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Substance Name: Fusidic acid [USAN:INN:BAN]
RN: 6990-06-3
UNII: 59XE10C19C
InChIKey: IECPWNUMDGFDKC-MZJAQBGESA-N

Note

  • An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis.

Molecular Formula

  • C31-H48-O6

Molecular Weight

  • 516.7142
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Protein Synthesis Inhibitors
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Fusidic acid
  • Fusidic acid [USAN:INN:BAN]

MeSH Heading

  • Fusidic acid

Synonyms

  • 3alpha,11alpha,16beta-Trihydroxy-29-nor-8alpha,9beta,13alpha,14beta-dammara-17(20),24-dien-21-oic acid 16-acetate
  • Acide fusidique
  • Acide fusidique [INN-French]
  • Acido fusidico
  • Acido fusidico [INN-Spanish]
  • Acidum fusidicum
  • Acidum fusidicum [INN-Latin]
  • C.A.S. 62,602; Diethanolamine fusidate
  • EINECS 230-256-0
  • Flucidin
  • Fucidic acid
  • Fucidin
  • Fucidin acid
  • Fucithalmic
  • Fusidic acid
  • Fusidine
  • Fusidinic acid
  • NSC 56192
  • Ramycin
  • SQ 16,603
  • SQ 16603
  • UNII-59XE10C19C

Systematic Names

  • 29-Nor-8alpha,9beta,13alpha,14beta-dammara-17(20),24-dien-21-oic acid, 3alpha,11alpha,16beta-trihydroxy-, 16-acetate, (Z)- (8CI)
  • 29-Nordammara-17(20),24-dien-21-oic acid, 16-(acetyloxy)-3,11-dihydroxy-, (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17Z)-
  • Fusidic acid

Registry Numbers

CAS Registry Number

  • 6990-06-3

FDA UNII

  • 59XE10C19C

Other Registry Numbers

  • 1386-65-8
  • 1404-47-3
  • 2618-21-5
  • 313340-66-8
  • 62-60-2

Related Registry Number

  • 751-94-0 (hydrochloride salt)

System Generated Number

  • 0006990063

Structure Descriptors

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

Smiles

C[C@@H]1[C@H](O)CC[C@@]2(C)[C@H]1CC[C@@]3(C)[C@H]2[C@H](O)C[C@H]4\C(=C(/CCC=C(C)C)\C(=O)O)\[C@H](C[C@]34C)OC(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 165mg/kg (165mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 157, 1981.
mouse LD50 intravenous 180mg/kg (180mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 156, 1981.
mouse LD50 oral 1500mg/kg (1500mg/kg)   Lancet. Vol. 1, Pg. 928, 1962.
mouse LD50 subcutaneous 1200mg/kg (1200mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 3, Pg. 1959, 1978.
women TDLo oral 420mg/kg/2W-I (420mg/kg) BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA		 Postgraduate Medical Journal. Vol. 67, Pg. 591, 1991.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 192.5 deg C   EXP
pKa Dissociation Constant 5.35 (none)   EXP
log P (octanol-water) 6.750 (none)   EST
Atmospheric OH Rate Constant 1.72E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.