Basic information
- CAS
6990-06-3- Standard SMILES
CC(=O)O[C@H]1C[C@@]2(C)[C@@H](C[C@@H](O)[C@H]3[C@@]4(C)CC[C@@H](O)[C@@H](C)[C@@H]4CC[C@@]32C)/C1=C(\CCC=C(C)C)C(=O)O- InChIKey
IECPWNUMDGFDKC-MZJAQBGESA-N- Molecular formula
- C31H48O6
- Average molar mass
- 516.7 g/mol
- Monoisotopic mass
- 516.34508925
Overview
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 Escherichia coli metabolite and an EC 2.7.1.33 (pantothenate kinase) inhibitor. It is an 11alpha-hydroxy steroid, a steroid antibiotic, a sterol ester, a 3alpha-hydroxy steroid, a steroid acid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a fusidate. It derives from a hydride of a 5alpha-cholestane.
Names & identifiers
- Preferred name
- Fusidic Acid
- IUPAC
- (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
- English name
- Fusidic Acid
- Molecular formula
- C31H48O6
- Molecular weight
- 516.71
Names & synonyms
fusidic acid6990-06-3RamycinFucidic acidFucidin acidFucithalmicTakstaAcide fusidiqueAcido fusidicoAcidum fusidicumAnhydrous Fusidic Acid(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
Show more names
FusidineFusidinic acid(Z)-2-((3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-Acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyldodecahydro-1H-cyclopenta[a]phenanthren-17(2H,10H,14H)-ylidene)-6-methylhept-5-enoic acidFusidic acid CRS29-NordaMMara-17(20),24-dien-21-oicacid, 16-(acetyloxy)-3,11-dihydroxy-, (3a,4a,8a,9b,11a,13a,14b,16b,17Z)-(3ALPHA,4ALPHA,8ALPHA,9BETA,11ALPHA,13ALPHA,14BETA,16BETA,17Z)-16-(ACETYLOXY)-3,11-DIHYDROXY-29-NORDAMMARA-17(20),24-DIEN-21-OIC ACIDsq16603Fuzidin
Fucidin cavijectNSC-56192SQ-1660359XE10C19CDTXSID0023086CHEBI:2901329-Nordammara-17(20),24-dien-21-oic acid, 16-(acetyloxy)-3,11-dihydroxy-, (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17Z)-Acid, Fusidic
Database identifiers
- CAS
6990-06-3- PubChem CID
- 3000226
- DTXSID
DTXSID0023086- ChEMBL
CHEMBL374975- ChEBI
CHEBI:29013- UNII
- 59XE10C19C
- EC Number
- 230-256-0
- Nikkaji
- J16.166G
Properties
Computed structural properties
- XLogP
- 5.5
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 994
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Antibiotics
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Solubility5.21e-03 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antibacterial Agents; Anti-Infective Agents; Protein Synthesis Inhibitors
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point192.5 °C
Physical DescriptionSolid
Dissociation Constants5.35
Collision Cross Section235.6 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 190 · 190-192°C
- Boiling point
- 521.49 °C · 521.49°C (rough estimate)
- alpha
- 20 · D20 -9° (chloroform)
- Density
- 1.0389 · 1.0389 (rough estimate)
- vapor pressure
- 0 · 0-0Pa at 25℃
- refractive index
- 1.489 · 1.4890 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Practically insoluble in water, freely soluble in ethanol (96 per cent)
- pka
- 5.35 in · pK: 5.35 in water
- form
- Solid
- color
- White to Off-White
- optical activity
- -920 · -920 (c 1, CHCl3)
- Water Solubility
- 2.376 · 2.376-525000μg/L at 25℃
- λmax
- 204 nm · 204nm(H2O)(lit.)
- Merck
- 14 · 14,4317
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- IECPWNUMDGFDKC-MZJAQBGESA-N
- SMILES
- [H][C@@]12CC[C@@]3(C)[C@@]([H])([C@H](O)C[C@@]4([H])\C([C@H](C[C@]34C)OC(C)=O)=C(/CC\C=C(\C)C)C(O)=O)[C@@]1(C)CC[C@@H](O)[C@H]2C
- LogP
- 2.68 · 2.68-6.75 at 20℃
- CAS DataBase Reference
- 6990 · 6990-06-3(CAS DataBase Reference)
- FDA UNII
- 59 XE10C19C · 59XE10C19C
- ATC code
- 6 AX01,D09AA02,J01XC01,S01AA13 · D06AX01,D09AA02,J01XC01,S01AA13
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312+P330-P501
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 36 · 36
- WGK Germany
- 3 · 3
- RTECS
- 1350000 · RC1350000
- HS Code
- 29419000 · 29419000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 in · LD50 in mice (g/kg): 1.2 s.c.; 1.5 orally (Godtfredsen)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (54.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 119 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
REACH registered substance: Fusidic acid (EC: 230-256-0)
Fusidic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (54.6%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Fusidic Acid
DILI Positive
Oral, Topical, Intravenous, optahlmic
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- rtecs
- RC1350000
- hs_code
- 29419000
- Toxicity
- LD50 in mice (g/kg): 1.2 s.c.; 1.5 orally (Godtfredsen)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312+P330-P501
Chemistry & industry
Pharmacology
ATC Code
D06AX01
S - Sensory organs
D - Dermatologicals
D - Dermatologicals
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding97 to 99%
PharmacodynamicsFusidic acid is a bacteriostatic antibiotic and helps prevent bacterial growth while the immune system clears the infection.
Mechanism of ActionFusidic 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.
Biological Half-LifeApproximately 5 to 6 hours in adults.
Metabolism/MetabolitesMetabolites include dicarboxylic ester/acid, 3-keto fusidic acid, hydroxy fusidic acid, glucuronide fusidic acid and a glycol metabolite.
MeSH Pharmacological Classification
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Substances that inhibit the growth or reproduction of BACTERIA.
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.
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >500
Applications
DescriptionFusidic Acid: An Inhibitor of the Elongation Factor G (EF-G)Fusidic acid is a steroidal antibiotic compound derived from the fungus Fusidium coccineum. The elongation factor G (EF-G) catalyzes the translocation of the tRNA and mRNA down the ribosome at the end of each round of polypeptide elongation. Fusidic acid binds to EF-G, preventing its release from the ribosome, thus stalling bacterial protein synthesis. Fusidic acid is mainly notable for its activity against staphylococci, whether or not they are resistant to methicillin and related penicillins. Fusidic acid was found in the culture broth of a fungus imperfectus, Fusidium coccineum, by Leo in 1962. It has a steroid structure but shows no hormonal activity.
Usesantibacterial
UsesFusidic acid is a bacteriostatic antibiotic. Fusidic Acid 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. Dyes and metabolites.
Preparation methods
PreparationFusidic acid (FA) is a tetracyclic triterpenoids isolated from fungi, which was first isolated from Fusidium coccineum in 1960 [1].
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Additional notes
DefinitionChEBI: A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.
Related reactions
2 records
Compound notes
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