Dihydrostreptomycin sesquisulfate
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| Category | Animal Health |
| Catalog number | BBF-03824 |
| CAS | 5490-27-7 |
| Molecular Weight | 730.71 |
| Molecular Formula | C21H41N7O12.3/2H2O4S |
| Purity | ≥95% |
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Description
Dihydrostreptomycin sesquisulfate is a semi-synthetic aminoglycoside antibiotic. Dihydrostreptomycin sesquisulfate is a derivative of Streptomycin used to treat bacterial diseases in cattle, pigs and sheep.
Specification
| Related CAS | 28779-37-5 (Deleted CAS) 7664-93-9 (free base) 1425-61-2 (x-sulfate) |
| Synonyms | D-Streptamine, O-2-deoxy-2-(methylamino)-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-(hydroxymethyl)-α-L-lyxofuranosyl-(1→4)-N1,N3-bis(aminoiminomethyl)-, sulfate (2:3); D-Streptamine, O-2-deoxy-2-(methylamino)-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-(hydroxymethyl)-α-L-lyxofuranosyl-(1→4)-N,N'-bis(aminoiminomethyl)-, sulfate (2:3) (salt); Streptomycin, dihydro-, sulfate (2:3) (salt); Didromycin; Didromycine; Dihydrostreptomycin 3/2 sulfate; Dihydrostreptomycin sulfate; Double-mycin; Panstreptin; Sol-Mycin; Streptomagna |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | Store at -20°C |
| IUPAC Name | 1,1'-((1R,2R,3S,4R,5R,6S)-4-(((2R,3R,4R,5S)-3-(((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-4-(hydroxymethyl)-5-methyltetrahydrofuran-2-yl)oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine sulfate;sulfuric acid |
| Canonical SMILES | CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(CO)O.CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(CO)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O |
| InChI | InChI=1S/2C21H41N7O12.3H2O4S/c2*1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;3*1-5(2,3)4/h2*5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7+,8-,9-,10-,11+, |
| InChI Key | CZWJCQXZZJHHRH-YCRXJPFRSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Application | An aminoglycoside antibiotic |
| Boiling Point | 954.5°C at 760 mmHg |
| Melting Point | >200°C |
| Solubility | Soluble in DMSO |
Reference Reading
1.Clinicopathological studies on facial eczema outbreak in sheep in Southwest Turkey.
Ozmen O;Sahinduran S;Haligur M;Albay MK Trop Anim Health Prod. 2008 Oct;40(7):545-51. doi: 10.1007/s11250-008-9132-7. Epub 2008 Jan 23.
After very hot summer, 22 sheep from 5 different flocks consisting of approximately 150-200 animals each were diagnosed with facial eczema in September 2005, in southwest Turkey. Photophobia, corneal opacity, severe ulcers of the facial skin, especially localized around the eyes and mouth, and 3% mortality were the most prominent clinical symptoms. GGT levels of the animals were very high and varying between 261- 328 U/l. While the activities of ALT and total bilirubin were elevated and AST was normal in affected sheep. Total bilirubin level was higher than normal. Seven of the 22 sheep were euthanatized and necropsy was performed on all of these animals. Severe icterus, hepatomegaly, enlarged gallbladder, congestion of mesenteric vessels were the common necropsy findings. Histopathological changes of the liver included necrosis of the hepatocytes, cholangiohepatitis characterized by mononuclear inflammatory cell infiltrate in the portal area and mild to severe fibrosis around bile ducts. A diagnosis of sporidesmin toxicosis was made based on the histopathology of the livers, the elevation in liver enzymes, and the development of cutaneous lesions consistent with photosensitization and high spore counts in the ruminal contents.
2.Concentrations of penicillin, streptomycin, and spiramycin in bovine udder tissue liquids.
Franklin A;Horn af Rantzien M;Obel N;Ostensson K;Aström G Am J Vet Res. 1986 Apr;47(4):804-7.
Concentrations of benzylpenicillin and spiramycin adipate were determined in bovine plasma and milk and in lymph draining the udder tissue after IM or IV administration. Combined benzylpenicillin and dihydrostreptomycin sulfate concentrations were also determined in the same fluids after intramammary injection. A superficial parenchymal lymph vessel, afferent to the supramammary lymph gland of the left quarters, was cannulated with a polythene catheter from which the lymph was allowed to drain freely. After injections of 9.5 mg of benzylpenicillin/kg of body weight IM, a mean peak concentration (PC) in lymph (3.7 micrograms/ml), constituting 77% of the PC in plasma (4.8 micrograms/ml), was obtained 0.5 to 1 hour after PC in the plasma. The benzylpenicillin lymph concentration was close to that in plasma for about 7 hours after injection. Thereafter, the benzylpenicillin lymph concentration continued to exceed that in plasma, but not that in milk. After IV administration of spiramycin adipate, the lymph concentration was almost identical to that in plasma. After intramammary injection of procaine benzylpenicillin (400 mg), in combination with the same amount of dihydrostreptomycin sulfate, into 2 udder quarters each, mean PC in the lymph of 3.
3.Determination of a ternary mixture of penicillin-G sodium salt, penicillin-G procain salt and dihydrostreptomycin sulphate, by third-derivative spectrophotometry.
Morelli B Talanta. 1994 Apr;41(4):479-83.
Ternary mixtures of antibiotics, i.e. penicillin-G sodium salt, penicillin-G procain salt and dihydrostreptomycin sulphate salt, are assayed by 'zero-crossing' third-derivative spectrophotometry. Calibration plots follows Beer's law up to 40 mug/ml of penicillin-G sodium at 222.5 nm (r = 0.9997), 46 mug/ml of penicillin-G procain at 217 nm (r = 0.9999) and 36 mug/ml of dihydrostreptomycin sulphate at 211.5 nm (r = 0.9999), in the presence of one another. Detection limits at p = 0.05 level of significance were calculated to be, respectively, 0.66, 0.41 and 0.25 mug/ml. The procedure is rapid, simple, nondestructive and does not require solution of equations. The method was successfully applied for determining laboratory mixtures and commercial injections.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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