This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Cyclopenthiazide
- DrugBank Accession Number
- DB13532
- Background
Cyclopenthiazide is a thiazide diuretic with antihypertensive properties. In a double blind, randomized crossover study, cyclopenthiazide was effective in reducing diastolic blood pressure in mildly hypertensive non-insulin dependent diabetic patients 2. It is a positive allosteric modulator at AMPA-A receptors 3.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cyclopenthiazide (DB13532)
- Weight
- Average: 379.87
Monoisotopic: 379.0427261 - Chemical Formula
- C13H18ClN3O4S2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- 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
Not Available
- Mechanism of action
- Not Available
- 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 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
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cyclopenthiazide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Abaloparatide Abaloparatide may increase the hypotensive activities of Cyclopenthiazide. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cyclopenthiazide. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Cyclopenthiazide. Acebutolol The therapeutic efficacy of Acebutolol can be increased when used in combination with Cyclopenthiazide. - Food Interactions
- Not Available
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.- International/Other Brands
- Navidrex
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- C03AB — Thiazides and potassium in combination
- C03A — LOW-CEILING DIURETICS, THIAZIDES
- C03 — DIURETICS
- C — CARDIOVASCULAR SYSTEM
- C03EA — Low-ceiling diuretics and potassium-sparing agents
- C03E — DIURETICS AND POTASSIUM-SPARING AGENTS IN COMBINATION
- C03 — DIURETICS
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Antihypertensive Agents
- Benzothiadiazines
- Cardiovascular Agents
- Diuretics
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Heterocyclic Compounds, Fused-Ring
- Hyperglycemia-Associated Agents
- Low-Ceiling Diuretics and Potassium-Sparing Agents
- Membrane Transport Modulators
- Natriuretic Agents
- Sodium Chloride Symporter Inhibitors
- Sulfonamides
- Sulfones
- Sulfur Compounds
- Thiazides
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Thiadiazines
- Sub Class
- Benzothiadiazines
- Direct Parent
- 1,2,4-benzothiadiazine-1,1-dioxides
- Alternative Parents
- Secondary alkylarylamines / Organosulfonamides / Benzenoids / Aryl chlorides / Aminosulfonyl compounds / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1,2,4-benzothiadiazine-1,1-dioxide / Amine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Hydrocarbon derivative / Organic nitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- VX4S2N85F5
- CAS number
- 742-20-1
- InChI Key
- BKYKPTRYDKTTJY-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H18ClN3O4S2/c14-9-6-10-12(7-11(9)22(15,18)19)23(20,21)17-13(16-10)5-8-3-1-2-4-8/h6-8,13,16-17H,1-5H2,(H2,15,18,19)
- IUPAC Name
- 6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide
- SMILES
- NS(=O)(=O)C1=CC2=C(NC(CC3CCCC3)NS2(=O)=O)C=C1Cl
References
- General References
- Johnston GD, Wilson R, McDermott BJ, McVeigh GE, Duffin D, Logan J: Low-dose cyclopenthiazide in the treatment of hypertension: a one-year community-based study. Q J Med. 1991 Feb;78(286):135-43. [Article]
- Passmore AP, Whitehead EM, Crawford V, McVeigh GE, Johnston GD: The antihypertensive and metabolic effects of low and conventional dose cyclopenthiazide in type II diabetics with hypertension. Q J Med. 1991 Nov;81(295):919-28. [Article]
- 37. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 455). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
- External Links
- PubChem Compound
- 2904
- PubChem Substance
- 347829304
- ChemSpider
- 2801
- 3000
- ChEBI
- 91686
- ChEMBL
- CHEMBL1373254
- Wikipedia
- Cyclopenthiazide
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
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
Property Value Source Water Solubility 0.279 mg/mL ALOGPS logP 1.88 ALOGPS logP 1.45 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 9.07 Chemaxon pKa (Strongest Basic) -2.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 118.36 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 88.97 m3·mol-1 Chemaxon Polarizability 36.83 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-f6d5745139a83de5c554 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-7d9bde571b3f839dabba Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-1009000000-8fef1e8bb5f1a301e150 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01q9-1009000000-441969b0fa73085c25d6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-6092000000-9b7ecf91bb3a6ac324af Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9021000000-484613ab5bbed4833f06 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 173.18163 predictedDeepCCS 1.0 (2019) [M+H]+ 175.84251 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.09657 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:43 / Updated at June 12, 2020 16:53