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Quinethazone

HCID 6307
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
73-49-4
Standard SMILES
CCC1NC(=O)c2cc(S(N)(=O)=O)c(Cl)cc2N1
InChIKey
AGMMTXLNIQSRCG-UHFFFAOYSA-N
Molecular formula
C10H12ClN3O3S
Average molar mass
289.74 g/mol
Monoisotopic mass
289.0287901

Overview

Fibrous crystals or white powder. (NTP, 1992)

Names & identifiers

Preferred name
Quinethazone
IUPAC
7-chloro-2-ethyl-4-oxo-2,3-dihydro-1H-quinazoline-6-sulfonamide
English name
QUINETHAZONE (1.5 G)
Molecular formula
C10H12ClN3O3S
Molecular weight
289.73858

Names & synonyms

QUINETHAZONE73-49-4HydromoxQuinethazonQuinethazonumAquamoxIdrokinQuinetazona7-chloro-2-ethyl-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamideCL 36010DTXSID90235487-Chloro-2-ethyl-1,2,3,4-tetrahydro-4-oxo-6-quinazolinesulfonamide
Show more names
cl36010ChinethazonumQUINETHAZONE (1.5 G)Quinethazone (1594007)
NSC-759904CHEBI:87177-Chloro-2-ethyl-1,2,3,4-tetrahydro-4-oxo-6-sulfamoylquinazoline7-Chloro-2-ethyl-6-sulfamoyl-1,2,3,4-tetrahydro-4-quinazolinone6-Quinazolinesulfonamide, 7-chloro-2-ethyl-1,2,3,4-tetrahydro-4-oxo-455E0S048WDTXCID7035487-chloro-2-ethyl-4-hydroxy-1,2-dihydroquinazoline-6-sulfonamide

Database identifiers

CAS
73-49-4
PubChem CID
6307
DTXSID
DTXSID9023548
ChEMBL
CHEMBL1532
ChEBI
CHEBI:8717
UNII
455E0S048W

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
110 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
18
Formal charge
0
Complexity
436

Experimental & physicochemical properties

OdorODORLESS
TasteBITTER TASTE
Color/Form · 2 items

Fibrous crystals from 50% acetone

WHITE TO YELLOWISH WHITE, CRYSTALLINE POWDER

Solubility · 5 items

less than 1 mg/mL at 67.1 °F (NTP, 1992)

Sol in acetone, alcohol.

1 G SOL IN 20 ML POLYETHYLENE GLYCOL 300

1 G SOL IN 125 ML PROPYLENE GLYCOL

1 G SOL IN 500 ML ALCOHOL

Human Drugs · 3 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point · 3 items

482 to 486 °F (NTP, 1992)

250-252 °C

251 °C

Physical Description · 2 items

Fibrous crystals or white powder. (NTP, 1992)

Solid

Stability/Shelf LifeDISCOLORS IN PRESENCE OF STRONG LIGHT & ALKALINE MATERIALS

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Other Safety InformationIMAP assessments - 6-Quinazolinesulfonamide, 7-chloro-2-ethyl-1,2,3,4-tetrahydro-4-oxo-: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: Symptoms of exposure to this compound may include allergies, skin rashes, thirst, epigastric pain, anorexia, gastric irritation, nausea, vomiting, diarrhea, constipation, photosensitivity, dryness, headache, muscle spasm, weakness, inflammation of the salivary gland, loss of libido, paresthesia, acute pancreatitis, pneumonitis, jaundice and other blood disorders. Other symptoms include cramping, hyperglycemia, glycosuria, vertigo, xanthopsia, leukopenia, thrombocytopenia, agranulocytosis, aplastic anemia, purpura, urticaria, necrotizing angiitis and restlessness.

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Reactive GroupAmides and Imides
Air and Water ReactionsInsoluble in water.

Safety & protection

Fire FightingFires involving this chemical may be controlled with a carbon dioxide, dry chemical or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 item

Quinethazone is a thiazide diuretic used to treat hypertension. It inhibits Na<sup>+</sup>/Cl<sup>-</sup> reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.

Mechanism of Action · 6 items

As a diuretic, quinethazone inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like quinethazone also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of quinethazone is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle.

...BENZOTHIADIAZIDES HAVE DIRECT EFFECT ON RENAL TUBULAR TRANSPORT OF SODIUM & CHLORIDE INDEPENDENT OF CARBONIC ANHYDRASE INACTIVATION. ...HAVE PARALLEL DOSE-RESPONSE CURVES & COMPARABLE MAX CHLORURETIC EFFECTS. /BENZOTHIADIAZIDES/

RENAL ACTIONS OF THIAZIDE DIURETICS DECR EXTRACELLULAR FLUID & PLASMA VOL, CARDIAC OUTPUT, & TOTAL EXCHANGEABLE SODIUM IN INDIVIDUALS WITHOUT ANY EVIDENCE OF CARDIAC FAILURE. ...SODIUM & WATER DEPLETION...BASIS FOR ANTIHYPERTENSIVE EFFECT. ...DIURETIC THIAZIDES RELAX PERIPHERAL ARTERIOLAR SMOOTH MUSCLE. /BENZOTHIADIAZIDES/

Decreased plasma volume and decreased extracellular fluid volume; decreased cardiac output initially, followed by decreased total peripheral resistance with normalization of cardiac output ... /from table/

