Apramycin (also known as Ai3-29795; Nebramycin II) is a broad spectrum and aminoglycoside class of antibiotic, which binds to the deep groove of the RNA. Apramycin consumption at farm level is most probably driving the increasing occurrence of apramycin/gentamicin cross-resistant [aac(3)-IV positive] E. coli in diseased pigs and healthy finishers at slaughter. Apramycin inhibits A. pleuropneumoniae FMV 87-682 with MIC50 of 8 mg/L. Apramycin (1/4 MIC) in the medium decreases the rate of growth of the bacterial strains tested, and causes the postantibiotic effect (PAE) up to 5 hours.

Physicochemical Properties

Molecular Formula	C21H43N5O15S
Molecular Weight	637.66
Exact Mass	637.247
Elemental Analysis	C, 39.56; H, 6.80; N, 10.98; O, 37.64; S, 5.03
CAS #	65710-07-8
Related CAS #	65710-07-8 (sulfate);37321-09-8;
PubChem CID	3081544
Appearance	White to yellow solid powder
Density	1.56
Boiling Point	949.8ºC at 760 mmHg
Melting Point	>168ºC (dec.)
Flash Point	528.2ºC
LogP	3.825
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	6
Heavy Atom Count	42
Complexity	841
Defined Atom Stereocenter Count	17
SMILES	S(=O)(=O)(O[H])O[H].O1[C@@]([H])([C@@]([H])(C([H])([H])[C@@]2([H])[C@@]1([H])[C@@]([H])([C@@]([H])([C@@]([H])(O[C@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)N([H])[H])O[H])O[H])O2)N([H])C([H])([H])[H])O[H])N([H])[H])O[C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])(C([H])([H])[C@]1([H])N([H])[H])N([H])[H])O[H])O[H]
InChi Key	WGLYHYWDYPSNPF-RQFIXDHTSA-N
InChi Code	InChI=1S/C21H41N5O11.H2O4S/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31;1-5(2,3)4/h5-21,26-32H,2-4,22-25H2,1H3;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-;/m1./s1
Chemical Name	(2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol sulfuric acid
Synonyms	Apramycin (sulfate); Apramycin sulphate; Apramycin Sulfate; Apramycin-Sulfate; ApramycinSulfate
HS Tariff Code	2934.99.03.00
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Aminoglycoside
ln Vitro	Apramycin consumption at farm level is most probably driving the increasing occurrence of apramycin/gentamicin cross-resistant [aac(3)-IV positive] E. coli in diseased pigs and healthy finishers at slaughter. Apramycin inhibits A. pleuropneumoniae FMV 87-682 with MIC50 of 8 mg/L. Apramycin (1/4 MIC) in the medium decreases the rate of growth of the bacterial strains tested, and causes the postantibiotic effect (PAE) up to 5 hours. Apramycin significantly reduces the haemolytic activity of A. pleuropneumoniae and affects the capsular material production of this isolate and of one isolate of P. multocida (type A). Apramycin induces translation errors, as assayed by incorporation of leucine, isoleucine and serine, although this effect occurs only to a limited extent, in cell-free systems from Escherichia coli programmed with poly(U). Apramycin inhibits the translocation step of protein synthesis both in vivo, in protoplasts of Bacillus megaterium, and in vitro, in cell-free systems from E. coli.
ln Vivo	Apramycin (225 mg/L) totally suppresses mortality and significantly reduces Salmonella excretion in comparison with non-treated chicks.
Animal Protocol	225 mg/L Chicks
References	[1]. J Antimicrob Chemother.2006 Jul;58(1):101-7. [2]. Int J Antimicrob Agents.1999 Aug;12(3):229-37. [3]. Immunopharmacol Immunotoxicol.1992;14(1-2):191-205.
Additional Infomation	Apramycin sulfate is a glycoside and an amino cyclitol.

Solubility Data

Solubility (In Vitro)	Water : 100~200 mg/mL(313.65 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 100 mg/mL (156.82 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication. Solubility in Formulation 2: PBS : 100 mg/mL (156.82 mM)  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.5682 mL	7.8412 mL	15.6823 mL
	5 mM	0.3136 mL	1.5682 mL	3.1365 mL
	10 mM	0.1568 mL	0.7841 mL	1.5682 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.