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 names	Diuril, others
Other names	6-Chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide
AHFS/Drugs.com	Monograph
MedlinePlus	a682341
Routes of administration	By mouth, IV
ATC code	C03AA04 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	low
Metabolism	Nil
Elimination half-life	45 to 120 minutes
Excretion	Renal
Identifiers
IUPAC name 6-chloro-1,1-dioxo-2H-1,2,4-benzothiadiazine-7-sulfonamide
CAS Number	58-94-6 Y
PubChem CID	2720
IUPHAR/BPS	4835
DrugBank	DB00880 Y
ChemSpider	2619 Y
UNII	77W477J15H
KEGG	D00519 Y
ChEBI	CHEBI:3640 Y
ChEMBL	ChEMBL842 Y
CompTox Dashboard (EPA)	DTXSID0022800
ECHA InfoCard	100.000.368
Chemical and physical data
Formula	C7H6ClN3O4S2
Molar mass	295.71 g·mol−1
3D model (JSmol)	Interactive image
Melting point	342.5–343 °C (648.5–649.4 °F)
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
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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

• Large amount of excess fluid including:
  • Heart failure
  • Peripheral edema
  • Hypertension

Contraindications

• Anuria^[5]
• Allergies to sulfa drugs^[5]

Side effects

• Nausea / Vomiting
• Headache
• Dizziness
• Excess urine production
• Dehydration
• Hypoelectrolytemia (esp. hypokalemia / hypomagnesia)

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

• Hydrochlorothiazide