FUSIDIC ACID

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21546624

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial elongation factor G 4 Target ID: Bacterial elongation factor G Sources: https://www.ncbi.nlm.nih.gov/pubmed/14709515 \| https://www.ncbi.nlm.nih.gov/pubmed/25451927	Inhibitor 8297		1.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin infections 59 Sources: http://www.csl.com.au/docs/518/291/Fucidin%20Topical%20PI%20-%20Approved%2023Dec2015.pdf	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.
Inflammatory dermatoses 4 Sources: http://www.medsafe.govt.nz/Profs/datasheet/f/fucicortcream.pdf	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

Title	Date	PubMed
Haematuria during methicillin therapy.	1971 Jul	5560145
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.	1973 Sep	4202339
Adverse reactions to intravenous administration of fusidic acid.	1981	7244561
Staphylococcal septicaemia complicated by probable cloxacillin neurotoxicity and by jaundice induced by fusidic acid.	1983 Apr	6867701
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Fusidic acid-induced hyperbilirubinemia.	1987 Aug	3608735
Inhibition of HIV replication in vitro by fusidic acid.	1987 Oct 10	2443777
Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent.	1989 Jan	2911579
Suppression of HIV replication in vitro by fusidic acid parallels cell toxicity.	1989 Jan	2745249
Susceptibility of mycobacteria to fusidic acid.	1990 Apr	2112466
Comparative in-vitro activities of ten fluoroquinolones and fusidic acid against Mycobacterium spp.	1990 Sep	2228828
Treatment of Crohn's disease with fusidic acid: an antibiotic with immunosuppressive properties similar to cyclosporin.	1992 Aug	1420741
Acute renal failure following intravenous fusidic acid.	1993	8394548
Anti-HIV activity of dideoxynucleosides, foscarnet and fusidic acid is potentiated by human leukocyte interferon in blood-derived macrophages.	1994 May-Jun	7515781
Acute renal failure in association with fusidic acid.	1997 Jun	9287276
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.	1997 May	9145860
In vitro susceptibility of Mycobacterium tuberculosis to fusidic acid.	2001 Dec	11843915
Antimycobacterial plant terpenoids.	2001 Nov	11731906
Hypocalcaemia during fusidic acid therapy.	2002 Feb	11823554
Inhibition of transport across the hepatocyte canalicular membrane by the antibiotic fusidate.	2002 Jul 1	12106615
[Cholestatic icterus induced by the administration of fusidic acid in a cirrhotic patient].	2002 Jun 29	12148265
Linezolid for the treatment of patients with endocarditis: a systematic review of the published evidence.	2006 Aug	16735427
Bacteremia and infective endocarditis caused by a non-daptomycin-susceptible, vancomycin-intermediate, and methicillin-resistant Staphylococcus aureus strain in Taiwan.	2008 Mar	18199793
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	19188393
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.	2010 Dec	20829430
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).	2013 Dec	24014644
Canine ocular thelaziosis caused by Thelazia callipaeda in Portugal.	2013 Jul	23067512
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013 Nov	23956101
Fusidic acid is an effective treatment against Toxoplasma gondii and Listeria monocytogenes in vitro, but not in mice.	2013 Nov	23949312
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	24085192

Patents

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 UTC 2023` Edited by `admin` on `Fri Dec 15 15:00:13 UTC 2023`
Record UNII	59XE10C19C
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FUSIDIC ACID

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 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

WHO-ATC

D09AA02

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

WHO-ATC

S01AA13

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

WHO-VATC

QD06AX01

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

NCI_THESAURUS

C28394

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

WHO-ATC

D06AX01

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

WHO-VATC

QS01AA13

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

NCI_THESAURUS

C52588

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

WHO-VATC

QJ01XC01

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

WHO-ATC

J01XC01

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

Code System Code Type Description

RXCUI

113608

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

ALTERNATIVE

CHEBI

71321

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

CHEBI

29013

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

DRUG CENTRAL

1261

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

EVMPD

SUB02292MIG

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

PUBCHEM

3000226

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

PRIMARY

INN

1431

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

LACTMED

Fusidic Acid

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

DAILYMED

59XE10C19C

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

ECHA (EC/EINECS)

230-256-0

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

MESH

D005672

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

PRIMARY

NSC

56192

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

PRIMARY

WIKIPEDIA

FUSIDIC ACID

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

PRIMARY

RXCUI

4608

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

PRIMARY

ChEMBL

CHEMBL374975

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

DRUG BANK

DB02703

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

FDA UNII

59XE10C19C

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

CAS

6990-06-3

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

EVMPD

SUB90515

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

MERCK INDEX

m5616

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

PRIMARY

Merck Index

EPA CompTox

DTXSID0023086

Created by admin on Fri Dec 15 15:00:13 UTC 2023 , Edited by admin on Fri Dec 15 15:00:13 UTC 2023

PRIMARY

NCI_THESAURUS

C65793

Created by admin on Fri Dec 15 15:00:14 UTC 2023 , Edited by admin on Fri Dec 15 15:00:14 UTC 2023

PRIMARY

Related Record Type Details


					7EB01222KN

FUSIDIC ACID PENTAHYDRATE

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					W540G73230

FUSIDIC ACID HEMIHYDRATE

SOLVATE->ANHYDROUS


					1XKK7J9CT6

DIETHANOLAMINE FUSIDATE

SALT/SOLVATE -> PARENT


					J7P3696BCQ

FUSIDATE SODIUM

SALT/SOLVATE -> PARENT


					7EB01222KN

FUSIDIC ACID PENTAHYDRATE

SOLVATE->ANHYDROUS

Related Record Type Details


					QL5YA4GBP8

16-Epideacetylfusidic acid

IMPURITY -> PARENT

Amount:


					WMU4BUR26K

11-Deoxyfusidic acid

IMPURITY -> PARENT

Amount:


					N6M6UV3TQW

16-epi-deacetylfusidic acid 21,16-lactone

IMPURITY -> PARENT

Amount:


					BH8KHH6DLM

11-Ketofusidic acid

IMPURITY -> PARENT

Amount:


					AKH44643KG

16-O-Deacetylfusidic acid

IMPURITY -> PARENT

Amount:


					LAN8V57VRJ

3-Didehydrofusidic acid

IMPURITY -> PARENT

Amount:


					G45GVV839F

26-hydroxyfusidic acid

IMPURITY -> PARENT

Amount:


					RZD6436JQV

9,11-Anhydrofusidic acid

IMPURITY -> PARENT

Amount:


					BX4P92XJ2U

Deacetylfusidic acid 21,16-lactone

IMPURITY -> PARENT

Amount:


					DHJ64Z35HB

26-oxofusidic acid

IMPURITY -> PARENT

Amount:

Related Record Type Details


					59XE10C19C

FUSIDIC ACID

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21546624

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21546624