Spectinomycin dihydrochloride pentahydrate Chemical Properties

Melting point:

205-207° (dec)

alpha 

D +14.8° (c = 0.42 in water)

storage temp. 

2-8°C

solubility 

H₂O: 50 mg/mL, clear, faintly yellow

form 

powder

color 

white to off-white

Water Solubility 

Soluble in water.Soluble in water, methanol, dimethyl sulfoxide, ethanol and dimethyl formamide.

Merck 

14,8739

BRN 

5684150

InChIKey

DCHJOVNPPSBWHK-UXXUFHFZSA-N

CAS DataBase Reference

22189-32-8

Safety Information

Safety Statements 

24/25

WGK Germany 

2

RTECS 

WG7400000

F 

10

HS Code 

29419090

Toxicity

mouse,LD50,intramuscular,> 5gm/kg (5000mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Japanese Journal of Antibiotics. Vol. 29, Pg. 43, 1976.

MSDS

• Language:English Provider:SigmaAldrich

Spectinomycin dihydrochloride pentahydrate Usage And Synthesis

Description

Spectinomycin was found in the culture broth of Streptomyces spectabilis by Upjohn Co. in 1961. This antibiotic was intended for use in treating various infections, as are the other aminoglycoside antibiotics, but its activity is insufficient for clinical efficacy except against gonorrhea. Spectinomycin does not develop crossresistance with any other antibiotic and shows low toxicity; it is used by deep intramuscular injection for “single-session,” bolusinjection therapy of gonorrhea.

Chemical Properties

White or almost white, slightly hygroscopic powder.

Originator

Trobicin,Upjohn,US,1971

Uses

Spectinomycin Dihydrochloride Pentahydrate is a new animal drug application (ANADA) administered in the drinking water of chickens as an aid in the control of airsacculitis; Also, it is an aminocylcitol antibiotic.

Uses

Spectinomycin is an aminocyclitol antibiotic produced by S. spectabilis that is active against Gram-negative and Gram-positive bacteria. Spectinomycin inhibits protein synthesis by binding to the 30S ribosomal subunit and interfering with peptidyl tRNA translocation. Mutations in the gene for ribosomal protein S5 prevents binding of spectinomycin and contributes to bacterial resistance.

Uses

Aminocyclotol antibacterial.

Definition

ChEBI: A hydrate that is the pentahydrate form of spectinomycin hydrochloride. An antibiotic that is active against gram-negative bacteria and used to treat gonorrhea.

Manufacturing Process

A lyophilized culture of Streptomyces spectabilis, NRRL 2792, was used to seed the following sterile agar medium on tubed slants:Tryptone 5 K2HPO4 0.5 NaCl 0.5 FeSO4 0.1 Agar 20
Deionized water to make 1 liter
The slants were incubated for 7 days at 30°C, after which time sporulation was complete. The spores from the agar slants were used, in an aqueous suspension, to inoculate 100 ml of preseed medium in a 500 ml Erlenmeyer flask. The sterile preseed medium consisted of:
Grams Dried whole yeast 10 Glucose 10 Pancreatic digest of 5 casein (N-Z-Amine B)
Tap water to make 1 liter adjusted to pH 7.2 before sterilizing
The seed flash was incubated for 24 hours at 32°C on a reciprocating shaker after which it was used as an inoculum for a 20 liter seed fermenter in the amount of approximately 5%. the 20 liter seed fermenter contained a sterile medium consisting of:
Grams Glucose 15 Cornstarch 25 Distiller's solubles 15 Brewer's yeast 10 Corn steep liquor 20
Tap water to make 1 liter adjusted to pH 7.2 before sterilizing
The 20 liter seed fermenter was incubated for 24 hours at 32°C and aerated at the rate of 6 standard liters or about 0.2 standard cubic feet of air per minute and agitated with a sweep stirrer. The 20 liter seed fermenter was used to inoculate 250 liters of the same medium in a 100 gallon fermentation tank. 1,200 ml of lard oil were added during the fermentation to control foaming. The tank was agitated with a propeller and aerated at the rate of 75 standard liters of air per minute. After 96 hours of fermentation the beer assayed 500 mcg/ml (18.3 mcg/mg on a dry basis) of actinospectacin. Actinospectacin is assayed by its activity against Klebsiella pneumoniae by standard agar diffusion procedure and based on crystalline actinospectacin sulfate according to US Patent 3,234,092.

Therapeutic Function

Antibacterial

General Description

A broad spectrum aminoglycoside antibiotic that contains two glucose moieties. Footprint studies indicate that spectinomycin exerts regional effects on ribosomal structure. A resistance gene (aph) which encodes a spectinomycin has been cloned from Legionella pneumophila (disease agent for Legionnaire’s disease) kinase and expressed in E. coli. Potency: ≥500 μg/mg.

Biological Activity

spectinomycin is an aminocyclitol antibiotic produced by s. spectabilis with activity against gram-negative bacterial species. spectinomycin has been used for the treatment of gonorrhea, where it inhibits microbial protein synthesis by binding to the 30s ribosomal subunit, protects the n‐7 position of e. coli 16s rrna residue g1064 from methylation by dimethyl sulfate. binding of spectinomycin at this location is thought to stabilize helix 34, inhibiting the binding of elongation factor g, thereby blocking translocation of peptidyl‐trnas from the ribosomal a site to the p site [1].spectinomycin selectively inhibited protein synthesis in cells and in extracts of e. coli. mutations to high-level resistance to this antibiotic map close to the streptomycin locus, and the site of action of spectinomycin, like that of streptomycin, is the 30s ribosomal subunit, as shown by experiments with reconstituted 70s ribosomes containing subunits from sensitive and from resistant ribosomes [2].

Biochem/physiol Actions

Mode of Action: Spectinomycin acts by inhibiting protein synthesis and elongation by binding to the bacterial 30S ribosomal subunit and interfering with peptidyl tRNA translocation.Mode of Resistance: A mutation in rpsE, the gene for ribosomal protein S5, prevents the binding of spectinomycin. Resistance is also conferred by the aminoglycoside-3′-adenyltransferase gene (aadA). Antimicrobial spectrum: Spectinomycin acts against gram-negative and gram-positive bacteria.

References

[1] zimmerman j m, maher l j. in vivo selection of spectinomycin‐binding rnas[j]. nucleic acids research, 2002, 30(24): 5425-5435.
[2] davies j, anderson p, davis b d. inhibition of protein synthesis by spectinomycin[j]. science, 1965, 149(3688): 1096-1098.

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