Basic information
- CAS
148-56-1- Standard SMILES
NS(=O)(=O)c1cc2c(cc1C(F)(F)F)NC=NS2(=O)=O- InChIKey
RGUQWGXAYZNLMI-UHFFFAOYSA-N- Molecular formula
- C8H6F3N3O4S2
- Average molar mass
- 329.3 g/mol
- Monoisotopic mass
- 328.97518251
Overview
Flumethiazide is a benzothiadiazine.
Names & identifiers
- Preferred name
- Flumethiazide
- IUPAC
- 1,1-dioxo-6-(trifluoromethyl)-4H-1λ6,2,4-benzothiadiazine-7-sulfonamide
- English name
- flumethiazide
- Molecular formula
- C8H6F3N3O4S2
- Molecular weight
- 329.278
Names & synonyms
FLUMETHIAZIDEAdemol148-56-1TrifluoromethylthiazideFlumethiazidFlumetiazidFludemilRoutraxAdemilFlumetiazidaFlumethiazidumFlumetiazide
Show more names
NSC44626NSC 446266-Trifluoromethyl-7-sulfamoyl-4H-1,2,4-benzothiazine 1,1-dioxide2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-(trifluoromethyl)-, 1,1-dioxide
Trifluoromethyl thiazide3PA0CDS0M5NSC-446266-(Trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide6-Trifluoromethyl-7-sulfamyl-1,2,4-benzothiadiazine 1,1-dioxideDTXSID601638626-Trifluoromethyl-7-sulfamoyl-4H-1,2,4-benzothiadiazine 1,1-dioxide7-Sulfamoyl-6-trifluoromethyl-2H-1,2,4-benzothiadiazine 1,1-dioxide
Database identifiers
- CAS
148-56-1- PubChem CID
- 8992
- DTXSID
DTXSID60163862- ChEMBL
CHEMBL2105128- ChEBI
CHEBI:135404- UNII
- 3PA0CDS0M5
- EC Number
- 205-717-4
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 617
Experimental & physicochemical properties
LogP0.32
Color/FormCRYSTALS
SolubilitySPARINGLY SOL IN WATER; 50 MG/ML IN BOILING WATER WITH DECOMP; PRACTICALLY INSOL IN ETHYL ACETATE, METHYL ETHYL KETONE, BENZENE, TOLUENE; SOL IN METHANOL, ETHANOL, DIMETHYL FORMAMIDE
Other Experimental PropertiesUNSTABLE IN ALKALINE SOLN, CONVERSION TO PRECURSOR ALPHA,ALPHA,ALPHA-TRIFLUORO-3-AMINO-4,6-DISULFAMOYLTOLUENE; DECOMP @ 305.4-307.8 °C
Physicochemical properties
- Melting point
- 306.6 °C · 306.6°C
- Boiling point
- 560 · 560.0±60.0 °C(Predicted)
- Density
- 1.6578 · 1.6578 (estimate)
- pka
- 6.3 · pKa 6.3(H2O) (Uncertain)
- Water Solubility
- 1.05 g/L · 1.05g/L(room temperature)
- FDA UNII
- 3 PA0CDS0M5 · 3PA0CDS0M5
- Hazardous Substances Data
- 148 · 148-56-1(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Interactions
TUBULAR TRANSPORT OF THIAZIDES MAY BE INHIBITED BY PROBENECID. /BENZOTHIADIAZIDES/
USE OF ENTERIC-COATED COMBINATIONS OF POTASSIUM CHLORIDE & THIAZIDE HAS BEEN ASSOC WITH HIGH INCIDENCE OF ULCERATION OF DISTAL JEJUNUM OR ILEUM. IT IS PREFERABLE TO PRESCRIBE PALATABLE SOLN OF POTASSIUM CHLORIDE... /BENZOTHIADIAZIDES/
...THIAZIDE DIURETICS HAVE BEEN PRESCRIBED IN COMBINATION WITH ALDOSTERONE ANTAGONIST OR OTHER POTASSIUM-SPARING DIURETIC IN ORDER TO OBTAIN ADDITIVE DIURETIC EFFECT WITH MAINTENANCE OF POTASSIUM BALANCE. /BENZOTHIADIAZIDES/
Human Toxicity Excerpts
