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58-93-5

Basic Information
CAS No.: 58-93-5
Name: Hydrochlorothiazide
Article Data: 49
Cas Database
Molecular Structure:
Molecular Structure of 58-93-5 (Hydrochlorothiazide)
Formula: C7H8ClN3O4S2
Molecular Weight: 297.743
Synonyms: 3,4-Dihydrochlorothiazide;Prestwick_263;6-Chloro-7-sulfamoyl-3, 4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide;Maschitt;Newtolide;3,4-Dihydro-6-chloro-7-sulfamyl-1,2, 4-benzothiadiazine-1,1-dioxide;component of Esimil;Dihydrochlorothiazid;Idrotiazide;Hydril;Drenol;Hydrochlorothiazid;Thiuretic;Hidrotiazida;Hydro-Diuril;Hydro-Aquil;Megadiuril;HCTZ;Aquarius;Component of Aldoril;2H-1,2,4-Benzothiadiazine-7-sulfonamide,6- chloro-3,4-dihydro-,1,1-dioxide;6-Chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide;Jen-Diril;Hidrochlortiazid;Esidrex;Disalunil;
EINECS: 200-403-3
Density: 1.693 g/cm3
Melting Point: 273 °C
Boiling Point: 577 °C at 760 mmHg
Flash Point: 577 °C at 760 mmHg
Solubility: 722mg/L(25 oC)
Appearance: white solid
Hazard Symbols: FlammableF, ToxicT, IrritantXi
Risk Codes: 22-42/43-36/38-23/25-36/37/38
Safety: 22-24-36/37-45-33-16-7-36/37/39-27-26
Transport Information: UN 1230 3/PG 2
PSA: 135.12000
LogP: 2.97740
Synthetic route
58-94-6

chlorothiazide

58-93-5

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

Conditions
ConditionsYield
With potassium borohydride; acetic acid In methanol at -10 - 5℃; for 4h; Reagent/catalyst; Solvent;93.9%
With hydrogen; platinum(IV) oxide In ethanol
121-30-2

chloraminophenamide

50-00-0

formaldehyd

58-93-5

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

Conditions
ConditionsYield
In water Reflux;92%
In ethanol at 90℃; for 384h;8.36%
With hydrogenchloride; ethyl acetate
121-30-2

chloraminophenamide

67-56-1

methanol

58-93-5

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

Conditions
ConditionsYield
With tert.-butylhydroperoxide at 110℃; for 12h;63%
50-00-0

formaldehyd

671-89-6

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

58-93-5

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

Conditions
ConditionsYield
With ammonium hydroxide Heating;

A

68905-61-3

C20H25NO5

B

58-93-5

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

Conditions
ConditionsYield
With water at 37℃; pH=7.4;

PMH

A

687620-14-0

C20H23NO5

B

58-93-5

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

Conditions
ConditionsYield
With water at 37℃; pH=7.4;

A

C24H25NO5

B

58-93-5

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

Conditions
ConditionsYield
With water at 37℃; pH=7.4;
88150-42-9

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

137862-53-4

N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine

58-93-5

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

58-93-5

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

7585-39-9

β‐cyclodextrin

175922-37-9

C7H8ClN3O4S2*C42H70O35

Conditions
ConditionsYield
In water for 4h;90%
In aq. phosphate buffer; water-d2 at 44.84℃; Temperature;
58-93-5

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

N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide

Conditions
ConditionsYield
Stage #1: 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide With sodium hydroxide In water at 20℃; for 0.333333h;
Stage #2: With bromine In water at 0℃;
90%
Stage #1: 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide With sodium hydroxide In water for 0.333333h;
Stage #2: With bromine In water
90%
Stage #1: 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide With sodium hydroxide In water at 20℃; for 0.5h;
Stage #2: With bromine In water at 0℃; for 0.25h;
90%
Downstream Products
50-00-0
121-30-2
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Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The IUPAC name of Hydrochlorothiazide is 6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide. With the CAS registry number 58-93-5, it is also named as 3,4-Dihydrochlorothiazide. The product's categories are Losartan Potassium & Hydrochlorothiazide; Xanthones; Heterocyclic Compounds; Heterocycles; Inhibitors; Ion transporter and other Ion Channel, and the other registry numbers are 125727-50-6; 8049-49-8. Besides, it is white solid, which should be stored in sealed and dark place at 2-8 °C. It is stable, and incompatible with strong oxidizing agents. In addition, its molecular formula is C7H8ClN3O4S2 and molecular weight is 297.73.

