Dihydrostreptomycin Chemical Properties

Melting point:

>300 °C

Boiling point:

641.09°C (rough estimate)

Density 

1.3963 (rough estimate)

refractive index 

1.6800 (estimate)

pka

pKa 7.8 (Uncertain)

MSDS

• Language:English Provider:2-[(1S,3R,4S,5R,6R)-5-(Diaminomethylideneamino)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-methylaminooxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-3,4,6-trihydroxycyclohexyl]guanidine

Dihydrostreptomycin Usage And Synthesis

Description

Dihydrostreptomycin was first synthesized by Parke Davis Co. in 1946by the reduction of streptomycin. Naturally occurring dihydrostreptomycin was found in the culture broth of Streptomyces humidus by Takeda Chemicals Industries in 1957. Its hydrochloride or sulfate is more easily crystallized and more stable under alkaline conditions than streptomycin. Dihydrostreptomycin has been used for therapy of tuberculosis, but because it has a higher ototoxicity than streptomycin its use is now restricted to animal therapy.

Originator

Dihydrostrepto,MSD ,US,1948

Uses

Antibacterial.

Definition

ChEBI: Dihydrostreptomycin is a member of streptomycins.

Manufacturing Process

Dihydrostreptomycin sulfate may be prepared from streptomycin sulfate by catalytic hydrogenation (Merck, Pfizer, Cyanamid), electrolytic reduction (Schenley, Olin Mathieson), or by sodium borohydride reduction (Bristol), or by isolation from a fermentation process (Takeda).

brand name

Abocillin;Biostrep;Complexobiotico;Diapenin 3;Diapenin balsamico;Diarrestival;Didromycin;Didrothenate;Dihydrocidan sulfato;Dihydrostreptofar;Diidro-pantostrept;Distreptopab;Dreiciclina balsamica;Dst;Entera-strept;Estreptoluy;Estreptosirup;Helle-strep-forte;Hp 48;Mastigun;Mixtencillin;Retromyopen;Rocopenstrep;Sanstrepto;Solmycin;Solvo-strept;Streptoduocin;Veticar;Veycil-as.

Therapeutic Function

Antibiotic

World Health Organization (WHO)

Dihydrostreptomycin, a derivative of the aminoglycoside antibiotic streptomycin with similar antibacterial activity, was first synthesized in 1947 and subsequently used in the treatment of tuberculosis and gram-negative infections. Preparations for systemic use have been widely withdrawn as a result of concern regarding their severe ototoxicity. Dihydrostreptomycin is poorly absorbed from the gastrointestinal tract. It remains available in oral preparations in some countries.

Safety Profile

Poison by intravenous and intramuscular routes. Moderately toxic by subcutaneous and intraperitoneal routes. Human teratogenic effects by unspecified route: developmental abnormahties of the eye and ear. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. A derivative of streptomycin; has anesthetic properties. When heated to decomposition it emits toxic fumes of NOx

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