Bendroflumethiazide

Base Information

• Chemical Name: Bendroflumethiazide
• CAS No.: 73-48-3
• Deprecated CAS: 96782-79-5
• Molecular Formula: C₁₅H₁₄F₃N₃O₄S₂
• Molecular Weight: 421.421
• Hs Code.: 2935904000
• European Community (EC) Number: 200-800-1
• NSC Number: 758229
• UNII: 5Q52X6ICJI
• DSSTox Substance ID: DTXSID5022647
• Nikkaji Number: J1.428A
• Wikipedia: Bendroflumethiazide
• Wikidata: Q1169164
• NCI Thesaurus Code: C47410
• RXCUI: 1369
• Pharos Ligand ID: T2CQHRL7XP2T
• Metabolomics Workbench ID: 145177
• ChEMBL ID: CHEMBL1684
• Mol file: 73-48-3.mol

Synonyms:Aprinox;Bendrofluazide;Bendroflumethiazide;Benzide;Benzide M;Benzide-M;Berkozide;Centyl;Esberizid;Naturetin;Naturine;Neo NaClex;Neo-NaClex;Pluryl;Urizid

Chemical Property of Bendroflumethiazide

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.88E-14mmHg at 25°C
• Melting Point: 205-207 °C
• Refractive Index: 1.583
• Boiling Point: 602.1 °C at 760 mmHg
• PKA: pKa 8.53±0.05(H2O t=25 I=0.2) (Uncertain)
• Flash Point: 317.9 °C
• PSA: 135.12000
• Density: 1.528 g/cm³
• LogP: 4.95410
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, freely soluble in acetone, soluble in ethanol (96 per cent).
• Water Solubility.: 40mg/L(room temperature)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 421.03778277
• Heavy Atom Count: 27
• Complexity: 740

Purity/Quality:

98%min ^*data from raw suppliers

rac bendroflumethiazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC2NC3=C(C=C(C(=C3)C(F)(F)F)S(=O)(=O)N)S(=O)(=O)N2
• Recent ClinicalTrials: Mechanisms of Diuretic Resistance in Heart Failure, Aim 2
• Recent EU Clinical Trials: BONATHIAD - Bone Association with Thiazide Diuretics.
• Description: Bendroflumethiazide (Item No. 21311) is an analytical reference standard categorized as a diuretic. Diuretics, including bendroflumethiazide, have been abused as performance-enhancing drugs and masking agents in sports doping. This product is intended for research and forensic applications.
• Uses: Bendroflumethiazide may be used for the same indications as the aforementioned drugs; however, it is primarily used as an adjuvant agent for relieving edema associated with cardiac insufficiency, liver cirrhosis, and edema caused by taking corticosteroids.
• Therapeutic Function: Diuretic, Antihypertensive
• Clinical Use: Thiazide diuretic: Hypertension Oedema
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of nephrotoxicity with NSAIDs; antagonism of diuretic effect. Anti-arrhythmics: hypokalaemia leads to increased cardiac toxicity; effects of lidocaine and mexiletine antagonised. Antibacterials: avoid administration with lymecycline. Antidepressants: increased risk of hypokalaemia with reboxetine; enhanced hypotensive effect with MAOIs; increased risk of postural hypotension with tricyclics. Antiepileptics: increased risk of hyponatraemia with carbamazepine. Antifungals: increased risk of hypokalaemia with amphotericin. Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotension with postsynaptic alpha-blockers like prazosin; hypokalaemia increases risk of ventricular arrhythmias with sotalol. Antipsychotics: hypokalaemia increases risk of ventricular arrhythmias with amisulpride; enhanced hypotensive effect with phenothiazines; hypokalaemia increases risk of ventricular arrhythmias with pimozide - avoid. Atomoxetine: hypokalaemia increases risk of ventricular arrhythmias. Cardiac glycosides: increased toxicity if hypokalaemia occurs. Ciclosporin: increased risk of nephrotoxicity and hypomagnesaemia. Cytotoxics: increased risk of ventricular arrhythmias due to hypokalaemia with arsenic trioxide; increased risk of nephrotoxicity and ototoxicity with platinum compounds. Lithium excretion reduced, increased toxicity.

Technology Process of Bendroflumethiazide

There total 3 articles about Bendroflumethiazide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-amino-6-(trifluoromethyl)-1,3-benzenedisulfonamide (654-62-6) + phenylacetaldehyde (122-78-1) → bendroflumethiazide (73-48-3,96782-95-5,96782-96-6)

Guidance literature:

With hydrogenchloride; In ethanol; Heating;

DOI:10.1021/jo01068a053

Reference yield:

4-amino-6-(trifluoromethyl)-1,3-benzenedisulfonamide (654-62-6) + phenylacetaldehyde dimethyl acetal (101-48-4) → bendroflumethiazide (73-48-3,96782-95-5,96782-96-6)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide;

Reference yield:

→ bendroflumethiazide (73-48-3,96782-95-5,96782-96-6)

Guidance literature:

/BRN= 370643/;

DOI:10.1021/ja01527a015

upstream raw materials:

4-amino-6-(trifluoromethyl)-1,3-benzenedisulfonamide

phenylacetaldehyde

phenylacetaldehyde dimethyl acetal

Downstream raw materials:

N-(3-benzyl-1,1-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydro-1λ⁶-benzo[1,2,4]thiadiazine-7-sulfonyl)-formimidic acid ethyl ester

4-amino-6-(trifluoromethyl)-1,3-benzenedisulfonamide

(R)-bendroflumethiazide

(S)-bendroflumethiazide

Refernces