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Chemistry

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Also known as: 1397-89-3, Amphotericin, Amphotericine b, Fungizone, Ambisome, Ampho-moronal
Molecular Formula
C47H73NO17
Molecular Weight
924.1  g/mol
InChI Key
APKFDSVGJQXUKY-INPOYWNPSA-N
FDA UNII
7XU7A7DROE

Amphotericin B
Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.
Amphotericin b is a Lipid-based Polyene Antifungal and Polyene Antifungal.
1 2D Structure

Amphotericin B

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
2.1.2 InChI
InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
2.1.3 InChI Key
APKFDSVGJQXUKY-INPOYWNPSA-N
2.1.4 Canonical SMILES
CC1C=CC=CC=CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC(C(CCC(CC(CC(=O)OC(C(C1O)C)C)O)O)O)O)O)O)O)C(=O)O)OC3C(C(C(C(O3)C)O)N)O
2.1.5 Isomeric SMILES
C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O
2.2 Other Identifiers
2.2.1 UNII
7XU7A7DROE
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Amphocil

2. Amphotericin

3. Amphotericin B Cholesterol Dispersion

4. Amphotericin B Colloidal Dispersion

5. Fungizone

2.3.2 Depositor-Supplied Synonyms

1. 1397-89-3

2. Amphotericin

3. Amphotericine B

4. Fungizone

5. Ambisome

6. Ampho-moronal

7. Halizon

8. Amfotericina B

9. Amphotericinum B

10. Amph-b

11. Liposomal Amphotericin B

12. Amphotericin-b

13. Abelcet

14. Amphotec

15. Fungilin

16. Mfcd00877763

17. 7xu7a7droe

18. Nsc 527017

19. Ncgc00090808-01

20. Dsstox_cid_2601

21. Dsstox_rid_76653

22. Amphotocerin

23. Dsstox_gsid_22601

24. Ambil

25. Ablc

26. Abelecet

27. Amphortericin B

28. Anfotericine B

29. Amphotericin B Liposome

30. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,19e,21e,23e,25e,27e,29e,31e,33r,35s,36r,37s)-33-(((2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic Acid

31. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,19e,21e,23e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic Acid

32. Amphotericin B Liposomal

33. Amphotericin B Trihydrate

34. Iab

35. Unii-7xu7a7droe

36. Fungisome

37. Amfotericina B [inn-spanish]

38. Amphotericine B [inn-french]

39. Amphotericinum B [inn-latin]

40. Ccris 5963

41. Hsdb 3008

42. Amphotericin B [usp:inn:jan]

43. Nsc-527017

44. Fungizone (tn)

45. Amphotec (tn)

46. (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic Acid

47. Ambisome (tn)

48. Amp B

49. Cas-1397-89-3

50. Einecs 215-742-2

51. Ns 718

52. Brn 0078342

53. Ai3-26528

54. Prestwick3_000410

55. Amphotericin B (85%)

56. Amphotericin B Solubilized

57. Amphotericin B [mi]

58. Schembl17973

59. Amphotericin B [inn]

60. Amphotericin B [jan]

61. Bspbio_000340

62. 5-18-10-00525 (beilstein Handbook Reference)

63. Amphotericin B [hsdb]

64. Bidd:gt0351

65. Amphotericin B [vandf]

66. Bpbio1_000374

67. Nktr-024

68. Amphotericin B [mart.]

69. Amphotericin B And Cinnamon Oil

70. Amphotericin B [usp-rs]

71. Amphotericin B [who-dd]

72. Amphotericin B [who-ip]

73. Dtxsid9022601

74. Hms2096a22

75. Hms3713a22

76. Amphotericin B (jp17/usp/inn)

77. Hy-b0221

78. Amphotericin B, Streptomyces Nodosus

79. Tox21_111027

80. Tox21_202484

81. Amphotericin B [orange Book]

82. Lmpk06000002

83. S1636

84. Amphotericin B [ep Monograph]

85. Akos024464746

86. Amphotericin B [usp Monograph]

87. Zinc253387843

88. Amphotericin B Liposome [vandf]

89. Ccg-220410

90. Db00681

91. Amphotericinum B [who-ip Latin]

92. Abelcet, Liposomal Amphotericin B

93. Ncgc00260033-01

94. (1r-(1r*,3s*,5r*,6r*,9r*,11r*,15s*,16r*,17r*,18s*,19e,21e,23e,25e,27e,29e,31e,33r*,35s*,36r*,37s*))-33-((3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic Acid

