Physicochemical Properties
Molecular Formula | C31H47NAO6 |
Molecular Weight | 538.69 |
Exact Mass | 538.327 |
Elemental Analysis | C, 69.12; H, 8.79; Na, 4.27; O, 17.82 |
CAS # | 751-94-0 |
Related CAS # | Fusidic acid;6990-06-3 |
PubChem CID | 23672955 |
Appearance | White to off-white solid powder |
Boiling Point | 635.6ºC at 760 mmHg |
Flash Point | 197.6ºC |
LogP | 4.331 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 6 |
Rotatable Bond Count | 6 |
Heavy Atom Count | 38 |
Complexity | 1000 |
Defined Atom Stereocenter Count | 10 |
SMILES | [Na+].O([H])[C@]1([H])C([H])([H])[C@@]2([H])/C(=C(/C(=O)[O-])\C([H])([H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H])/[C@]([H])(C([H])([H])[C@]2(C([H])([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]3([H])[C@]([H])(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])[C@@]21[H])O[H])OC(C([H])([H])[H])=O |
InChi Key | HJHVQCXHVMGZNC-JCJNLNMISA-M |
InChi Code | InChI=1S/C31H48O6.Na/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32;/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36);/q;+1/p-1/b26-20-;/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-;/m0./s1 |
Chemical Name | sodium (Z)-2-((3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-ylidene)-6-methylhept-5-enoate |
Synonyms | Fusidate Sodium; CEM102; CEM 102; CEM-102 |
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
Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Fusidic acid is not approved for marketing in the United States by the U.S. Food and Drug Administration, but is available in other countries as topical and systemic dosage forms. Data on excretion of fusidic acid into breastmilk are quite old and not from a well-designed study, but levels in breastmilk after intravenous fusidic acid appear to be low. With topical products, ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking. Fusidic acid applied topically to the nipples appears to be relatively ineffective as a treatment for sore, cracked nipples. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk A small, randomized, unblinded trial of mothers with sore, cracked nipples was performed. Fusidic acid ointment applied to the nipples after each feeding was much less effective (36% vs 79%) than an oral antibiotic (cloxacillin or erythromycin for 10 days) in resolving the problem. Additionally, 43% of patients had no improvement with fusidic acid compared with 16% with oral antibiotics; 21% worsened with fusidic acid compared with 5% with oral antibiotics. |
References |
[1]. A Critical Review of the Properties of Fusidic Acid and Analytical Methods for Its Determination. Crit Rev Anal Chem. 2016;46(4):352-360. [2]. Fusidic acid is an effective treatment against Toxoplasma gondii and Listeria monocytogenes in vitro, but not in mice. Parasitol Res. 2013;112(11):3859-3863. [3]. Fernandes P. Fusidic Acid: A Bacterial Elongation Factor Inhibitor for the Oral Treatment of Acute and Chronic Staphylococcal Infections. Cold Spring Harb Perspect Med. 2016 Jan 4;6(1):a025437 |
Additional Infomation |
Fusidate Sodium is a sodium salt form of fusidic acid, a bacteriostatic antibiotic derived from the fungus Fusidium coccineum and used as a topical medication to treat skin infections. An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis. See also: Fusidic Acid (has active moiety). |
Solubility Data
Solubility (In Vitro) |
H2O : ≥ 100 mg/mL (~185.64 mM) DMSO : ≥ 100 mg/mL (~185.64 mM) |
Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.64 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 (4.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (4.64 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 4: 100 mg/mL (185.64 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 | 1.8564 mL | 9.2818 mL | 18.5636 mL | |
5 mM | 0.3713 mL | 1.8564 mL | 3.7127 mL | |
10 mM | 0.1856 mL | 0.9282 mL | 1.8564 mL |