Streptomycin sulfate

Description

Streptomycin was found in the culture broth of Streptomyces griseus by S. A. Waksman of Rutgers University in 1944; it was the second antibiotic introduced clinically (after penicillin). This drug is a water soluble, basic substance having an aminoglycoside structure and showing strong activity against a wide range of gram-positive and gram-negative bacteria including Mycobacterium. Streptomycin is the first choice among antituberculotic antibiotics and has been used for the therapy of Spirochaeta and Treponema infections.

Chemical properties

White to off-white powder

The Uses of Streptomycin sulfate

Streptomycin sulfate is a sulfate salt of streptomycin that is a protein synthesis inhibitor. Streptomycin is an antibiotic drug, the first of a class of drugs called aminoglycosides to be discovered, and was the first antibiotic remedy for tuberculosis.

The Uses of Streptomycin sulfate

Antibiotic substance produced by aerobic fermentation. Antibacterial (tuberculostatic).

The Uses of Streptomycin sulfate

Triacetine

What are the applications of Application

Streptomycin sulfate is An antibiotic for cell culture

Definition

ChEBI: Streptomycin sulfate is an aminoglycoside sulfate salt. It is functionally related to a streptomycin.

brand name

Strycin (Bristol-Myers Squibb).

General Description

An antibacterial. White to light gray or pale buff powder with faint amine-like odor.

Air & Water Reactions

Hygroscopic. Water soluble.

Reactivity Profile

Streptomycin sulfate is a medicinal amino saccharide.

Health Hazard

SYMPTOMS: Symptoms of exposure to Streptomycin sulfate include skin rashes, eosinophilia, blood dyscrasias, stomatitis, anaphylactic shock, pruritus, scaling, and fever.

Fire Hazard

Flash point data for Streptomycin sulfate are not available, however Streptomycin sulfate is probably combustible.

Clinical Use

Streptomycin sulfate is a white, odorless powder that is hygroscopicbut stable toward light and air. It is freely solublein water, forming solutions that are slightly acidic or nearlyneutral. It is very slightly soluble in alcohol and is insolublein most other organic solvents. Acid hydrolysis yields streptidineand streptobiosamine, the compound that is a combinationof L-streptose and N-methyl-L-glucosamine.
Streptomycin acts as a triacidic base through the effectof its two strongly basic guanidino groups and the moreweakly basic methylamino group. Aqueous solutions maybe stored at room temperature for 1 week without any lossof potency, but they are most stable if the pH is between 4.5and 7.0. The solutions decompose if sterilized by heating,so sterile solutions are prepared by adding sterile distilledwater to the sterile powder. The early salts of streptomycincontained impurities that were difficult to remove andcaused a histamine-like reaction. By forming a complexwith calcium chloride, it was possible to free the streptomycinfrom these impurities and to obtain a product thatwas generally well tolerated.
The organism that produces streptomycin, S. griseus, alsoproduces several other antibiotic compounds: hydroxystreptomycin,mannisidostreptomycin, and cycloheximide (q.v.).Of these, only cycloheximide has achieved importance as amedicinally useful substance. The term streptomycin A hasbeen used to refer to what is commonly called streptomycin,and mannisidostreptomycin has been called streptomycin B.Hydroxystreptomycin differs from streptomycin in having ahydroxyl group in place of one of the hydrogen atoms of thestreptose methyl group. Mannisidostreptomycin has a mannoseresidue attached in glycosidic linkage through the hydroxylgroup at C-4 of the N-methyl-L-glucosamine moiety.The work of Dyer et al. to establish the stereochemicalstructure of streptomycin has been completed, and confirmedwith the total synthesis of streptomycin and dihydrostreptomycinby Japanese scientists.

Safety Profile

Poison by ingestion and intravenous routes. Moderately toxic by subcutaneous route. An experimental teratogen. Human systemic effects by intraperitoneal route: flaccid paralysis without anesthesia, motor activity changes and pulmonary changes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also STREPTOMYCIN and SULFATES.

Purification Methods

The sulfate is recrystallised from H2O/EtOH, washed with a little EtOH, Et2O and dried in a vacuum. [UV and IR: Grove & Randall Antibiotics Monographs 2 163 1855, Heuser et al. J Am Chem Soc 75 4013 1953, Kuehl et al. J Am Chem Soc 68 1460 1946, Regna et al. J Biol Chem 165 631 1946.] During protein synthesis it inhibits initiation and causes misreading of mRNA [Zierhut et al. Eur J Biochem 98 577 1979, Chandra & Gray Methods Enzymol 184 70 1990]. [Beilstein 18/11 V 82.]