95. 14,39-dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,2 7,29,31-heptaene-36-carboxylic Acid, 33-((3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-(1r-(1r*,3s*,5r*,6r*,9r*,11r*,15s*,16r*,17r*,18s*,19e,21e,23e, 25e-27e,29e,31e,33r*,35s*,36r*,37s*))-

96. Amphotericin B Lipid Complex [mi]

97. Ab00513832

98. Amphotericin B Deoxycholate [who-dd]

99. Amphotericin B Lipid Complex [vandf]

100. Amphotericin B Liposomal Complex [mi]

101. C06573

102. D00203

103. Ab00513832_02

104. 397a893

105. Q412223

106. 1397-89-3, C47h73no17

107. Amphotericin B From Streptomyces Sp., ~80% (hplc), Powder

108. Amphotericin B From Streptomyces Sp., Bioreagent, Suitable For Cell Culture, ~80% (hplc)

109. Amphotericin B Solubilized, Powder, Gamma-irradiated, Bioxtra, Suitable For Cell Culture

110. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,19e,21e,23e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,

111. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,19e,21e,23e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic Acid

112. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,19e,21e,23e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(3-amino-3,6-dideoxy-?-d-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic Acid

113. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,19e,21e,23e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-he

114. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,19e,21e,23e,25e,27e,29e,31e,33r,35s,36r,37s)-33-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-hept

115. (1r,3s,5r,6r,9r,11r,15s,16r,17r,18s,33r,35s,36r,37s)-33-{[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carbo

116. (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-

117. 23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic Acid

118. Amphotericin B From Streptomyces Sp., Vetec(tm) Reagent Grade, Bioreagent, Suitable For Cell Culture, ~80%

119. Amphotericin B Solution, 250 Mug/ml In Deionized Water, Sterile-filtered, Bioreagent, Suitable For Cell Culture

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 924.1 g/mol
Molecular Formula C47H73NO17
XLogP30
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count18
Rotatable Bond Count3
Exact Mass923.48784986 g/mol
Monoisotopic Mass923.48784986 g/mol
Topological Polar Surface Area320 Ų
Heavy Atom Count65
Formal Charge0
Complexity1670
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count7
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameAbelcet
PubMed HealthAmphotericin B Lipid Complex (Injection)
Drug ClassesAntifungal, Antiprotozoal
Active IngredientAmphotericin b
Dosage FormInjectable, lipid complex
RouteInjection
Strength5mg/ml
Market StatusPrescription
CompanySigma Tau

2 of 8  
Drug NameAmbisome
PubMed HealthAmphotericin B Liposome (Injection)
Drug ClassesAntifungal, Antiprotozoal
Active IngredientAmphotericin b
Dosage FormInjectable, liposomal
RouteInjection
Strength50mg/vial
Market StatusPrescription
CompanyAstellas

3 of 8  
Drug NameAmphotec
PubMed HealthAmphotericin B Cholesteryl Sulfate Complex (Injection)
Drug ClassesAntifungal, Antiprotozoal
Drug LabelAMPHOTEC is a sterile, pyrogen-free, lyophilized powder for reconstitution and intravenous (IV) administration. AMPHOTEC consists of a 1:1 (molar ratio) complex of amphotericin B and cholesteryl sulfate. Upon reconstitution, AMPHOTEC forms a colloi...
Active IngredientAmphotericin b
Dosage FormInjectable, lipid complex
RouteInjection
Strength100mg/vial; 50mg/vial
Market StatusPrescription
CompanyAlkopharma Usa

4 of 8  
Drug NameAmphotericin b
PubMed HealthAmphotericin B (Injection)
Drug ClassesAntifungal, Antiprotozoal
Drug LabelAmphotericin B for Injection USP contains amphotericin B, an antifungal polyene antibiotic obtained from a strain of Streptomyces nodosus. Amphotericin B is designated chemically as [1R- (1R*, 3S*, 5R*, 6R*, 9R*, 11R*, 15S*, 16R*, 17R*, 18S*, 19E, 21...
Active IngredientAmphotericin b
Dosage FormInjectable
RouteInjection
Strength50mg/vial
Market StatusPrescription
CompanyX Gen Pharms

