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Trichlormethiazide

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Trichlormethiazide
Clinical data
AHFS/Drugs.comMicromedex 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
BioavailabilityVariably absorbed from GI tract
ExcretionPrimarily 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
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.004.654Edit this at Wikidata
Chemical and physical data
FormulaC8H8Cl3N3O4S2
Molar mass380.64 g·mol−1
 ☒NcheckY (what is this?)  (verify)

Trichlormethiazide (INN, currently being sold under the brand names ofAchletin,Diu-Hydrin andTriflumen) is adiuretic with properties similar to those ofhydrochlorothiazide.[1] It is usually administered for the treatment ofoedema (including that which is associated withheart failure,hepatic cirrhosis andcorticosteroid therapy) andhypertension.[1] Inveterinary medicine, trichlormethiazide can be combined withdexamethasone to be used on horses with mild swelling ofdistal limbs and generalbruising.[2]

As a diuretic (in particular athiazide), trichlormethiazide encourages water loss from the body.[1] Trichlormethiazide works byinhibiting Na+/Cl ion reabsorption from thedistaltubules of thekidneys.[1] In addition, trichlormethiazide increases theexcretion ofpotassium.[1]

Mechanism

[edit]

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, itshypotensive effects may not necessarily be due to its role as a diuretic.[1] Thiazides in general causevasodilation by activating calcium-activated potassium channels in vascular smooth muscles and inhibiting variouscarbonic anhydrases invascular tissue.[1]

Synthesis

[edit]
Trichlormethiazide synthesis:[3][4][5][6][7][8]

References

[edit]
  1. ^abcdefgh"DrugBank: DB01021 (Trichlormethiazide)". DrugBank. Retrieved2008-01-23.
  2. ^"Trichlormethiazide and Dexamethasone for veterinary use". Wedgewood Pharmacy. Retrieved2008-01-24.
  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 
Sulfonamides
(andetacrynic acid)
CA inhibitors (atPT)
Loop (Na-K-Cl atAL)
Thiazides (Na-Cl atDCT,
Calcium-sparing)
Thiazide-likes (primarilyDCT)
Potassium-sparing (atCD)
ESC blockers
Aldosterone antagonists
Osmotic diuretics (PT,DL)
Vasopressin receptor inhibitors
(DCT andCD)
Other
Combination products
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