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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H48O6
Molecular Weight 516.7092
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FUSIDIC ACID

SMILES

[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=IECPWNUMDGFDKC-MZJAQBGESA-N
InChI=1S/C31H48O6/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)/b26-20-/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1

HIDE SMILES / InChI
Molecular Formula C31H48O6
Molecular Weight 516.7092
Charge 0
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
Adverse reactions to intravenous administration of fusidic acid.
1981
Screening for new compounds with antiherpes activity.
1984 Oct
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 in association with fusidic acid.
1997 Jun
In vitro susceptibility of Mycobacterium tuberculosis to fusidic acid.
2001 Dec
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
Canine ocular thelaziosis caused by Thelazia callipaeda in Portugal.
2013 Jul
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 15:00:13 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:13 GMT 2023
Record UNII
59XE10C19C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FUSIDIC ACID
EP   INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
fusidic acid [INN]
Common Name English
FUCITHALMIC
Brand Name English
FUSIDIC ACID [EP IMPURITY]
Common Name English
FUSIDIC ACID [USAN]
Common Name English
FUSIDIC ACID [EP MONOGRAPH]
Common Name English
SQ-16603
Code English
3α,11α,16β-Trihydroxy-29-nor-8α,9β,13α,14β-dammara-17(20),24-dien-21-oic acid 16-acetate
Common Name English
TAKSTA
Brand Name English
Fusidic acid [WHO-DD]
Common Name English
CEM-102
Code English
RAMYCIN
Common Name English
FUSIDATE
Common Name English
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)
Common Name English
NSC-56192
Code English
FUSIDIC ACID [MI]
Common Name English
ANHYDROUS FUSIDIC ACID
Common Name English
Classification Tree Code System Code
WHO-VATC QD09AA02
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
WHO-ATC D09AA02
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
WHO-ATC S01AA13
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
WHO-VATC QD06AX01
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
WHO-ATC D06AX01
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
WHO-VATC QS01AA13
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
NCI_THESAURUS C52588
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
WHO-VATC QJ01XC01
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
WHO-ATC J01XC01
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
Code System Code Type Description
RXCUI
113608
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
ALTERNATIVE
CHEBI
71321
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
CHEBI
29013
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
DRUG CENTRAL
1261
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
EVMPD
SUB02292MIG
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
PUBCHEM
3000226
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
PRIMARY
INN
1431
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
LACTMED
Fusidic Acid
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
DAILYMED
59XE10C19C
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
230-256-0
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
MESH
D005672
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
PRIMARY
NSC
56192
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
PRIMARY
WIKIPEDIA
FUSIDIC ACID
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
PRIMARY
RXCUI
4608
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL374975
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
DRUG BANK
DB02703
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
FDA UNII
59XE10C19C
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
CAS
6990-06-3
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
EVMPD
SUB90515
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
MERCK INDEX
m5616
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID0023086
Created by admin on Fri Dec 15 15:00:13 GMT 2023 , Edited by admin on Fri Dec 15 15:00:13 GMT 2023
PRIMARY
NCI_THESAURUS
C65793
Created by admin on Fri Dec 15 15:00:14 GMT 2023 , Edited by admin on Fri Dec 15 15:00:14 GMT 2023
PRIMARY
Related Record Type Details
Structure of FUSIDIC ACID PENTAHYDRATE
SALT/SOLVATE -> PARENT
Structure of FUSIDIC ACID HEMIHYDRATE
SOLVATE->ANHYDROUS
Structure of DIETHANOLAMINE FUSIDATE
SALT/SOLVATE -> PARENT
Structure of FUSIDATE SODIUM
SALT/SOLVATE -> PARENT
Structure of FUSIDIC ACID PENTAHYDRATE
SOLVATE->ANHYDROUS
Related Record Type Details
Structure of 16-Epideacetylfusidic acid
IMPURITY -> PARENT
Structure of 11-Deoxyfusidic acid
IMPURITY -> PARENT
Structure of 16-epi-deacetylfusidic acid 21,16-lactone
IMPURITY -> PARENT
Structure of 11-Ketofusidic acid
IMPURITY -> PARENT
Structure of 16-O-Deacetylfusidic acid
IMPURITY -> PARENT
Structure of 3-Didehydrofusidic acid
IMPURITY -> PARENT
Structure of 26-hydroxyfusidic acid
IMPURITY -> PARENT
Structure of 9,11-Anhydrofusidic acid
IMPURITY -> PARENT
Structure of Deacetylfusidic acid 21,16-lactone
IMPURITY -> PARENT
Structure of 26-oxofusidic acid
IMPURITY -> PARENT
Related Record Type Details
Structure of FUSIDIC ACID
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