Details of the Drug

General Information of Drug (ID: DMWVCF3)

Drug Name
Fusidic Acid
Synonyms
FUCIDIN; Fucidate; Fucithalmic; Fusidate; Fusidine; Ramycin; Diethanolamine fusidate; Fucidate Sodium; Fucidic acid; Fucidin acid; Fuci (TN); Fucibet (TN); Fucicort (TN); Fucidin (TN); Fucidin Cream 2%; Fucidine (TN); Fucithalmic (TN); Fucizon (TN); Fudic (TN); Fusiderm (TN); Fusidin (TN); SQ 16,603; Fusidic acid (USAN/INN); C.A.S. 62,602; (2Z)-2-[(17Z)-16beta-acetoxy-3alpha,11alpha-dihydroxy-4alpha,8alpha,10,14beta-tetramethyl-5alpha,9beta,13alpha-gonan-17-ylidene]-6-methylhept-5-enoic acid; (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid; (2Z)-2-[(3alpha,4alpha,5alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17Z)-16-(acetyloxy)-3,11-dihydroxy-4,8,10,14-tetramethylgonan-17-ylidene]-6-methylhept-5-enoic acid; 16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid; 3.alpha.,11.alpha.,16.beta.-Trihydroxy-29-nor-8.alpha.,9.beta.,13.alpha.,14.beta.-dammara-17(20),24-dien-21-oic acid 16-acetate
Indication
Disease Entry ICD 11 Status REF
Acne vulgaris ED80 Approved [1]
Actinomycosis N.A. Approved [2]
Acute gonococcal cervicitis N.A. Approved [3]
Acute gonococcal epididymo-orchitis N.A. Approved [3]
Anthrax 1B97 Approved [4]
Bacteremia 1A73 Approved [5]
Bacterial infection 1A00-1C4Z Approved [6]
Bartonellosis N.A. Approved [3]
Blepharoconjunctivitis N.A. Approved [7]
Boutonneuse fever N.A. Approved [3]
Brill-Zinsser disease N.A. Approved [3]
Bronchitis CA20 Approved [8]
Brucellosis N.A. Approved [3]
Chancroid N.A. Approved [3]
Chlamydiaceae infections N.A. Approved [9]
Cholangitis N.A. Approved [3]
Corneal abrasion NA06.4 Approved [10]
Cutaneous anthrax N.A. Approved [3]
Dacryocystitis N.A. Approved [11]
Demodex blepharitis 1G07 Approved [3]
Endemic typhus N.A. Approved [3]
Epidemic louse-borne typhus N.A. Approved [3]
Folliculitis N.A. Approved [12]
Gastrointestinal anthrax N.A. Approved [3]
Inhalational anthrax N.A. Approved [3]
Listeriosis N.A. Approved [13]
Lymphogranuloma venereum N.A. Approved [3]
Mycoplasma pneumoniae pneumonia N.A. Approved [3]
Neonatal sepsis N.A. Approved [14]
Ornithosis N.A. Approved [3]
Paronychia 1F23.13 Approved [15]
Peritonitis N.A. Approved [16]
Pneumococcal infection CA00-CA40 Approved [17]
Pneumonia CA40 Approved [18]
Pseudomonas aeruginosa infectious disease N.A. Approved [19]
Q fever N.A. Approved [3]
Relapsing fever N.A. Approved [3]
Rickettsialpox N.A. Approved [3]
Rickettsiosis N.A. Approved [3]
Rocky mountain spotted fever N.A. Approved [3]
Rosacea ED90.0 Approved [20]
Staphylococcal pneumonia N.A. Approved [21]
Staphylococcus aureus infection N.A. Approved [22]
Streptococcus infection 1B53 Approved [23]
Syphilis N.A. Approved [24]
Trachoma N.A. Approved [3]
Tularemia 1B94 Approved [3]
Typhus N.A. Approved [3]
Urinary tract infection GC08 Approved [25]
Yaws N.A. Approved [3]
MRSA infection 1D01.0Y Phase 3 [26]
Sinusitis CA0A.Z Investigative [27]
Vibrio cholerae infection 1A00 Investigative [3]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
D06AX01: Fusidic Acid
D06AX: Other antibiotics for topical use
D06A: ANTIBIOTICS FOR TOPICAL USE
D06: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
D: DERMATOLOGICALS
D09AA02: Fusidic Acid