5 of 8  
Drug NameAbelcet
PubMed HealthAmphotericin B Lipid Complex (Injection)
Drug ClassesAntifungal, Antiprotozoal
Active IngredientAmphotericin b
Dosage FormInjectable, lipid complex
RouteInjection
Strength5mg/ml
Market StatusPrescription
CompanySigma Tau

6 of 8  
Drug NameAmbisome
PubMed HealthAmphotericin B Liposome (Injection)
Drug ClassesAntifungal, Antiprotozoal
Active IngredientAmphotericin b
Dosage FormInjectable, liposomal
RouteInjection
Strength50mg/vial
Market StatusPrescription
CompanyAstellas

7 of 8  
Drug NameAmphotec
PubMed HealthAmphotericin B Cholesteryl Sulfate Complex (Injection)
Drug ClassesAntifungal, Antiprotozoal
Drug LabelAMPHOTEC is a sterile, pyrogen-free, lyophilized powder for reconstitution and intravenous (IV) administration. AMPHOTEC consists of a 1:1 (molar ratio) complex of amphotericin B and cholesteryl sulfate. Upon reconstitution, AMPHOTEC forms a colloi...
Active IngredientAmphotericin b
Dosage FormInjectable, lipid complex
RouteInjection
Strength100mg/vial; 50mg/vial
Market StatusPrescription
CompanyAlkopharma Usa

8 of 8  
Drug NameAmphotericin b
PubMed HealthAmphotericin B (Injection)
Drug ClassesAntifungal, Antiprotozoal
Drug LabelAmphotericin B for Injection USP contains amphotericin B, an antifungal polyene antibiotic obtained from a strain of Streptomyces nodosus. Amphotericin B is designated chemically as [1R- (1R*, 3S*, 5R*, 6R*, 9R*, 11R*, 15S*, 16R*, 17R*, 18S*, 19E, 21...
Active IngredientAmphotericin b
Dosage FormInjectable
RouteInjection
Strength50mg/vial
Market StatusPrescription
CompanyX Gen Pharms

4.2 Therapeutic Uses

Ambecides; Antibiotics, Antifungal; Antibiotics, Macrolide; Antiprotozoal Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


MEDICATION: Antifungal; (VET): Antifungal

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 98


MEDICATION (VET): ... Blastomycosis, histoplasmosis.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 18


Parenteral amphotericin B is used as a secondary agent in the treatment of paracoccidioidomycosis caused by Paracoccidioide brasillensis. /NOT included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 131


For more Therapeutic Uses (Complete) data for AMPHOTERICIN B (19 total), please visit the HSDB record page.


4.3 Drug Warning

Rash (including maculopapular or vesiculobullous rash), purpura, pruritus, urticaria, sweating, exfoliative dermatitis, erythema multiforme, alopecia, dry skin, and skin discoloration or ulcer, have been reported in patients receiving amphotericin B.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 538


IV administration of conventional amphotericin B, amphotericin B cholesteryl sulfate complex, amphotericin B lipid complex, or amphotericin B liposomal may cause erythema, pain, or inflammation at the injection site. Phlebitis or thrombophlebitis has been reported with conventional IV amphotericin B. The manufacturer of conventional IV amphotericin B and some clinicians suggest that the addition of 500-1000 units of heparin to the amphotericin B infusion, the use of a pediatric scalp-vein needle, or alternate-day therapy may decrease the incidence of thrombophlebitis. Extravasation of the drug causes local irritation.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 538


