Identification
- Summary
Thiothixene is an antipsychotic indicated for the management of schizophrenia.
- Brand Names
- Navane
- Generic Name
- Thiothixene
- DrugBank Accession Number
- DB01623
- Background
A thioxanthine used as an antipsychotic agent. Its effects are similar to the phenothiazine antipsychotics.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Thiothixene (DB01623)
- Weight
- Average: 443.625
Monoisotopic: 443.170118567 - Chemical Formula
- C23H29N3O2S2
- Synonyms
- cis-thiothixene
- Thiothixene
- Tiotixene
- Tiotixeno
- Tiotixenum
- External IDs
- CP-12252-1
- NSC-108165
- P-4657 B
- P-4657B
Pharmacology
- Indication
For the management of schizophrenia.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Schizophrenia •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Thiothixene is an antipsychotic of the thioxanthene series. Navane possesses certain chemical and pharmacological similarities to the piperazine phenothiazines and differences from the aliphatic group of phenothiazines. Although widely used in the treatment of schizophrenia for several decades, thiothixene is seldom used today in favor of atypical antipsychotics such as risperidone.
- Mechanism of action
Thiothixene 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).
Target Actions Organism ADopamine D2 receptor antagonistHumans ADopamine D1 receptor antagonistHumans U5-hydroxytryptamine receptor 2A antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
10-20 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include central nervous system depression, coma, difficulty swallowing, dizziness, drowsiness, head tilted to the side, low blood pressure, muscle twitching, rigid muscles, salivation, tremors, walking disturbances, and weakness.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Thiothixene is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Thiothixene can be increased when it is combined with Abametapir. Abatacept The metabolism of Thiothixene can be increased when combined with Abatacept. Abiraterone The serum concentration of Thiothixene can be increased when it is combined with Abiraterone. Acenocoumarol The metabolism of Thiothixene can be decreased when combined with Acenocoumarol. - Food Interactions
- Avoid alcohol.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Thiothixene hydrochloride B3CRJ1EWJU 22189-31-7 MEUAAEMCZUPORO-LRSHZYOCSA-N - International/Other Brands
- Navan / Navaron / Orbinamon
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Navane Capsule 20 mg/1 Oral Roerig 1967-07-24 2012-08-01 US 
Navane Capsule 2 mg/1 Oral Roerig 1967-07-24 2012-08-01 US Navane Capsule 10 mg/1 Oral Roerig 1967-07-24 2012-08-01 US Navane Capsule 1 mg/1 Oral Roerig 1967-07-24 2012-08-01 US Navane Capsule 5 mg Oral Searchlight Pharma Inc 1969-12-31 Not applicable Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Thiothixene Capsule 5 mg/1 Oral Golden State Medical Supply, Inc. 2019-04-05 Not applicable US Thiothixene Capsule 2 mg/1 Oral Sandoz Inc 1987-06-24 2016-01-31 US Thiothixene Capsule 10 mg/1 Oral REMEDYREPACK INC. 2019-10-02 2023-10-31 US Thiothixene Capsule 1 mg/1 Oral REMEDYREPACK INC. 2017-11-09 2020-05-06 US Thiothixene Capsule 2 mg/1 Oral Novitium Pharma Llc 2019-04-05 Not applicable US
Categories
- ATC Codes
- N05AF04 — Tiotixene
- Drug Categories
- Antidepressive Agents
- Antipsychotic Agents
- Antipsychotic Agents (First Generation [Typical])
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Drugs causing inadvertant photosensitivity
- Heterocyclic Compounds, Fused-Ring
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- Photosensitizing Agents
- Potential QTc-Prolonging Agents
- Psycholeptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Sulfur Compounds
- Thioxanthene Derivatives
- Thioxanthenes
- Tranquilizing Agents
- Xanthenes
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiopyrans
- Sub Class
- 1-benzothiopyrans
- Direct Parent
- Thioxanthenes
- Alternative Parents
- Diarylthioethers / N-methylpiperazines / Organosulfonamides / Benzenoids / Aminosulfonyl compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1,4-diazinane / Amine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative / N-alkylpiperazine
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7318FJ13YJ
- CAS number
- 3313-26-6
- InChI Key
- GFBKORZTTCHDGY-UWVJOHFNSA-N
- InChI
- InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3/b19-8-
- IUPAC Name
- (9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide
- SMILES
- CN(C)S(=O)(=O)C1=CC2=C(SC3=CC=CC=C3\C2=C\CCN2CCN(C)CC2)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015560
- KEGG Drug
- D00374
- PubChem Compound
- 941651
- PubChem Substance
- 46505564
- ChemSpider
- 819430
- BindingDB
- 78576
- 10510
- ChEBI
- 9571
- ChEMBL
- CHEMBL1201
- ZINC
- ZINC000030690433
- Therapeutic Targets Database
- DAP000318
- PharmGKB
- PA451669
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Tiotixene
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count Not Available Completed Not Available Bipolar Disorder (BD) / Psychosis / Schizoaffective Disorders / Schizophrenia / Type 2 Diabetes Mellitus 1 Not Available Completed Not Available Schizophrenia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advanced Pharmaceutical Services Inc.
- Comprehensive Consultant Services Inc.
- Direct Dispensing Inc.
- Heartland Repack Services LLC
- Major Pharmaceuticals
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Pfizer Inc.
- Physicians Total Care Inc.
