Fusidic Acid - Moligand™, ≥98% , Elongation factor G inhibitor, CAS No.6990-06-3, Elongation factor G inhibitor

CAS: 6990-06-3 Cat. No.: F134821 Molecular Weight: 516.71 EC Number: 230-256-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

fusidic acid | Q-201141 | (2Z)-2-[(17Z)-16beta-acetoxy-3alpha,11alpha-dihydroxy-4alpha,8alpha,10,14beta-tetramethyl-5alpha,9beta,13alpha-gonan-17-ylidene]-6-methylhept-5-enoic acid | 59XE10C19C | GTPL10815 | Acido fusidico | 3.alpha.,16.beta.-Trihydroxy-2

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Fusidic acid is bacteriostatic antibiotic that only works on gram-positive bacteria. It limits the growth of bacteria by inhibiting bacterial protein synthesis in a number of ways. It binds to the ribosome-elongation factor G complex, thereby inhibiti.
A bacteriostatic antibiotic that only works on gram-positive bacteria.

Specifications

Synonyms

fusidic acid | Q-201141 | (2Z)-2-[(17Z)-16beta-acetoxy-3alpha, 11alpha-dihydroxy-4alpha, 8alpha, 10, 14beta-tetramethyl-5alpha, 9beta, 13alpha-gonan-17-ylidene]-6-methylhept-5-enoic acid | 59XE10C19C | GTPL10815 | Acido fusidico | 3.alpha., 16.beta.-Trihydroxy-2

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Suppresses nitric oxide lysis of pancreatic islet cells. Inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G factor and translocation of peptidyl-tRNA.

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Elongation factor G inhibitor

Purity

≥98%

Product Properties

• ALogP: 5.5

Names and Identifiers

• Pubchem Sid: 488194132
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488194132
• Canonical Smiles: CC1C2CCC3(C(C2(CCC1O)C)C(CC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)O)C
• IUPAC Name: (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
• InChIKey: IECPWNUMDGFDKC-MZJAQBGESA-N
• 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
• Isomeric SMILES: C[C@H]1[C@@H]2CC[C@]3([C@H]([C@]2(CC[C@H]1O)C)[C@@H](C[C@@H]\4[C@@]3(C[C@@H](/C4=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)O)C
• WGK Germany: 3
• RTECS: RC1350000
• Alternate CAS: 6990-06-3,751-94-0 (hydrochloride salt)
• NSC Number: 56192
• MeSH Entry Terms: Acid, Fusidic;Fucithalmic;Fusidate Sodium;Fusidate, Silver;Fusidate, Sodium;Fusidic Acid;Fusidic Acid, Sodium Salt;Fusidin;Silver Fusidate;Sodium Fusidate;Sodium, Fusidate;Stanicide
• Molecular Weight: 516.71
• Reaxy-Rn: 36058977
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=36058977&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Steroid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Steroid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Steroid esters
• Alternative Parents: 3-alpha-hydroxysteroids 11-alpha-hydroxysteroids Medium-chain fatty acids Methyl-branched fatty acids Hydroxy fatty acids Unsaturated fatty acids Dicarboxylic acids and derivatives Secondary alcohols Cyclic alcohols and derivatives Carboxylic acid esters Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Steroid ester - 3-hydroxysteroid - 3-alpha-hydroxysteroid - 11-hydroxysteroid - 11-alpha-hydroxysteroid - Hydroxysteroid - Medium-chain fatty acid - Branched fatty acid - Methyl-branched fatty acid - Hydroxy fatty acid - Fatty acyl - Fatty acid - Unsaturated fatty acid - Dicarboxylic acid or derivatives - Cyclic alcohol - Carboxylic acid ester - Secondary alcohol - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Organic oxide - Alcohol - Organooxygen compound - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
• External Descriptors: Prostostane and fusidane triterpenoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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ALB Tchem Serum albumin (2651 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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Homo sapiens (32628 Activities)

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MKN-45 (2102 Activities)

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U-87 MG (3946 Activities)

