Diazoxide

Base Information

• Chemical Name: Diazoxide
• CAS No.: 364-98-7
• Deprecated CAS: 1342899-70-0
• Molecular Formula: C8H7 Cl N2 O2 S
• Molecular Weight: 230.675
• Hs Code.: 2934990002
• European Community (EC) Number: 206-668-1
• NSC Number: 759574,76130,64198
• UNII: O5CB12L4FN
• DSSTox Substance ID: DTXSID7022914
• Nikkaji Number: J5.703G
• Wikipedia: Diazoxide
• Wikidata: Q420009
• NCI Thesaurus Code: C428
• RXCUI: 3327
• Pharos Ligand ID: 47G3UKW9W9HH
• Metabolomics Workbench ID: 43344
• ChEMBL ID: CHEMBL181,CHEMBL1518123
• Mol file: 364-98-7.mol

Synonyms:Diazoxide;Hyperstat;Proglycem

Chemical Property of Diazoxide

Chemical Property:

• Melting Point: >310°C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 414.8°Cat760mmHg
• PKA: pKa 8.5 (Uncertain)
• Flash Point: 204.7°C
• PSA: 66.91000
• Density: 1.61g/cm³
• LogP: 2.52700
• Storage Temp.: Store at RT
• Solubility.: 0.1 M NaOH: soluble
• Water Solubility.: Soluble in 0.1M NaOH. Insoluble in water or in methanol.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 229.9916763
• Heavy Atom Count: 14
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Diazoxide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NS(=O)(=O)C2=C(N1)C=CC(=C2)Cl
• Recent ClinicalTrials: Novel Approach for the Prevention of Hypoglycemia Associated Autonomic Failure (HAAF)
• Recent EU Clinical Trials: Use of diazoxide in hypoglycaemia
• Description: Diazoxide is a nondiuretic derivative of thiazides that dramatically reduces blood pressure by direct relaxation of smooth muscles of the arterioles, possibly as a result of calcium channel activation of smooth musculature in arterioles. It has a weak effect on the venous system and on the heart. In addition to hypotensive action, diazoxide causes a sharp increase in the level of glucose in the blood as a result of the inhibition of insulin release from adrenal glands. Some of the undesirable effects are water and sodium ion retention in the body and increased concentrations of uric acid in the blood. It is used in urgent situations where blood pressure needs to be reduced in severe hypertension. Diazoxide is not used for essential hypertension. A synonym of this drug is hyperstat.
• Uses: Diazoxide has traditionally been used therapeutically for its antihypertensive and hyperglycemic properties. It acts as a potent arteriolar vasodilator in the short-term treatment of acute hypertension, malignant hypertension, and occasionally, in cases of pregnancy-induced hypertension. By relaxing peripheral arterioles of smooth muscle cells, peripheral vascular resistance is reduced. In rare cases, cardiac and pulmonary effects have occurred in neonates and in infants. In the treatment of hypertensive crisis with 300 mg of IV diazoxide, angina, myocardial and cerebral infarction, ischemia, and optic nerve damage could ensue. Diazoxide is used also in the management of hypoglycemia secondary to hyperinsulinism in adults with inoperable islet cell adenoma or carcinoma, or extrapancreatic malignancy; and in infants and children with leucine sensitivity, islet cell hyperplasia, nesidioblastosis, extrapancreatic malignancy, islet cell adenoma, or adenomatosis. In the treatment of hypoglycemia due to hyperinsulinism, diazoxide is an oral agent that decreases insulin release from the pancreas, enhancing glycogenolysis and inhibiting the uptake of glucose. wound healing agent Diazoxide reduces status epilepticus neuron damage in diabetes.
• Therapeutic Function: Antihypertensive
• Biological Functions: Diazoxide (Hyperstat) is chemically similar to the thiazide diuretics. It is devoid of diuretic activity and causes Na+ and water retention. Diazoxide is a very potent vasodilator and is available only for intravenous use in the treatment of hypertensive emergencies. The mechanism by which diazoxide relaxes vascular smooth muscle is related to its ability to activate potassium channels and produce a hyperpolarization of the cell membrane.
• Clinical Use: Diazoxide is used by intravenous injection as a rapidly acting antihypertensiveagent for emergency reduction of blood pressurein hospitalized patients with accelerated or malignanthypertension. More than 90% is bound to serum protein, andcaution is needed when it is used in conjunction with otherprotein-bound drugs that may be displaced by diazoxide.The injection is given rapidly by the intravenous route toensure maximal effect. The initial dose is usually 1 mg/kg ofbody weight, with a second dose given if the first injectiondoes not lower blood pressure satisfactorily within 30 minutes.Further doses may be given at 4- to 24-hour intervalsif needed. Oral antihypertensive therapy is begun as soon aspossible. In contrast to the acute clinical uses of glucagon, diazoxidefinds use in chronic hypoglycemic conditions: inoperableislet cell adenoma or carcinomas, extrapancreatic malignanciesof insulin-secreting cells, or islet cell hyperplasias. Inchildren, additional indications include congenital hyperinsulinemia124and leucine sensitivity. Experimentally, diazoxideis among an array of ATP-sensitive potassium channel openersbeing studied for intermittently bringing aboutβ-cell rest.
• Drug interactions: Potentially hazardous interactions with other drugsAntihypertensives and vasodilators: enhanced hypotensive effect.MAOIs: withdraw at least 14 days before starting diazoxidePhenytoin: may reduce phenytoin levels.

Technology Process of Diazoxide

There total 15 articles about Diazoxide 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: 98.0%

2-amino-5-chlorobenzenesulfonamide (5790-69-2) + N,N-dimethyl acetamide (127-19-5,116057-81-9) → diazoxide (364-98-7)

Guidance literature:

With Imidazole hydrochloride; for 7h; Reflux;

Reference yield: 90.0%

3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide (360-81-6) → diazoxide (364-98-7)

Guidance literature:

With chlorine; In N,N-dimethyl-formamide; at 0 ℃;

Reference yield: 87.0%

acetic acid (64-19-7,77671-22-8) + 7-chloro-2,3-dihydro-3-oxo-4H-1,2,4-benzothiadiazine (5800-59-9) → diazoxide (364-98-7)

Guidance literature:

With sulfuric acid; at 120 ℃; for 2h;

upstream raw materials:

2-amino-5-chlorobenzenesulfonamide

acetic acid

3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

2-(acetylamino)benzenesulfonamide

Refernces

• 1、 -. "Diazoxide preparation method". Paragraph 0023; 0024; 0025. . Retrieved 2018/07/30.
• 2、 -. "SALTS OF POTASSIUM ATP CHANNEL OPENERS AND USES THEREOF". Page/Page column 152; 155-156. . Retrieved 2008/06/13.