Thiazide diuretics increase urinary excretion of sodium and water by inhibiting sodium reabsorption in the early distal tubules. They increase the rate of delivery of tubular fluid and electrolytes to the distal sites of hydrogen and potassium ion secretion, while plasma volume contraction increases aldosterone production. The increased delivery and increase in aldosterone levels promote sodium reabsorption at the distal tubules, thus increasing the loss of potassium and hydrogen ions. /Thiazide diuretics/

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
EC Number
200-801-7
Nikkaji
J1.429J
Other Experimental PropertiesIT DIFFERS CHEMICALLY FROM THE BENZOTHIAZIDE TYPE ONLY IN REPLACEMENT OF SULFUR ATOM BY CARBON

Physicochemical properties

Melting point
250 · 250-252°
Density
1.4208 · 1.4208 (rough estimate)
refractive index
1.63 · 1.6300 (estimate)
storage temp.
Refrigerator
solubility
DMSO (Slightly), Methanol (Slightly, Sonicated)
form
Solid
pka
9.3 · pKa 9.3 (Uncertain);10.7 (Uncertain)
color
Pale Beige to Brown
Water Solubility
0.15 g/L · 0.15g/L(25 ºC)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
FDA UNII
455 E0S048W · 455E0S048W
ATC code
3 BA02 · C03BA02
EPA Substance Registry System
Quinethazone (73-49-4)
Hazardous Substances Data
73 · 73-49-4(Hazardous Substances Data)
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, dampen the solid spill material with 5% ammonium hydroxide, then transfer the dampened material to a suitable container. Use absorbent paper dampened with 5% ammonium hydroxide to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with 5% ammonium hydroxide followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Interactions · 5 items

MANY DIABETIC PT REGULATED BY CHLORPROPAMIDE OR OTHER SULFONYLUREAS EXHIBIT IMPAIRED DIABETIC CONTROL WHEN ANY THIAZIDE DIURETIC IS ADDED TO DRUG REGIMEN. /QUINETHAZONE/...SHOULD BE EXPECTED TO INTERACT IN A SIMILAR MANNER.

PT RECEIVING /THIAZIDES & RELATED DIURETICS/...MAY DEVELOP ELECTROLYTE DISTURBANCES...WHICH MAY ENHANCE CARDIOTOXICITY OF DIGITALIS. /QUINETHAZONE/...CAN CAUSE HYPOKALEMIA, & MAY BE EXPECTED TO INTERACT WITH CARDIAC GLYCOSIDES.

THIAZIDES ENHANCE ANTIHYPERTENSIVE ACTION OF GUANETHIDINE... /QUINETHAZONE/...SHOULD BE EXPECTED TO INTERACT WITH GUANETHIDINE ALSO.

/QUINETHAZONE/...MAY ENHANCE NEUROMUSCULAR BLOCKADE PRODUCED BY TUBOCURARINE...

For more Interactions (Complete) data for QUINETHAZONE (20 total), please visit the HSDB record page.

Human Toxicity ExcerptsCLINICAL TOXICITY...USUALLY RESULTS FROM UNEXPECTED HYPERSENSITIVITY. CASES HAVE BEEN REPORTED WITH PURPURA, DERMATITIS WITH PHOTOSENSITIVITY, DEPRESSION OF FORMED ELEMENTS OF BLOOD, & NECROTIZING VASCULITIS. /BENZOTHIADIAZIDES/
Antidote and Emergency TreatmentThiazide diuretic overdose should be treated by ... supportive symptomatic treatment and monitoring of serum electrolyte concentrations and renal function. /Thiazide diuretic/

Regulatory information

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety data

Hazardous Substances Data
73-49-4(Hazardous Substances Data)

For more Mechanism of Action (Complete) data for QUINETHAZONE (7 total), please visit the HSDB record page.

MeSH Pharmacological ClassificationAgents that inhibit SODIUM CHLORIDE SYMPORTERS. They act as DIURETICS. Excess use is associated with HYPOKALEMIA.
Absorption, Distribution and Excretion...RAPIDLY ABSORBED FROM GI TRACT...
Cellular LocationsCytoplasm
Metabolite PathwaysQuinethazone Action Pathway

Uses & manufacturing

Uses · 2 items

Therap cat: Diuretic, Antihypertensive

...an orally effective benzothiadiazine diuretic and antihypertensive drug.

Methods of Manufacturing · 2 items

Cohen et al, J Am Chem Soc 82, 2731 (1960); Cohen, Vaughan, Jr, US patent 2,976,289 (1961 to Am Cyanamid).

4'-CHLORO-O-ACETOTOLUIDIDE IS SUBJECTED TO CHLOROSULFONATION & SUBSEQUENT AMINATION TO FORM 2-AMINO-4-CHLORO-5-SULFAMOYLBENZAMIDE. REFLUXING WITH AN ACIDULATED ALCOHOLIC SOLUTION OF THE DIETHYLACETAL OF PROPIONALDEHYDE EFFECTS THE REQUIRED CONDENSATION CYCLIZATION TO YIELD QUINETHAZONE.

Use ClassificationPharmaceuticals

Applications

UsesQuinethazone is a thiazide diuretic used to treat hypertension.

General DescriptionFibrous crystals or white powder.

Suppliers15 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
陕西缔都医药化工有限公司+86-29-87569262 +86-15003564040 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
BOC Sciences[email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Quinethazone is a member of the class of quinazolines that is quinazolin-4-one substituted at positions 2, 6 and 7 by ethyl, sulfamoyl and chloro groups respectively; a thiazide-like diuretic used to treat hypertension. It has a role as an antihypertensive agent and a diuretic.