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    ??????????

    ??????????
    ?????????? ??? ???
    ?? ??:
    58-93-5
    ???:
    ??????????
    ???(??):
    ??????????
    ???:
    Hydrochlorothiazide
    ???(??):
    HCZ;HCTZ;Ziac;Zide;Nefrix;Oretic;roxane;su5879;Bremil;Cidrex
    CBNumber:
    CB5383966
    ???:
    C7H8ClN3O4S2
    ??? ??:
    297.74
    MOL ??:
    58-93-5.mol

    ?????????? ??

    ???
    273 °C
    ?? ?
    577.0±60.0 °C(Predicted)
    ??
    1.6761 (rough estimate)
    ???
    1.6100 (estimate)
    ???
    9℃
    ?? ??
    2-8°C
    ???
    Very slightly soluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides
    ?? ?? (pKa)
    7.9, 9.2(at 25℃)
    ??? ??
    solid
    ???
    722mg/L(25 ºC)
    ?? ??(λmax)
    318nm(H2O)(lit.)
    Merck
    14,4781
    BRN
    625101
    ???
    Stable. Incompatible with strong oxidizing agents.
    InChIKey
    JZUFKLXOESDKRF-UHFFFAOYSA-N
    CAS ??????
    58-93-5(CAS DataBase Reference)
    IARC
    2B (Vol. 50, 108) 2016
    NIST
    6-Chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide(58-93-5)
    EPA
    Hydrochlorothiazide (58-93-5)
    ??
    • ?? ? ?? ??
    • ?? ? ???? ?? (GHS)
    ??? ?? Xi,T,F,Xn
    ?? ???? ?? 22-42/43-36/38-23/25-36/37/38-39/23/24/25-23/24/25-11
    ????? 22-24-36/37-45-33-16-7-36/37/39-27-26
    ????(UN No.) UN 1230 3/PG 2
    WGK ?? 2
    RTECS ?? DK9100000
    ?? ?? ?? Irritant
    TSCA Yes
    HS ?? 29350090
    ?? ?? ??? 58-93-5(Hazardous Substances Data)
    ?? LD50 in mice (mg/kg): 590 i.v.; >8000 orally (Piala)
    ????(GHS):
    ?? ?: Danger
    ??·?? ??:
    ?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
    H225 ???? ?? ? ?? ??? ?? ?? 2 ?? P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
    H302 ??? ??? ?? ?? ?? - ?? ?? 4 ?? P264, P270, P301+P312, P330, P501
    H303 ??? ??? ? ?? ?? ?? ?? - ?? ?? 5 P312
    H370 ??(??, ??? ?? ??? ?? ??? ??)? ??? ???(????? ?? ???? ??? ???? ???? ???? ????? ??? ????? ??) ?? ???? ?? - 1? ?? ?? 1 ?? P260, P264, P270, P307+P311, P321,P405, P501
    ??????:
    P210 ?·???·??·????? ????? - ?? ???.
    P260 ??·?·??·???·??·...·????? ???? ???.
    P280 ????/???/???/?????? ?????.
    P311 ????(??)? ??? ????.
    P301+P310 ???? ?? ????(??)? ??? ????.
    NFPA 704
    1
    2 0

    ?????????? MSDS


    Hydrochlorothiazide

    ?????????? C??? ??, ??, ??

    ??? ??

    White Solid

    Originator

    Hydrodiuril,MSD,US,1959

    ??

    Hydrochlorothiazide is one of the most widely used drugs of this series, and it is used for the same indications, as is chlorothiazide. Hydrochlorothiazide causes less inhibition of carbonic anhydrase, but causes 5–10 times more diuresis of sodium ions than chlorothiazide using the same dose.

    ??

    A carbonic anhydrase inhibitor. Diuretic.

    ??

    Labelled Hydrochlorothiazide (H714560). Hydrochlorothiazide is a carbonic anhydrase inhibitor as a diuretic.

    ??

    ChEBI: A benzothiadiazine that is 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted by a chloro group at position 6 and a sulfonamide at 7. It is diuretic used for the treatment of hypertension and congestive heart failure.

