NAV

Phenothiazine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Phenothiazine
DrugBank Accession Number
DB11447
Background

Phenothiazine (PTZ) is an organic thiazine compound.

Type
Small Molecule
Groups
Experimental, Vet approved
Structure
3D
Similar Structures
Weight
Average: 199.27
Monoisotopic: 199.045570468
Chemical Formula
C12H9NS
Synonyms
  • 10H-phenothiazine
  • dibenzo-1,4-thiazine
  • Fenotiazina
  • Phenothiazine
  • Phenothiazinum
  • Thiodiphenylamin
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
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
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Toxicity

Not Available

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.
DrugInteraction
Integrate drug-drug
interactions in your software
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Phenothiazine.
AmifampridineThe risk or severity of seizure can be increased when Phenothiazine is combined with Amifampridine.
AmitriptylineThe serum concentration of Nortriptyline, an active metabolite of Amitriptyline, can be decreased when used in combination with Phenothiazine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Phenothiazine.
BrexanoloneThe therapeutic efficacy of Brexanolone can be decreased when used in combination with Phenothiazine.
Food Interactions
Not Available

Categories

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
Diarylthioethers / Benzenoids / 1,4-thiazines / Secondary amines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazine (CHEBI:37931)
Affected organisms
Not Available

Chemical Identifiers

UNII
GS9EX7QNU6
CAS number
92-84-2
InChI Key
WJFKNYWRSNBZNX-UHFFFAOYSA-N
InChI
InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H
IUPAC Name
10H-phenothiazine
SMILES
N1C2=CC=CC=C2SC2=CC=CC=C12

References

General References
  1. Authors unspecified: Phenothiazine. Can J Comp Med Vet Sci. 1940 Dec;4(12):332. [Article]
  2. Authors unspecified: PHENOTHIAZINE. Bull Am Pharm Assoc. 1946 Jul-Aug;14(7-8):158. [Article]
  3. Boet DJ: Phenothiazine retinopathy. Ophthalmologica. 1969;158 Suppl:574-82. [Article]
  4. RAPPAPORT R: [Phenothiazine derivatives]. Fr Med. 1957 Aug-Sep;20(8-9):23-6. [Article]
  5. Alkemade PP: Phenothiazine-retinopathy. Ophthalmologica. 1968;155(1):70-6. [Article]
  6. LONGMORE DB: PHENOTHIAZINE PIGMENTATION. Lancet. 1965 Apr 17;1(7390):854. [Article]
  7. RICHARDS F: PHENOTHIAZINE PIGMENTATION. Lancet. 1965 Aug 28;2(7409):437. [Article]
  8. Singh SD, Varma A: Phenothiazine poisoning. Indian Pediatr. 1986 Oct;23 Suppl:172-3. [Article]
  9. McNeill DL: Phenothiazine resistance. Br Med J. 1977 Jul 9;2(6079):127-8. [Article]
  10. DELGADO JN, COSGROVE FP, ISAACSON EI: PHENOTHIAZINE DERIVATIVES. Tex Med. 1964 Mar;60:315-8. [Article]
  11. Filip IH, Gal E, Lupan I, Perde-Schrepler M, Lonnecke P, Surducan M, Gaina LI, Hey-Hawkins E, Silaghi-Dumitrescu L: Tuning the coordination properties of phenothiazine by regioselective introduction of diphenylphosphanyl groups. Dalton Trans. 2015 Jan 14;44(2):615-29. doi: 10.1039/c4dt02665a. Epub 2014 Nov 10. [Article]
  12. Musah RA, Lesiak AD, Maron MJ, Cody RB, Edwards D, Fowble KL, Dane AJ, Long MC: Mechanosensitivity below Ground: Touch-Sensitive Smell-Producing Roots in the Shy Plant Mimosa pudica. Plant Physiol. 2016 Feb;170(2):1075-89. doi: 10.1104/pp.15.01705. Epub 2015 Dec 9. [Article]
KEGG Drug
D02601
ChemSpider
21106365
BindingDB
50012855
ChEBI
37931
ChEMBL
CHEMBL828
ZINC
ZINC000100009616
Wikipedia
Phenothiazine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.39 mg/mLALOGPS
logP4.19ALOGPS
logP3.63Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)17.91Chemaxon
pKa (Strongest Basic)-0.95Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area12.03 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity61.17 m3·mol-1Chemaxon
Polarizability21.6 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0006-2920000000-abe97627fbae89daa0db
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014j-2900000000-0c8015640d3d05a50f86
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-247dcbbacbccc1f11a32
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-9650ce22215267e5e099
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-9650ce22215267e5e099
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-040382568166268e6635
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-4920000000-adaa9ed0dfa95f945c3d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006t-0900000000-f3d902db716a75a3baaa
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]-140.6551771
predicted
DarkChem Lite v0.1.0
[M-H]-145.0318521
predicted
DarkChem Lite v0.1.0
[M-H]-131.44435
predicted
DeepCCS 1.0 (2019)
[M+H]+146.0195251
predicted
DarkChem Lite v0.1.0
[M+H]+145.5611521
predicted
DarkChem Lite v0.1.0
[M+H]+134.19081
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.1682865
predicted
DarkChem Lite v0.1.0
[M+Na]+145.1262521
predicted
DarkChem Lite v0.1.0
[M+Na]+143.1389
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 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 February 25, 2016 18:50 / Updated at February 21, 2021 18:53