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MedKoo Cat#: 329855 | Name: Neomycin sulfate
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Description:

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

Neomycin is an aminoglycoside antibiotic found in many topical medications such as creams, ointments, and eyedrops. The discovery of neomycin dates back to 1949. It was discovered in the lab of Selman Waksman. Neomycin belongs to aminoglycoside class of antibiotics that contain two or more aminosugars connected by glycosidic bonds.

Chemical Structure

Neomycin sulfate
Neomycin sulfate
CAS#1405-10-3 (sulfate)

Theoretical Analysis

MedKoo Cat#: 329855

Name: Neomycin sulfate

CAS#: 1405-10-3 (sulfate)

Chemical Formula: C23H52N6O25S3

Exact Mass: 614.3123

Molecular Weight: 908.87

Elemental Analysis: C, 30.40; H, 5.77; N, 9.25; O, 44.01; S, 10.58

Price and Availability

Size Price Availability Quantity
25g USD 90.00 Ready to ship
50g USD 150.00 Ready to ship
100g USD 225.00 Ready to ship
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Related CAS #
55298-68-5 (palmitate) 1406-04-8 (undecylenate) 119-04-0 (free base) 1405-10-3 (sulfate) 4146-30-9 (B sulfate)
Synonym
Neomycin; Framycetin; Neomycin B; Mycifradin; Soframycin;
IUPAC/Chemical Name
(2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol trisulfate
InChi Key
KWBUARAINLGYMG-JGMIRXPNSA-N
InChi Code
InChI=1S/C23H46N6O13.3H2O4S/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22;3*1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;3*(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;;;/m1.../s1
SMILES Code
O[C@@H]1[C@@H](CN)O[C@H](O[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]4N)[C@H]3O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@H]1O.O=S(O)(O)=O.O=S(O)(O)=O.O=S(O)(O)=O
Appearance
Solid powder
Purity
>90% (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
Certificate of Analysis
View CoA: current batch, Lot# CMC80921
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Neomycin sulfate, an aminoglycoside antibiotic, exerts antibacterial activity and is a known phospholipase C (PLC) inhibitor.
In vitro activity:
To examine the effect of antibiotics on plaque formation of strain Nancy of coxsackievirus B3 (CVB3-Nancy), a monolayer of HeLa cells were infected that had been pretreated or not with 1 mg/ml of an antibiotic cocktail consisting of vancomycin, ampicillin, neomycin, and streptomycin. Following adsorption for 30 min, the inoculum was removed, and an agar overlay with or without antibiotics was added. Treatment with vancomycin, ampicillin, or streptomycin alone did not confer the large-plaque phenotype (Fig. 1A), but treatment with neomycin was sufficient for the large plaque phenotype (Fig. 1B). Lower concentrations of neomycin were also sufficient for large-plaque formation (Fig. 1B).Neomycin treatment increased plaque size of type 3 Dearing reovirus, a doublestranded RNA virus (Fig. 1D). Plaque size was quantified and found that when cells were exposed to neomycin, CVB3-Nancy plaques were 63-fold larger than in untreated cells and reovirus plaques were 2.6-fold larger than in untreated cells, but there was no significant effect on poliovirus plaque size (Fig. 1E). Overall, these data indicate that treatment with neomycin is capable of increasing plaque size CVB3-Nancy and reovirus but not poliovirus. Neomycin treatment did not alter viral attachment, translation, or replication. However, it was found that the positive charge of neomycin and other positively charged compounds enhanced viral diffusion by overcoming the negative inhibitory effect of sulfated polysaccharides present in agar overlays. Neomycin and the positively charged compound protamine also enhanced plaque formation of reovirus. Reference: mSphere. 2019 Jan-Feb; 4(1): e00632-18. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6382971/
In vivo activity:
This study in the rats established the effect of a broad spectrum and poorly absorbed antibiotic, neomycin sulfate on the toxicity of vicine. The results showed extreme decrease in mortality rate in the group pretreated with neomycin. Hemoglobin (Hb) concentration, hematocrit (Hct) value, and red blood cells (RBCs) count were significantly decreased after injection of vicine and the improvement of these values in the group pretreated with neomycin. The same results were observed in white blood cells (WBCs). The results showed a significant decrease in glucose level and returned to normal in group pretreated with neomycin. Glutathione (GSH) was significantly decreased in the vicine group and returned to normal value in the group pretreated with neomycin. Lipid peroxide (TBARs) was significantly increased in the group treated with vicine and neomycin pretreated group decreased to the normal level. Glucose-6phosphate dehydrogenase (G6-PD) activity was significantly decreased and returned to normal level in rats pretreated with neomycin. Serum protein and globulin were significantly decreased but serum albumin showed insignificant decrease in vicine and neomycin groups compared to control. Alanine aminotransferase (ALT) and aspartate aminotransferase (AST) were significantly decreased in the vicine group. The group pretreated with neomycin showed significantly increased activities of AST and ALT compared with vicine group. In conclusion, neomycin pretreatment of rats injected with glycoside vicine decreased to a great extent of its toxic and mortality effects and is useful in favism and hemolytic anemia. Reference: J Toxicol. 2013;2013:913128. https://pubmed.ncbi.nlm.nih.gov/23840205/
Solvent mg/mL mM
Solubility
H2O 31.0 34.10
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 908.87 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.