D09AA: Medicated dressings with antiinfectives
D09A: MEDICATED DRESSINGS
D09: MEDICATED DRESSINGS
D: DERMATOLOGICALS
J01XC01: Fusidic Acid
J01XC: Steroid antibacterials
J01X: OTHER ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
J01XC01: Fusidic Acid
J01XC: Steroid antibacterials
J01X: OTHER ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
S01AA13: Fusidic Acid
S01AA: Antibiotics
S01A: ANTIINFECTIVES
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 516.7
Logarithm of the Partition Coefficient (xlogp) 5.5
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [28]
Bioavailability
91% of drug becomes completely available to its intended biological destination(s) [29]
Half-life
The concentration or amount of drug in body reduced by one-half in 5 - 6 hours [30]
Chemical Identifiers
Formula
C31H48O6
IUPAC Name
(2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
Canonical SMILES
C[C@H]1[C@@H]2CC[C@]3([C@H]([C@]2(CC[C@H]1O)C)[C@@H](C[C@@H]\\4[C@@]3(C[C@@H](/C4=C(/CCC=C(C)C)\\C(=O)O)OC(=O)C)C)O)C
InChI
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
InChIKey
IECPWNUMDGFDKC-MZJAQBGESA-N
Cross-matching ID
PubChem CID
3000226
ChEBI ID
CHEMBL374975
CAS Number
6990-06-3
UNII
59XE10C19C
DrugBank ID
DB02703
TTD ID
D0X7XG
INTEDE ID
DR0758
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Streptococcus Elongation factor G (Stre-coc fusA) TT6HP1T EFG_STRZJ Inhibitor [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [31]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [32]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [33]
Solute carrier organic anion transporter family member 1B1 (SLCO1B1) OTNEN8QK SO1B1_HUMAN Gene/Protein Processing [34]
Solute carrier organic anion transporter family member 1B3 (SLCO1B3) OTOM3BUH SO1B3_HUMAN Gene/Protein Processing [34]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Curcumin/Fusidic Acid Bitherapy Loaded Mixed Micellar Nanogel for Acne Vulgaris Treatment: In Vitro and In Vivo Studies. AAPS PharmSciTech. 2023 Sep 11;24(7):182.
2 [In vitro sensitivity of Actinomyces israelii, Actinobacillus actinomycetem-comitans and Bacteroides melaninogenicus to cephalothin, cephaloridine, gentamicin, fusidic acid and lincomycin]. Int Z Klin Pharmakol Ther Toxikol. 1970 Oct;3(4):318-20.
3 A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
4 Cationic quaternized aminocalix[4]arenes: cytotoxicity, haemolytic and antibacterial activities. Int J Pharm. 2013 Dec 15;458(1):25-30.
5 Genetic determinants of resistance to fusidic acid among clinical bacteremia isolates of Staphylococcus aureus. Antimicrob Agents Chemother. 2009 May;53(5):2059-65.
6 Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
7 Fusidic acid viscous eyedrops--an evaluation of pharmacodynamics, pharmacokinetics and clinical use for UK optometrists. Ophthalmic Physiol Opt. 2006 Jul;26(4):343-61.
8 [Interferon-gamma receptor 1 deficiency in a 19-month-old child: case report and literature review]. Zhonghua Er Ke Za Zhi. 2014 May;52(5):387-91.
9 The in vitro effects of proxymetacaine, fluorescein, and fusidic acid on real-time PCR assays used for the diagnosis of Feline herpesvirus 1 and Chlamydophila felis infections. Vet Ophthalmol. 2011 Sep;14 Suppl 1:5-8.
