CAS No.58-93-5,Hydrochlorothiazide Suppliers

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Basic Information

Molecular Structure:
CAS No.:	58-93-5
Name:	Hydrochlorothiazide
Article Data:	49

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:	F, T, Xi
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With ammonium hydroxide Heating;

: 1318259-41-4
PSH

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

Conditions	Yield
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

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

: 1318259-49-2
PPH

A: C24H25NO5

B: 58-93-5
6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Raw Materials

671-89-6

121-30-2

50-00-0

58-94-6

137862-53-4

88150-42-9

Downstream Products

121-30-2

50-00-0

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Consensus Reports

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.