Spectinomycin dihydrochloride pentahydrate

Spectinomycin dihydrochloride pentahydrate

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Spectinomycin dihydrochloride pentahydrate
Category Antibiotics
Catalog number BBF-04648
CAS 22189-32-8
Molecular Weight 495.35
Molecular Formula C14H24N2O7.2HCl.5H2O
Purity 98%

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Description

The dihydrochloride pentahydrate salt form of Spectinomycin, an aminoglycoside antibiotic isolated from Streptomyces spectabilis, has been found to be effective against gram-negative bacteria.

Specification

Related CAS 1695-77-8 (free base) 21736-83-4 (dihydrochloride)
Synonyms Spectam; Spectogard; Spectinomycin HCl pentahydrate; Togamycin dihydrochloride pentahydrate; [2R-(2α,4aβ,5aβ,6β,7β,8β,9α,9aα,10aβ)]-Decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-4H-pyrano[2,3-b][1,4]benzodioxin-4-one Dihydrochloride Pentahydrate; Actinospectacin dihydrochloride pentahydrate
Storage Store at -20°C under inert atmosphere
IUPAC Name (1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one;pentahydrate;dihydrochloride
Canonical SMILES CC1CC(=O)C2(C(O1)OC3C(C(C(C(C3O2)NC)O)NC)O)O.O.O.O.O.O.Cl.Cl
InChI InChI=1S/C14H24N2O7.2ClH.5H2O/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14;;;;;;;/h5,7-13,15-16,18-20H,4H2,1-3H3;2*1H;5*1H2/t5-,7-,8+,9+,10+,11-,12-,13+,14+;;;;;;;/m1..../s1
InChI Key DCHJOVNPPSBWHK-UXXUFHFZSA-N
Source Streptomyces spectabilis

Properties

Appearance White to Off-white Solid
Application Anti-Bacterial Agents
Antibiotic Activity Spectrum Gram-negative bacteria
Boiling Point 583.1°C at 760 mmHg
Melting Point 196-198°C
Solubility Slightly soluble in Methanol, Water (Sonicated)

Reference Reading

1.[Characteristics of the E. coli strains isolated from calves].
Petkov M Vet Med Nauki. 1980;17(6-7):12-6.
A study was carried out on E. coli strains eliminated in the Pleven District. It was proved that 19.4% of the strains were enteropathogenic. The enteropathogenic E. coli provoked dilatation of the ligated intestinal segments. All enteropathogenic E. coli proved positive for K 99 antigen. For the non-enteropathogenic E. coli K 99 antigen was not proved. The enteropathogenic E. coli strains referred to the serotypes O 101, O 8, O 9 and O 11, whereas the non-enteropathogenic ones referred to the serotypes O 78, O 35, O 117, O 26, O 111 and O 86. The strains under consideration were not haemolytic. The prevailing part were sensitive to kanamycin, ampicillin, spectam, medium sensitive to streptomycin and slightly sensitive to furazolin and erythran. No differences were proved with regard to sensitivity both of enteropathogenic and nonenteropathogenic E. coli strains to antibiotics.
2.Comparison of spectinomycin hydrochloride and aqueous procaine penicillin G in the treatment of uncomplicated gonorrhea.
Duanćić A;Fiumara NJ;Alpert S;Lee YH;Tarr PI;Rosner B;McCormack WM Antimicrob Agents Chemother. 1974 Oct;6(4):512-5.
Men and women with uncomplicated gonorrhea were randomly assigned to receive aqueous procaine penicillin G (2,400,000 U for men; 2,400,000 U daily for 2 days for women) or spectinomycin hydrochloride (2.0 g for men; 4.0 g for women). Among men who returned for post-treatment evaluation within 10 days, treatment failures were noted among 16 (20.3%) of 79 men who received penicillin and 8 (9.5%) of 84 men who received spectinomycin (P < 0.1). Similarly, 6 (13.3%) of 45 women who received penicillin and 3 (6.5%) of 46 women who received spectinomycin had positive endocervical cultures for Neisseria gonorrhoeae at the time of the post-treatment examination (P = not significant).
3.Treatment of gonorrhea with spectinomycin hydrochloride: comparison with standard penicillin schedules.
Duncan WC;Holder WR;Roberts DP;Knox JM Antimicrob Agents Chemother. 1972 Mar;1(3):210-4.
Spectinomycin hydrochloride, a new parenteral antibiotic prepared from Streptomyces spectabilis, was compared with standard U.S. Public Health Service-recommended dosages of aqueous procaine penicillin G in the treatment of uncomplicated gonorrhea in 353 men and 314 women. Of the 314 women, 130 had a pretreatment positive rectal culture. All diagnoses were proven by culture on Thayer-Martin selective medium. Minimal inhibitory concentrations of both drugs were determined. Single doses of 2 and 4 g of spectinomycin were compared with 2.4 million units of procaine penicillin in males and with both 2.4 and 4.8 million units of procaine penicillin in females. Both spectinomycin schedules, 2.4 million units of penicillin in males and 4.8 million units of penicillin in females, resulted in cure rates in excess of 90%. There were no failures at the rectal site only in those women with positive rectal cultures. There was no advantage to using the larger amount of spectinomycin in either sex.

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