基本情報
- CAS
6990-06-3- 標準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- 分子式
- C31H48O6
- 平均分子量
- 516.7 g/mol
- 単同位体質量
- 516.34508925
概要
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.
名称と識別子
- 優先名称
- 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
- 現地名
- フシジン酸
- 英語名
- Fusidic Acid
- 分子式
- C31H48O6
- 分子量
- 516.71
名称と別名
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
名称をさらに表示
ラマイシン(8α,9β,13α,14β,Z)-16β-アセチルオキシ-3α,11α-ジヒドロキシ-29-ノルダンマラ-17(20),24-ジエン-21-酸(4α,8α,9β,13α,14β,17Z)-16β-(アセチルオキシ)-3α,11α-ジヒドロキシ-29-ノル-5α-ダンマラ-17(20),24-ジエン-21-酸フシジン酸フジジンフシド酸(4S,8α,9β,13α,14β,17Z)-16β-アセトキシ-3α,11α-ジヒドロキシ-29-ノル-5α-ダンマラ-17(20),24-ジエン-21-酸(17Z)-3α,11α-ジヒドロキシ-16β-アセトキシ-5α-フシダ-17(20),24-ジエン-21-酸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
データベース識別子
- CAS
6990-06-3- PubChem CID
- 3000226
- DTXSID
DTXSID0023086- ChEMBL
CHEMBL374975- ChEBI
CHEBI:29013- UNII
- 59XE10C19C
- EC Number
- 230-256-0
- Nikkaji
- J16.166G
物性
構造計算による物性
- XLogP
- 5.5
- 極性表面積
- 104 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 6
- 回転可能結合数
- 6
- 重原子数
- 37
- 形式電荷
- 0
- 複雑度
- 994
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 190 · 190-192°C
- 沸点
- 521.49 °C · 521.49°C (rough estimate)
- 比旋光度
- 20 · D20 -9° (chloroform)
- 比重(密度)
- 1.0389 · 1.0389 (rough estimate)
- 蒸気圧
- 0 · 0-0Pa at 25℃
- 屈折率
- 1.489 · 1.4890 (estimate)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- 水にほとんど溶けず、エタノールに溶けやすい (96%)
- 酸解離定数(Pka)
- 5.35 in · pK: 5.35 in water
- 外見
- Solid
- 色
- ホワイトからオフホワイト
- 水溶解度
- 2.376 · 2.376-525000μg/L at 25℃
- Merck
- 14 · 14,4317
- 安定性
- 吸湿性
- 主な用途
- 医薬品（低分子化合物）
- 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 データベース
- 6990 · 6990-06-3(CAS DataBase Reference)
化学的性質
化学的特性White Solid
安全と法規制
GHS分類
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.
危険有害性情報
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%)
毒性情報
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
安全データ
- wgk
- 3
- rtecs
- RC1350000
- 毒性
- LD50 in mice (g/kg): 1.2 s.c.; 1.5 orally (Godtfredsen)
- hs_code
- 29419000
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 36
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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
用途と製造
UsesUse (kg; approx.) in Germany (2009): >500
応用分野
解説C31H48O6(516.69)．Fusidium coccineumの産生する抗生物質．耐性ぶどう球菌感染症に効力がある．生合成的にはプロトラノスタン誘導体と考えられる．"融点192～193 ℃．[α]20D－9°(クロロホルム)．λmax 210，240 nm(ε 9400，9900)．エタノール，アセトン，クロロホルム，ピリジン，ジオキサンに可溶．タンパク質合成系の伸長因子に結合して，タンパク質合成を阻害する．LD50 1.2 g/kg(マウス，経口)．[CAS 6990-06-3]森北出版「化学辞典（第2版）
説明Fusidic 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.
調製方法
製造方法Fusidic acid (FA) is a tetracyclic triterpenoids isolated from fungi, which was first isolated from Fusidium coccineum in 1960 [1].
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補足説明
定義ChEBI: A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.
関連反応
2 件
化合物ノート
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