Gentamicin C1
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| Category | Antibiotics |
| Catalog number | BBF-04433 |
| CAS | 25876-10-2 |
| Molecular Weight | 477.59 |
| Molecular Formula | C21H43N5O7 |
| Purity | 90% |
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Description
It is a broad-spectrum aminoglycoside antibiotic produced by the strain of Micromonospora spp. One of several components of the gentamicin C complex which comprises approximately 80% gentamicin and exhibits the most potent antimicrobial activity.
Specification
| Related CAS | 38539-12-7 (monosulfate salt) |
| Synonyms | O-2-Amino-2,3,4,6,7-pentadeoxy-6-(methylamino)-α-D-ribo-heptopyranosyl-(14)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(16)]-2-deoxy-D-streptamine |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol |
| Canonical SMILES | CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC |
| InChI | InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1 |
| InChI Key | CEAZRRDELHUEMR-CAMVTXANSA-N |
| Source | Micromonospora spp. |
Properties
| Appearance | White-slightly yellow, crystalline powder |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 669.4±55.0°C (Predicted) |
| Melting Point | 94-100°C |
| Density | 1.30±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Dimethylformamide, Pyridine, Water |
Reference Reading
1. Microbial biosynthesis and applications of gentamicin: a critical appraisal
C Ganesh Kumar, M Himabindu, Annapurna Jetty Crit Rev Biotechnol . 2008;28(3):173-212. doi: 10.1080/07388550802262197.
Gentamicin is an aminoglycoside antibiotic produced by various species of the genus Micromonospora and has received much attention in the recent years as a broad-spectrum antibiotic for treatment of various infections. It exists as a complex of closely related aminoglycoside structures and the clinically significant one is the gentamicin C complex. This review article focuses attention on the present status of knowledge and the main advancements achieved in the last few decades on the subject of gentamicin with regard to its production, biosynthetic pathway, mode of action, and uses. The various nutritional and environmental parameters affecting gentamicin production and the factors affecting the release of bound gentamicin are discussed. Further, strain improvement using UV and/or chemical mutagenesis can be applied to augment the efficiency of the producer strain and a number of case studies are presented. Different detection and quantitative methods for gentamicin estimation and the mode of action of gentamicin are discussed in detail. This antibiotic finds extensive use in combination chemotherapy and as a drug for different delivery agents for treatment of osteomyelitis and other recent applications in gene therapy.
2. Methyltransferases of gentamicin biosynthesis
Peter F Leadlay, Fanglu Huang, Sicong Li, Anna Reva, Yuhui Sun, Binbin Xiong, Yuanzhen Liu, Junhong Guo, Zixin Deng Proc Natl Acad Sci U S A . 2018 Feb 6;115(6):1340-1345. doi: 10.1073/pnas.1711603115.
Gentamicin C complex fromMicromonospora echinosporaremains a globally important antibiotic, and there is revived interest in the semisynthesis of analogs that might show improved therapeutic properties. The complex consists of five components differing in their methylation pattern at one or more sites in the molecule. We show here, using specific gene deletion and chemical complementation, that the gentamicin pathway up to the branch point is defined by the selectivity of the methyltransferases GenN, GenD1, and GenK. Unexpectedly, they comprise a methylation network in which early intermediates are ectopically modified. Using whole-genome sequence, we have also discovered the terminal 6'-N-methyltransfer required to produce gentamicin C2b from C1a or gentamicin C1 from C2, an example of an essential biosynthetic enzyme being located not in the biosynthetic gene cluster but far removed on the chromosome. These findings fully account for the methylation pattern in gentamicins and open the way to production of individual gentamicins by fermentation, as starting materials for semisynthesis.
3. Gentamicin and gentamicin C1 in the treatment of complicated urinary tract infections: comparative study of efficacy, tolerance, and pharmacokinetics
P G Welling, A Mosegaard, P O Madsen Antimicrob Agents Chemother . 1975 Mar;7(3):328-32. doi: 10.1128/AAC.7.3.328.
The clinical efficacy, patient tolerance, and pharmacokinetics of gentamicin and the single component gentamicin C(1) were studied after single and multiple doses in elderly male patients. Patient tolerance was extremely good at the dose levels used. There was some evidence of renal function impairment due to repeated intramuscular doses of gentamicin, but not gentamicin C(1). The antibiotics were equally effective against the organisms present in the urine of these patients. The pharmacokinetics of the two antibiotic forms were similar, although gentamicin C(1) appeared to have a larger distribution space.
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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 ╳
