Synonym
Netilmicin Sulfate, Netilmicin-Sulfate; Sch-20569
IUPAC/Chemical Name
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-Amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol sulfate
InChi Key
PQHZSWZPVGHDEZ-UIQTUGNFSA-N
InChi Code
InChI=1S/C21H41N5O7.H2O4S/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20;1-5(2,3)4/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3;(H2,1,2,3,4)/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+;/m1./s1
SMILES Code
O[C@H]1[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@@H]3[C@H](N)CC=C(CN)O3)[C@@H](N)C[C@H]2NCC)OC[C@@](O)(C)[C@@H]1NC.O=S(O)(O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Netilmicin (sulfate) (SCH-20569 (sulfate)) is an active aminoglycoside antibiotic.
In vitro activity:
The aim of this work was to examine the impact of netilmicin on melanogenesis in cultured normal human melanocytes (HEMa-LP). The WST-1 assay was used to detect netilmicin cytotoxic effect. Netilmicin induced concentration-dependent loss in melanocytes viability.
Reference: Acta Pol Pharm. 2013 Sep-Oct;70(5):803-8. https://pubmed.ncbi.nlm.nih.gov/24147358/
In vivo activity:
The total phospholipid contents of the mitochondrial, microsomal, brush border membrane and basolateral membrane fractions of netilmicin-injected rats were higher by approximately 10% than the respective fractions of control rats and each fraction exhibited a significant increase of one or more of the four phospholipids elevated in the renal cortical homogenate and in the lysosomal fraction. The data indicate that the myeloid body is the primary source of the lysosomal phospholipidosis induced by netilmicin which provides support for the hypothesis that the lysosomal phospholipidosis is secondary to aminoglycoside-induced inhibition of phospholipid degradation.
Reference: J Pharmacol Exp Ther. 1985 Dec;235(3):810-9. https://pubmed.ncbi.nlm.nih.gov/3001278/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
1.0 |
1.39 |
| Water |
194.0 |
338.18 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
573.66
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Wrześniok D, Beberok A, Otreba M, Buszman E. Netilmicin-induced modulation of melanogenesis in HEMa-LP melanocytes. Acta Pol Pharm. 2013 Sep-Oct;70(5):803-8. PMID: 24147358.
2. Bonfiglio G, Scuderi AC, Russo G. Netilmicin: in vitro activity, time-kill evaluation and postantibiotic effect on microorganisms isolated from ocular infections. Chemotherapy. 2001 Mar-Apr;47(2):117-22. doi: 10.1159/000048510. PMID: 11173813.
3. Josepovitz C, Farruggella T, Levine R, Lane B, Kaloyanides GJ. Effect of netilmicin on the phospholipid composition of subcellular fractions of rat renal cortex. J Pharmacol Exp Ther. 1985 Dec;235(3):810-9. PMID: 3001278.
In vitro protocol:
1. Wrześniok D, Beberok A, Otreba M, Buszman E. Netilmicin-induced modulation of melanogenesis in HEMa-LP melanocytes. Acta Pol Pharm. 2013 Sep-Oct;70(5):803-8. PMID: 24147358.
2. Bonfiglio G, Scuderi AC, Russo G. Netilmicin: in vitro activity, time-kill evaluation and postantibiotic effect on microorganisms isolated from ocular infections. Chemotherapy. 2001 Mar-Apr;47(2):117-22. doi: 10.1159/000048510. PMID: 11173813.
In vivo protocol:
1. Josepovitz C, Farruggella T, Levine R, Lane B, Kaloyanides GJ. Effect of netilmicin on the phospholipid composition of subcellular fractions of rat renal cortex. J Pharmacol Exp Ther. 1985 Dec;235(3):810-9. PMID: 3001278.
1: Wrześniok D, Buszman E, Grzegorczyk M, Grzegorczyk A, Hryniewicz T. Impact of metal ions on netilmicin-melanin interaction. Acta Pol Pharm. 2012 Jan-Feb;69(1):41-5. PubMed PMID: 22574505.
2: Kolate A, Kore G, Lesimple P, Baradia D, Patil S, Hanrahan JW, Misra A. Polymer assisted entrapment of netilmicin in PLGA nanoparticles for sustained antibacterial activity. J Microencapsul. 2015;32(1):61-74. doi: 10.3109/02652048.2014.944951. Epub 2014 Sep 19. PubMed PMID: 25238317.
3: Joseph A, Patel S, Rustum A. Development and validation of a RP-HPLC method for the estimation of netilmicin sulfate and its related substances using charged aerosol detection. J Chromatogr Sci. 2010 Aug;48(7):607-12. PubMed PMID: 20819288.
4: Takeichi Y, Miki K, Uyama M. [Morphological change in the retina after injection of calcium and netilmicin sulfate in the rabbit vitreous body]. Nippon Ganka Gakkai Zasshi. 1994 Feb;98(2):150-6. Japanese. PubMed PMID: 8109459.
5: Craig WA, Gudmundsson S, Reich RM. Netilmicin sulfate: a comparative evaluation of antimicrobial activity, pharmacokinetics, adverse reactions and clinical efficacy. Pharmacotherapy. 1983 Nov-Dec;3(6):305-15. Review. PubMed PMID: 6361701.
6: Chaudry IA, Bruey KP, Hurlburt LE, Oden EM. Compatibility of netilmicin sulfate injection with commonly used intravenous injections and additives. Am J Hosp Pharm. 1981 Nov;38(11):1737-42. PubMed PMID: 7304628.
7: Sandal G, Akbay Ş, Ozen M. Acquired Bartter-like syndrome association with netilmicin therapy in an extremely low birth weight infant. Ren Fail. 2014 Feb;36(1):123-5. doi: 10.3109/0886022X.2013.832861. Epub 2013 Sep 24. PubMed PMID: 24059693.
8: Santos Navarro M, Zarzuelo Castañeda A, López FG, Sánchez Navarro A, Arévalo M, Lanao JM. Pharmacokinetic parameters of netilmicin and protective effect of piperacillin regarding nephrotoxicity caused by netilmicin. Eur J Drug Metab Pharmacokinet. 1998 Apr-Jun;23(2):143-7. PubMed PMID: 9725472.
9: Takeichi Y, Miki K, Uyama M. [Morphological changes in the retina following one-shot injection of netilmicin sulfate into the vitreous]. Nippon Ganka Gakkai Zasshi. 1991 Jul;95(7):669-77. Japanese. PubMed PMID: 1927747.
10: LeFrock JL, Carr BB, Blias F, Schell RF, Dematteo C, Tillotson JR. A comparative study of gentamicin and netilmicin in the treatment of gram-negative infections. Drug Intell Clin Pharm. 1985 Apr;19(4):309-15. PubMed PMID: 3891278.
