Gentamicin X2

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Gentamicin X2
Category Antibiotics
Catalog number BBF-04476
CAS 36889-17-5
Molecular Weight 482.53
Molecular Formula C19H38N4O10
Purity ≥98.0%

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Description

One of several different components found in standard grade Gentamicin. Gentamicin is an aminoglycoside antibiotic.

Specification

Related CAS 57793-88-1 (monosulfate salt)
Synonyms O-2-Amino-2-deoxy-α-D-glucopyranosyl-(1→4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)]-2-deoxy-D-streptamine; Gentamicin X
Storage Store at -20°C under inert atmosphere
IUPAC Name (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
Canonical SMILES CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CO)O)O)N)N)N)O
InChI InChI=1S/C19H38N4O10/c1-19(29)5-30-18(13(28)16(19)23-2)33-15-7(21)3-6(20)14(12(15)27)32-17-9(22)11(26)10(25)8(4-24)31-17/h6-18,23-29H,3-5,20-22H2,1-2H3/t6-,7+,8+,9+,10+,11+,12-,13+,14+,15-,16+,17+,18+,19-/m0/s1
InChI Key HFLKNINDVFJPQT-ZFAMMYHGSA-N
Source Micromonospora spp.

Properties

Appearance Off-white to Light Beige Solid
Boiling Point 762.7±60.0°C (Predicted)
Melting Point >90°C (dec.)
Density 1.50±0.1 g/cm3 (Predicted)
Solubility Slightly soluble in Water

Reference Reading

1. Application of Box-Behnken design to prepare gentamicin-loaded calcium carbonate nanoparticles
Solmaz Maleki Dizaj, Mohammad Barzegar-Jalali, Khosro Adibkia, Farzaneh Lotfipour, Mohammad-Hossein Zarrintan Artif Cells Nanomed Biotechnol . 2016 Sep;44(6):1475-81. doi: 10.3109/21691401.2015.1042108.
The aim of this research was to prepare and optimize calcium carbonate (CaCO3) nanoparticles as carriers for gentamicin sulfate. A chemical precipitation method was used to prepare the gentamicin sulfate-loaded CaCO3 nanoparticles. A 3-factor, 3-level Box-Behnken design was used for the optimization procedure, with the molar ratio of CaCl2: Na2CO3 (X1), the concentration of drug (X2), and the speed of homogenization (X3) as the independent variables. The particle size and entrapment efficiency were considered as response variables. Mathematical equations and response surface plots were used, along with the counter plots, to relate the dependent and independent variables. The results indicated that the speed of homogenization was the main variable contributing to particle size and entrapment efficiency. The combined effect of all three independent variables was also evaluated. Using the response optimization design, the optimized Xl-X3 levels were predicted. An optimized formulation was then prepared according to these levels, resulting in a particle size of 80.23 nm and an entrapment efficiency of 30.80%. It was concluded that the chemical precipitation technique, together with the Box-Behnken experimental design methodology, could be successfully used to optimize the formulation of drug-incorporated calcium carbonate nanoparticles.
2. Micromonospora-produced gentamicin components
G H Wagman, E Katz, R G Condon, B K Lee Antimicrob Agents Chemother . 1976 Jan;9(1):151-9. doi: 10.1128/AAC.9.1.151.
After the chromatographic separation of [methyl-(14)C]gentamicin major (C) components from a large-scale radioactive fermentation (Lee et al., 1974), [methyl-(14)C]gentamicin minor (polar) components (A, B, B(1), X(2), and G-418) were isolated from subsequent chromatography of the remaining antibiotic mixture. When l-[methyl-(14)C]methionine was added at the onset of biosynthesis of the gentamicin components, incorporation of label into the minor components preceded incorporation into the major components. Degradation occurred when [methyl-(14)C]gentamicin major components (C(1), C(2) and C(1)a) were added respectively to the gentamicin-producing culture medium and shaken.
3. Daily gentamicin using ideal body weight demonstrates lower risk of postpartum endometritis and increased chance of successful outcome compared with traditional 8-hour dosing for the treatment of intrapartum chorioamnionitis
Meera Kesavan Nasir, Juliette Kim, Jeanne Carey, Audrey Renson, Shailini Singh, Daniel Martingano, Sharon Rogoff J Matern Fetal Neonatal Med . 2019 Oct;32(19):3204-3208. doi: 10.1080/14767058.2018.1460348.
Background:Clinical chorioamnionitis complicates approximately 1-4% of pregnancies overall. Although universal agreement does not exist regarding the antibiotic regimen of choice, most studies have evaluated intravenous ampicillin dosed at 2 g every 6 hours plus gentamicin dosed every 8 hours. Only three studies have examined daily gentamicin for the treatment of intrapartum chorioamnionitis and thus is insufficiently investigated.Objective:This study seeks to determine whether daily dosing of gentamicin using ideal body weight for the treatment of intrapartum chorioamnionitis is more or equivalently efficacious when compared to traditional 8-hour dosing regimens.Materials and methods:We conducted a retrospective cohort study and reviewed charts on all women receiving treatment for intrapartum chorioamnionitis, which included intravenous gentamicin daily dosing calculated using 5 mg/kg ideal body weight or receiving traditional every 8 hours dosing of gentamicin at two large academic centers. Our primary outcomes were resolution of infection following delivery without the development of maternal endometritis and/or neonatal sepsis. Baseline characteristics were compared between dosing groups using Welch two-samplet-tests for continuous variables, uncorrected X2test and exact binomial 95% confidence intervals. We calculated the risk ratios of each outcome in the ideal versus traditional dosing groups using modified Poisson regression, both crude and adjusted. Adjusted models were controlled for variables determined to be potential confounders, which included BMI, diabetes mellitus, gestational blood pressure >140/90, group β-Streptococcusstatus, race, advanced maternal age (>34 y), and parity.Results:The study included 500 patients with 255 patients receiving daily dosing of gentamicin and 245 receiving traditional dosing of gentamicin. Of the patients receiving daily gentamicin compared to traditional dosing, 95.7% (95% CI 94.9-96.6%) achieved the primary outcome versus 92% (95% CI 90.8 - 93.2%), 2.4% (95% CI 1.8-3%) developed endometritis versus 5.6% (4.5-6.7%), 1.6% (95% CI 1.1-2.1%) delivered neonates with sepsis versus 3.3% (CI 2.5-4.1%), and 36.9% required cesarean delivery versus 41.4%. In crude analysis, compared to traditional dosing, IDW daily dosing was associated with a lower risk of postpartum endometritis (RR 0.42, 95% CI 0.16-1.10,p= .032). After adjusting for BMI, diabetes mellitus, gestational blood pressure >140/90, group β-Streptococcusstatus, race, advanced maternal age (>34 y), and parity, the IDW daily dosing group had a 5% greater chance of successful outcome (RR 1.05, 95% CI 1.00-1.10,p= .046) and a 64% lower risk of endometritis (RR 0.35, 95% CI 0.15-0.83,p= .017).Conclusion:Daily dosing of gentamicin using ideal body weight is associated with a lower risk of postpartum endometritis and high chance of a successful outcome in the treatment of intrapartum chorioamnionitis compared with traditional 8-hour dosing in our ethnically diverse, urban population and thus may be considered a superior option to every 8 hours dosing regimens.

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