Chlorothiazide

Chlorothiazide
Names
	Other names 6-Chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
Identifiers
CAS Number	58-94-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3640 ;
ChEMBL	ChEMBL842 ;
ChemSpider	2619 ;
DrugBank	DB00880 ;
ECHA InfoCard	100.000.368
KEGG	D00519 ;
PubChem CID	2720;
UNII	77W477J15H ;
CompTox Dashboard (EPA)	DTXSID0022800 ;
	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) Key: JBMKAUGHUNFTOL-UHFFFAOYSA-N ;
	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).

Chlorothiazide
Clinical data
Trade names	Diuril, others
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 ;
PubChem CID	2720;
IUPHAR/BPS	4835;
DrugBank	DB00880 ;
ChemSpider	2619 ;
UNII	77W477J15H;
KEGG	D00519 ;
ChEBI	CHEBI:3640 ;
ChEMBL	ChEMBL842 ;
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;
	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) ; Key:JBMKAUGHUNFTOL-UHFFFAOYSA-N ;
	(verify)

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

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]

Indications

Large amount of excess fluid including:

Contraindications

Anuria ^[4]
Allergies to sulfa drugs^[4]

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.^[5]

The structure has been determined by X-ray crystallography.^[6]

References

^ 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.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 456. ISBN 9783527607495.
^ ^a ^b "Diuril (Chlorothiazide): Side Effects, Interactions, Warning, Dosage & Uses". RxList. Retrieved 2019-10-07.
^ "Historical Awards - The Lasker Foundation". The Lasker Foundation.
^ 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.

[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.

[:0-4] "Diuril (Chlorothiazide): Side Effects, Interactions, Warning, Dosage & Uses". RxList. Retrieved 2019-10-07.

[5] "Historical Awards - The Lasker Foundation". The Lasker Foundation.

[6] 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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