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    Fusidic Acid

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: Fusidine, 6990-06-3, Ramycin, Fucithalmic, Fusidate, Fucidic acid
    Molecular Formula
    C31H48O6
    Molecular Weight
    516.7  g/mol
    InChI Key
    IECPWNUMDGFDKC-MZJAQBGESA-N
    FDA UNII
    59XE10C19C
    An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 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
    2.1.2 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
    2.1.3 InChI Key
    IECPWNUMDGFDKC-MZJAQBGESA-N
    2.1.4 Canonical SMILES
    CC1C2CCC3(C(C2(CCC1O)C)C(CC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)O)C
    2.1.5 Isomeric 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
    2.2 Other Identifiers
    2.2.1 UNII
    59XE10C19C
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Acid, Fusidic

    2. Fucithalmic

    3. Fusidate, Silver

    4. Fusidin

    5. Silver Fusidate

    6. Sodium Fusidate

    7. Stanicide

    2.3.2 Depositor-Supplied Synonyms

    1. Fusidine

    2. 6990-06-3

    3. Ramycin

    4. Fucithalmic

    5. Fusidate

    6. Fucidic Acid

    7. Fucidin Acid

    8. Fucidin

    9. Flucidin

    10. Fucidate

    11. Taksta

    12. Sodium Fusidate

    13. Sq 16,603

    14. (-)-fusidic Acid

    15. (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

    16. Anhydrous Fusidic Acid

    17. Cem-102

    18. Nsc-56192

    19. Sq 16603

    20. Mls001332649

    21. Chebi:29013

    22. 59xe10c19c

    23. Smr000857101

    24. Sq-16603

    25. (2e)-2-[(3r,4s,5s,8s,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

    26. Acide Fusidique

    27. Acido Fusidico

    28. Fusidinic Acid

    29. Acidum Fusidicum

    30. Mfcd00865135

    31. (-)-16beta-acetoxy-3alpha,11alpha-dihydroxyfusida-17(20)z,24-diene-21-oic Acid

    32. (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

    33. (2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetoxy-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-methyl-hept-5-enoic Acid

    34. (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17z)-16-(acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid

    35. (z)-2-((3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyldodecahydro-1h-cyclopenta[a]phenanthren-17(2h,10h,14h)-ylidene)-6-methylhept-5-enoic Acid

    36. Fusidic Acid (usan/inn)

    37. Fusidic-acid

    38. Fusidate Acid

    39. 1qca

    40. Fusidicacid

    41. C.a.s. 62,602

    42. Prestwick2_000390

    43. Fusidic Acid [mi]

    44. Fusidic Acid [inn]

    45. Fusidic Acid [usan]

    46. Schembl25646

    47. Mls001332650

    48. Mls002207094

    49. Unii-59xe10c19c

    50. Acide Fusidique [inn-french]

    51. Acido Fusidico [inn-spanish]

    52. Acidum Fusidicum [inn-latin]

    53. Fusidic Acid [who-dd]

    54. Cem102

    55. Chembl374975

    56. Dtxsid0023086

    57. Fusidic Acid [usan:inn:ban]

    58. Bdbm58924

    59. Cid_3000226

    60. Gtpl10815

    61. Hms2235b11

    62. Fusidic Acid [ep Impurity]

    63. Act03304

    64. Ex-a3797

    65. Fusidic Acid [ep Monograph]

    66. Hy-b1350

    67. Nsc56192

    68. Zinc8143796

    69. Einecs 230-256-0

    70. Fusidic Acid For Peak Identification

    71. Nsc 56192

    72. S3971

    73. 16-(acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid

    74. Akos005146257

    75. Ccg-269829

    76. Db02703

    77. Ds-3261

    78. Lmpr0106040001

    79. Ncgc00485232-01

    80. (2z)-2-[(17z)-16beta-acetoxy-3alpha,11alpha-dihydroxy-4alpha,8alpha,10,14beta-tetramethyl-5alpha,9beta,13alpha-gonan-17-ylidene]-6-methylhept-5-enoic Acid

    81. 29-nordammara-17(20),24-dien-21-oic Acid, 16-(acetyloxy)-3,11-dihydroxy-, (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,14beta,16beta,17z)-