- Prepak Systems Inc.
- Qualitest
- Rebel Distributors Corp.
- Remedy Repack
- Sandhills Packaging Inc.
- Sandoz
- Tya Pharmaceuticals
- UDL Laboratories
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Capsule Oral 1 mg/1 Capsule Oral 20 mg/1 Capsule Oral 5 mg Solution, concentrate Oral 5 mg/1mL Capsule Oral 2 mg Capsule Oral 10 mg Capsule Oral 10 mg/1 Capsule Oral 2 mg/1 Capsule Oral 5 mg/1 - Prices
Unit description Cost Unit Navane 20 mg capsule 3.15USD capsule Navane 10 mg capsule 1.66USD capsule Navane 5 mg capsule 1.2USD capsule Navane 2 mg capsule 0.8USD capsule Thiothixene 10 mg capsule 0.67USD capsule Thiothixene 5 mg capsule 0.47USD capsule Thiothixene 2 mg capsule 0.31USD capsule Thiothixene 1 mg capsule 0.24USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0139 mg/mL ALOGPS logP 4.01 ALOGPS logP 3.36 Chemaxon logS -4.5 ALOGPS pKa (Strongest Basic) 8.16 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 43.86 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 137.85 m3·mol-1 Chemaxon Polarizability 50.35 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9969 Blood Brain Barrier + 0.9437 Caco-2 permeable - 0.6277 P-glycoprotein substrate Substrate 0.8707 P-glycoprotein inhibitor I Inhibitor 0.9247 P-glycoprotein inhibitor II Inhibitor 0.9036 Renal organic cation transporter Non-inhibitor 0.5373 CYP450 2C9 substrate Non-substrate 0.7951 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Substrate 0.5269 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8933 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5406 Ames test Non AMES toxic 0.651 Carcinogenicity Non-carcinogens 0.8173 Biodegradation Not ready biodegradable 0.947 Rat acute toxicity 2.7586 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5093 hERG inhibition (predictor II) Non-inhibitor 0.7259
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 227.1014217 predictedDarkChem Lite v0.1.0 [M-H]- 223.2769217 predictedDarkChem Lite v0.1.0 [M-H]- 201.6591 predictedDeepCCS 1.0 (2019) [M+H]+ 227.3568217 predictedDarkChem Lite v0.1.0 [M+H]+ 222.6235217 predictedDarkChem Lite v0.1.0 [M+H]+ 204.05466 predictedDeepCCS 1.0 (2019) [M+Na]+ 226.9817217 predictedDarkChem Lite v0.1.0 [M+Na]+ 223.5196217 predictedDarkChem Lite v0.1.0 [M+Na]+ 209.98012 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Shultz PJ, Sedor JR, Abboud HE: Dopaminergic stimulation of cAMP accumulation in cultured rat mesangial cells. Am J Physiol. 1987 Aug;253(2 Pt 2):H358-64. [Article]
- Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. [Article]
- Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [Article]
- Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. [Article]
- Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. doi: 10.3371/CSRP.4.1.5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled amine receptor activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name
- DRD1
- Uniprot ID
- P21728
- Uniprot Name
- D(1A) dopamine receptor
- Molecular Weight
- 49292.765 Da
References
- Shultz PJ, Sedor JR, Abboud HE: Dopaminergic stimulation of cAMP accumulation in cultured rat mesangial cells. Am J Physiol. 1987 Aug;253(2 Pt 2):H358-64. [Article]
- Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm (Vienna). 2000;107(3):295-302. [Article]
- Kroeze WK, Hufeisen SJ, Popadak BA, Renock SM, Steinberg S, Ernsberger P, Jayathilake K, Meltzer HY, Roth BL: H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. Neuropsychopharmacology. 2003 Mar;28(3):519-26. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Shin JG, Soukhova N, Flockhart DA: Effect of antipsychotic drugs on human liver cytochrome P-450 (CYP) isoforms in vitro: preferential inhibition of CYP2D6. Drug Metab Dispos. 1999 Sep;27(9):1078-84. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Xie C, Pogribna M, Word B, Lyn-Cook L Jr, Lyn-Cook BD, Hammons GJ: In vitro analysis of factors influencing CYP1A2 expression as potential determinants of interindividual variation. Pharmacol Res Perspect. 2017 Mar 2;5(2):e00299. doi: 10.1002/prp2.299. eCollection 2017 Apr. [Article]
- Thiothixene [Link]
- CYP1A2 cancer.gov document [File]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Kitamura K, Omran AA, Nagata C, Kamijima Y, Tanaka R, Takegami S, Kitade T: Effects of inorganic ions on the binding of triflupromazine and chlorpromazine to bovine serum albumin studied by spectrometric methods. Chem Pharm Bull (Tokyo). 2006 Jul;54(7):972-6. [Article]
- Rukhadze MD, Bezarashvili GS, Sidamonidze NS, Tsagareli SK: Investigation of binding process of chlorpromazine to bovine serum albumin by means of passive and active experiments. Biomed Chromatogr. 2001 Oct;15(6):365-73. [Article]
- Silva D, Cortez CM, Louro SR: Quenching of the intrinsic fluorescence of bovine serum albumin by chlorpromazine and hemin. Braz J Med Biol Res. 2004 Jul;37(7):963-8. Epub 2004 Jun 22. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [Article]
Drug created at August 29, 2007 20:17 / Updated at February 20, 2024 23:55