Netilmicin Sulfate | CAS#56391-57-2 | aminoglycoside antibiotic

Netilmicin Sulfate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561029

CAS#: 56391-57-2

Description: Netilmicin Sulfate is a semisynthetic, water soluble aminoglycoside antibiotic obtained by chemical modification of sisomicin. It is active against both Gram-positive and Gram-negative bacteria, including strains which are resistant to other aminoglycosides.

Chemical Structure

Netilmicin Sulfate

CAS# 56391-57-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561029
Name: Netilmicin Sulfate
CAS#: 56391-57-2
Chemical Formula: C21H43N5O11S
Exact Mass: 0.00
Molecular Weight: 573.659
Elemental Analysis: C, 43.97; H, 7.56; N, 12.21; O, 30.68; S, 5.59

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 260
25mg	USD 610
50mg	USD 680
100mg	USD 1200
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Appearance: Solid powder

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

More Info:

Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	1.0	1.39
	Water	194.0	338.18

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.

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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.

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Netilmicin Sulfate featured