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Amphotericin B information


Amphotericin B
Clinical data
Trade namesFungizone, Mysteclin-F, AmBisome and other
AHFS/Drugs.comMonograph
MedlinePlusa682643
License data
  • US DailyMed: Amphotericin_B
Pregnancy
category
  • AU: B2[1]
Routes of
administration
Intravenous infusion
ATC code
  • A01AB04 (WHO) A07AA07 (WHO), G01AA03 (WHO), J02AA01 (WHO)
Legal status
Legal status
  • US: ℞-only[2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability100% (IV)
Metabolismkidney
Elimination half-life
  • Initial phase: 24 hours
  • Second phase: approximately 15 days
Excretion
  • 40% found in urine after single cumulated over several days
  • Biliar excretion also important
Identifiers
IUPAC name
  • (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- β-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
CAS Number
  • 12633-72-6 checkY
PubChem CID
  • 14956
DrugBank
  • DB00681 checkY
ChemSpider
  • 10237579 checkY
UNII
  • 7XU7A7DROE
KEGG
  • D00203 checkY
ChEBI
  • CHEBI:2682 checkY
ChEMBL
  • ChEMBL267345 checkY
NIAID ChemDB
  • 000096
CompTox Dashboard (EPA)
  • DTXSID9022601 Edit this at Wikidata
ECHA InfoCard100.014.311 Edit this at Wikidata
Chemical and physical data
FormulaC47H73NO17
Molar mass924.091 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point170 °C (338 °F)
SMILES
  • O=C(O)[C@@H]3[C@@H](O)C[C@@]2(O)C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@@H](C)[C@H](C)[C@H](O)[C@@H](C)C=CC=CC=CC=CC=CC=CC=C[C@H](O[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O)C[C@@H]3O2
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 checkY
  • Key:APKFDSVGJQXUKY-INPOYWNPSA-N checkY
  (verify)

Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis.[3] The fungal infections it is used to treat include mucormycosis, aspergillosis, blastomycosis, candidiasis, coccidioidomycosis, and cryptococcosis.[4] For certain infections it is given with flucytosine.[5] It is typically given intravenously (injection into a vein).[4]

Common side effects include a reaction with fever, chills, and headaches soon after the medication is given, as well as kidney problems.[4] Allergic symptoms including anaphylaxis may occur.[4] Other serious side effects include low blood potassium and myocarditis (inflammation of the heart).[3] It appears to be relatively safe in pregnancy.[4] There is a lipid formulation that has a lower risk of side effects.[4] It is in the polyene class of medications and works in part by interfering with the cell membrane of the fungus.[3][4]

Amphotericin B was isolated from Streptomyces nodosus in 1955 at the Squibb For Medical Research Institute from cultures isolated from the streptomycete obtained from the river bed of Orinoco in that region of Venezuela[6] and came into medical use in 1958.[7][8] It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication.[4][10]

  1. ^ "Updates to the Prescribing Medicines in Pregnancy database". Therapeutic Goods Administration (TGA). 12 May 2022. Retrieved 13 May 2022.
  2. ^ "Ambisome- amphotericin b injection, powder, lyophilized, for solution". DailyMed. Retrieved 11 August 2021.
  3. ^ a b c World Health Organization (March 2010). Control of the leishmaniasis: report of a meeting of the WHO Expert Committee on the Control of Leishmaniases. Geneva: World Health Organization. pp. 55, 88, 186. hdl:10665/44412. ISBN 9789241209496.
  4. ^ a b c d e f g h "Amphotericin B". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-01. Retrieved January 1, 2015.
  5. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 145. hdl:10665/44053. ISBN 9789241547659.
  6. ^ Velázquez L (1976). Farmacología y su proyección a la clínica 13a ed (in Spanish). Oteo. p. 966. ISBN 8485152050.
  7. ^ Walker SR (2012). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN 9789400926592. Archived from the original on 2017-09-10.
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 477. ISBN 9783527607495.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.

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Amphotericin B

Last Update:

Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include mucormycosis...

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Mucor mucedo

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the consumption of cheese contaminated with M. mucedo mould growth. Amphotericin B, a drug primarily used for treatment of patients with progressive and...

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Coccidioidomycosis

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cytotoxicity. These include liposomal amphotericin B, amphotericin B lipid complex such as Abelcet (brand) amphotericin B phospholipid complex also as AmBisome...

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Neutropenia

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review found that lipid formulations of amphotericin B had fewer side effects than conventional amphotericin B, though it is not clear whether there are...

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Coccidioides immitis

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including these newer drugs. In very severe cases, combination therapy with amphotericin B and an azole have been postulated, although no trials have been conducted...

