| Identification | More | [Name]
Fusidine | [CAS]
6990-06-3 | [Synonyms]
(3ALPHA,4ALPHA,8ALPHA,9BETA,11ALPHA,13ALPHA,14BETA,16BETA,17Z)-16-(ACETYLOXY)-3,11-DIHYDROXY-29-NORDAMMARA-17(20),24-DIEN-21-OIC ACID
FUSIDIC ACID
24-dien-21-oicacid,16-(acetyloxy)-3,11-dihydroxy-29-nordammara-17(20(3-al
4-alpha,8-alpha,9-beta,11-alpha,13-alpha,14-beta,16-beta,17z)-ph
ramycin
sq16603
FUSIDIC ACID IP
(3a,4a,8a,9b,11a,13a,14b,16b,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid
Flucidin
Fucithalmic
Fusidinic acid
NSC 56192
29-Nordammara-17(20),24-dien-21-oic acid, 16-(acetyloxy)-3,11-dihydroxy-, (3.alpha.,4.alpha.,8.alpha.,9.beta.,11.alpha.,13.alpha.,14.beta.,16.beta.,17Z)-
16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid
Fusidine
(3alpha,4alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17Z)-16-(acetyloxy)-3,11-dihydroxy-29-Nordammara-17(20),24-dien-21-oic acid
Pyzidieb acid
(3a,4a,8a,9,11a,13a,147,167,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid
(4S,8α,9β,13α,14β,17Z)-16β-Acetoxy-3α,11α-dihydroxy-29-nor-5α-dammara-17(20),24-dien-21-oic acid
(8α,9β,13α,14β,Z)-16β-Acetyloxy-3α,11α-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid | [EINECS(EC#)]
230-256-0 | [Molecular Formula]
C31H48O6 | [MDL Number]
MFCD00865135 | [Molecular Weight]
516.71 | [MOL File]
6990-06-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
190-192°C | [alpha ]
D20 -9° (chloroform) | [Boiling point ]
521.49°C (rough estimate) | [density ]
1.0389 (rough estimate) | [vapor pressure ]
0-0Pa at 25℃ | [refractive index ]
1.4890 (estimate) | [storage temp. ]
2-8°C | [solubility ]
Practically insoluble in water, freely soluble in ethanol (96 per cent) | [form ]
neat | [pka]
pK: 5.35 in water | [color ]
White to Off-White | [optical activity]
-920 (c 1, CHCl3) | [Water Solubility ]
2.376-525000μg/L at 25℃ | [Usage]
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 | [λmax]
204nm(H2O)(lit.) | [Merck ]
14,4317 | [Stability:]
Hygroscopic | [LogP]
2.68-6.75 at 20℃ | [CAS DataBase Reference]
6990-06-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [RTECS ]
RC1350000 | [HS Code ]
29181990 | [Toxicity]
LD50 in mice (g/kg): 1.2 s.c.; 1.5 orally (Godtfredsen) |
| Hazard Information | Back Directory | [Hazard]
Moderately toxic inhibitor of translocation
during protein synthesis. | [Description]
Fusidic acid was found in the culture broth of a fungus imperfectus, Fusidium coccineum, by Leo in 1962. It has a steroid struc ture but shows no hormonal activity.
| [Chemical Properties]
White Solid | [Uses]
antibacterial | [Uses]
Fusidic 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. | [Definition]
ChEBI: A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum. | [Brand name]
Fucidine (Bristol-Myers Squibb). | [Biological Activity]
Fusidic acid shows very strong activity against Staphy lococcus aureus and weak activity against other gram-positive bacteria and gram-negative cocci and Mycobacterium.
| [Biochem/physiol Actions]
Fusidic acid is a tetracyclic triterpenoid with antibiotic activity against Gram-positive bacteria. It is derived from Fusidium coccineum. It shows its activity against anaerobes, corynebacterial, Nocardia, and Neisseria species. Fusidic acid exhibits therapeutic effects against Staphylococcal infections, skin infections. |
| Questions And Answer | Back Directory | [Mode of action]
Fusidic acid forms a stable complex with an elongation factor (EF-G) involved in translocation and with guanosine triphosphate (GTP), which provides energy for the translocation process. One round of translocation occurs, with hydrolysis of GTP, but the fusidic acid–EF-G–GDP complex cannot dissociate from the ribosome, thereby blocking further chain elongation and leaving peptidyl-tRNA in the P site.
Although protein synthesis in Gram-negative bacilli–and, indeed, mammalian cells–is susceptible to fusidic acid, the antibiotic penetrates poorly into these cells and the spectrum of action is virtually restricted to Gram-positive bacteria, notably staphylococci.
| [Structure]
Fusidic acid 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. Fusidic acid has an asteroid-type structure, as do some other antibiotics produced by fungi, but does not possess any steroid activity. The structure is thought to be responsible for the steroid-like high penetration.
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