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HEK293 (82097 Activities)

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HeLa (62764 Activities)

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ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

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Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Salmonella typhimurium (15756 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Staphylococcus intermedius (187 Activities)

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Acinetobacter baumannii (41033 Activities)

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Neisseria gonorrhoeae (1461 Activities)

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Neisseria meningitidis (411 Activities)

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Escherichia coli (133304 Activities)

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Chlamydia trachomatis (699 Activities)

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Streptococcus pyogenes (16140 Activities)

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Clostridioides difficile (2968 Activities)

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Corynebacterium xerosis (106 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Enterococcus faecalis (29875 Activities)

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Streptomyces coelicolor (161 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Toxoplasma gondii (4585 Activities)

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Oryctolagus cuniculus (11301 Activities)

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Mus musculus (284745 Activities)

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Staphylococcus saprophyticus (562 Activities)

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CHO (4503 Activities)

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CHO-K1 (1115 Activities)

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RAW264.7 (28094 Activities)

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Vero (26788 Activities)

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Staphylococcus lugdunensis (349 Activities)

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Mammaliicoccus sciuri (248 Activities)

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Brain (1 Activities)

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Plasma (328 Activities)

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Serum (58 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in alcohol (1:5), chloroform (1:4), ether (1:60), and ethanol (50 mg/ml). Insoluble in water.
• Sensitivity: Heat sensitive；Moisture sensitive
• Specific Rotation[α]: -7° (C=1,CHCl3)
• Melt Point(°C): 193 °C
• Molecular Weight: 516.700 g/mol
• XLogP3: 5.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 516.345 Da
• Monoisotopic Mass: 516.345 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 994.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Haohua Liu, Yue Cai, Yuteng Chu, Xiaojie Yu, Fuhang Song, Hong Wang, Huawei Zhang, Xuanrong Sun.  (2022)  Formulation of Chrysomycin A Cream for the Treatment of Skin Infections.  MOLECULES,  27  (14): (4613).  [PMID:35889485] [10.3390/molecules27144613]

2. Xueer Zhou, Meng Wang, Yue Wang, Jianhong Liu, Chaoliang Zhang, Jian Pan, Qiang Peng.  (2024)  Albumin as a functional carrier solubilizing and facilitating fusidic acid transmembrane delivery into Gram-negative bacteria.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39059524] [10.1016/j.ijbiomac.2024.134019]

3. Yue Cai, Xinrui Zhang, Wentao Hu, Fuhang Song, Hong Wang, Huawei Zhang, Xuanrong Sun.  (2024)  Enhancing transdermal delivery of chrysomycin A for the treatment of cutaneous melanoma and MRSA infections using Skin-Penetrating Peptide-Functionalized deformable liposomes.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,      [PMID:39722374] [10.1016/j.ijpharm.2024.125130]

4. Jianhong Liu, Xuyang Lai, Yuanhong Li, Zhuohang Yu, Xuan Wang, Chaoliang Zhang, Qiang Peng.  (2024)  Reversing the Natural Drug Resistance of Gram-Negative Bacteria to Fusidic Acid via Forming Drug–Phospholipid Complex.  Bioengineering-Basel,  11  (2): (177).  [PMID:38391663] [10.3390/bioengineering11020177]

5. Xiaxia Fan, Dan Guo, Songtao Li, Jinmiao Tian, Chaotong Zhang, Zhuoyu Li.  (2025)  Fusidic Acid Reverses Chemoresistance in Breast Cancer via Targeting DDX6 to Downregulate GSK-3β/β-Catenin Signaling.  Advanced Science,      [PMID:40757496] [10.1002/advs.202504680]

6. Yi Jintao, Fu Nani, Zhong Wenhui, Liu Xia, Zhou Anqi, Li Xun.  (2026)  A CQDs-doped europium-DPA framework for fluorescence and colorimetric dual-mode sensing of amoxicillin and ciprofloxacin.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:41718751] [10.1007/s00216-026-06405-5]