Cyclopenthiazide

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

Identification

Name
Cyclopenthiazide
Accession Number
DB13532
Type
Small Molecule
Groups
Approved
Description

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].

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Navidrex
Categories
UNII
VX4S2N85F5
CAS number
742-20-1
Weight
Average: 379.87
Monoisotopic: 379.0427261
Chemical Formula
C13H18ClN3O4S2
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1S,6R)-3-{[3-(TRIFLUOROMETHYL)-5,6-DIHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]CARBONYL}-6-(2,4,5-TRIFLUOROPHENYL)CYCLOHEX-3-EN-1-AMINEThe therapeutic efficacy of (1S,6R)-3-{[3-(TRIFLUOROMETHYL)-5,6-DIHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]CARBONYL}-6-(2,4,5-TRIFLUOROPHENYL)CYCLOHEX-3-EN-1-AMINE can be decreased when used in combination with Cyclopenthiazide.
(4R)-limoneneThe therapeutic efficacy of Cyclopenthiazide can be decreased when used in combination with (4R)-limonene.
16-Bromoepiandrosterone16-Bromoepiandrosterone may increase the hypokalemic activities of Cyclopenthiazide.
19-norandrostenedione19-norandrostenedione may increase the hypokalemic activities of Cyclopenthiazide.
1alpha-Hydroxyvitamin D5The risk or severity of hyperkalemia can be increased when 1alpha-Hydroxyvitamin D5 is combined with Cyclopenthiazide.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Cyclopenthiazide.
5-androstenedione5-androstenedione may increase the hypokalemic activities of Cyclopenthiazide.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Cyclopenthiazide.
AbediterolAbediterol may increase the hypokalemic activities of Cyclopenthiazide.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Cyclopenthiazide.
Food Interactions
Not Available

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. [PubMed:2031076]
  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. [PubMed:1808632]
  3. 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
ChEBI
91686
ChEMBL
CHEMBL1373254
Wikipedia
Cyclopenthiazide
ATC Codes
C03AB07 — Cyclopenthiazide and potassiumC03AA07 — CyclopenthiazideG01AE10 — Combinations of sulfonamidesC03EA07 — Cyclopenthiazide and potassium-sparing agents

Clinical Trials

Clinical Trials
Not Available

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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Secondary aliphatic/aromatic amine / Aryl chloride / Aryl halide / Organosulfonic acid amide / Benzenoid / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Aminosulfonyl compound / Sulfonyl
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on June 23, 2017 14:43 / Updated on September 07, 2018 03:27