Grundinformationen
- 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- Summenformel
- C31H48O6
- Durchschnittliche Molmasse
- 516,7 g/mol
- Monoisotopische Masse
- 516,34508925
Überblick
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.
Namen und Bezeichner
- Bevorzugter 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
- Lokaler Name
- Fusidinsure
- Englischer Name
- Fusidic Acid
- Summenformel
- C31H48O6
- Molmasse
- 516.71
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
6990-06-3- PubChem CID
- 3000226
- DTXSID
DTXSID0023086- ChEMBL
CHEMBL374975- ChEBI
CHEBI:29013- UNII
- 59XE10C19C
- EC Number
- 230-256-0
- Nikkaji
- J16.166G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,5
- Polarare Oberfläche (TPSA)
- 104 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 37
- Formalladung
- 0
- Komplexität
- 994
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 190 · 190-192°C
- Siedepunkt
- 521.49 °C · 521.49°C (rough estimate)
- Dichte
- 1.0389 · 1.0389 (rough estimate)
- Dampfdruck
- 0 · 0-0Pa at 25℃
- Brechungsindex
- 1.489 · 1.4890 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- Practically insoluble in water, freely soluble in ethanol (96 per cent)
- pka
- 5.35 in · pK: 5.35 in water
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Wasserlöslichkeit
- 2.376 · 2.376-525000μg/L at 25℃
- Merck
- 14 · 14,4317
- Stabilität
- 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 Datenbank
- 6990 · 6990-06-3(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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%)
Toxikologische Informationen
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
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29419000
- RTECS-Nr.
- RC1350000
- risk_code
- 22
- Toxizität
- LD50 in mice (g/kg): 1.2 s.c.; 1.5 orally (Godtfredsen)
- hazard_code
- Xn
- safety_code
- 36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
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
Verwendung und Herstellung
UsesUse (kg; approx.) in Germany (2009): >500
Anwendungen
BeschreibungFusidic 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.
Darstellung
synthetischeFusidic acid (FA) is a tetracyclic triterpenoids isolated from fungi, which was first isolated from Fusidium coccineum in 1960 [1].
Anbieter100 Anbieter
北京华美互利生物化工010-56205725 · [email protected]
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湖北恒化科技有限公司18064208139 · [email protected]
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TCI AMERICA800-4238616 · [email protected]
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TCI Europe320-37350700 · [email protected]
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广州市慈铭生物科技有限公司020-38082199,29065168,38082986,29878298,29866629,4000192398
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池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
铜陵恒优生物科技有限公司021-50426030 13856289449;13124863828 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
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成都艾娜华化学制剂有限公司028-86612776; 13699069380 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
Target molecule Corp.857-239-0968 · [email protected]
沧州恩科医药科技有限公司0317-5296180 15533709196 · [email protected]
成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
南京罗迈美生物科技有限公司[email protected]
Ergänzende Hinweise
DefinitionChEBI: A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.
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