Recalculate based on batch purity %
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. Woods Acevedo MA, Erickson AK, Pfeiffer JK. The Antibiotic Neomycin Enhances Coxsackievirus Plaque Formation. mSphere. 2019 Feb 20;4(1):e00632-18. doi: 10.1128/mSphere.00632-18. PMID: 30787120; PMCID: PMC6382971. 2. Raghavan D, Starcher BC, Vyavahare NR. Neomycin binding preserves extracellular matrix in bioprosthetic heart valves during in vitro cyclic fatigue and storage. Acta Biomater. 2009 May;5(4):983-92. doi: 10.1016/j.actbio.2008.11.004. Epub 2008 Nov 27. PMID: 19091637; PMCID: PMC2702722. 3. Arbid MS, Koriem KM, Asaad GF, Megahed HA. Effect of the antibiotic neomycin on the toxicity of the glycoside vicine in rats. J Toxicol. 2013;2013:913128. doi: 10.1155/2013/913128. Epub 2013 Jun 12. PMID: 23840205; PMCID: PMC3694484. 4. Tsai MC. Effect of neomycin on post-tetanic twitch tension of the mouse diaphragm preparation. Br J Pharmacol. 1987 Apr;90(4):625-33. doi: 10.1111/j.1476-5381.1987.tb11214.x. PMID: 3580702; PMCID: PMC1917201.
In vitro protocol:
1. Woods Acevedo MA, Erickson AK, Pfeiffer JK. The Antibiotic Neomycin Enhances Coxsackievirus Plaque Formation. mSphere. 2019 Feb 20;4(1):e00632-18. doi: 10.1128/mSphere.00632-18. PMID: 30787120; PMCID: PMC6382971. 2. Raghavan D, Starcher BC, Vyavahare NR. Neomycin binding preserves extracellular matrix in bioprosthetic heart valves during in vitro cyclic fatigue and storage. Acta Biomater. 2009 May;5(4):983-92. doi: 10.1016/j.actbio.2008.11.004. Epub 2008 Nov 27. PMID: 19091637; PMCID: PMC2702722.
In vivo protocol:
1. Arbid MS, Koriem KM, Asaad GF, Megahed HA. Effect of the antibiotic neomycin on the toxicity of the glycoside vicine in rats. J Toxicol. 2013;2013:913128. doi: 10.1155/2013/913128. Epub 2013 Jun 12. PMID: 23840205; PMCID: PMC3694484. 2. Tsai MC. Effect of neomycin on post-tetanic twitch tension of the mouse diaphragm preparation. Br J Pharmacol. 1987 Apr;90(4):625-33. doi: 10.1111/j.1476-5381.1987.tb11214.x. PMID: 3580702; PMCID: PMC1917201.
1: Elliott JF, Abbas M, Hull P, de Gannes G, Toussi R, Milani A. Decreasing Rates of Neomycin Sensitization in Western Canada. J Cutan Med Surg. 2016 Sep;20(5):446-52. doi: 10.1177/1203475415623512. Epub 2015 Dec 23. Review. PubMed PMID: 26700538. 2: Leise MD, Poterucha JJ, Kamath PS, Kim WR. Management of hepatic encephalopathy in the hospital. Mayo Clin Proc. 2014 Feb;89(2):241-53. doi: 10.1016/j.mayocp.2013.11.009. Epub 2014 Jan 8. Review. PubMed PMID: 24411831; PubMed Central PMCID: PMC4128786. 3: Zhu GQ, Shi KQ, Huang S, Wang LR, Lin YQ, Huang GQ, Chen YP, Braddock M, Zheng MH. Systematic review with network meta-analysis: the comparative effectiveness and safety of interventions in patients with overt hepatic encephalopathy. Aliment Pharmacol Ther. 2015 Apr;41(7):624-35. doi: 10.1111/apt.13122. Epub 2015 Feb 13. Review. PubMed PMID: 25684317. 4: Cohen PR. Follicular contact dermatitis revisited: A review emphasizing neomycin-associated follicular contact dermatitis. World J Clin Cases. 2014 Dec 16;2(12):815-21. doi: 10.12998/wjcc.v2.i12.815. Review. PubMed PMID: 25516854; PubMed Central PMCID: PMC4266827. 5: Ellul MA, Gholkar SA, Cross TJ. Hepatic encephalopathy due to liver cirrhosis. BMJ. 2015 Aug 11;351:h4187. doi: 10.1136/bmj.h4187. Review. PubMed PMID: 26265724. 6: Marie C, Petri WA Jr. Amoebic dysentery. BMJ Clin Evid. 2013 Aug 30;2013. pii: 0918. Review. PubMed PMID: 23991750; PubMed Central PMCID: PMC3758071. 