(S)-Bendroflumethiazide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (S)-Bendroflumethiazide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (S)-Bendroflumethiazide?

The molecule (S)-Bendroflumethiazide presents a molecular formula of C15H14F3N3O4S2 and its IUPAC name is (3S)-3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide.

Bendroflumethiazide is a thiazide diuretic with antihypertensive and diuretic properties. It is marketed under the brand name Naturetin. The drug acts by inhibiting the reabsorption of sodium and chloride in the distal convoluted tubule, which leads to increased urinary output..

The thiazide diuretics are a class of drugs commonly used to treat hypertension (high blood pressure) and edema (fluid retention). The mechanism of action of thiazide diuretics is to inhibit the reabsorption of sodium and chloride in the distal convoluted tubule of the nephron. This action leads to an increase in urinary output and a decrease in extracellular fluid volume..

Bendroflumethiazide is a relatively potent thiazide diuretic with a long duration of action. The drug is well absorbed from the gastrointestinal tract and has a bioavailability of approximately 100%. Peak plasma concentrations are achieved within 2-4 hours of oral administration..

The half-life of bendroflumethiazide is 12-24 hours. The drug is eliminated primarily by the kidneys via urinary excretion..

Bendroflumethiazide is indicated for the treatment of hypertension and edema. The usual starting dose is 2.5 mg once daily. The dose may be increased to 5 mg once daily if needed..

The most common side effects of bendroflumethiazide include dizziness, lightheadedness, headache, and diarrhea. Bendroflumethiazide can also cause electrolyte imbalances, including hypokalemia and hyponatremia..

Bendroflumethiazide is contraindicated in patients with hypersensitivity to the drug. The thiazide diuretics are also contraindicated in patients with anuria (absent urine output), severe renal impairment, or severe liver disease..

Bendroflumethiazide can interact with other medications. The thiazide diuretics can increase the risk of hyperkalemia when used with potassium-sparing diuretics, ACE inhibitors, and angiotensin II receptor antagonists. The thiazide diuretics can also increase the risk of hypokalemia when used with corticosteroids, estrogens, and digoxin..

Bendroflumethiazide should be used with caution in patients with renal impairment, liver disease, or diabetes. The thiazide diuretics can also cause photosensitivity..

3D structure

Cartesian coordinates

Geometry of (S)-Bendroflumethiazide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(S)-Bendroflumethiazide HDWIHXWEUNVBIY-AWEZNQCLSA-N chemical compound 2D structure molecule svg
(S)-Bendroflumethiazide

 

Molecule descriptors

 
IUPAC name(3S)-3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide
InChI codeInChI=1S/C15H14F3N3O4S2/c16-15(17,18)10-7-11-13(8-12(10)26(19,22)23)27(24,25)21-14(20-11)6-9-4-2-1-3-5-9/h1-5,7-8,14,20-21H,6H2,(H2,19,22,23)/t14-/m0/s1
InChI KeyHDWIHXWEUNVBIY-AWEZNQCLSA-N
SMILESNS(=O)(=O)c1cc2c(cc1C(F)(F)F)N[C@H](Cc1ccccc1)NS2(=O)=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (3S)-3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide
  • (S)-Bendroflumethiazide
  • 1245935-40-3
  • 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3,4-dihydro-3-(phenylmethyl)-6-(trifluoromethyl)-, 1,1-dioxide, (3S)-
  • 8G2L3JUW5S
  • Bendroflumethiazide, (S)-
  • NCGC00016312-01
  • NCGC00018194-01
  • NCGC00018194-05
  • Q27126564

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC897222
  • CAS-73-48-3
  • UNII-8G2L3JUW5S
  • DTXSID10424975
  • CHEMBL1336812
  • CHEBI:59244
  • SCHEMBL44537

Physico-Chemical properties

IUPAC name(3S)-3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide
Molecular formulaC15H14F3N3O4S2
Molecular weight421.415
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity96.86
LogP5.0
Topological polar surface area135.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.