6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 872
• Molecular Formular: C7H8ClN3O4S2
• Molecular Mass: 297.73912
• Monoisotopic Mass: 296.96447543
• SMILES: Clc1c(S(=O)(=O)N)cc2S(=O)(=O)NCNc2c1
• Canonical SMILES: Clc1cc2NCNS(=O)(=O)c2cc1S(=O)(=O)N
• InChI: InChI=1S/C7H8ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-2,10-11H,3H2,(H2,9,12,13)
• InChIKey: JZUFKLXOESDKRF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide; 6-chloro-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: hydrochlorothiazide; 6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• Brand Name: Acuretic; Aldoril; Apresazide; Aquarills; Aquarius; Bremil; Caplaril; Capozide; Chlorosulthiadil; Chlorzide; Cidrex; Dichlorosal; Dichlorotride; Dichlotiazid; Dichlotride; Diclotride; Dicyclotride; Direma; Disalunil; Diu-Melusin; Drenol; Esidrex; Esimil; Fluvin; Hidril; Hidrochlortiazid; Hidroronol; Hidrotiazida; Hydril; Hydro-Aquil; Hydro-Diuril; Hydrodiuretic; Hydropres; Hydrosaluric; Hydrothide; Hydrozide; Hypothiazid; Hypothiazide; Idrotiazide; Ivaugan; Jen-Diril; Lotensin Hct; Maschitt; Megadiuril; Moduretic; Nefrix; Neo-Codema; Neoflumen; Newtolide; Panurin; Ro-Hydrazide; Servithiazid; Thiaretic; Thiuretic; Thlaretic; Timolide; Urodiazin; Vetidrex; Ziac
• Synonyms: 6-chloro-1,1-dioxo-1,2,3,4-tetrahydro-1lambda~6~,2,4-benzothiadiazine-7-sulfonamide; HCTZ; HCZ; Dihydroxychlorothiazidum; Dihydrochlorurite; Dihydrochlorothiazidum; Dihydrochlorothiazid; Dihydrochlorothiazide; Dihydrochlorurit; Hydrochlorothiazid; Hydrochlorthiazide; Hydrochlorothiazide; Aquazide H; Carozide; Diaqua; Esidrix; Ezide; Hydrochlorothiazide; 6-Chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide; 6-Chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; Esidrex; Vetidrex; Aquarius; Bremil; Cidrex; Dichlotride; Diurizid; Drenol; Hidrochlortiazid; Hydrex; Oretic; Pantemon; Thiuretic; 6-Chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide; 6-氯-3,4-二氢-2H-1,2,4-苯并噻二嗪-7-磺酰胺-1,1-二氧化物; 6-氯-7-磺酰胺-3,4-二氢-1,2,4-苯并噻二嗪-1,1-二氧化物; 氢氯噻嗪

Database IDs

• CAS Number: 58-93-5
• EC Number: 200-403-3
• MDL Number: MFCD00051765
• Beilstein Number: 625101
• Merck Index: 144781
• PubChem SID: 160964335; 24277806; 24895542
• PubChem CID: 3639

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.087113
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.57571745
• LogD (pH = 7.4): -0.5834805
• Log P: -0.5756178
• Molar Refractivity: 63.1096 cm^3
• Polarizability: 25.34669 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.16
• LOG S: -2.12
• Solubility (Water): 2.24e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.7 mg/mL; Methanol
• Apperance: crystalline; White Solid
• Melting Point: 266-272°C; 273-275°C; 273-277°C
• Hydrophobicity(logP): -0.5

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: Irritant
• RTECS: DK9100000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ALB(213), CA1(759), CA11(770), CA12(771), CA13(377677), CA14(23632), CA2(760), CA3(761), CA4(762), CA5A(763), CA6(765), CA7(766), CA8(767), CA9(768); human ... ALB(213), CA1(759), CA2(760), CA4(762)
• Mechanism of Action: Carbonic anhydrase inhibitor

