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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H48O6.C4H11NO2
Molecular Weight 621.8449
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DIETHANOLAMINE FUSIDATE

SMILES

OCCNCCO.[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=OQZZCXRLEFBPLZ-JCJNLNMISA-N
InChI=1S/C31H48O6.C4H11NO2/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;6-3-1-5-2-4-7/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36);5-7H,1-4H2/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

Molecular Formula C4H11NO2
Molecular Weight 105.1356
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

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

Substance Class Chemical
Created
by admin
on Fri Dec 15 20:31:41 GMT 2023
Edited
by admin
on Fri Dec 15 20:31:41 GMT 2023
Record UNII
1XKK7J9CT6
Record Status Validated (UNII)
Record Version
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Name Type Language
DIETHANOLAMINE FUSIDATE
WHO-DD  
Common Name English
FUSIDATE DIOLAMINE
Common Name English
29-NORDAMMARA-17(20),24-DIEN-21-OIC ACID, 16-(ACETYLOXY)-3,11-DIHYDROXY-, (3.ALPHA.,4.ALPHA.,8.ALPHA.,9.ALPHA.,11.ALPHA.,13.ALPHA.,14.BETA.,16.BETA.,17Z)-, COMPD. WITH 2,2'-IMINOBIS(ETHANOL) (1:1)
Common Name English
FUSIDATE DIETHANOLAMINE
Common Name English
Diethanolamine fusidate [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
100000079554
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
FDA UNII
1XKK7J9CT6
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
240-442-3
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
EVMPD
SUB13572MIG
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
MESH
C013483
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
CAS
16391-75-6
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
PUBCHEM
46174083
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID701020012
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY
RXCUI
22971
Created by admin on Fri Dec 15 20:31:41 GMT 2023 , Edited by admin on Fri Dec 15 20:31:41 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE