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Fusidic Acid

Synopsis, Chemistry

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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

Fusidic Acid

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 Formula	C₃₁H₄₈O₆
Molecular Weight	516.7 g/mol
XLogP3	5.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	516.34508925 g/mol
Monoisotopic Mass	516.34508925 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	994
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.