Cyclopenthiazide

Base Information

• Chemical Name: Cyclopenthiazide
• CAS No.: 742-20-1
• Deprecated CAS: 96782-85-3
• Molecular Formula: C₁₃H₁₈ClN₃O₄S₂
• Molecular Weight: 379.889
• European Community (EC) Number: 212-012-5
• NSC Number: 107679
• UNII: VX4S2N85F5,T7817XC41U,866GEV195O
• DSSTox Substance ID: DTXSID4022868
• Nikkaji Number: J3.318I
• Wikipedia: Cyclopenthiazide
• Wikidata: Q3676519
• NCI Thesaurus Code: C80839
• Metabolomics Workbench ID: 71453
• ChEMBL ID: CHEMBL1373254
• Mol file: 742-20-1.mol

Synonyms:Cyclomethiazide;Cyclopenthiazide

Chemical Property of Cyclopenthiazide

Chemical Property:

• Appearance/Colour: crystals
• Vapor Pressure: 1.29E-14mmHg at 25°C
• Melting Point: 238-242ºC
• Refractive Index: 1.6
• Boiling Point: 605.6 °C at 760 mmHg
• PKA: 9.00±0.40(Predicted)
• Flash Point: 320.1 °C
• PSA: 135.12000
• Density: 1.471 g/cm³
• LogP: 4.92630
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Sparingly)
• Water Solubility.: 50mg/L(room temperature)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 379.0427261
• Heavy Atom Count: 23
• Complexity: 637

Purity/Quality:

99% ^*data from raw suppliers

Cyclopenthiazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C1)CC2NC3=CC(=C(C=C3S(=O)(=O)N2)S(=O)(=O)N)Cl
• Uses: Cyclopenthiazide is a thiazide diuretic. Cyclopenthiazide is used in the treatment of oedema caused by conditions such as kidney disease, liver cirrhosis and pre-menstrual syndrome as well as in the treatment of hypertension. Antihypertensive;Sodium Chloride Symporter Inhibitor
• Clinical Use: Thiazide diuretic: Hypertension Heart failure 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 possibly 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 Cyclopenthiazide

There total 3 articles about Cyclopenthiazide 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:

6-chloro-3-cyclopentylmethyl-1,1-dioxo-1,2(4)-dihydro-1λ6-benzo[1,2,4]thiadiazine-7-sulfonic acid amide (92017-67-9) → cyclopenthiazide (742-20-1,96783-05-0,96783-06-1)

Guidance literature:

With sodium tetrahydroborate; aluminium trichloride; In tetrahydrofuran;

DOI:10.1021/jo01066a046

Reference yield:

chloraminophenamide (121-30-2) + 2-cyclopentylacetaldehyde (5623-81-4) → cyclopenthiazide (742-20-1,96783-05-0,96783-06-1)

Guidance literature:

With hydrogenchloride; In ethanol; for 12h; Ambient temperature;

DOI:10.1021/jo01066a046

Reference yield:

→ cyclopenthiazide (742-20-1,96783-05-0,96783-06-1)

Guidance literature:

upstream raw materials:

chloraminophenamide

2-cyclopentylacetaldehyde

6-chloro-3-cyclopentylmethyl-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-7-sulfonic acid amide