Fusidic Acid (Fucidin; SQ-16603), a bacteriostatic antibiotic isolated from the Fusidium coccineum fungus, is a protein synthesis inhibitor of the steroidal class used to treat bacterial infections. It acts by inhibiting translocation during protein synthesis.
Physicochemical Properties
| Molecular Formula | C31H48O6 |
| Molecular Weight | 516.7092 |
| Exact Mass | 516.345 |
| Elemental Analysis | C, 72.06; H, 9.36; O, 18.58 |
| CAS # | 6990-06-3 |
| Related CAS # | Fusidic acid sodium salt;751-94-0;Fusidic acid-d6 |
| PubChem CID | 3000226 |
| Appearance | Solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 635.6±55.0 °C at 760 mmHg |
| Melting Point | 190-192ºC |
| Flash Point | 197.7±25.0 °C |
| Vapour Pressure | 0.0±4.2 mmHg at 25°C |
| Index of Refraction | 1.558 |
| LogP | 6.41 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 37 |
| Complexity | 994 |
| Defined Atom Stereocenter Count | 10 |
| SMILES | O([H])[C@]1([H])C([H])([H])[C@@]2([H])/C(=C(/C(=O)O[H])\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 | IECPWNUMDGFDKC-CDSRIIBBSA-N |
| InChi Code | InChI=1S/C31H48O6/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)/b26-20-/t18-,21?,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1 |
| Chemical Name | (Z)-2-((3R,4S,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-enoic acid |
| Synonyms | Anhydrous Fusidic Acid; Fucidin; Fucidine; SQ-16603; CEM-102; SQ 16603; CEM 102; SQ16603; CEM102 |
| 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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | Bacterial |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion Sodium fusidic acid tablets have a 91% oral bioavailability. Absorption of the film-coated tablets is complete when compared to a solution, however oral absorption is variable. Oral fusidic acid hemihydrate (suspension) achieved a 22.5% bioavailability in pediatric patients following a 20 milligram/kilogram dose. Metabolism / Metabolites Metabolites include dicarboxylic ester/acid, 3-keto fusidic acid, hydroxy fusidic acid, glucuronide fusidic acid and a glycol metabolite. Biological Half-Life Approximately 5 to 6 hours in adults. |
| 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. Protein Binding 97 to 99% |
| 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. |
| Additional Infomation |
Fusidic acid is a steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum. It has a role as a protein synthesis inhibitor, an EC 2.7.1.33 (pantothenate kinase) inhibitor and an Escherichia coli metabolite. It is a 3alpha-hydroxy steroid, an 11alpha-hydroxy steroid, a sterol ester, a steroid acid, an alpha,beta-unsaturated monocarboxylic acid and a steroid antibiotic. It is a conjugate acid of a fusidate. It derives from a hydride of a 5alpha-cholestane. An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed) It acts by inhibiting translocation during protein synthesis. It is often used topically in creams and eyedrops but is available in systemic formulations including tablets and injections. Fusidic acid has been reported in Stilbella aciculosa, Microsporum canis, and other organisms with data available. Fusidic Acid is a bacteriostatic antibiotic derived from the fungus Fusidium coccineum and used as a topical medication to treat skin infections. Fusidic acid acts as a bacterial protein synthesis inhibitor by preventing the turnover of elongation factor G (EF-G) from the ribosome. Fusidic acid is effective primarily on gram-positive bacteria. 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: Fusidate Sodium (active moiety of). Drug Indication For the treatment of bacterial infections. Mechanism of Action Fusidic acid works by interfering with bacterial protein synthesis, specifically by preventing the translocation of the elongation factor G (EF-G) from the ribosome. It also can inhibit chloramphenicol acetyltransferase enzymes. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~193.53 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.84 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 (4.84 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: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (4.84 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9353 mL | 9.6766 mL | 19.3532 mL | |
| 5 mM | 0.3871 mL | 1.9353 mL | 3.8706 mL | |
| 10 mM | 0.1935 mL | 0.9677 mL | 1.9353 mL |