Chlorothiazide

Chlorothiazide, sold under the brand name Diuril among others, is an organic compound used as a diuretic and as an antihypertensive.[1][2]

Chlorothiazide
Clinical data
Trade namesDiuril, others
AHFS/Drugs.comMonograph
MedlinePlusa682341
Routes of
administration		By mouth, IV
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilitylow
MetabolismNil
Elimination half-life45 to 120 minutes
ExcretionRenal
Identifiers
IUPAC name
  • 6-chloro-1,1-dioxo-2H-1,2,4-benzothiadiazine-7-sulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.368
Chemical and physical data
FormulaC7H6ClN3O4S2
Molar mass295.71 g·mol−1
3D model (JSmol)
SMILES
  • O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)/N=C\N2)N
InChI
  • 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) Y
  • Key:JBMKAUGHUNFTOL-UHFFFAOYSA-N Y
  (verify)
Chlorothiazide
Names
Other names
6-Chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.368
KEGG
PubChem CID
UNII
InChI
  • 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) Y
    Key: JBMKAUGHUNFTOL-UHFFFAOYSA-N Y
SMILES
  • O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)/N=C\N2)N
Properties
Melting point 342.5–343 °C (648.5–649.4 °F; 615.6–616.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is used both within the hospital setting or for personal use to manage excess fluid associated with congestive heart failure. Most often taken in pill form, it is usually taken orally once or twice a day. In the ICU setting, chlorothiazide is given to diurese a patient in addition to furosemide (Lasix). Working in a separate mechanism from furosemide and absorbed enterically as a reconstituted suspension administered through a nasogastric tube (NG tube), the two drugs potentiate one another.

It was patented in 1956 and approved for medical use in 1958.[3] It is on the World Health Organization's List of Essential Medicines.[4]

Indications

Contraindications

Side effects

History

The research team of Merck Sharp and Dohme Research Laboratories of Beyer, Sprague, Baer, and Novello created a new series of medications, the thiazide diuretics, which includes chlorothiazide. They won an Albert Lasker Special Award in 1975 for this work.[6]

The structure has been determined by X-ray crystallography.[7]

See also

References
  1. Ernst ME, Grimm J, Richard H (November 2008). "Thiazide diuretics: 50 years and beyond". Current Hypertension Reviews. 4 (4): 256–65. doi:10.2174/157340208786241264.
  2. Duarte JD, Cooper-DeHoff RM (June 2010). "Mechanisms for blood pressure lowering and metabolic effects of thiazide and thiazide-like diuretics". Expert Review of Cardiovascular Therapy. 8 (6): 793–802. doi:10.1586/erc.10.27. PMC 2904515. PMID 20528637.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 456. ISBN 9783527607495.
  4. World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  5. "Diuril (Chlorothiazide): Side Effects, Interactions, Warning, Dosage & Uses". RxList. Retrieved 2019-10-07.
  6. "Historical Awards - The Lasker Foundation". The Lasker Foundation.
  7. Johnston A, Bardin J, Johnston BF, Fernandes P, Kennedy AR, Price SL, Florence AJ (2011). "Experimental and Predicted Crystal Energy Landscapes of Chlorothiazide". Crystal Growth & Design. 11 (2): 405–413. doi:10.1021/cg1010049.
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