    82. 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

    83. C.a.s. 62,602; Diethanolamine Fusidate

    84. Cs-0013095

    85. F1007

    86. C06694

    87. D04281

    88. 990f063

    89. Q259930

    90. Q-201141

    91. Fusidic Acid, European Pharmacopoeia (ep) Reference Standard

    92. Fusidic Acid For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    93. (2z)-2-[(3beta,4beta,5alpha,8alpha,9beta,11beta,13alpha,16beta,17z)-16-(acetyloxy)-3,11-dihydroxy-4,8,10,14-tetramethylgonan-17-ylidene]-6-methylhept-5-enoic Acid

    94. (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-methyl-5-heptenoic Acid

    95. (2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-4,8,10,14-tetramethyl-3,11-bis(oxidanyl)-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-hept-5-enoic Acid

    96. (3alpha,4alpha,8alpha,9beta,11alpha,13alpha,147beta,167beta,17z)-16-(acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid

    97. 29-nor-8.alpha.,13.alpha.,14.beta.-dammara-17(20),24-dien-21-oic Acid, 3.alpha.,11.alpha.,16.beta.-trihydroxy-, 16-acetate, (z)-

    98. 29-nor-8alpha,9beta,13alpha,14beta-dammara-17(20),24-dien-21-oic Acid, 3alpha,11alpha,16beta-trihydroxy-, 16-acetate, (z)-

    99. 29-nordammara-17(20), 16-(acetyloxy)-3,11-dihydroxy-, (3.alpha.,4.alpha.,8.alpha.,9.beta.,11.alpha.,13.alpha.,14.beta.,16.beta.,17z)-

    100. 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)

    101. 29-nordammara-17(20),24-dien-21-oic Acid, 16-(acetyloxy)-3,11-dihydroxy-, (3a,4a,8a,9b,11a,13a,14b,16b,17z)-

    102. 3.alpha.,16.beta.-trihydroxy-29-nor-8.alpha.,9.beta.,13.alpha.,14.beta.-dammara-17(20),24-dien-21-oic Acid 16-acetate

    103. 3alpha,11alpha,16beta-trihydroxy-29-nor-8alpha,9beta,13alpha,14beta-dammara-17(20),24-dien-21-oic Acid 16-acetate

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 516.7 g/mol
    Molecular Formula C31H48O6
    XLogP35.5
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass516.34508925 g/mol
    Monoisotopic Mass516.34508925 g/mol
    Topological Polar Surface Area104 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity994
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of bacterial infections.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Fusidic acid is a bacteriostatic antibiotic and helps prevent bacterial growth while the immune system clears the infection.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    Protein Synthesis Inhibitors

    Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

    5.3 ATC Code

    D - Dermatologicals

    D06 - Antibiotics and chemotherapeutics for dermatological use

    D06A - Antibiotics for topical use

    D06AX - Other antibiotics for topical use

    D06AX01 - Fusidic acid

    D - Dermatologicals

    D09 - Medicated dressings

    D09A - Medicated dressings

    D09AA - Medicated dressings with antiinfectives

    D09AA02 - Fusidic acid

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01X - Other antibacterials

    J01XC - Steroid antibacterials

    J01XC01 - Fusidic acid

    S - Sensory organs

    S01 - Ophthalmologicals

    S01A - Antiinfectives

    S01AA - Antibiotics

    S01AA13 - Fusidic acid

    5.4 Absorption, Distribution and Excretion

    Absorption

    Sodium fusidic acid tablets have a 91% oral bioavailability. Absorption of the film-coated tablets is complete when compared to a solution, however oral absorption is variable. Oral fusidic acid hemihydrate (suspension) achieved a 22.5% bioavailability in pediatric patients following a 20 milligram/kilogram dose.

    5.5 Metabolism/Metabolites

    Metabolites include dicarboxylic ester/acid, 3-keto fusidic acid, hydroxy fusidic acid, glucuronide fusidic acid and a glycol metabolite.

    5.6 Biological Half-Life

    Approximately 5 to 6 hours in adults.

    5.7 Mechanism of Action

    Fusidic acid works by interfering with bacterial protein synthesis, specifically by preventing the translocation of the elongation factor G (EF-G) from the ribosome. It also can inhibit chloramphenicol acetyltransferase enzymes.