Fusidic Acid| Fucidin | SQ-16603 | CAS#6990-06-3 | Protein Synthesis Inhibitor

MedKoo Cat#: 328808 | Name: Fusidic Acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Anhydrous Fusidic Acid, also known as Fucidin and SQ-16603, is a protein synthesis inhibitor used to treat bacterial infections. It acts by inhibiting translocation during protein synthesis.

Chemical Structure

Fusidic Acid

CAS#6990-06-3

Theoretical Analysis

MedKoo Cat#: 328808

Name: Fusidic Acid

CAS#: 6990-06-3

Chemical Formula: C31H48O6

Exact Mass: 516.3451

Molecular Weight: 516.72

Elemental Analysis: C, 72.06; H, 9.36; O, 18.58

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 350.00	2 Weeks
1g	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Anhydrous Fusidic Acid; Fucidin; Fucidine; SQ-16603; CEM-102; SQ 16603; CEM 102; SQ16603; CEM102

IUPAC/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

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

SMILES Code

C[C@@H](C1CC[C@]([C@@](C[C@@H]/2OC(C)=O)3C)4C)[C@H](O)CC[C@]1(C)[C@]4([H])[C@H](O)C[C@@]3([H])C2=C(C(O)=O)/CC/C=C(C)\C

Appearance

Solid powder

Purity

>97% (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

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Fusidic acid (Fusidate) a bacteriostatic antibiotic produced from the Fusidium coccineum fungus, belongs to the class of steroids.

In vitro activity:

Fusidic acid treatment decreased the number of T. gondii plaques in a dose-dependent manner, with a half maximal inhibitory concentration (IC50) of ~4 μg/ml (Fig. 1). Fusidic acid inhibited a T. gondii mutant with a dramatic reduction in TgEFG levels, highlighting that either TgEFG levels are in excess of that required for tissue culture growth or that TgEFG is not the only target of fusidic acid. Overall, these results show that fusidic acid is effective against T. gondii in tissue culture, and suggest that it might be a useful treatment against T. gondii during animal infection. Reference: Parasitol Res. 2013 Nov; 112(11): 3859–3863. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4096717/

In vivo activity:

Untreated EAM animals exhibited discolored areas over the cardiac surface (mean macroscopic score 1.8) and severe inflammatory lesions were observed microscopically in the myocardium (Fig. 1a). These lesions were composed of marked infiltration by inflammatory cells including lymphocytes, macrophages and neutrophils. In contrast, in the EAM rats treated with fusidine from days 0 to 10 (group A) there was little inflammatory cells infiltration in the myocardium and cardiac myocytes were well preserved (Fig. 1b). In late treatment group B, only focal infiltration by inflammatory cells was detected and necrosis limited to cardiac myocytes that were in contact with the inflammatory cells (Fig. 1f). The mean microscopic score was still markedly lower than that of untreated animals (Table 1). Reference: Pharmacol Res. 2005 Dec;52(6):491-6. https://pubmed.ncbi.nlm.nih.gov/16216521/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	193.53

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 516.72 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

Formulation protocol:

1. Park E, Kim DK, Kim CS, Kim JS, Kim S, Chun HS. Protective effects of fusidic acid against sodium nitroprusside-induced apoptosis in C6 glial cells. Neuroreport. 2019 Dec 10;30(17):1222-1229. doi: 10.1097/WNR.0000000000001354. PMID: 31651708. 2. Payne AJ, Neal LM, Knoll LJ. Fusidic acid is an effective treatment against Toxoplasma gondii and Listeria monocytogenes in vitro, but not in mice. Parasitol Res. 2013 Nov;112(11):3859-63. doi: 10.1007/s00436-013-3574-1. Epub 2013 Aug 16. PMID: 23949312; PMCID: PMC4096717. 3. Milenkovć M, Arsenović-Ranin N, Vucićević D, Bufan B, Stojić-Vukanić Z. Fusidin ameliorates experimental autoimmune myocarditis in rats by inhibiting TNF-alpha production. Pharmazie. 2007 Jun;62(6):445-8. PMID: 17663192. 4. Milenković M, Vucićević D, Milosavljević P, Ranin NA, Vukanić ZS, Colić M. Suppression of experimental autoimmune myocarditis by sodium fusidate (fusidin). Pharmacol Res. 2005 Dec;52(6):491-6. doi: 10.1016/j.phrs.2005.08.001. Epub 2005 Oct 7. PMID: 16216521.