Conventional IV amphotericin B is associated with a high incidence of adverse effects, and most patients who receive the drug experience potentially severe adverse effects at some time during the course of therapy. Acute infusion reactions (e.g., fever, chills, headache, nausea, vomiting) and nephrotoxicity are the most frequent adverse reactions to conventional IV amphotericin B. Although clinical experience with amphotericin B cholesteryl sulfate complex, amphotericin B lipid complex, and amphotericin B liposomal is limited to date, these drugs appear to be better tolerated than conventional IV amphotericin B. As with conventional IV amphotericin B, the most frequent adverse reactions to amphotericin B cholesteryl sulfate complex, amphotericin B lipid complex, or amphotericin B liposomal are acute infusion reactions; however, data accumulated to date indicate that lipid-based and liposomal formulations of amphotericin B may be associated with a lower overall incidence of adverse effects and a lower incidence of hematologic and renal toxicity than the conventional formulation of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 537


Acute infusion reactions consisting of fever, shaking chills, hypotension, anorexia, nausea, vomiting, headache, dyspnea, and tachypnea may occur 1-3 hours after initiation of IV infusions of conventional amphotericin B, amphotericin B cholesteryl sulfate, amphotericin B lipid complex, or amphotericin B liposomal. These reactions are most severe and occur most frequently with initial doses and usually lessen with subsequent doses. Fever (with or without shaking chills) may occur as soon as 15-20 minutes after IV infusions of conventional amphotericin B are started. The majority of patients receiving conventional IV amphotericin B (50-90%) exhibit some degree of intolerance to initial doses of the drug, even when therapy is initiated with low doses. Although these reactions become less frequent following subsequent doses or administration of the drug on alternate days, they recur if conventional IV amphotericin B therapy is interrupted and then reinstituted.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 537


For more Drug Warnings (Complete) data for AMPHOTERICIN B (18 total), please visit the HSDB record page.


4.4 Drug Indication

Used to treat potentially life threatening fungal infections.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Amphotericin B shows a high order of in vitro activity against many species of fungi. Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL in vitro. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses.


5.2 MeSH Pharmacological Classification

Amebicides

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)


Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)


Anti-Bacterial Agents

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


Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
AMPHOTERICIN B
5.3.2 FDA UNII
7XU7A7DROE
5.3.3 Pharmacological Classes
Polyene Antifungal [EPC]; Polyenes [CS]; Lipid-based Polyene Antifungal [EPC]
5.4 ATC Code

A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB04 - Amphotericin B


A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07A - Intestinal antiinfectives

A07AA - Antibiotics

A07AA07 - Amphotericin B


G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AA - Antibiotics

G01AA03 - Amphotericin B


J - Antiinfectives for systemic use

J02 - Antimycotics for systemic use

J02A - Antimycotics for systemic use

J02AA - Antibiotics

J02AA01 - Amphotericin B


5.5 Absorption, Distribution and Excretion

Absorption

Bioavailability is 100% for intravenous infusion.


Clearance

39 +/- 22 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day at Day 1]

17 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day 3-20 days later]

51 +/- 44 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day at Day 1]

22 +/- 15 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day 3-20 days later]

21 +/- 14 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day at Day 1]

11 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day 3-20 days later]


The pharmacokinetics of amphotericin B vary substantially depending on whether the drug is administered as conventional amphotericin B (formulated with sodium desoxycholate), amphotericin B cholesteryl sulfate complex, amphotericin B lipid complex, or amphotericin B liposomal, and pharmacokinetic parameters reported for one amphotericin B formulation should not be used to predict the pharmacokinetics of any other amphotericin B formulation.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 541


Amphotericin B is poorly absorbed from the GI tract and must be given parenterally to treat systemic fungal infections. In one study, immediately after completion of iv infusion of 30 mg of amphotericin B (administered over a period of several hours), average peak serum concentrations were about 1 ug/ml; when the dose was 50 mg, average peak serum concentrations were approximately 2 ug/ml. Immediately after infusion, no more than 10% of the amphotericin B dose can be accounted for in serum. Average minimum serum concentrations (recorded just prior to the next drug infusion) of approximately 0.4 ug/ml have been reported when doses of 30 mg were given daily or when doses of 60 mg were given every other day.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 541


