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
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)
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
Title | Date | PubMed |
---|---|---|
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 |
|
Iliacus haematoma syndrome as a complication of anticoagulant therapy. | 1968 Oct 12 |
|
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 |
|
Diuretic-associated pancreatitis: a collective review and illustrative cases. | 1987 Sep |
|
Milk-alkali syndrome associated with use of chlorothiazide and calcium carbonate. | 1989 Mar |
|
Thiazide therapy for ACTH-induced hypercalciuria and nephrolithiasis. | 1992 Mar |
|
Are certain diuretics also anticonvulsants? | 2001 Oct |
|
Hyperinsulinism in tyrosinaemia type I. | 2005 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Releasing the flood waters: diuril and the reshaping of hypertension. | 2005 Winter |
|
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 |
|
Healing virtue: Saludadores versus witches in early modern Spain. | 2009 |
|
Expression of therapeutic misconception amongst Egyptians: a qualitative pilot study. | 2009 Jun 30 |
|
Do new drugs increase life expectancy? A critique of a Manhattan Institute paper. | 2009 May |
|
Formulation optimization of hydrodynamically balanced oral controlled release bioadhesive tablets of tramadol hydrochloride. | 2010 Apr-Jun |
|
Impacts of intensive agricultural irrigation and livestock farming on a semi-arid Mediterranean catchment. | 2010 Aug |
|
Transparotid approach for mandibular condylar neck and subcondylar fractures. | 2010 Dec |
|
Buccal fat pad versus sandwich graft for treatment of oroantral defects: A comparison. | 2010 Jan |
|
Running away experience and psychoactive substance use among adolescents in Taiwan: multi-city street outreach survey. | 2010 Jan 20 |
|
Thiazide-induced hyponatremia. | 2010 Jun |
|
Speeding up the process urine sample pre-treatment: some perspectives on the use of microwave assisted extraction in the anti-doping field. | 2010 Jun 15 |
|
Surgical anatomy of the lower eyelid relating to lower blepharoplasty. | 2010 Mar |
|
Hypertension, antihypertensive medication use, and breast cancer risk in the California Teachers Study cohort. | 2010 Oct |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
C03AB04
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
WHO-ATC |
C03AA04
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
NDF-RT |
N0000166469
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
WHO-VATC |
QC03AB04
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
NCI_THESAURUS |
C49185
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
NDF-RT |
N0000175419
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
CFR |
21 CFR 520.420
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
WHO-VATC |
QC03AA04
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
NDF-RT |
N0000166469
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
LIVERTOX |
194
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
WHO-VATC |
QC03AH01
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
NDF-RT |
N0000175359
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
||
|
WHO-ATC |
C03AH01
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
636
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
SUB06198MIG
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
D002740
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
58-94-6
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
CHLOROTHIAZIDE
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
58-94-6
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
200-404-9
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
DB00880
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
58-94-6
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
58-94-6
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
CHEMBL842
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
M3441
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | Merck Index | ||
|
2396
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | RxNorm | ||
|
4835
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
C28924
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY | |||
|
2720
Created by
admin on Tue Oct 22 00:48:18 UTC 2019 , Edited by admin on Tue Oct 22 00:48:18 UTC 2019
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)