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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H47O6.Na
Molecular Weight 538.691
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FUSIDATE SODIUM

SMILES

[Na+].C[C@@H]1[C@H](O)CC[C@@]2(C)[C@H]1CC[C@@]3(C)[C@H]2[C@H](O)C[C@H]4\C([C@H](C[C@]34C)OC(C)=O)=C(/CCC=C(C)C)C([O-])=O

InChI

InChIKey=HJHVQCXHVMGZNC-JCJNLNMISA-M
InChI=1S/C31H48O6.Na/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);/q;+1/p-1/b26-20-;/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-;/m0./s1

HIDE SMILES / InChI

Description

Fusidic acid is a anti-bacterial agent, initially isolated from Fusidium coccineum by Godtfredsen et al (Leo Pharma) in 1960. It is discussed that fusidic acid exerts its anti-microbial effect by inhibiting bacterial elongation factor G, thus suppressing the protein synthesis. Fusidic acid is widely used in Europe under the names Fucidin H(fusidic acid / hydrocortisone acetate), Fucidin (fusidic acid / sodium fusidate) and Fucicort (fusidic acid / betamethasone valerate) for the treatment of primary/secondary skin infections and inflammatory dermatoses.

CNS Activity

CNS Penetrant
2588
Curator's Comment: CNS penetration is low.

Originator

Approval Year

2013
589
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
FUCIDIN

Approved Use

For use in the treatment of primary and secondary skin infections caused by sensitive strains of Staphylococcus aureus, Streptococcusspp and Corynebacterium minutissimum. Primary skin infections that may be expected to respond to treatment with FUCIDIN OINTMENT (sodium fusidate) and CREAM (fusidic acid) include: impetigo contagiosa, erythrasma and secondary skin infections such as infected wounds and infected burns.
Curative
Approved
8583
FUCICORT

Approved Use

FUCICORT is indicated in inflammatory dermatoses where bacterial infection is present or likely to occur. Inflammatory dermatoses include atopic eczema, discoid eczema, seborrheic dermatitis, contact dermatitis, lichen simplex chronicus, psoriasis, discoid lupus erythematosus
PubMed

PubMed

TitleDatePubMed
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014-01
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013-12
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013-11
Fusidic acid is an effective treatment against Toxoplasma gondii and Listeria monocytogenes in vitro, but not in mice.
2013-11
Canine ocular thelaziosis caused by Thelazia callipaeda in Portugal.
2013-07
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010-12
Severe statin-induced rhabdomyolysis mimicking Guillain-Barré syndrome in four patients with diabetes mellitus treated with fusidic acid.
2010-06
Intracellular activity of antibiotics in a model of human THP-1 macrophages infected by a Staphylococcus aureus small-colony variant strain isolated from a cystic fibrosis patient: pharmacodynamic evaluation and comparison with isogenic normal-phenotype and revertant strains.
2009-04
A case of recurrent rapidly progressive lower limb weakness.
2008-07
Bacteremia and infective endocarditis caused by a non-daptomycin-susceptible, vancomycin-intermediate, and methicillin-resistant Staphylococcus aureus strain in Taiwan.
2008-03
Linezolid for the treatment of patients with endocarditis: a systematic review of the published evidence.
2006-08
Sideroblastic anaemia during fusidic acid treatment.
2004-05
Sideroblastic anaemia and fusidic acid.
2003-02
Inhibition of transport across the hepatocyte canalicular membrane by the antibiotic fusidate.
2002-07-01
[Cholestatic icterus induced by the administration of fusidic acid in a cirrhotic patient].
2002-06-29
Hypocalcaemia during fusidic acid therapy.
2002-02
In vitro susceptibility of Mycobacterium tuberculosis to fusidic acid.
2001-12
Antimycobacterial plant terpenoids.
2001-11
Acute renal failure in association with fusidic acid.
1997-06
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997-05
Anti-HIV activity of dideoxynucleosides, foscarnet and fusidic acid is potentiated by human leukocyte interferon in blood-derived macrophages.
1994-05-01
Acute renal failure following intravenous fusidic acid.
1993
Treatment of Crohn's disease with fusidic acid: an antibiotic with immunosuppressive properties similar to cyclosporin.
1992-08
Comparative in-vitro activities of ten fluoroquinolones and fusidic acid against Mycobacterium spp.
1990-09
Susceptibility of mycobacteria to fusidic acid.
1990-04
Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent.
1989-01
Suppression of HIV replication in vitro by fusidic acid parallels cell toxicity.
1989-01
Inhibition of HIV replication in vitro by fusidic acid.
1987-10-10
Fusidic acid-induced hyperbilirubinemia.
1987-08
Screening for new compounds with antiherpes activity.
1984-10
Staphylococcal septicaemia complicated by probable cloxacillin neurotoxicity and by jaundice induced by fusidic acid.
1983-04
Adverse reactions to intravenous administration of fusidic acid.
1981
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.
1973-09
Haematuria during methicillin therapy.
1971-07
Fusidic acid: a new antibiotic.
1962-03-10
Patents