    Manufacturing Process

    As described in US Patent 3,163,645, a mixture of 2.9 grams of 5-chloro-2,4- disulfamyl aniline in 15 ml of anhydrous diethyleneglycol dimethyl ether, 0.5 ml of an ethyl acetate solution containing 109.5 grams of hydrogen chloride per 1,000 ml and 0.33 grams (0.011 mol) of paraformaldehyde is heated to 80° to 90°C and maintained at that temperature for 1 hour. The resulting mixture is cooled to room temperature and concentrated to one-third of its volume under reduced pressure, diluted with water, then allowed to crystallize. The product is filtered off and recrystallized from water, to yield the desired 6-chloro-7-sulfamyl-3,4-dihydro-2H-[1,2,4]-benzothiadiazine-1,1- dioxide, MP 266° to 268°C, yield 1.4 grams. By replacing paraformaldehyde by 0.84 gram of 1,1 -dimethoxymethane and proceeding as above, the same compound is obtained.
    As described in US Patent 3,025,292, the desired product may be made by hydrogenation of chlorothiazide. Three grams of 6-chloro-7-sulfamyl-1,2,4- benzothiadiazine-1,1-dioxide (chlorothiazide) is suspended in 100 ml of methanol. Then 1.0 gram of a 5% ruthenium on charcoal catalyst is added, and the mixture is reduced at room temperature and at an initial hydrogen pressure of 39 psig. The theoretical amount of hydrogen to form the 3,4- dihydro derivative is absorbed after a period of about 10 hours.
    The reduction mixture then is heated to boiling and filtered hot to remove the catalyst. The catalyst is washed with a little methanol and the combined filtrate is concentrated to a volume of about 25 ml by evaporation on a steam bath. Upon cooling to room temperature, white crystals separate which are filtered, washed with water, and dried in vacuo at room temperature over phosphorus pentoxide overnight. The weight of 6-chloro-7-sulfamyl 3,4- dihydro-1,2,4-benzothiadiazine-1,1-dioxide obtained is 1.26 grams; MP 268.5° to 270°C. Dilution of the above filtrate with water to a volume of about 125 ml gives a second crop of product having the same melting point and weighing 1.22 grams, giving a combined yield of 83%. When the product is mixed with an authentic sample of 6-chloro-7-sulfamyl-3,4-dihydro-1,2,4- benzothiadiazine-1,1-dioxide, prepared by another method, the melting point is not depressed.

    ???

    Esidrix (Novartis); Hydro-D (Halsey); Hydrodiuril (Merck); Microzide (Watson); Oretic (Abbott); Zide (Solvay Pharmaceuticals).

    Therapeutic Function

    Diuretic

    ?? ??

    Crystals or white powder.

    ??? ?? ??

    Insoluble in water.

    ?? ???

    Strong reducing agents will produce toxic gases ammonia and hydrogen sulfide.

    ????

    Flash point data for Hydrochlorothiazide are not available but Hydrochlorothiazide is probably combustible.

    Safety Profile

    Poison bp intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. Human systemic effects by ingestion: sodum level changes, chlorine level changes, acute pulmonary edema, nausea or vomiting. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A duetic. When heated to decomposition it emits very toxic fumes of SOx, Cl-, and NOx.

    Chemical Synthesis

    Hydrochlorothiazide, 1,1-dioxide 6-chloro-3,4-dihydro-2H-1,2,4- benzothiadiazin-7-sulfonamide (21.3.4), is synthesized either by cyclization of 4,6-sulfonamido- 3-chloroaniline (21.3.2) using paraformaldehyde, during which simultaneous reduction of the double bond occurs at position C3–C4, or the drug is synthesized by reduction of the same double bond in chlorothiazide (21.3.3) by formaldehyde. This small change in structure increases activity of the drug in comparison with chlorothiazide, and increases its absorbability when used orally.

    Veterinary Drugs and Treatments

    In veterinary medicine, furosemide has largely supplanted the use of thiazides as a general diuretic (edema treatment). Thiazides are still used for the treatment of systemic hypertension, nephrogenic diabetes insipidus, and to help prevent the recurrence of calcium oxalate uroliths in dogs.

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