Acetazolamide

Base Information

• Chemical Name: Acetazolamide
• CAS No.: 59-66-5
• Deprecated CAS: 5661-25-6,8017-69-4,909032-78-6,8017-69-4
• Molecular Formula: C4H6N4O3S2
• Molecular Weight: 222.249
• Hs Code.: 29350090
• European Community (EC) Number: 200-440-5
• NSC Number: 755854,145177
• UNII: O3FX965V0I
• DSSTox Substance ID: DTXSID7022544
• Nikkaji Number: J1.395A
• Wikipedia: Acetazolamide
• Wikidata: Q413690
• NCI Thesaurus Code: C28809
• RXCUI: 167
• Pharos Ligand ID: 9XY1117CMPQQ
• Metabolomics Workbench ID: 43109
• ChEMBL ID: CHEMBL20
• Mol file: 59-66-5.mol

Synonyms:Acetamide, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)- (8CI);2-Acetamido-1,3,4-thiadiazole-5-sulfonamide;2-Acetylamino-1,3,4-thiadiazole-5-sulfonamide;5-Acetamide-1,3,4-thiadiazole-2-sulfonamide;5-Acetylamino-1,3,4-thiadiazol-2-ylsulfonamide;Acetamox;Acetazolamid;Acetazolamide;Atenezol;Cidamex;Diakarb;Diamox;Diluran;Diuramide;Diuriwas;Diutazol;Eumicton;Glaupax;L 579486;N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide;N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide;NSC 145177;Natrionex;Phonurit;

Chemical Property of Acetazolamide

Chemical Property:

• Appearance/Colour: White to yellowish-white fine crystalline powder
• Melting Point: 256-261 °C
• Refractive Index: 1.6270 (estimate)
• PKA: 7.2(at 25℃)
• PSA: 151.66000
• Density: 1.744 g/cm³
• LogP: 0.99800
• Storage Temp.: Refrigerator
• Solubility.: Soluble in NH4OH (50 mg/mL), DMSO, Methanol and slightly soluble
• Water Solubility.: <0.1 g/100 mL at 22℃
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 221.98813241
• Heavy Atom Count: 13
• Complexity: 297

Purity/Quality:

98.5%-101%, ^*data from raw suppliers

Acetazolamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=NN=C(S1)S(=O)(=O)N
• Recent ClinicalTrials: Bioavailability, Bioequivalence and Tolerability of IHL-42X Compared to the Reference Drugs
• Recent EU Clinical Trials: Prospective clinical trial to evaluate the efficacy of acetazolamide for the treatment of cystoid macular edema in inherited retinal dystrophies: the CAR trial
• Recent NIPH Clinical Trials: The Clinical Efficacy of Carbonic Anhydrase Inhibitors and Steroids in the Management of Cystoid Macular Edema in Patients with Retinitis Pigmentosa
• Description: Acetazolamide is a drug used for the treatment of glaucoma,epilepsy,altitude sickness,periodic paralysis, chronic macular edema, idiopathic intracranial hypertension, andheart failure. It can also been used for the treatment of altitude sickness, increased intracranial pressure and neuromuscular disorders. In addition, it also has significant effect of diuretic. It belongs to the carbonic anhydrase inhibitorfamilies of medication. It works by decreasing the amount ofhydrogen ionsandbicarbonatein the body. Acetazolamide is a weak diuretic with limited use in edema associated with cardiac insufficiency, glaucoma, minor epileptic attacks, and altitude sickness.
• Uses: Acetazolamide acts as a carbonic anhydrase inhibitor which increases cerebral blood flow. It inhibits water permeability of membranes by interacting with aquaporins. It is used for the medical treatment of glaucoma, epileptic seizure, idiopathic intracranial hypertension, altitude sickness, cystinuria. carbonic anhydrase inhibitor, diuretic, antiglaucoma Acetazolamide is used for epilepsy in the absence of attacks and also in conjunction with other antiepileptic drugs.
• Therapeutic Function: Carbonic anhydrase inhibitor, Diuretic, Antiglaucoma
• Clinical Use: Acetazolamide was the first of the carbonic anhydrase inhibitors to be introduced as an orally effective diuretic, with a diuretic effect that lasts approximately 8 to 12 hours. As mentioned earlier, its diuretic action is limited because of the systemic acidosis it produces. Acetazolamide reduces the rate of aqueous humor formation and is used primarily for reducing intraocular pressure in the treatment of glaucoma. The dose is 250 mg to 1 g per day.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: high dose aspirin reduces excretion (risk of toxicity). Anti-arrhythmics: increased toxicity if hypokalaemia occurs. Antibacterials: effects of methenamine antagonised. Antiepileptics: increased risk of osteomalacia with phenytoin and phenobarbital; concentration of carbamazepine and possibly fosphenytoin and phenytoin increased. Antihypertensives: enhanced hypotensive effect. Antipsychotics: increased risk of ventricular arrhythmias due to hypokalaemia. Atomoxetine: increased risk of ventricular arrhythmias due to hypokalaemia. Beta-blockers: increased risk of ventricular arrhythmias due to hypokalaemia with sotalol. Cardiac glycosides: increased toxicity if hypokalaemia occurs. Ciclosporin: possibly increases ciclosporin concentration. Cytotoxics: alkaline urine increases methotrexate excretion; increased risk of ventricular arrhythmias due to hypokalaemia with arsenic trioxide; increased risk of nephrotoxicity and ototoxicity with platinum compounds. Lithium: lithium excretion increased.

Technology Process of Acetazolamide

There total 7 articles about Acetazolamide 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: 76.0%

5-amino-1, 3, 4-thiadiazole-2-sulfonamide (14949-00-9) + tiolacetic acid (507-09-5) → acetazolamide (59-66-5,8017-69-4)

Guidance literature:

With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; In acetonitrile; at 20 ℃; for 5h; Irradiation;

DOI:10.1021/acs.orglett.9b03905

Reference yield: 74.0%

5-acetamido-1,3,4-thiadiazolyl-2-sulfonyl chloride (32873-57-7) → acetazolamide (59-66-5,8017-69-4)

Guidance literature:

With 1,1,1-triphenylsilylamine; In acetonitrile; for 1h; Reflux; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.08.034

Reference yield:

2-acetylamino-5-benzylmercapto-1,3,4-thiadiazole (64387-67-3) → acetazolamide (59-66-5,8017-69-4)

Guidance literature:

With chlorine; acetic acid; anschliessendes Behandeln mit fluessigem NH₃;

DOI:10.1021/ja01599a033

upstream raw materials:

5-acetamido-1,3,4-thiadiazolyl-2-sulfonyl chloride

2-acetylamino-5-benzylmercapto-1,3,4-thiadiazole

PSA

PPA

Downstream raw materials:

PPA

C₁₁H₉ClN₄O₄S₂

C₁₁H₉N₅O₆S₂

C₁₁H₉N₅O₆S₂

Refernces

• 1、 -. "Preparation process for intermediate of acetazolamide". Paragraph 0052; 0053. . Retrieved 2017/09/13.
• 2、 -. "Compositions and methods for the suppression of carbonic anhydrase activity". Page/Page column 27; 28. . Retrieved 2016/04/05.