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Antifungal

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concentration required in that region for therapeutic benefit. Example(s): amphotericin B. This may be used to treat some fungal infections of the vaginal region...

Word Count : 2564

Mucormycosis

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It may appear similar to aspergillosis. Treatment is generally with amphotericin B and surgical debridement. Preventive measures include wearing a face...

Word Count : 5584

Aspergillosis

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aggressive invasive aspergillosis include voriconazole and liposomal amphotericin B in combination with surgical debridement. For the less aggressive allergic...

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Polyene

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bonds. The following polyenes are used as antimycotics for humans: amphotericin B, nystatin, candicidin, pimaricin, methyl partricin, and trichomycin...

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Sporotrichosis

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surgery. Systemic medications used include Itraconazole, posaconazole and amphotericin B. With treatment, most people will recover, but an immunocompromised...

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Histoplasmosis

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preparations of amphotericin B have risk of nephrotoxicity. Individuals taking amphotericin B are monitored for renal function. Liposomal amphotericin B is better...

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Visceral leishmaniasis

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"IL-10- and TGF-B-Mediated Susceptibility in Kala-azar and Post-kala-azar Dermal Leishmaniasis: The Significance of Amphotericin B in the Control of...

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Cryptococcosis

Last Update:

cerebrospinal fluid, sputum, and skin biopsy. Treatment is with fluconazole or amphotericin B. Data from 2009 estimated that of the almost one million cases of cryptococcal...

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Candidiasis

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usually effective. Oral or intravenous fluconazole, itraconazole, or amphotericin B may be used if these do not work. A number of topical antifungal medications...

Word Count : 6310

Candida tropicalis

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bloodstream to peripheral organs. For invasive disease, treatments include amphotericin B, echinocandins, or extended-spectrum triazole antifungals. In the history...

Word Count : 2783

Leishmaniasis

Last Update:

Some possible medications used for visceral disease include liposomal amphotericin B, a combination of pentavalent antimonials and paromomycin, and miltefosine...

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Drugs for Neglected Diseases Initiative

Last Update:

the first-line treatment for VL. Single dose amphotericin B and paromomycin/miltefosine/amphotericin B combinations were recommended by the WHO Expert...

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Naegleriasis

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basis of the laboratory evidence and case reports, heroic doses of amphotericin B have been the traditional mainstay of PAM treatment since the first...

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Cryptococcus neoformans

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cryptococcal meningitis. A new study found that brain glucose can trigger amphotericin B (AmB) tolerance of C. neoformans during meningitis which means it needs...

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Blastomycosis

Last Update:

mild or moderate disease. In severe cases, patients are treated with amphotericin B before azole treatment. In either event, the azole treatment lasts for...

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Nephrotoxicity

Last Update:

Proximal convoluted tubule: Aminoglycoside antibiotics (e.g., gentamicin), amphotericin B, cisplatin, radiocontrast media, immunoglobulins, mannitol Distal tubule:...

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Nystatin

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activity than colloidal formulations of amphotericin B, and demonstrated effectiveness against some amphotericin B-resistant forms of fungi. It offers an...

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Aspergillus terreus

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people with deficient immune systems. It is relatively resistant to amphotericin B, a common antifungal drug. Aspergillus terreus also produces aspterric...

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Leishmania donovani

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this therapy. Another antimicrobial drug amphotericin B is also commonly used. Liposomal amphotericin B (L-AmB) has been a drug of choice in India, but...

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Ergosterol

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the use of some antifungals against West African sleeping sickness. Amphotericin B, an antifungal drug, targets ergosterol. It binds physically to ergosterol...

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Clavispora lusitaniae

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2013. Some investigators have theorized that the widespread use of Amphotericin B empiric antifungal therapy selects for infections with Candida lusitaniae...

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Nakaseomyces glabratus

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medications such as amphotericin B and nystatin, along with variable vulnerability to flucytosine and caspofungin. However, intravenous amphotericin B is a medication...

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List of infectious diseases

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"Rabies". www.who.int. Retrieved 2023-06-16. Lindell, D. M.; Morris, S. B.; White, M. P.; Kallal, L. E.; Lundy, P. K.; Hamouda, T.; Baker, J. R.; Lukacs...

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Pichia kudriavzevii

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 rugosa. P. kudriavzevii can be successfully treated with voriconazole, amphotericin B, and echinocandins (micafungin, caspofungin, and anidulafungin).[citation...

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Macrolide

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have similar activity to ciclosporin. Polyene antimycotics, such as amphotericin B, nystatin etc., are a subgroup of macrolides. Cruentaren is another...

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