Cyclopenthiazide

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
Weight
Average: 379.87
Monoisotopic: 379.0427261
Chemical Formula
C13H18ClN3O4S2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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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
AbacavirCyclopenthiazide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AbaloparatideAbaloparatide may increase the hypotensive activities of Cyclopenthiazide.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cyclopenthiazide.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Cyclopenthiazide.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Cyclopenthiazide.
Food Interactions
Not Available

Products

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International/Other Brands
Navidrex

Categories

ATC Codes
G01AE10 — Combinations of sulfonamidesC03AB07 — Cyclopenthiazide and potassiumC03EA07 — Cyclopenthiazide and potassium-sparing agentsC03AA07 — Cyclopenthiazide
Drug Categories
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
  1. 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]
  2. 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]
  3. 37. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 455). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
PubChem Compound
2904
PubChem Substance
347829304
ChemSpider
2801
RxNav
3000
ChEBI
91686
ChEMBL
CHEMBL1373254
Wikipedia
Cyclopenthiazide

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 Solubility0.279 mg/mLALOGPS
logP1.88ALOGPS
logP1.45Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.07Chemaxon
pKa (Strongest Basic)-2.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area118.36 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity88.97 m3·mol-1Chemaxon
Polarizability36.83 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-f6d5745139a83de5c554
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-7d9bde571b3f839dabba
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1009000000-8fef1e8bb5f1a301e150
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-1009000000-441969b0fa73085c25d6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-6092000000-9b7ecf91bb3a6ac324af
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9021000000-484613ab5bbed4833f06
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]-173.18163
predicted
DeepCCS 1.0 (2019)
[M+H]+175.84251
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.09657
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:43 / Updated at June 12, 2020 16:53