Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H5ClN3O4S2.Na |
Molecular Weight | 317.705 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].NS(=O)(=O)C1=C(Cl)C=C2N=C[N-]S(=O)(=O)C2=C1
InChI
InChIKey=CPIWHAFLBZQYLQ-UHFFFAOYSA-N
InChI=1S/C7H5ClN3O4S2.Na/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5;/h1-3H,(H2-,9,10,11,12,13);/q-1;+1
DescriptionSources: http://www.drugbank.ca/drugs/DB00880Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/diuril-injection.html
Sources: http://www.drugbank.ca/drugs/DB00880
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/diuril-injection.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13802826
Curator's Comment: Chlorothiazide was synthesized by Novello and Sprague in 1957
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL261 Sources: http://www.drugbank.ca/drugs/DB00880 |
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Target ID: CHEMBL205 Sources: http://www.drugbank.ca/drugs/DB00880 |
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Target ID: CHEMBL3729 Sources: http://www.drugbank.ca/drugs/DB00880 |
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Target ID: CHEMBL1876 Sources: http://www.drugbank.ca/drugs/DB00880 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Diuril Approved UseIntravenous Sodium DIURIL is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy.
Intravenous Sodium DIURIL has also been found useful in edema due to various forms of renal dysfunction such as nephrotic syndrome, acute glomerulonephritis, and chronic renal failure. Launch Date1958 |
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Primary | Diuril Approved UseIntravenous Sodium DIURIL is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy.
Intravenous Sodium DIURIL has also been found useful in edema due to various forms of renal dysfunction such as nephrotic syndrome, acute glomerulonephritis, and chronic renal failure. Launch Date1958 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
682.97 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19902362 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLOROTHIAZIDE plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
806.27 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19902362 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLOROTHIAZIDE plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19902362 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLOROTHIAZIDE plasma | Sus scrofa population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1000 mg 2 times / day multiple, oral Recommended Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Edema|Hypertension Sources: Page: p.4 |
Disc. AE: Hypersensitivity, Azotemia... AEs leading to discontinuation/dose reduction: Hypersensitivity Sources: Page: p.4Azotemia Systemic lupus erythematosus reactivation |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Azotemia | Disc. AE | 1000 mg 2 times / day multiple, oral Recommended Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Edema|Hypertension Sources: Page: p.4 |
Hypersensitivity | Disc. AE | 1000 mg 2 times / day multiple, oral Recommended Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Edema|Hypertension Sources: Page: p.4 |
Systemic lupus erythematosus reactivation | Disc. AE | 1000 mg 2 times / day multiple, oral Recommended Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Edema|Hypertension Sources: Page: p.4 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
weak [IC50 2205 uM] | |||
Page: abstract |
weak [IC50 2632 uM] | |||
Page: 9.0 |
yes [IC50 212 uM] | |||
Page: abstract |
yes [IC50 3.78 uM] | |||
Page: abstract |
yes [IC50 65.3 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
Page: 3.0 |
yes | |||
Page: S34 |
yes | |||
Page: S34 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Metabolic and hormonal studies in a patient with primary aldosteronism, presenting with acute hypokalaemic paresis induced by chlorothiazide. | 1968 May |
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Cimetidine and visual hallucinations. | 1978 Jul 21 |
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Milk-alkali syndrome associated with use of chlorothiazide and calcium carbonate. | 1989 Mar |
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Electrochemical behavior of the antituberculosis drug isoniazid and its square-wave adsorptive stripping voltammetric estimation in bulk form, tablets and biological fluids at a mercury electrode. | 2003 Nov 24 |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Thiazide diuretics and the risk of gallbladder disease requiring surgery in women. | 2005 Mar 14 |
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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 |
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Expression of therapeutic misconception amongst Egyptians: a qualitative pilot study. | 2009 Jun 30 |
|
Formulation optimization of hydrodynamically balanced oral controlled release bioadhesive tablets of tramadol hydrochloride. | 2010 Apr-Jun |
|
Surgical anatomy of the lower eyelid relating to lower blepharoplasty. | 2010 Mar |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/diuril-injection.html
The usual adult dosage is 0.5 to 1 g once or twice a day.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8914012
Chlorothiazide (1000 uM) inhibited osteocalcin secretion (-42 +/- 12.7%) in human model cell line MG-63
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C49185
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SN86FG7N2K
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DTXSID00221091
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C65319
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CHEMBL842
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ACTIVE MOIETY
SUBSTANCE RECORD