The other characteristics of Hydrochlorothiazide can be summarized as:
(1)EINECS: 200-403-3; (2)ACD/LogP: -0.07; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): -0.07; (5)ACD/LogD (pH 7.4): -0.09; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 21.8; (9)ACD/KOC (pH 7.4): 21.06; (10)#H bond acceptors: 7; (11)#H bond donors: 4; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.632; (14)Molar Refractivity: 62.71 cm3; (15)Molar Volume: 175.8 cm3; (16)Surface Tension: 62 dyne/cm; (17)Density: 1.693 g/cm3; (18)Flash Point: 302.7 °C; (19)Melting point: 273-275 °C; (20)Water Solubility: 722 mg/L at 25 °C; (21)Enthalpy of Vaporization: 86.38 kJ/mol; (22)Boiling Point: 577 °C at 760 mmHg; (23)Vapour Pressure: 2.6E-13 mmHg at 25 °C.

Preparation of Hydrochlorothiazide:
First, you can use m-Chloroaniline to produce 5-Chloro-2,4-chloro sulfonyl aniline by chlorosulfonation. Then use it to produce 5-Chloro-2,4-amino-sulfo-aniline. At last, you can get this chemical by the reaction of 5-Chloro-2,4-amino-sulfo-aniline with Formaldehyde.

Uses of Hydrochlorothiazide:
 This chemical is a first line diuretic drug of the thiazide class that acts by inhibiting the kidneys' ability to retain water. It is also used to treat hypertension such as Diovan HCT, Zestoretic, Benicar HCT, Atacand HCT, and Lotensin HCT, Temax-H and others in combination with many popular drugs. Furthermore, it can be used in the treatment of osteoporosis.

Safety information of Hydrochlorothiazide:
When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. It is also toxic by inhalation and if swallowed. Please do not breathe dust. Moreover, it is irritating to eyes, respiratory system and skin. It may cause sensitization by inhalation and skin contact. Please keep container tightly closed away from sources of ignition. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin. Additionally, please take off immediately all contaminated clothing. And take precautionary measures against static discharges. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1NC2=CC(=C(C=C2S(=O)(=O)N1)S(=O)(=O)N)Cl
(2)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)
(3)InChIKey: JZUFKLXOESDKRF-UHFFFAOYSA-N

The toxicity data of Hydrochlorothiazide is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 250mg/kg (250mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 124, 1973.
man TDLo oral 12857ug/kg/9D (12.857mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Medicine. Vol. 70, Pg. 1163, 1981.
man TDLo oral 75mg/kg/30W-I (75mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: OTHER CHANGES
Rinsho Shinkeigaku. Clinical Neurology. Vol. 17, Pg. 162, 1977.
mouse LD50 intraperitoneal 578mg/kg (578mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 77, 1965.
mouse LD50 intravenous 590mg/kg (590mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 134, Pg. 273, 1961.
mouse LD50 oral 1175mg/kg (1175mg/kg)   Farmatsevtichnii Zhurnal Vol. (1), Pg. 44, 1983.
mouse LD50 subcutaneous 1470mg/kg (1470mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 124, 1973.
mouse LD50 unreported 1100mg/kg (1100mg/kg)   Farmatsevtichnii Zhurnal Vol. (5), Pg. 26, 1983.
rabbit LD50 intravenous 461mg/kg (461mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 124, 1973.
rat LD50 intraperitoneal 234mg/kg (234mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 124, 1973.
rat LD50 intravenous 990mg/kg (990mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 140, Pg. 249, 1963.
rat LD50 oral 2750mg/kg (2750mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 333, 1959.
rat LD50 subcutaneous 1270mg/kg (1270mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 124, 1973.
women LDLo oral 2500ug/kg/5D- (2.5mg/kg) BEHAVIORAL: COMA American Journal of Medicine. Vol. 70, Pg. 1163, 1981.
women TDLo oral 250ug/kg (0.25mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

VASCULAR: SHOCK
Annals of Pharmacotherpy. Vol. 29, Pg. 701, 1995.
women TDLo oral 500ug/kg (0.5mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Lancet. Vol. 348, Pg. 1035, 1996.
women TDLo oral 500ug/kg (0.5mg/kg)   Israel Journal of Medical Sciences. Vol. 28, Pg. 880, 1992.
women TDLo oral 500ug/kg (0.5mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Annals of Emergency Medicine. Vol. 16, Pg. 901, 1987.
women TDLo oral 500ug/kg (0.5mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

GASTROINTESTINAL: NAUSEA OR VOMITING
Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 238, 1984.
women TDLo oral 2mg/kg/12H-I (2mg/kg)   Southern Medical Journal. Vol. 76, Pg. 1363, 1983.
women TDLo oral 2mg/kg/12H-I (2mg/kg)   Southern Medical Journal. Vol. 76, Pg. 1363, 1983.
women TDLo oral 34884ug/kg/30 (34.884mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"
Tokyo Joshi Ika Daigaku Zasshi. Journal of Tokyo Women's Medical College. Vol. 53, Pg. 1226, 1983.