NAV

Acetophenazine

Identification

Generic Name
Acetophenazine
DrugBank Accession Number
DB01063
Background

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
3D
Similar Structures
Weight
Average: 411.56
Monoisotopic: 411.198047877
Chemical Formula
C23H29N3O2S
Synonyms
  • Acetophenazina
  • Acetophenazine
  • Acetophenazinum
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

For the treatment of disorganized and psychotic thinking. Also used to help treat false perceptions (e.g. hallucinations or delusions.)

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
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.

TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
UAndrogen receptorNot AvailableHumans
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
Integrate drug-drug
interactions in your software
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with 1,2-Benzodiazepine.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Acetophenazine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Acetophenazine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Acetophenazine.
AgomelatineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Agomelatine.
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Acetophenazine maleate3P5HNU5JTC5714-00-1NUKVZKPNSKJGBK-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)
Affected organisms
  • Humans and other mammals

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
  1. 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. [Article]
  2. 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. [Article]
Human Metabolome Database
HMDB0015196
KEGG Compound
C06807
PubChem Compound
17676
PubChem Substance
46507036
ChemSpider
16708
BindingDB
82475
RxNav
16735
ChEBI
2401
ChEMBL
CHEMBL1085
ZINC
ZINC000022446634
Therapeutic Targets Database
DAP000844
PharmGKB
PA164781360
Wikipedia
Acetophenazine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)167-168.5Sherlock, M.H. and Sperber, N.;U .S. Patent 2,985,654; May 23,1961; assigned to Schering Corporation
logP2.62SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0601 mg/mLALOGPS
logP3.48ALOGPS
logP2.65Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.46Chemaxon
pKa (Strongest Basic)7.78Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area47.02 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity121.7 m3·mol-1Chemaxon
Polarizability46.68 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9893
Blood Brain Barrier+0.9469
Caco-2 permeable-0.5303
P-glycoprotein substrateSubstrate0.846
P-glycoprotein inhibitor IInhibitor0.8809
P-glycoprotein inhibitor IIInhibitor0.6834
Renal organic cation transporterInhibitor0.5248
CYP450 2C9 substrateNon-substrate0.6788
CYP450 2D6 substrateSubstrate0.7697
CYP450 3A4 substrateNon-substrate0.644
CYP450 1A2 substrateInhibitor0.8354
CYP450 2C9 inhibitorNon-inhibitor0.9186
CYP450 2D6 inhibitorInhibitor0.8979
CYP450 2C19 inhibitorNon-inhibitor0.8746
CYP450 3A4 inhibitorNon-inhibitor0.7426
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.817
CarcinogenicityNon-carcinogens0.891
BiodegradationNot ready biodegradable0.9893
Rat acute toxicity2.7720 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8509
hERG inhibition (predictor II)Inhibitor0.7117
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001j-2349000000-75f8347d32e98e5870c4
GC-MS Spectrum - EI-BGC-MSsplash10-0h2f-7962200000-29f2e9055979e0add70b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0010900000-b65755ffc15b092a990b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0000900000-2cf55f6de92bf8d2b32c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0243900000-2c679e7cd2fbd23bbbce
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009600000-51760108e6ee66c7266a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-1219100000-f4df167c648039e9e4a0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ukm-1097000000-9e5cb028427823dd7d5e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-216.8111544
predicted
DarkChem Lite v0.1.0
[M-H]-219.1193544
predicted
DarkChem Lite v0.1.0
[M-H]-194.38283
predicted
DeepCCS 1.0 (2019)
[M+H]+217.1070544
predicted
DarkChem Lite v0.1.0
[M+H]+219.1464544
predicted
DarkChem Lite v0.1.0
[M+H]+196.74086
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.4242544
predicted
DarkChem Lite v0.1.0
[M+Na]+219.3956544
predicted
DarkChem Lite v0.1.0
[M+Na]+203.52684
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Dopamine D2 receptor
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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. [Article]
  3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [Article]
  4. 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. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details2. Androgen receptor
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
  1. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:54