CLINICAL TOXICITY IS RELATIVELY RARE & USUALLY RESULTS FROM UNEXPECTED HYPERSENSITIVITY. CASES HAVE BEEN REPORTED WITH PURPURA, DERMATITIS WITH PHOTOSENSITIVITY, DEPRESSION OF FORMED ELEMENTS OF BLOOD, & NECROTIZING VASCULITIS... /BENZOTHIADIAZIDES/
PLASMA URIC ACID IS FREQUENTLY ELEVATED & IN SUSCEPTIBLE PT MAY BE ASSOCIATED WITH ATTACKS OF GOUT. ... MANY OBSERVERS HAVE NOTED CORRELATION WITH HYPOKALEMIA & ALKALOSIS. INCR CONCN OF BLOOD AMMONIA HAVE BEEN REPORTED. /BENZOTHIADIAZIDES/
IN PT...WITH HYPERTENSIVE DISEASE & DECR RENAL RESERVE, MANIFESTATIONS OF RENAL INSUFFICIENCY MAY BE AGGRAVATED AFTER INTENSIVE OR PROLONGED COURSES OF THIAZIDES THAT LEAD TO EXCESSIVE DEPLETION OF FLUID & ELECTROLYTE. /BENZOTHIADIAZIDES/
IN CIRRHOSIS OF LIVER, DETERIORATIONG OF MENTAL FUNCTION, INCL ONSET OF COMA, HAS BEEN ATTRIBUTED TO THIAZIDE THERAPY. ... CHOLESTATIC HEPATITIS HAS ALSO BEEN REPORTED. THIAZIDES MAY INDUCE HYPERGLYCEMIA & AGGRAVATE PREEXISTING DIABETES MELLITUS. /BENZOTHIADIAZIDES/
Safety data
- Hazardous Substances Data
- 148-56-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Mechanism of Action
INHIBITION OF CARBONIC ANHYDRASE DECR CONCN OF HYDROGEN ION AVAILABLE FOR EXCHANGE. DECR HYDROGEN-ION CONCN LEADS TO NATRIURESIS & THEREFORE DIURESIS. USE OF CARBONIC ANHYDRASE INHIBITOR DOES NOT GREATLY ALTER CHLORIDE EXCRETION. HOWEVER, THERE MAY BE MARKED POTASSIUM LOSS WITH RESULTING HYPOKALEMIA. /DIURETICS/
DOMINANT ACTION OF THIAZIDES IS TO INCR RENAL EXCRETION OF SODIUM & CHLORIDE & ACCOMPANYING VOL OF WATER. UNLIKE BOTH MERCURIALS & CARBONIC ANHYDRASE INHIBITORS, ACTION OF THIAZIDES IS VIRTUALLY INDEPENDENT OF ACID-BASE BALANCE. THIAZIDES ALSO EVOKE SIGNIFICANT AUGMENTATION OF POTASSIUM EXCRETION... /BENZOTHIADIAZIDES/
THIAZIDES ARE...SECRETED INTO TUBULAR FLUID BY ACTIVE PROCESS LOCATED IN PROXIMAL SEGMENT. ... THIAZIDES INHIBIT REABSORPTION OF SODIUM & ITS ATTENDANT ANION, CHLORIDE, IN DISTAL SEGMENT. ... AUGMENTED EXCRETION OF.../POTASSIUM/ RESULTS FROM ITS INCR SECRETION BY DISTAL TUBULE. /BENZOTHIADIAZIDES/
Absorption, Distribution and Excretion
THIAZIDES ARE ABSORBED FROM GASTROINTESTINAL TRACT & OWE THEIR USEFULNESS LARGELY TO THEIR EFFECTIVENESS BY ORAL ROUTE. ABSORPTION IS RELATIVELY RAPID. ... DRUG PASSES READILY THROUGH PLACENTAL BARRIER TO FETUS. ... MOST COMPD ARE RAPIDLY EXCRETED WITHIN 3-6 HR. /BENZOTHIADIAZIDES/
Uses & manufacturing
Uses
CARBONIC ANHYDRASE INHIBITOR
MEDICATION
Methods of ManufacturingHOLDREDGE ET AL, J AM CHEM SOC 81, 4807 (1959); YALE ET AL, IBID, 82, 2042 (1960); US PATENT 3,040,042 (1962 TO OLIN MATHIESON); BRITISH PATENT 861,809 (1961 TO SK&F).
General Manufacturing InformationMOST COMPD OF THIS GROUP ARE ANALOGS OF 1,2,4-BENZOTHIADIAZINE-1,1-DIOXIDE... AS GROUP THEY CAN BE DESIGNATED AS "BENZOTHIADIAZIDE," OR "THIAZIDE," DIURETICS. /BENZOTHIADIAZIDES/
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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