Trichlormethiazide

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Trichlormethiazide
Trichlormethiazide.svg
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Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy
category
  • B (D if used to treat pregnancy-induced hypertension)
Routes of
administration
Oral (capsules, tablets, oral solution)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability Variably absorbed from GI tract
Excretion Primarily excreted unchanged in urine
Identifiers
  • 6-Chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-benzo[e] [1,2,4]thiadiazine-7-sulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.654 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C8H8Cl3N3O4S2
Molar mass 380.64 g·mol−1
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Trichlormethiazide (INN, currently being sold under the brand names of Achletin, Diu-Hydrin and Triflumen) is a diuretic with properties similar to those of hydrochlorothiazide. [1] It is usually administered for the treatment of oedema (including that which is associated with heart failure, hepatic cirrhosis and corticosteroid therapy) and hypertension. [1] In veterinary medicine, trichlormethiazide can be combined with dexamethasone to be used on horses with mild swelling of distal limbs and general bruising. [2]

Contents

As a diuretic (in particular a thiazide), trichlormethiazide encourages water loss from the body. [1] Trichlormethiazide works by inhibiting Na+/Cl ion reabsorption from the distal tubules of the kidneys. [1] In addition, trichlormethiazide increases the excretion of potassium. [1]

Mechanism

Trichlormethiazide appears to block the active reabsorption of chloride and possibly sodium in the ascending loop of Henle. This results in excretion of sodium, chloride and water, and thus acts as a diuretic. [1] Although trichlormethiazide is used to treat hypertension, its hypotensive effects may not necessarily be due to its role as a diuretic. [1] Thiazides in general cause vasodilation by activating calcium-activated potassium channels in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue. [1]

Synthesis

Trichlormethiazide synthesis: Trichlormethiazide synthesis.svg
Trichlormethiazide synthesis:

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In physiology, aldosterone escape is a term that has been used to refer to two distinct phenomena involving aldosterone that are exactly opposite each other:

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A diuretic is any substance that promotes diuresis, the increased production of urine. This includes forced diuresis. A diuretic tablet is sometimes colloquially called a water tablet. There are several categories of diuretics. All diuretics increase the excretion of water from the body, through the kidneys. There exist several classes of diuretic, and each works in a distinct way. Alternatively, an antidiuretic, such as vasopressin, is an agent or drug which reduces the excretion of water in urine.

References

  1. 1 2 3 4 5 6 7 8 "DrugBank: DB01021 (Trichlormethiazide)". DrugBank. Retrieved 2008-01-23.
  2. "Trichlormethiazide and Dexamethasone for veterinary use". Wedgewood Pharmacy. Retrieved 2008-01-24.
  3. GB 949373,"Benzthiadiazine derivatives and processes for their manufacture",published 1960, assigned to Scherico Ltd.
  4. DE 1147233,de Stevens G, Werner LH,"Verfahren zur Herstellung von 2-Alkenyl-7-sulfamyl-3, 4-dihydro-1, 2, 4-benzothiadiazin-1, 1-dioxyden",published 1960, assigned to Ciba Geigy
  5. De Stevens G, Werner LH, Barrett WE, Chart JJ, Renzi AH (March 1960). "The chemistry and pharmacology of hydrotrichlorothiazide". Experientia. 16 (3): 113–4. doi:10.1007/bf02158094. PMID   13815073. S2CID   35063235.
  6. Sherlock MH, Sperber N, Topliss J (May 1960). "3-Haloalkyl-dihydrobenzothiadiazine dioxides as potent diuretic agents". Experientia. 16 (5): 184–5. doi:10.1007/BF02178974. S2CID   3086415.
  7. GB 954023,"Novel process for preparation of dihydrobenzothiadiazines",published 1960, assigned to Scherico Ltd.
  8. US 3264292,Close WJ,published 1960, assigned to Abbott Labs