Information on the distribution of amphotericin B is limited, although distribution is apparently multicompartmental. The volume of distribution of the drug following administration of conventional amphotericin B has been reported to be 4 L/kg; the volume of distribution at steady state after administration of amphotericin B cholesteryl sulfate is reported to be 3.8-4.1 L/kg. Amphotericin B concentrations attained in inflamed pleura, peritoneum, synovium, and aqueous humor following IV administration of conventional amphotericin B reportedly are about 60% of concurrent plasma concentrations; the drug also is distributed into vitreous humor, pleural, pericardial, peritoneal, and synovial fluid. Amphotericin B reportedly crosses the placenta and low concentrations are attained in amniotic fluid.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 541


Following IV administration of conventional amphotericin B, CSF concentrations of the drug are approximately 3% of concurrent serum concentrations. To achieve fungistatic CSF concentrations, the drug must usually be administered intrathecally. In patients with meningitis, intrathecal administration of 0.2-0.3 mg of conventional amphotericin B via a subcutaneous reservoir has produced peak CSF concentrations of 0.5-0.8 ug/mL; 24 hours after the dose, CSF concentrations were 0.11-0.29 ug/mL. Amphotericin B is removed from the CSF by arachnoid villi and appears to be stored in the extracellular compartment of the brain, which may act as a reservoir for the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 541


For more Absorption, Distribution and Excretion (Complete) data for AMPHOTERICIN B (14 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Exclusively renal


5.7 Biological Half-Life

An elimination half-life of approximately 15 days follows an initial plasma half-life of about 24 hours.


Amphotericin B cholesteryl sulfate complex has a distribution half-life of 3.5 minutes and an elimination half-life of 27.5-28.2 hours. /Amphotericin B cholesteryl sulfate complex/

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 541


Following IV administration of conventional amphotericin B in patients whose renal function is normal prior to therapy, the initial plasma half-life is approximately 24 hours. After the first 24 hours, the rate at which amphotericin B is eliminated decreases and an elimination half-life of approximately 15 days has been reported.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 541


Elimination, half life: Neonates: Variable (range, 18 to 62.5 hours). Children: Variable (range, 5.5 to 40.3 hours). Adults: Approximately 24 hours. Terminal half life: Approximately 15 days. NOTE: There is large interindividual variation among neonates in the elimination of amphotericin B. Amphotericin B may persist in the circulation of neonates for up to 17 days after it has been discontinued.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 131


. The half life of elimination of amphotericin B from the lungs /of rats/ was 4.8 days according to serial sacrifices done after a single dose of 3.2 mg of aerosol doses of amphotericin B per kg.

PMID:2327759 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC171515 Niki Y et al; Antimicrob Agents Chemother 34 (1): 29-32 (1990)


5.8 Mechanism of Action

Amphotericin B is fungistatic or fungicidal depending on the concentration obtained in body fluids and the susceptibility of the fungus. The drug acts by binding to sterols (ergosterol) in the cell membrane of susceptible fungi. This creates a transmembrane channel, and the resultant change in membrane permeability allowing leakage of intracellular components. Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of amphotericin B and the azoles. Amphotericin B, a polyene, binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death.


Amphotericin B usually is fungistatic in action at concentrations obtained clinically, but may be fungicidal in high concentrations or against very susceptible organisms. Amphotericin B exerts its antifungal activity principally by binding to sterols (e.g., ergosterol) in the fungal cell membrane. As a result of this binding, the cell membrane is no longer able to function as a selective barrier and leakage of intracellular contents occurs. Cell death occurs in part as a result of permeability changes, but other mechanisms also may contribute to the in vivo antifungal effects of amphotericin B against some fungi. Amphotericin B is not active in vitro against organisms that do not contain sterols in their cell membranes (eg, bacteria).

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 540


Binding to sterols in mammalian cells (such as certain kidney cells and erythrocytes) may account for some of the toxicities reported with conventional amphotericin B therapy. At usual therapeutic concentrations of amphotericin B, the drug does not appear to hemolyze mature erythrocytes, and the anemia seen with conventional IV amphotericin B therapy may result from the action of the drug on actively metabolizing and dividing erythropoietic cells.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 540


...Nephrotoxicity associated with conventional IV amphotericin B appears to involve several mechanisms, including a direct vasoconstrictive effect on renal arterioles that reduces glomerular and renal tubular blood flow and a lytic action on cholesterol-rich lysosomal membranes of renal tubular cells. ...

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 537


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29-Jan-2021
31-Aug-2024
KGS
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