Gentamicin B
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| Category | Antibiotics |
| Catalog number | BBF-01868 |
| CAS | 36889-15-3 |
| Molecular Weight | 482.53 |
| Molecular Formula | C19H38N4O10 |
| Purity | 95% |
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Description
Gentamicin A is one of the antibiotics originally isolated from Micromonos poraechinospora NRRL 2985. It is used to treat respiratory and urinary tract, blood, bone and soft tissues infections.
Specification
| Related CAS | 43169-50-2 (sulfate) |
| Synonyms | Betamicine; O-6-Amino-6-deoxy-α-D-glucopyranosyl-(1→4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)]-2-deoxy-D-streptamine; Betamicin; Sch 14342; (1R,2R,3S,4R,6S)-4,6-Diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl 6-amino-6-deoxy-α-D-glucopyranoside |
| IUPAC Name | (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol |
| Canonical SMILES | CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CN)O)O)O)N)N)O |
| InChI | InChI=1S/C19H38N4O10/c1-19(29)5-30-17(13(28)16(19)23-2)32-14-6(21)3-7(22)15(12(14)27)33-18-11(26)10(25)9(24)8(4-20)31-18/h6-18,23-29H,3-5,20-22H2,1-2H3/t6-,7+,8-,9-,10+,11-,12-,13-,14+,15-,16-,17-,18-,19+/m1/s1 |
| InChI Key | RHRAMPXHWHSKQB-GGEUKFTFSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi |
| Boiling Point | 751.2°C at 760 mmHg |
| Density | 1.5 g/cm3 |
Reference Reading
1.Once daily isepamicin treatment in complicated urinary tract infections.
Lee SS1, Liu YC, Wann SR, Lin WR, Tsai TH, Lin HH, Chen YS, Yen MY. J Microbiol Immunol Infect. 1999 Jun;32(2):105-10.
Isepamicin is a new aminoglycoside, derived from gentamicin B, which is more stable than other aminoglycosides against inactivating enzymes, and is less nephrotoxic. We evaluated the efficacy and safety of a once daily isepamicin in the treatment of complicated urinary tract infections (UTIs), as compared with amikacin. During the period May, 1997, to January, 1998, a total of 52 patients with similar demographic and baseline characteristics were enrolled into a prospective, randomized, open-label, single-center trial at the Veterans General Hospital-Kaohsiung. Eleven patients were excluded for protocol violation. The remaining 41 patients were included in the efficacy analysis. Study subjects included 16 men and 25 women, with a mean age of 57.9 (range 18-95) years. Clinical improvement was noted in 100% of patients in both the isepamicin and amikacin group. No statistically significant difference was observed between the 2 groups in regard to the rapidity of defervescence, relief of dysuria and urinary frequency, and clearance of bacteriuria and pyuria.
2.Accessibility of aminoglycosides, isolated and in interaction with phosphatidylinositol, to water. A conformational analysis using the concept of molecular hydrophobicity potential.
Mingeot-Leclercq MP1, Tulkens PM, Brasseur R. Biochem Pharmacol. 1992 Nov 17;44(10):1967-75.
The mode of interaction between aminoglycosides and negatively charged phospholipids plays a critical role in the inhibition of lysosomal phospholipases induced by these antibiotics and therefore in their nephrotoxicity. Previous works suggested that accessibility of the drug interacting with phospholipids to water could be crucial in this respect. We have used the concept of molecular hydrophobicity potential described by Brasseur [J Med Chem 266: 16120-16127, 1991] to visualize the hydrophobic and hydrophilic envelopes around aminoglycosides assembled with phosphatidylinositol molecules, and to obtain a three-dimensional representation of the complex formed. Using a series of different aminoglycosides, we showed that molecules with a lower inhibitory potential (gentamicin B, amikacin and isepamicin) are surrounded by both hydrophobic and hydrophilic envelopes whereas aminoglycosides which are more inhibitory are enveloped primarily by either hydrophilic (kanamycin A or B) or hydrophobic (gentamicin C1a) envelopes.
3.Assembly of a novel biosynthetic pathway for gentamicin B production in Micromonospora echinospora.
Ni X1, Sun Z2, Gu Y3, Cui H4, Xia H5. Microb Cell Fact. 2016 Jan 5;15(1):1. doi: 10.1186/s12934-015-0402-6.
BACKGROUND: Isepamicin is a weakly toxic but highly active aminoglycoside antibiotic derivative of gentamicin B. Gentamicin B is a naturally occurring minor component isolated from Micromonospora echinospora. 2'-NH2-containing gentamicin C complex is a dominant compound produced by wild-type M. echinospora; by contrast, 2'-OH-containing gentamicin B is produced as a minor component. However, the biosynthetic pathway of gentamicin B remains unclear. Considering that gentamicin B shares a unique C2' hydroxyl group with kanamycin A, we aimed to design a new biosynthetic pathway of gentamicin B by combining twelve steps of gentamicin biosynthesis and two steps of kanamycin biosynthesis.
4.[Microbial drug resistance and the presence of plasmids in Salmonella strains isolated from different sources].
Luque A1, Moriñigo MA, Rodríguez-Avial C, Picazo JJ, Borrego JJ. Enferm Infecc Microbiol Clin. 1994 Apr;12(4):187-92.
BACKGROUND: To establish the relationship between the presence of plasmid and their antimicrobial resistance of Salmonella strains.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
