FUSIDIC ACID HEMIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C31H48O6.H2O
Molecular Weight	1051.4337
Optical Activity	UNSPECIFIED
Defined Stereocenters	20 / 20
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[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.[H][C@@]56C[C@@H](O)[C@@]7([H])[C@@]8(C)CC[C@@H](O)[C@@H](C)[C@]8([H])CC[C@]7(C)[C@@]5(C)C[C@H](OC(C)=O)\C6=C(\CCC=C(C)C)C(O)=O

InChI

InChIKey=CSXHKOSAWQTJBT-YDYKLMMDSA-N

InChI=1S/2C31H48O6.H2O/c2*1-17(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;/h2*9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36);1H2/b2*26-20-;/t2*18-,21-,22-,23+,24+,25-,27-,29-,30-,31-;/m00./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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Fusidic acid: a new antibiotic.	1962 Mar 10	13899435
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
Sideroblastic anaemia and fusidic acid.	2003 Feb	12602389
Sideroblastic anaemia during fusidic acid treatment.	2004 May	15059072
Linezolid for the treatment of patients with endocarditis: a systematic review of the published evidence.	2006 Aug	16735427
A case of recurrent rapidly progressive lower limb weakness.	2008 Jul	18487263
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
Severe statin-induced rhabdomyolysis mimicking Guillain-Barré syndrome in four patients with diabetes mellitus treated with fusidic acid.	2010 Jun	20546290
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 17:17:48 UTC 2023` Edited by `admin` on `Fri Dec 15 17:17:48 UTC 2023`
Record UNII	W540G73230
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FUSIDIC ACID HEMIHYDRATE

Common Name

English

Fusidic acid hemihydrate [WHO-DD]

Common Name

English

29-NORDAMMARA-17(20),24-DIEN-21-OIC ACID, 16-(ACETYLOXY)-3,11-DIHYDROXY-, HYDRATE (2:1), (3.ALPHA.,4.ALPHA.,8.ALPHA.,9.BETA.,11.ALPHA.,13.ALPHA.,14.BETA.,16.BETA.,17Z)-

Common Name

English

FUSIDIC ACID (HEMIHYDRATE)

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID50169257