goldberger N, May LT, Christopoulos A, Dalton JT, Sexton PM, Zhang XK, Abagyan R: Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs. Proc Natl Acad Sci U S A. 2007 Jul 17;104(29):11927-32. Epub 2007 Jul 2. [PubMed:17606915]
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51
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