Oxacillin sodium monohydrate is an antibiotic, similar to Flucloxacillin, that may be utilized to treat drug-resistant Staphylococcus aureus infections.

Physicochemical Properties

Molecular Formula	C19H20N3NAO6S
Molecular Weight	441.4334
Exact Mass	441.097
CAS #	7240-38-2
Related CAS #	Oxacillin sodium salt;1173-88-2;Oxacillin;66-79-5
PubChem CID	23694213
Appearance	Typically exists as solid at room temperature
Boiling Point	686.8ºC at 760 mmHg
Melting Point	188ºC
Flash Point	369.2ºC
Index of Refraction	205 ° (C=1, H2O)
LogP	0.992
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Heavy Atom Count	30
Complexity	687
Defined Atom Stereocenter Count	3
SMILES	S1C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C(=O)[O-])N2C([C@]([H])([C@@]12[H])N([H])C(C1=C(C([H])([H])[H])ON=C1C1C([H])=C([H])C([H])=C([H])C=1[H])=O)=O.[Na+].O([H])[H]
InChi Key	ZVIYWUUZWWBNMB-VICXVTCVSA-M
InChi Code	InChI=1S/C19H19N3O5S.Na.H2O/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22;;/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1
Chemical Name	sodium;(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrate
Synonyms	oxacillin sodium monohydrate; Oxacillin sodium hydrate; Bactocill; OXACILLIN SODIUM; Oxacillin sodium salt monohydrate; Cryptocillin; Penstapho
HS Tariff Code	2934.99.9001
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

ln Vitro	Four clinical isolates of S. aureus that carry the mecA gene (SA 1306, SA 1326, SA 1552, and SA 4666) show MIC values of less than 1 μg/mL for oxacillin[1]. Tol+ and Tol-strains undergo lysis when exposed to oxacillin (5 μg/mL) for 0-90 min[2].
Cell Assay	Cell Line: Cells of S. aureus which had grown for six to eight generations in [14C]glycerol. Concentration: 5 μg/mL. Incubation Time: 0, 30, 60, 90 min. Result: The rates at which the cells lysed allowed for the easy separation of Tol+ isolates from Tol- isolates.
References	[1]. Antimicrob Agents Chemother. 2008 Nov;52(11):3905-8. [2]. Antimicrob Agents Chemother. 1979 Aug;16(2):134-40. [3]. J Antibiot (Tokyo). 1976 Apr;29(4):460-5.
Additional Infomation	Oxacillin sodium monohydrate is a hydrate. It contains an oxacillin sodium. Oxacillin Sodium is the sodium salt form of oxacillin, a semisynthetic penicillinase-resistant and acid-stable penicillin with an antimicrobial activity. Oxacillin binds to penicillin-binding proteins in the bacterial cell wall, thereby blocking the synthesis of peptidoglycan, a critical component of the bacterial cell wall. This leads to inhibition of cell growth and causes cell lysis. An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections. See also: Oxacillin Sodium (annotation moved to).

Solubility Data

Solubility (In Vitro)

H2O : ≥ 100 mg/mL (~226.54 mM) DMSO : ~50 mg/mL (~113.27 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.66 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 3: 110 mg/mL (249.19 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.2654 mL	11.3268 mL	22.6536 mL
	5 mM	0.4531 mL	2.2654 mL	4.5307 mL
	10 mM	0.2265 mL	1.1327 mL	2.2654 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.