Synonym
Neamine sulfate; Neomycin A sulfate
IUPAC/Chemical Name
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol sulfate
InChi Key
UPUAISIJDDQCRN-SQAHNGQVSA-N
InChi Code
InChI=1S/C12H26N4O6.H2O4S/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20;1-5(2,3)4/h3-12,17-20H,1-2,13-16H2;(H2,1,2,3,4)/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-;/m1./s1
SMILES Code
NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O.OS(=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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
420.43
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 |
1: Yang ZJ, Concilio MG, Ramesh V, Zhang LH. Synthesis and Evaluation of Novel Neamine-Nucleoside Conjugates as Potential Antibiotic Targets for Escherichia coli 16S Ribosomal RNA. Methods Mol Biol. 2019;1870:151-163. doi: 10.1007/978-1-4939-8808-2_11. PMID: 30539553.
2: Swain J, El Khoury M, Flament A, Dezanet C, Briée F, Van Der Smissen P, Décout JL, Mingeot-Leclercq MP. Antimicrobial activity of amphiphilic neamine derivatives: Understanding the mechanism of action on Gram-positive bacteria. Biochim Biophys Acta Biomembr. 2019 Oct 1;1861(10):182998. doi: 10.1016/j.bbamem.2019.05.020. Epub 2019 May 31. PMID: 31153908.
3: Liu YP, Wu YL, Zhang XY, Hu GF, Wu YX. Neamine inhibits growth of pancreatic cancer cells in vitro and in vivo. J Huazhong Univ Sci Technolog Med Sci. 2016 Feb;36(1):82-87. doi: 10.1007/s11596-016-1546-2. Epub 2016 Feb 3. PMID: 26838745.
4: Liu Y, Zhang X, An S, Wu Y, Hu G, Wu Y. Pharmacokinetics of neamine in rats and anti-cervical cancer activity in vitro and in vivo. Cancer Chemother Pharmacol. 2015 Mar;75(3):465-74. doi: 10.1007/s00280-014-2658-7. Epub 2015 Jan 1. PMID: 25552400.
5: Kishimoto K, Yoshida S, Ibaragi S, Yoshioka N, Hu GF, Sasaki A. Neamine inhibits oral cancer progression by suppressing angiogenin-mediated angiogenesis and cancer cell proliferation. Anticancer Res. 2014 May;34(5):2113-21. PMID: 24778013; PMCID: PMC4757496
