Hydrochlorothiazide

Base Information

• Chemical Name: Hydrochlorothiazide
• CAS No.: 58-93-5
• Deprecated CAS: 125727-50-6,8049-49-8,8049-49-8
• Molecular Formula: C7H8ClN3O4S2
• Molecular Weight: 297.743
• Hs Code.: 29350090
• European Community (EC) Number: 200-403-3
• NSC Number: 757059,53477
• UNII: 0J48LPH2TH
• DSSTox Substance ID: DTXSID2020713
• Nikkaji Number: J1.920H
• Wikipedia: Hydrochlorothiazide
• Wikidata: Q423930
• NCI Thesaurus Code: C29098
• RXCUI: 5487
• Pharos Ligand ID: 26SQGNMSGNQT
• Metabolomics Workbench ID: 37935
• ChEMBL ID: CHEMBL435
• Mol file: 58-93-5.mol

Synonyms:Dichlothiazide;Dihydrochlorothiazide;Esidrex;Esidrix;HCTZ;Hydrochlorothiazide;HydroDIURIL;Hypothiazide;Oretic;Sectrazide

Chemical Property of Hydrochlorothiazide

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 273 °C
• Refractive Index: 1.632
• Boiling Point: 577 °C at 760 mmHg
• PKA: 7.9, 9.2(at 25℃)
• Flash Point: 577 °C at 760 mmHg
• PSA: 135.12000
• Density: 1.693 g/cm³
• LogP: 2.97740
• Storage Temp.: 2-8°C
• Solubility.: Very slightly soluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides
• Water Solubility.: 722mg/L(25 oC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 296.9644758
• Heavy Atom Count: 17
• Complexity: 494

Purity/Quality:

99% ^*data from raw suppliers

Hydrochlorothiazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, T, Xi
• Hazard Codes: Xi,T,F,Xn
• Statements: 22-42/43-36/38-23/25-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 22-24-36/37-45-33-16-7-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1NC2=CC(=C(C=C2S(=O)(=O)N1)S(=O)(=O)N)Cl
• Recent ClinicalTrials: HYDROchlorothiazide to PROTECT Polycystic Kidney Disease Patients and Improve Their Quality of Life
• Recent EU Clinical Trials: The effects of medication induced blood pressure reduction on cerebral hemodynamics in hypertensive frail elderly
• Recent NIPH Clinical Trials: Randomized controlled trials of the renal protective effects of exerenone versus hydrochlorothiazide in hypertensive patients with CKD already on ACEI or ARB therapy.
• description: Hydrochlorothiazide is a kind of thiazide diuretic drugs with moderate diuretic effect. It exert is diuretic effect through acting on the medullary ascending limb cortical segment, inhibiting the active re-absorption of Cl-and passive absorption of Na+ at this site. In addition, the product also has a hypotensive effect and anti-diuretic effect. It is suitable for treating a variety of edema, particularly for cardiogenic edema. It can also be used as antihypertensive agents, for treatment light, medium hypertension. It also has certain efficacy in treating diabetes insipidus, and idiopathic hypercalciuria. Commonly used thiazide diuretics include hydrochlorothiazide, chlorthalidone, indapamide and the like.
• Indications: 1. Edema disease: including congestive heart failure, cirrhosis, nephrotic syndrome, acute and chronic nephritis edema, chronic renal failure early, adrenocorticotropic hormone and estrogen therapy caused retention of sodium and water. 2. High blood pressure: it can be used alone or in combination with other antihypertensive drugs. It is mainly used for the treatment of essential hypertension. 3. Central or nephrogenic diabetes insipidus. 4. Kidney stone disease: it is mainly used for the prevention of calcium stone formation.
• Uses: The product is a typical representative in the thiazide diuretic drug with its pharmaceutical sales in United States ranking first in 1985. Owing to its easy administration, moderate action as well as being suitable for all kinds of edema, it is most often clinically applied. Owing to adverse reactions like potassium secretion, we should pay attention to supplement potassium salt during the application. Intravenous injection-mice-LD50: 590mg/kg, oral LD50: greater than 8000mg/kg. Diuretics It mainly inhibits the re-absorption on Na+ and Cl-by the proximal end of the distal convoluted tubule so that renal excretion of sodium chloride is increased to produce a diuretic effect. It is a kind of diuretic drugs of moderate effect. This product has antihypertensive effect with the effect being enhanced when being use in combination with Lee medicine paste, antihypertensive shen paste or apocynum venetum and other traditional Chinese medicine. This product also has anti-diuretic effect and can be used for the treatment of diabetes insipidus Hydrochlorothiazide is one of the most widely used drugs of this series, and it is used for the same indications, as is chlorothiazide. Hydrochlorothiazide causes less inhibition of carbonic anhydrase, but causes 5–10 times more diuresis of sodium ions than chlorothiazide using the same dose. A carbonic anhydrase inhibitor. Diuretic.
• Production method: It is produced by: m-Chlorosulfonated goes through chlorosulfonation to give 5-chloro-2,4-chloro-anilide, and further reacted with ammonia to form 5-chloro-2,4-sulfamoyl aniline which finally reacts with formaldehyde to obtain the final product.
• Therapeutic Function: Diuretic

Technology Process of Hydrochlorothiazide

There total 10 articles about Hydrochlorothiazide 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: 93.9%

chlorothiazide (58-94-6) → 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (58-93-5,8049-49-8)

Guidance literature:

With potassium borohydride; acetic acid; In methanol; at -10 - 5 ℃; for 4h; Reagent/catalyst; Solvent;

Reference yield: 92.0%

chloraminophenamide (121-30-2) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (58-93-5,8049-49-8)

Guidance literature:

In water; Reflux;

Reference yield: 63.0%

chloraminophenamide (121-30-2) + methanol (67-56-1) → 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (58-93-5,8049-49-8)

Guidance literature:

With tert.-butylhydroperoxide; at 110 ℃; for 12h;

DOI:10.1016/j.tetlet.2018.04.054

upstream raw materials:

chloraminophenamide

formaldehyd

4-amino-6-chloro-benzene-1,3-disulfonyl chloride

chlorothiazide

Downstream raw materials:

C₇H₈ClN₃O₄S₂*C₃₃H₃₀N₄O₂

chloraminophenamide

formaldehyd

4-amino-1,3-benzenedisulfonamide

Refernces

• 1、 Kitanosono, Taku,Cho, Soo Min,Kobayashi, Shū. "A convenient and mild cyclocondensation using water-soluble aldehydes in water". . p. 7237 - 7241. Retrieved 2018/11/21.
• 2、 Sun, Jinwei,Tao, Tao,Xu, Dan,Cao, Hui,Kong, Qinggang,Wang, Xinyu,Liu, Yun,Zhao, Jianglin,Wang, Yi,Pan, Yi. "Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues". . p. 2099 - 2102. Retrieved 2018/05/04.