In vitro protocol:

In vivo protocol:

1. Milenkovć M, Arsenović-Ranin N, Vucićević D, Bufan B, Stojić-Vukanić Z. Fusidin ameliorates experimental autoimmune myocarditis in rats by inhibiting TNF-alpha production. Pharmazie. 2007 Jun;62(6):445-8. PMID: 17663192. 2. Milenković M, Vucićević D, Milosavljević P, Ranin NA, Vukanić ZS, Colić M. Suppression of experimental autoimmune myocarditis by sodium fusidate (fusidin). Pharmacol Res. 2005 Dec;52(6):491-6. doi: 10.1016/j.phrs.2005.08.001. Epub 2005 Oct 7. PMID: 16216521.

1: 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. doi: 10.1101/cshperspect.a025437. Review. PubMed PMID: 26729758. 2: Chan JF, Ma MK, Chan GS, Chan GC, Choi GK, Chan KH, Cheng VC, Chan KW, Choy BY, Yuen KY. Rapid reduction of viruria and stabilization of allograft function by fusidic acid in a renal transplant recipient with JC virus-associated nephropathy. Infection. 2015 Oct;43(5):577-81. doi: 10.1007/s15010-015-0721-x. Epub 2015 May 6. PubMed PMID: 25944568. 3: Zhang S, Wang S, Zhang Q, Chang CW, Zhan J. Three new fusidic acid derivatives and their antibacterial activity. Bioorg Med Chem Lett. 2015 May 1;25(9):1920-4. doi: 10.1016/j.bmcl.2015.03.033. Epub 2015 Mar 20. PubMed PMID: 25824664; PubMed Central PMCID: PMC4408258. 4: Ellington MJ, Reuter S, Harris SR, Holden MT, Cartwright EJ, Greaves D, Gerver SM, Hope R, Brown NM, Török ME, Parkhill J, Köser CU, Peacock SJ. Emergent and evolving antimicrobial resistance cassettes in community-associated fusidic acid and meticillin-resistant Staphylococcus aureus. Int J Antimicrob Agents. 2015 May;45(5):477-84. doi: 10.1016/j.ijantimicag.2015.01.009. Epub 2015 Feb 19. PubMed PMID: 25769787; PubMed Central PMCID: PMC4415905. 5: Lapham K, Novak J, Marroquin LD, Swiss R, Qin S, Strock CJ, Scialis R, Aleo MD, Schroeter T, Eng H, Rodrigues AD, Kalgutkar AS. Inhibition of Hepatobiliary Transport Activity by the Antibacterial Agent Fusidic Acid: Insights into Factors Contributing to Conjugated Hyperbilirubinemia/Cholestasis. Chem Res Toxicol. 2016 Oct 4. PubMed PMID: 27676153. 6: Yu F, Liu Y, Lu C, Lv J, Qi X, Ding Y, Li D, Huang X, Hu L, Wang L. Dissemination of fusidic acid resistance among Staphylococcus aureus clinical isolates. BMC Microbiol. 2015 Oct 13;15:210. doi: 10.1186/s12866-015-0552-z. PubMed PMID: 26463589; PubMed Central PMCID: PMC4604626. 7: Bachoumas K, Fiancette M, Lascarrou JB, Lacherade JC, Leclair F, Reignier J. Fatal rhabdomyolysis following the co-prescription of fusidic acid and pravastatin. Med Mal Infect. 2015 Oct;45(10):417-9. doi: 10.1016/j.medmal.2015.09.006. Epub 2015 Oct 21. PubMed PMID: 26472060. 8: Chen HJ, Hung WC, Lin YT, Tsai JC, Chiu HC, Hsueh PR, Teng LJ. A novel fusidic acid resistance determinant, fusF, in Staphylococcus cohnii. J Antimicrob Chemother. 2015 Feb;70(2):416-9. doi: 10.1093/jac/dku408. Epub 2014 Oct 13. PubMed PMID: 25313205. 9: Gurel MS, Naycı S, Turgut AV, Bozkurt ER. Comparison of the effects of topical fusidic acid and rifamycin on wound healing in rats. Int Wound J. 2015 Feb;12(1):106-10. doi: 10.1111/iwj.12060. Epub 2013 Mar 13. PubMed PMID: 23489386. 10: Hung WC, Chen HJ, Lin YT, Tsai JC, Chen CW, Lu HH, Tseng SP, Jheng YY, Leong KH, Teng LJ. Skin Commensal Staphylococci May Act as Reservoir for Fusidic Acid Resistance Genes. PLoS One. 2015 Nov 18;10(11):e0143106. doi: 10.1371/journal.pone.0143106. eCollection 2015. PubMed PMID: 26581090; PubMed Central PMCID: PMC4651549.