Patents

06054711
5
20090131389
4
8933063
4
WO2007051468A2
4

Sample Use Guides

In Vivo Use Guide
A small amount of fucidin ointment(sodium fusidate) or cream (fusidic acid) should be applied to the lesion 3 or 4 times daily until favourable results are achieved. Futicort cream (fusidic acid / betamethasone valerate) is applied 2 times daily.
Route of Administration: Topical
In Vitro Use Guide
In vitro fusidic acid inhibited S. aureus (minimum inhibitory concentration [MIC], 0.25 ug/mL), Micrococcus luteus (MIC, 0.25–0.5 ug/mL), Corynebacterium spp. (MIC, 0.06–0.12 ug/mL), Moraxella catarrhalis (MIC, 0.06–0.12 ug/mL), and Neisseria meningitidis (MIC, 0.12–0.25 ug/mL).
Name Type Language
SODIUM FUSIDATE
EP   MART.  
Preferred Name English
FUSIDATE SODIUM
USAN   WHO-DD  
USAN  
Official Name English
Fusidate sodium [WHO-DD]
Common Name English
SQ 16360
Code English
FUCIDIN LEO
Brand Name English
FUCIDINE
Brand Name English
SODIUM FUSIDATE [EP MONOGRAPH]
Common Name English
SODIUM FUSIDATE [JAN]
Common Name English
FUSIDATE SODIUM [USAN]
Common Name English
FUSIDIC ACID, SODIUM SALT
Common Name English
29-NORDAMMARA-17(20),24-DIEN-21-OIC ACID, 16-(ACETYLOXY)-3,11-DIHYDROXY-, MONOSODIUM SALT, (3.ALPHA.,4.ALPHA.,8.ALPHA.,9.BETA.,11.ALPHA.,13.ALPHA.,14.BETA.,16.BETA.,17Z)-
Common Name English
ZN-6
Code English
SODIUM FUSIDATE [MART.]
Common Name English
Sodium 3?,11?,16?-trihydroxy-29-nor-8?,9?,13?,14?-dammara-17(20),24-dien-21-oate 16-acetate
Common Name English
SQ-16360
Code English
FUCIDIN
Brand Name English
FUSIDIC ACID SODIUM SALT [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
FDA ORPHAN DRUG 723519
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
FDA ORPHAN DRUG 400513
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
NCI_THESAURUS C52588
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
Code System Code Type Description
PUBCHEM
23672955
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
EVMPD
SUB12288MIG
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
SMS_ID
100000079317
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
212-030-3
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
MERCK INDEX
m5616
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY Merck Index
FDA UNII
J7P3696BCQ
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID9045552
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
DAILYMED
J7P3696BCQ
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
RXCUI
9874
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY RxNorm
CAS
751-94-0
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
ChEMBL
CHEMBL383466
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
DRUG BANK
DBSALT000340
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
NCI_THESAURUS
C65792
Created by admin on Mon Mar 31 17:35:24 GMT 2025 , Edited by admin on Mon Mar 31 17:35:24 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of FUSIDIC ACID
SUBSTANCE RECORD
Structure of FUSIDATE SODIUM
NIH
NCATS
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