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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+].[H][C@@]12C[C@@H](O)[C@@]3([H])[C@@]4(C)CC[C@@H](O)[C@@H](C)[C@]4([H])CC[C@]3(C)[C@@]1(C)C[C@H](OC(C)=O)\C2=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
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C31H47O6
Molecular Weight 515.7013
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 1
Optical Activity UNSPECIFIED

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
2554
Curator's Comment: CNS penetration is low.

Originator

Approval Year

2013
596
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 1.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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
8429
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
Fusidic acid: a new antibiotic.
1962 Mar 10
Haematuria during methicillin therapy.
1971 Jul
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.
1973 Sep
Adverse reactions to intravenous administration of fusidic acid.
1981
Staphylococcal septicaemia complicated by probable cloxacillin neurotoxicity and by jaundice induced by fusidic acid.
1983 Apr
Screening for new compounds with antiherpes activity.
1984 Oct
Fusidic acid-induced hyperbilirubinemia.
1987 Aug
Inhibition of HIV replication in vitro by fusidic acid.
1987 Oct 10
Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent.
1989 Jan
Suppression of HIV replication in vitro by fusidic acid parallels cell toxicity.
1989 Jan
Susceptibility of mycobacteria to fusidic acid.
1990 Apr
Comparative in-vitro activities of ten fluoroquinolones and fusidic acid against Mycobacterium spp.
1990 Sep
Treatment of Crohn's disease with fusidic acid: an antibiotic with immunosuppressive properties similar to cyclosporin.
1992 Aug
Acute renal failure following intravenous fusidic acid.
1993
Anti-HIV activity of dideoxynucleosides, foscarnet and fusidic acid is potentiated by human leukocyte interferon in blood-derived macrophages.
1994 May-Jun
Acute renal failure in association with fusidic acid.
1997 Jun
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997 May
In vitro susceptibility of Mycobacterium tuberculosis to fusidic acid.
2001 Dec
Antimycobacterial plant terpenoids.
2001 Nov
Hypocalcaemia during fusidic acid therapy.
2002 Feb
Inhibition of transport across the hepatocyte canalicular membrane by the antibiotic fusidate.
2002 Jul 1
[Cholestatic icterus induced by the administration of fusidic acid in a cirrhotic patient].
2002 Jun 29
Sideroblastic anaemia and fusidic acid.
2003 Feb
Sideroblastic anaemia during fusidic acid treatment.
2004 May
Linezolid for the treatment of patients with endocarditis: a systematic review of the published evidence.
2006 Aug
A case of recurrent rapidly progressive lower limb weakness.
2008 Jul
Bacteremia and infective endocarditis caused by a non-daptomycin-susceptible, vancomycin-intermediate, and methicillin-resistant Staphylococcus aureus strain in Taiwan.
2008 Mar
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 Apr
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010 Dec
Severe statin-induced rhabdomyolysis mimicking Guillain-Barré syndrome in four patients with diabetes mellitus treated with fusidic acid.
2010 Jun
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Canine ocular thelaziosis caused by Thelazia callipaeda in Portugal.
2013 Jul
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 Nov
Fusidic acid is an effective treatment against Toxoplasma gondii and Listeria monocytogenes in vitro, but not in mice.
2013 Nov
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 Jan
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:01:08 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:08 GMT 2023
Record UNII
J7P3696BCQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
SODIUM FUSIDATE
EP   MART.  
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 3α,11α,16β-trihydroxy-29-nor-8α,9β,13α,14β-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 Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
FDA ORPHAN DRUG 723519
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
FDA ORPHAN DRUG 400513
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
NCI_THESAURUS C52588
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
Code System Code Type Description
PUBCHEM
23672955
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
EVMPD
SUB12288MIG
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
SMS_ID
100000079317
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-030-3
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
MERCK INDEX
m5616
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY Merck Index
FDA UNII
J7P3696BCQ
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID9045552
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
DAILYMED
J7P3696BCQ
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
RXCUI
9874
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY RxNorm
CAS
751-94-0
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL383466
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
DRUG BANK
DBSALT000340
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
NCI_THESAURUS
C65792
Created by admin on Fri Dec 15 15:01:08 GMT 2023 , Edited by admin on Fri Dec 15 15:01:08 GMT 2023
PRIMARY
Related Record Type Details
Structure of FUSIDIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of FUSIDIC ACID
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