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Details

Stereochemistry RACEMIC
Molecular Formula C9H11Cl2N3O4S2
Molecular Weight 360.2397
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYCLOTHIAZIDE

SMILES

CN1C(CCl)Nc2cc(c(cc2S1(=O)=O)S(=O)(=O)N)Cl

InChI

InChIKey=CESYKOGBSMNBPD-UHFFFAOYSA-N
InChI=1S/C9H11Cl2N3O4S2/c1-14-9(4-10)13-6-2-5(11)7(19(12,15)16)3-8(6)20(14,17)18/h2-3,9,13H,4H2,1H3,(H2,12,15,16)

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/methyclothiazide.html

Methyclothiazide, a diuretic-antihypertensive agent, is a member of the benzothiadiazine (thiazide) class of drugs. Methyclothiazide has a per mg natriuretic activity approximately 100 times that of the prototype thiazide, chlorothiazide. At maximal therapeutic dosages, all thiazides are approximately equal in their diuretic/natriuretic effects. Like other benzothiadiazines, methyclothiazide also has antihypertensive properties, and may be used for this purpose either alone or to enhance the antihypertensive action of other drugs. Methyclothiazide 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, methyclothiazide 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 methyclothiazide 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 methyclothiazide 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. Methyclothiazide is used in the management of hypertension either as the sole therapeutic agent or to enhance the effect of other antihypertensive drugs in the more severe forms of hypertension. Also used as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Methyclothiazide

Approved Use

Methyclothiazide tablets are indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effect of other antihypertensive drugs in the more severe forms of hypertension. Methyclothiazide tablets are indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. Methyclothiazide tablets have also been found useful in edema due to various forms of renal dysfunction such as the nephrotic syndrome, acute glomerulonephritis, and chronic renal failure.

Launch Date

3.98303986E11
Doses

Doses

DosePopulationAdverse events​
10 mg 2 times / day multiple, oral
Highest studied dose
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
unhealthy, 22-68
n = 25
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 22-68
Sex: M+F
Population Size: 25
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Antihypertensive properties of cryptenamine used with reserpine and methyclothiazide.
1971 Aug
Patents

Sample Use Guides

2.5 to 5 mg orally once a day
Route of Administration: Oral
Methyclothiazide (10(-4) M) induced endothelium-dependent inhibition of the vasoconstrictor responses to NE and AVP in aortas from SHR (spontaneously hypertensive rats), and the maximal vasoconstrictive effect of NE and AVP was decreased by 59 +/- 11% and 32.3 +/- 13%, respectively
Name Type Language
METHYCLOTHIAZIDE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
METHYCLOTHIAZIDE COMPONENT OF DIUTENSEN-R
Common Name English
METHYCLOTHIAZIDE COMPONENT OF ENDURONYL
Common Name English
METHYCLOTHIAZIDE [ORANGE BOOK]
Common Name English
METHYCLOTHIAZIDE [USP-RS]
Common Name English
METHYCLOTHIAZIDE [JAN]
Common Name English
2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE, 6-CHLORO-3-(CHLOROMETHYL)-3,4-DIHYDRO-2-METHYL-, 1,1-DIOXIDE, (+/-)-
Systematic Name English
ENDURON
Brand Name English
METHYCLOTHIAZIDE [MART.]
Common Name English
METHYCLOTHIAZIDE COMPONENT OF EUTRON
Common Name English
EUTRON COMPONENT METHYCLOTHIAZIDE
Common Name English
METHYCLOTHIAZIDE [USP]
Common Name English
NSC-110431
Code English
METHYCLOTHIAZIDE [INN]
Common Name English
DIUTENSEN-R COMPONENT METHYCLOTHIAZIDE
Common Name English
METHYCLOTHIAZIDE [HSDB]
Common Name English
METHYCLOTHIAZIDE [WHO-DD]
Common Name English
ENDURONYL COMPONENT METHYCLOTHIAZIDE
Common Name English
AQUATENSEN
Brand Name English
METHYCLOTHIAZIDE [USAN]
Common Name English
METHYCLOTHIAZIDE [VANDF]
Common Name English
METHYCLOTHIAZIDE [MI]
Common Name English
(+/-)-6-CHLORO-3-(CHLOROMETHYL)-3,4-DIHYDRO-2-METHYL-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1-DIOXIDE
Systematic Name English
Classification Tree Code System Code
WHO-ATC C03AB08
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
NDF-RT N0000175359
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
NDF-RT N0000166469
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
NCI_THESAURUS C49185
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
NDF-RT N0000175419
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
WHO-VATC QC03AA08
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
WHO-ATC C03AA08
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
WHO-VATC QC03AB08
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
LIVERTOX 623
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
NDF-RT N0000166469
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
Code System Code Type Description
USP_CATALOG
1424007
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M7349
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY Merck Index
PUBCHEM
4121
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
CAS
135-07-9
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
LACTMED
Methyclothiazide
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
IUPHAR
7235
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
WIKIPEDIA
METHYCLOTHIAZIDE
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
EVMPD
SUB08861MIG
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
DRUG CENTRAL
1759
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
DRUG BANK
DB00232
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
EPA CompTox
135-07-9
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
MESH
D008736
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
NCI_THESAURUS
C47614
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-172-2
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
HSDB
3363
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
FDA UNII
L3H46UAC61
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
RXCUI
6860
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL1577
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY
INN
1050
Created by admin on Sat Jun 26 15:06:39 UTC 2021 , Edited by admin on Sat Jun 26 15:06:39 UTC 2021
PRIMARY