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Details

Stereochemistry ACHIRAL
Molecular Formula C7H6ClN3O4S2
Molecular Weight 295.723
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROTHIAZIDE

SMILES

NS(=O)(=O)C1=C(Cl)C=C2N=CNS(=O)(=O)C2=C1

InChI

InChIKey=JBMKAUGHUNFTOL-UHFFFAOYSA-N
InChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13)

HIDE SMILES / InChI

Description

Like other thiazides, chlorothiazide promotes water loss from the body (diuretics). It inhibits Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue. Chlorothiazide affects the distal renal tubular mechanism of electrolyte reabsorption. At maximal therapeutic dosages, all thiazides are approximately equal in their diuretic efficacy. Chlorothiazide increases excretion of sodium and chloride in approximately equivalent amounts. Natriuresis may be accompanied by some loss of potassium and bicarbonate. After oral doses, 10-15 percent of the dose is excreted unchanged in the urine. Chlorothiazide crosses the placental but not the blood-brain barrier and is excreted in breast milk. As a diuretic, chlorothiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like chlorothiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of chlorothiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle. It is marketed under the brand name Diuril.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Toxic effects of a chlorothiazide-diazoxide combination on adipose tissue and kidneys of intact rats.
1968 Jun
Metabolic and hormonal studies in a patient with primary aldosteronism, presenting with acute hypokalaemic paresis induced by chlorothiazide.
1968 May
Chlorothiazide-induced hypercalcemia in juvenile osteoporosis and hyperparathyroidism.
1969 Jul 10
Lithium-induced diabetes insipidus: manic symptoms, brain and electrolyte correlates, and chlorothiazide treatment.
1973 Sep
On the mechanism of lithium-induced diabetes insipidus in man and the rat.
1974 Apr
Cimetidine and visual hallucinations.
1978 Jul 21
Hyperosmolality complicating recovery from lithium toxicity.
1978 Jun 10
Renal calcifications: a complication of long-term furosemide therapy in preterm infants.
1982 Sep
Reversal of vitamin-D2-induced hypercalciuria by chlorothiazide.
1983 Feb
Thiazide-induced hyponatremia.
1983 Nov
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Fast gas chromatographic/mass spectrometric determination of diuretics and masking agents in human urine: Development and validation of a productive screening protocol for antidoping analysis.
2006 Dec 1
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
The usual adult dosage is 0.5 to 1 g once or twice a day.
Route of Administration: Intravenous
In Vitro Use Guide
Chlorothiazide (1000 uM) inhibited osteocalcin secretion (-42 +/- 12.7%) in human model cell line MG-63
Name Type Language
CHLOROTHIAZIDE
EP   GREEN BOOK   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
CHLOROTHIAZIDE [ORANGE BOOK]
Common Name English
CHLOROTHIAZIDE [VANDF]
Common Name English
CHLOROTHIAZIDE [JAN]
Common Name English
6-CHLORO-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1-DIOXIDE
Systematic Name English
CHLOROTHIAZIDE [USP-RS]
Common Name English
CHLOROTHIAZIDE [EP]
Common Name English
CHLOROTHIAZIDE [GREEN BOOK]
Common Name English
DIURIL
Brand Name English
CHLOROTHIAZIDE [WHO-DD]
Common Name English
CHLOROTHIAZIDE [HSDB]
Common Name English
NSC-25693
Code English
2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE, 6-CHLORO-, 1,1-DIOXIDE
Systematic Name English
CHLOROTHIAZIDE [INN]
Common Name English
HYDROCHLOROTHIAZIDE IMPURITY, CHLOROTHIAZIDE- [USP]
Common Name English
CHLOROTHIAZIDE [MART.]
Common Name English
CHLOROTHIAZIDE [USP]
Common Name English
HYDROCHLOROTHIAZIDE SPECIFIED IMPURITY A [EP]
Common Name English
CHLOROTHIAZIDE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC C03AB04
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
WHO-ATC C03AA04
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
NDF-RT N0000166469
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
WHO-VATC QC03AB04
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
NDF-RT N0000175419
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
CFR 21 CFR 520.420
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
WHO-VATC QC03AA04
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
NDF-RT N0000166469
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
LIVERTOX 194
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
WHO-VATC QC03AH01
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
NDF-RT N0000175359
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
WHO-ATC C03AH01
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
Code System Code Type Description
INN
636
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
EVMPD
SUB06198MIG
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
MESH
D002740
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
LactMed
58-94-6
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
WIKIPEDIA
CHLOROTHIAZIDE
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
HSDB
58-94-6
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-404-9
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
DRUG BANK
DB00880
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
EPA CompTox
58-94-6
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
CAS
58-94-6
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
ChEMBL
CHEMBL842
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
MERCK INDEX
M3441
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY Merck Index
RXCUI
2396
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY RxNorm
IUPHAR
4835
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
NCI_THESAURUS
C28924
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY
PUBCHEM
2720
Created by admin on Tue Mar 06 10:25:58 UTC 2018 , Edited by admin on Tue Mar 06 10:25:58 UTC 2018
PRIMARY SWITZERF