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Details

Stereochemistry RACEMIC
Molecular Formula C8H8Cl3N3O4S2
Molecular Weight 380.656
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICHLORMETHIAZIDE

SMILES

NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C(Cl)Cl

InChI

InChIKey=LMJSLTNSBFUCMU-UHFFFAOYSA-N
InChI=1S/C8H8Cl3N3O4S2/c9-3-1-4-6(2-5(3)19(12,15)16)20(17,18)14-8(13-4)7(10)11/h1-2,7-8,13-14H,(H2,12,15,16)

HIDE SMILES / InChI

Molecular Formula C8H8Cl3N3O4S2
Molecular Weight 380.656
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Trichloromethiazide, previously sold under the brand names of NAQUA, METAHYDRIN and TRICHLOREX, is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. Trichloromethiazide has also been found useful in edema due to various forms of renal dysfunction such as nephrotic syndrome, acute glomer-ulonephritis, and chronic renal failure. Trichloromethiazide is also indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effectiveness of other antihypertensive drugs in the more severe forms of hypertension. Like other thiazides, Trichloromethiazide promotes water loss from the body (diuretics). They inhibit 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. Trichlormethiazide appears to block the active reabsorption of chloride and possibly sodium in the ascending loop of Henle, altering electrolyte transfer in the proximal tubule. This results in excretion of sodium, chloride, and water and, hence, diuresis. As a diuretic, Trichloromethiazide 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 Trichloromethiazide 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 Trichloromethiazide 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.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Sinus arrest following diuretic therapy in a patient with myxedema and hypertension.
1975
Vasodilator effect of indapamide in dog mesenteric vasculature.
1985 Nov
Depression after treatment with thiazide diuretics for hypertension.
1985 Sep
Renal arteriolar diameters in spontaneously hypertensive rats. Vascular cast study.
1991 Jul
Effects of KW-3902, a novel adenosine A1-receptor antagonist, on cephaloridine-induced acute renal failure in rats.
1994 Jan
Inhibition of human thiopurine methyltransferase by furosemide, bendroflumethiazide and trichlormethiazide.
1996
Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4.
2000 Sep 29
A case of exercise-induced acute renal failure in a patient with idiopathic renal hypouricemia developed during antihypertensive therapy with losartan and trichlormethiazide.
2003 Jun
Endothelin 1 activation of endothelin A receptor/NADPH oxidase pathway and diminished antioxidants critically contribute to endothelial progenitor cell reduction and dysfunction in salt-sensitive hypertension.
2012 May
Patents

Sample Use Guides

In Vivo Use Guide
Usual adult dose Diuretic or [Antidiuretic (central or nephrogenic diabetes insipidus)] Oral, 1 to 4 mg once a day, once every other day, or once a day for three to five days a week. Antihypertensive Oral, 2 to 4 mg once a day, the dosage being adjusted according to response.
Route of Administration: Oral
In Vitro Use Guide
Trichloromethiazide (100 uM) in the lumen increased net Ca2+ absorption (JCa) in isolated rabbit connecting tubules (CNT).
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:41:30 UTC 2019
Edited
by admin
on Tue Oct 22 00:41:30 UTC 2019
Record UNII
Q58C92TUN0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICHLORMETHIAZIDE
GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
(+/-)-6-CHLORO-3-(DICHLOROMETHYL)-3,4-DIHYDRO-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1-DIOXIDE
Systematic Name English
TRICHLORMETHIAZIDE COMPONENT OF NAQUIVAL
Common Name English
TRICHLORMETHIAZIDE [GREEN BOOK]
Common Name English
TRICHLORMETHIAZIDE [USP]
Common Name English
TRICHLORMETHIAZIDE [VANDF]
Common Name English
TRICHLORMETHIAZIDE [USP-RS]
Common Name English
NAQUIVAL COMPONENT TRICHLORMETHIAZIDE
Common Name English
METAHYDRIN
Brand Name English
TRICHLORMETHIAZIDE [INN]
Common Name English
NSC-61560
Code English
TRICHLORMETHIAZIDE [WHO-DD]
Common Name English
TRICHLORMETHIAZIDE [MART.]
Common Name English
TRICHLORMETHIAZIDE [MI]
Common Name English
2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE, 6-CHLORO-3-(DICHLOROMETHYL)-3,4-DIHYDRO-, 1,1-DIOXIDE, (+/-)-
Systematic Name English
METATENSIN COMPONENT TRICHLORMETHIAZIDE
Common Name English
TRICHLORMETHIAZIDE COMPONENT OF METATENSIN
Common Name English
TRICHLORMETHIAZIDE [ORANGE BOOK]
Common Name English
TRICHLORMETHIAZIDE [HSDB]
Common Name English
TRICHLOROMETHIAZIDE
Common Name English
NAQUA
Brand Name English
Classification Tree Code System Code
WHO-ATC C03EA02
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
WHO-ATC C03AA06
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
WHO-VATC QC03AA56
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
NCI_THESAURUS C49185
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
WHO-VATC QC03AA06
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
WHO-ATC C03AB06
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
WHO-VATC QC03EA02
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
WHO-VATC QC03AB06
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
Code System Code Type Description
PUBCHEM
5560
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
NCI_THESAURUS
C47769
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
HSDB
133-67-5
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
LactMed
133-67-5
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
CAS
133-67-5
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
ChEMBL
CHEMBL1054
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
WIKIPEDIA
TRICHLORMETHIAZIDE
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
MERCK INDEX
M11059
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY Merck Index
DRUG BANK
DB01021
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
ECHA (EC/EINECS)
205-118-8
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
EVMPD
SUB11263MIG
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
INN
1012
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
IUPHAR
7314
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
RXCUI
10772
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY RxNorm
MESH
D014237
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
EPA CompTox
133-67-5
Created by admin on Tue Oct 22 00:41:31 UTC 2019 , Edited by admin on Tue Oct 22 00:41:31 UTC 2019
PRIMARY
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