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| Benzamidine hydrochloride Basic information |
| Benzamidine hydrochloride Chemical Properties |
| Melting point | 86-88 °C(lit.) | | storage temp. | 2-8°C | | solubility | DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 3 mg/ml | | form | Powder | | color | White to off-white | | PH | 4.0 to 6.5(50g/L, 25 ℃) | | Water Solubility | soluble | | BRN | 3594959 | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily | | InChIKey | LZCZIHQBSCVGRD-UHFFFAOYSA-N | | CAS DataBase Reference | 1670-14-0(CAS DataBase Reference) | | EPA Substance Registry System | Benzenecarboximidamide, monohydrochloride (1670-14-0) |
| Benzamidine hydrochloride Usage And Synthesis |
| Description | Benzamidine hydrochloride is a reversible inhibitor of trypsin, trypsin-like enzymes, and serine proteases. A concentration of approximately 1 mM is used for general protease inhibition. To inhibit proteases from yeast, a range of 0.5 to 4.0 mM is used and it is for the most part interchangeable with pepstatin A.In addition to being a strong competitive inhibitor of trypsin, benzamidine HCl has been also shown to be a strong competitive inhibitor of thrombin and plasmin. It was also found to be as effective as aprotinin in the prevention of glucagon degradation in human plasma. | | Chemical Properties | white to off-white powder | | Uses | Benzamidine is a reversible inhibitor of serine proteases, including trypsin, plasmin, and thrombin (Kis = 35, 350, and 220 μM, respectively). In addition to its use as a general serine protease inhibitor, benzamidine is used, when immobilized, to purify novel proteases. | | Preparation | To a stainless steel rocking autoclave equipped with a stirrer is added 103.0 gm (1.0 mole) of benzonitrile, 214.0 gm (4.0 mole) of ammonium chloride, and 306.0 gm (18.0 mole) of ammonia is introduced by means of a transfer bomb. The reaction mixture is heated at 150°C for 18 hr (pressure: 1300-6500 psig), cooled, and, with appropriate precautions for the safe control of the excess ammonia, is vented to atmospheric pressure. The reaction mixture is extracted with ether to remove approximately 5% unreacted benzonitrile, and then extracted with hot acetonitrile or ethanol to separate the amidine hydrochloride from the unreacted ammonium chloride. Concentration of the latter affords 120.5 gm (77%) of benzamidine hydrochloride, m.p. 161-163°C.
| | Biological Activity | Benzamidine hydrochloride is an reversible competitive inhibitor of trypsin-like serine proteases, with Kis of 97 μM, 21 μM, 20 μM and 110 μM for uPA, trypsin, tryptase and factor Xa, respectively. | | Safety Profile | Moderately toxic byintraperitoneal route. When heated to decomposition itemits toxic vapors of NOx, HCl, and Cl-. | | in vitro | Benzamidine hydrochloride has weak inhibition for tPA and thrombin, with Kis of 750 μM and 320 μM, respectively. | | References | 1) Markwardt?et al. (1968)?Comparative studies on the inhibition of trypsin, plasmin, and thrombin by derivatives of benzylamine and benzamide; Eur. J. Biochem.,?6?502
2) Deutscher?et al.?(1990),?Maintaining protein stability; Methods Enzymol.,?182?83
3) Jaswinski?et al.?(1990),?Preparations of extracts from yeast; Methods Enzymol.,?182?154
4) Ensinck?et al.?(1972),?Use of Benzamidine as a proteolytic inhibitor in the radioimmunoassay of glucagon in plasma; J. Clin. Endocrinol. Metab.,?35?463
5) Jeffcoate?et al. (1974),?Use of benzamidine to prevent the destruction of thyrotropin-releasing hormone (TRH) by blood; Endocrinol. Metab,?38?155 |
| Benzamidine hydrochloride Preparation Products And Raw materials |
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