7: Schaefer P, Baugh RF. Acute otitis externa: an update. Am Fam Physician. 2012 Dec 1;86(11):1055-61. Review. PubMed PMID: 23198673. 8: Daneman N, Sarwar S, Fowler RA, Cuthbertson BH; SuDDICU Canadian Study Group. Effect of selective decontamination on antimicrobial resistance in intensive care units: a systematic review and meta-analysis. Lancet Infect Dis. 2013 Apr;13(4):328-41. doi: 10.1016/S1473-3099(12)70322-5. Epub 2013 Jan 25. Review. PubMed PMID: 23352693. 9: Jawaro T, Yang A, Dixit D, Bridgeman MB. Management of Hepatic Encephalopathy: A Primer. Ann Pharmacother. 2016 Jul;50(7):569-77. doi: 10.1177/1060028016645826. Epub 2016 Apr 28. Review. PubMed PMID: 27126547. 10: McGarry GW. Recurrent epistaxis in children. BMJ Clin Evid. 2013 Oct 30;2013:0311. Review. PubMed PMID: 24172703; PubMed Central PMCID: PMC3812896. 11: Cash BD. Emerging role of probiotics and antimicrobials in the management of irritable bowel syndrome. Curr Med Res Opin. 2014 Jul;30(7):1405-15. doi: 10.1185/03007995.2014.908278. Epub 2014 Apr 14. Review. PubMed PMID: 24666019. 12: Görsch I, Loth C, Haritoglou C. [Chalazion - diagnosis and therapy]. MMW Fortschr Med. 2016 Jun 23;158(12):52-5. doi: 10.1007/s15006-016-8447-y. Review. German. PubMed PMID: 27324006. 13: Mohammad RA, Regal RE, Alaniz C. Combination therapy for the treatment and prevention of hepatic encephalopathy. Ann Pharmacother. 2012 Nov;46(11):1559-63. doi: 10.1345/aph.1R146. Epub 2012 Oct 23. Review. PubMed PMID: 23092866. 14: Park SR, Park JW, Ban YH, Sohng JK, Yoon YJ. 2-Deoxystreptamine-containing aminoglycoside antibiotics: recent advances in the characterization and manipulation of their biosynthetic pathways. Nat Prod Rep. 2013 Jan;30(1):11-20. doi: 10.1039/c2np20092a. Review. PubMed PMID: 23179168. 15: Sundar S, Chakravarty J. Leishmaniasis: an update of current pharmacotherapy. Expert Opin Pharmacother. 2013 Jan;14(1):53-63. doi: 10.1517/14656566.2013.755515. Epub 2012 Dec 21. Review. PubMed PMID: 23256501. 16: Burden-Teh E, Wootton CI, Williams HC. Can a simple outpatient-based treatment be used to treat cutaneous leishmaniasis in young children? A Critically Appraised Topic. Br J Dermatol. 2015 Apr;172(4):861-6. doi: 10.1111/bjd.13496. Review. PubMed PMID: 25354137. 17: Murai A, Kitahara K, Okumura S, Kobayashi M, Horio F. Oral antibiotics enhance antibody responses to keyhole limpet hemocyanin in orally but not muscularly immunized chickens. Anim Sci J. 2016 Feb;87(2):257-65. doi: 10.1111/asj.12424. Epub 2015 Aug 24. Review. PubMed PMID: 26304689. 18: Dat AD, Poon F, Pham KB, Doust J. Aloe vera for treating acute and chronic wounds. Cochrane Database Syst Rev. 2012 Feb 15;(2):CD008762. doi: 10.1002/14651858.CD008762.pub2. Review. PubMed PMID: 22336851. 19: Gluud LL, Vilstrup H, Morgan MY. Non-absorbable disaccharides versus placebo/no intervention and lactulose versus lactitol for the prevention and treatment of hepatic encephalopathy in people with cirrhosis. Cochrane Database Syst Rev. 2016 May 6;(5):CD003044. doi: 10.1002/14651858.CD003044.pub4. Review. PubMed PMID: 27153247. 20: Iakobson LM. [International standardization of the neomycin B reference preparation and the composition of neomycin used in medical practice in different countries (brief review of data from WHO)]. Antibiotiki. 1971 Jul;16(7):667-70. Review. Russian. PubMed PMID: 4945582.