Netilmicin

Structural formula
General
Non-proprietary name	Netilmicin
other names	[2,6-diamino-2,3,4,6-tetradeoxy-α- D -glycero-hex-4-enopyranosyl- (1 → 4)] - [3-deoxy-4- C- methyl-3-methylamino -β-l-arabinopyranosyl- (1 → 6)] - 2-deoxy- N 1-ethyl- D -streptamine (2 R , 3 R , 4 R , 5 R ) -2 - [(1 S , 2 S , 3 R , 4 S , 6 R ) -4-amino-3 - ((2 S , 3 R ) -3 -amino-6-aminomethyl-3,4-dihydro-2 H -pyran-2-yloxy) -6-ethylamino-2-hydroxycyclohexyloxy] -5-methyl-4-methylaminotetrahydropyran-3,5-diol
Molecular formula	C 21 H 41 N 5 O 7
External identifiers / databases
CAS number 56391-56-1 EC number 260-146-8 ECHA InfoCard 100.054.661 PubChem 441306 ChemSpider 38195 DrugBank DB00955 Wikidata Q2553496
Drug information
ATC code	S01 AA23 J01 GB07
Drug class	Aminoglycoside antibiotics
properties
Molar mass	475.58 g mol −1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Netilmicin sulfate danger H and P phrases H: 312-332-360 P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Netilmicin is an antibiotic belonging to the group of aminoglycoside antibiotics . Due to its very low oral bioavailability , the active ingredient is only suitable for intravenous or topical use .

The spectrum of activity includes numerous gram-negative bacteria, including those with gentamicin resistance. Netilmicin is less effective than other aminoglycosides against Pseudomonas aeruginosa . According to some studies, the toxicity (inner ear, kidney) is somewhat less pronounced than with tobramycin or gentamicin.

Netilmicin sulfate , a white to yellowish white, very hygroscopic powder, which is very easily soluble in water and practically insoluble in acetone and ethanol 96%, is used pharmaceutically .

Netilmicin is produced semi-synthetically from sisomicin (4,5-dehydrogentamicin-C _1a ), which is obtained from Micromonospora species by fermentation .

Individual evidence

1. ↑ There is not yet a harmonized classification for this substance . A labeling of D-streptamine, O-3-deoxy-4-C-methyl-3- (methylamino) -β-l-arabinopyranosyl- (1 → 6) -O- [2, is shown, which is derived from a self-classification by the distributor 6-diamino-2,3,4,6-tetradeoxy-α-d-glycero-hex-4-enopyranosyl- (1 → 4)] -2-deoxy-N1-ethyl-, sulfate (2: 5) (salt ) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 15, 2020.
2. ^ GC McCormick, E. Weinberg, RJ Szot, E. Schwartz: Comparative ototoxicity of netilmicin, gentamicin, and tobramycin in cats . In: Toxicology and Applied Pharmacology . tape 77 , no. 3 , March 15, 1985, ISSN  0041-008X , p. 479-489 , doi : 10.1016 / 0041-008X (85) 90188-7 .
3. ↑ GH Hottendorf, D Barnett, LL Gordon, EF Christensen, H Madissoo: Nonparallel nephrotoxicity dose-response curves of aminoglycosides. In: Antimicrobial Agents and Chemotherapy . tape 19 , no. 6 , June 1981, ISSN  0066-4804 , pp. 1024-1028 , PMID 7271271 , PMC 181601 (free full text).
4. ↑ JM Bernstein, GJ Gorse, MI Linzmayer, PS Pegram, RD Levin: Relative efficacy and toxicity of netilmicin and tobramycin in oncology patients . In: Archives of Internal Medicine . tape 146 , no. December 12 , 1986, ISSN  0003-9926 , pp. 2329-2334 , PMID 3535719 .
5. ↑ External identifiers or database links for netilmicin sulfate : CAS number: 56391-57-2, EC number: 260-147-3, ECHA InfoCard: 100.054.662 , PubChem : 62115 , ChemSpider : 55951 , Wikidata : Q27288755 . Other name: 2-Deoxy-6- O - [3-deoxy-4- C -methyl-3- (methylamino) -β- L -arabinopyranosyl] -4- O - (2,6-diamino-2,3, 4,6-tetradeoxy-α- D -glycero-hex-4-enopyranosyl) -1- N -ethyl- D -streptamine sulfate. Molecular formula: C ₄₂ H ₉₂ N ₁₀ O ₃₄ S ₅ . Molar mass: 1442 g mol ⁻¹ .
6. ↑ ^{a b} Netilmicinsulfat (Ph.Eur.), European Pharmacopoeia , 8th edition, Grundwerk 2014, p. 4290 f.