Product Information

• Purity: 97%; 98%
• Salt Data: Free Base
• Suitability: meets USP testing specifications
• Application(s): Chloruretic; Diuretic and antihypertensive agent; Kaliuretic.; Natriuretic
• Pharmacopeia Traceability: traceable to BP 186; traceable to PhEur H1200000; traceable to USP 1314009
• Empirical Formula (Hill Notation): C7H8ClN3O4S2

DETAILS

MP Biomedicals - 02157403

Crystalline
A carbonic anhydrase inhibitor

DrugBank - DB00999

• Drug Groups: approved
• Description: A thiazide diuretic often considered the prototypical member of this class. It reduces the reabsorption of electrolytes from the renal tubules. This results in increased excretion of water and electrolytes, including sodium, potassium, chloride, and magnesium. It has been used in the treatment of several disorders including edema, hypertension, diabetes insipidus, and hypoparathyroidism. [PubChem]
• Indication: For the treatment of high blood pressure and management of edema.
• Pharmacology: Thiazides such as hydrochlorothiazide promote water loss from the body (diuretics). They inhibit Na^+/Cl^- 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.
• Toxicity: The most common signs and symptoms observed are those caused by electrolyte depletion (hypokalemia, hypochloremia, hyponatremia) and dehydration resulting from excessive diuresis. If digitalis has also been administered, hypokalemia may accentuate cardiac arrhythmias. The oral LD50 of hydrochlorothiazide is greater than 10 g/kg in the mouse and rat.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hydrochlorothiazide is not metabolized.
• Absorption: 50-60%
• Half Life: 5.6 and 14.8 hours
• Protein Binding: 67.9%
• Elimination: Hydrochlorothiazide is not metabolized but is eliminated rapidly by the kidney. Hydrochlorothiazide crosses the placental but not the blood-brain barrier and is excreted in breast milk.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1708

Research Area: Cardiovascular Disease
Biological Activity:
Ibuprofen Lysine (NeoProfen) is a non-selective COX inhibitor with an IC50 of 0.33 mM. It is known to have an antiplatelet effect, though Ibuprofen Lysine (NeoProfen) is relatively mild and short-lived when compared with that of aspirin or other better-known antiplatelet agents. [1] Ibuprofen, indomethacin, and meclofenamate were potent inhibitors of the microsomal cyclooxygenase prepared from feline lung with IC50 of 0.33 mM, 29 μM, and 4.7 μM, respectively. [2]

Sigma Aldrich - H149

Biochem/physiol Actions
碳酸酐酶抑制剂

Sigma Aldrich - 08213

Biochem/physiol Actions
Carbonic anhydrase inhibitor

Sigma Aldrich - H2910

Biochem/physiol Actions
碳酸酐酶抑制剂

Sigma Aldrich - H4759

Biochem/physiol Actions
碳酸酐酶抑制剂

Toronto Research Chemicals - H714560

Hydrochlorothiazide is a carbonic anhydrase inhibitor as a diuretic.

REFERENCES

• http://en.wikipedia.org/wiki/Hydrochlorothiazide
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• Deppeler, H.P., et al.: Anal. Profiles Drug Subs., 10, 405 (1961)
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• Dupont, L. et al., Acta Cryst. B, 1972, 28, 2340, (cryst struct)
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• Deppeler, H.P., Anal. Profiles Drug Subst., 1981, 10, 405, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 681, (synonyms)
• IARC Monog., 1990, 50, 293, (rev, tox)
• Danielsen-Runge, W., Dtsch. Apoth. -Ztg., 1992, 132, 1950, (rev)
• Kountourellis, J.E. et al., J. Chem. Eng. Data, 1992, 37, 187, (cryst struct)
• Diuretics IV: Proc. Int. Conf. Diuretics, 4th, 1992, (eds. Puschett, J.B. et al), Excerpta Medica, Amsterdam, 1993, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 818
• Gottdiener, J.S. et al., Circulation, 1997, 95, 2007, (use)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CFY000