Trichlormethiazide

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Trichlormethiazide
Trichlormethiazide.svg
Trichlormethiazide-3D-spacefill.png
Systematic (IUPAC) name
6-chloro-3-(dichloromethyl)-1,1-dioxo-
3,4-dihydro-2H-benzo[e] [1,2,4]thiadiazine-
7-sulfonamide
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy
category
  • B (D if used to treat pregnancy-induced hypertension)
Legal status
  • (Prescription only)
Routes of
administration
Oral (capsules, tablets, oral solution)
Pharmacokinetic data
Bioavailability Variably absorbed from GI tract
Excretion Primarily excreted unchanged in urine
Identifiers
CAS Registry Number 133-67-5 YesY
ATC code C03AA03
PubChem CID: 5560
IUPHAR/BPS 7314
DrugBank DB01021 N
ChemSpider 5359 N
UNII Q58C92TUN0 N
KEGG D00658 N
ChEMBL CHEMBL1054 N
Chemical data
Formula C8H8Cl3N3O4S2
Molecular mass 380.6558 g/mol
 N (what is this?)  (verify)

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]

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[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

Synthesis[edit]

Trichlormethiazide is 1,1-dioxide 3,4-dihydro-3-(dichlormethyl)-6-chloro-2H-1,2,4-benzothiadiazin-7-sulfonamide.

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

Synonyms of this drug are esmarin, esmalorid, anatran, carvacron, intromene, sanamirone, methahydrin, naqua, triazide, and others.

See also[edit]

References[edit]

  1. ^ a b c d e f "DrugBank: DB01021 (Trichlormethiazide)". DrugBank. Retrieved 2008-01-23. 
  2. ^ "Trichlormethiazide and Dexamethasone for veterinary use". Wedgewood Pharmacy. Retrieved 2008-01-24. 
  3. ^ Scherico Ltd., Br. GB 949373  (1960).
  4. ^ G. de Stevens, L.H. Werner, Ger. DE 1147233  (1960).
  5. ^ De Stevens, G; Werner, L. H.; Barrett, W. E.; Chart, J. J.; Renzi, A. H. (1960). "The chemistry and pharmacology of hydrotrichlorothiazide". Experientia 16: 113–4. PMID 13815073.  edit
  6. ^ M.H. Sherlock, N. Sperber, J. Topliss, Experientia, 16, 184 (1960).
  7. ^ Scherico Ltd., GB 954023  (1960).
  8. ^ W.J. Close, U.S. Patent 3,264,292 (1960).
  9. ^ "Epithiazide". Drugfuture.com. Retrieved 2015-05-05.