10 Antibiotic prophylaxis for corneal abrasion. Cochrane Database Syst Rev. 2022 May 27;5(5):CD014617.
11 [Susceptibility of drug-resistant staphylococci isolated from different parts of the ocular anterior segment to common ophthalmic antibiotics]. Zhonghua Yan Ke Za Zhi. 2022 Aug 11;58(8):598-605.
12 Fusidic acid betamethasone lipid cream. Int J Clin Pract. 2016 May;70 Suppl 184:4-13.
13 Antimicrobial Resistance of Listeria monocytogenes from Animal Foods to First- and Second-Line Drugs in the Treatment of Listeriosis from 2008 to 2021: A Systematic Review and Meta-Analysis. Can J Infect Dis Med Microbiol. 2022 Oct 7;2022:1351983.
14 Microbiological Characteristics and Resistance Patterns in a Neonatal Intensive Care Unit: A Retrospective Surveillance Study. Cureus. 2024 Mar 12;16(3):e56027.
15 Extensive pyomyositis secondary to paronychia-related MRSA infection: A case report. Medicine (Baltimore). 2022 Jan 14;101(2):e28431.
16 An experimental evaluation of the pharmacokinetics of fusidic acid in peritoneal dialysis. J Med Microbiol. 1992 Feb;36(2):71-7.
17 Epidemiology of penicillin resistant pneumococci in Iceland. Microb Drug Resist. 1995 Summer;1(2):121-5.
18 Mycoplasma pneumoniae-associated mucositis. BMJ Case Rep. 2021 Apr 15;14(4):e239086.
19 Bacterial profile of diabetic foot infections and antibiotic susceptibility in a specialized diabetes centre in Cameroon. Pan Afr Med J. 2022 May 18;42:52.
20 Placebo controlled trial of fusidic acid gel and oxytetracycline for recurrent blepharitis and rosacea. Br J Ophthalmol. 1995 Jan;79(1):42-5.
21 Fusidic acid in other infections. Int J Antimicrob Agents. 1999 Aug;12 Suppl 2:S11-5.
22 Registered and investigational drugs for the treatment of methicillin-resistant Staphylococcus aureus infection. Recent Pat Antiinfect Drug Discov. 2008 Jan;3(1):10-33.
23 Impetigo: diagnosis and treatment. Am Fam Physician. 2014 Aug 15;90(4):229-35.
24 Balanoposthitis and Penile Edema: Atypical Manifestations of Primary Syphilis. Sex Transm Dis. 2015 Sep;42(9):524-5.
25 Isolation of Staphylococcus aureus Urinary Tract Infections at a Community-Based Healthcare Center in Riyadh. Cureus. 2023 Feb 18;15(2):e35140.
26 Application of pharmacokinetic-pharmacodynamic modeling and the justification of a novel fusidic acid dosing regimen: raising Lazarus from the dead. Clin Infect Dis. 2011 Jun;52 Suppl 7:S513-9.
27 Facial cellulitis associated with Pseudomonas aeruginosa complicating ophthalmic herpes zoster. Dermatol Online J. 2004 Oct 15;10(2):20.
28 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
29 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
30 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
31 The potent mechanism-based inactivation of CYP2D6 and CYP3A4 with fusidic acid in in vivo bioaccumulation. Xenobiotica. 2018 Oct;48(10):999-1005.
32 Fusidic acid inhibits hepatic transporters and metabolic enzymes: potential cause of clinical drug-drug interaction observed with statin coadministration. Antimicrob Agents Chemother. 2016 Sep 23;60(10):5986-94.
33 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
34 Inhibition of Hepatobiliary Transport Activity by the Antibacterial Agent Fusidic Acid: Insights into Factors Contributing to Conjugated Hyperbilirubinemia/Cholestasis. Chem Res Toxicol. 2016 Oct 17;29(10):1778-1788. doi: 10.1021/acs.chemrestox.6b00262. Epub 2016 Oct 4.