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1397-89-3

1397-89-3 structure
1397-89-3 structure
  • Name: Amphotericin B
  • Chemical Name: amphotericin B
  • CAS Number: 1397-89-3
  • Molecular Formula: C47H73NO17
  • Molecular Weight: 924.079
  • Catalog: API Antibiotics Polyene
  • Create Date: 2018-09-28 00:16:24
  • Modify Date: 2024-01-02 09:45:05
  • Amphotericin B is a polyene antifungal agent against a wide variety of fungal pathogens. It binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death.
Name amphotericin B
Synonyms Ampho-moronal
LNS-AmB
(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
Amphocin
Amphotec
MFCD00877763
Halizon
(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-diox abicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
abicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
Fungilin
EINECS 215-742-2
Amphozone
Amphotericin B
14,39-Dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid, 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-, (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-
AmBisome
(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
FUNGIZONE
ns718
Abelcet
Abelecet
(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-b-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
14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid, 33-[(3-amino-3,6-dideoxy-b-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-, (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-
Description Amphotericin B is a polyene antifungal agent against a wide variety of fungal pathogens. It binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death.
Related Catalog
Target

Fungal[1]
In Vitro Amphotericin B administration is limited by infusion-related toxicity, including fever and chills, an effect postulated to result from proinflammatory cytokine production by innate immune cells. Amphotericin B induces signal transduction and inflammatory cytokine release from cells expressing TLR2 and CD14[1]. Amphotericin B interacts with cholesterol, the major sterol of mammal membranes, thus limiting the usefulness of Amphotericin B due to its relatively high toxicity. Amphotericin B is dispersed as a pre-micellar or as a highly aggregated state in the subphase[2]. Amphotericin B only kills unicellular Leishmania promastigotes (LPs) when aqueous pores permeable to small cations and anions are formed. Amphotericin B (0.1 mM) induces a polarization potential, indicating K+ leakage in KCl-loaded liposomes suspended in an iso-osmotic sucrose solution. Amphotericin B (0.05 mM) exhibits a nearly total collapse of the negative membrane potential, indicating Na+ entry into the cells[3].
In Vivo Amphotericin B results in prolonging the incubation time and decreasing PrPSc accumulation in the hamster scrapie model. Amphotericin B markedly reduces PrPSc levels in mice with transmissible subacute spongiform encephalopathies (TSSE)[4]. Amphotericin B exerts a direct effect on Plasmodium falciparum and influences eryptosis of infected erythrocytes, parasitemia and hostsurvival in murine malaria. Amphotericin B tends to delay the increase of parasitemia and significantly delays host death plasmodium berghei-infected mice[5].
Kinase Assay THP-1 and HEK293 cells are transiently transfected using DEAE-dextran and Polyfect reagent, respectively. Plasmids transfected contain genes coding for the NF-κB-dependent pELAM-luc luciferase reporter, TLR2, TLR4, CD14, and MD2. Cells (5×105 THP-1 or 1×105 HEK293) are added to 12-well plates, washed after 18 h, and stimulated for 5 h. Cells are then lysed with reporter lysis buffer as directed, and lysates are analyzed for luminescence using Promega luciferase substrate and a Monolight 3010 luminometer.
Cell Assay The kinetics of cell death induced by AmB against Leishmania promastigotes is followed by using fluorometry with the DNA-binding compound ethidium bromide (EB). Fluorescence measurements are performed on a SPEX Fluorolog II spectrophotometer at 365-580 nm excitation-emission wavelengths. Promastigotes at a final concentration of 25×106 cells/mL are incubated for 5 min with gentle stirring in the fluorescence cuvette with 2 mL of different buffered solutions but always containing 10 mM glucose and EB (50 mM). After signal stabilization is achieved, AmB is added and dissolved in dimethylsulfoxide. Maximal EB incorporation is always obtained by adding digitonin (50 mg/mL). All solutions used are buffered with 75 mM TRIS (pH 4 7.6) and contain 150 mM NaCl (BNa+), 150 mM KCl (BK+), 150 mM choline chloride, and 100 mM sucrose, 100 mM NaCl. The osmolarity of all solutions is always adjusted to 390±5 mOsm using an advanced instrument SW2 osmometer.
References

[1]. Sau K, et al. The antifungal drug amphotericin B promotes inflammatory cytokine release by a Toll-like receptor- and CD14-dependent mechanism. J Biol Chem. 2003 Sep 26;278(39):37561-8. Epub 2003 Jul 14.

[2]. Barwicz J, et al. The effect of aggregation state of amphotericin-B on its interactions with cholesterol- or ergosterol-containing phosphatidylcholine monolayers. Chem Phys Lipids. 1997 Feb 28;85(2):145-55.

[3]. Ramos H, et al. Amphotericin B kills unicellular leishmanias by forming aqueous pores permeable to small cations and anions. J Membr Biol. 1996 Jul;152(1):65-75.

[4]. Demaimay R, et al. Pharmacological studies of a new derivative of amphotericin B, MS-8209, in mouse and hamster scrapie. J Gen Virol. 1994 Sep;75 (Pt 9):2499-503.

[5]. Adams ML, et al. Amphotericin B encapsulated in micelles based on poly(ethylene oxide)-block-poly(L-amino acid) derivatives exerts reduced in vitro hemolysis but maintains potent in vivo antifungal activity. Biomacromolecules. 2003 May-Jun;4(3):750-7.
Density 1.3±0.1 g/cm3
Boiling Point 1140.4±65.0 °C at 760 mmHg
Melting Point >170°C
Molecular Formula C47H73NO17
Molecular Weight 924.079
Flash Point 643.5±34.3 °C
Exact Mass 923.487854
PSA 319.61000
LogP 1.16
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.614
Stability Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
Water Solubility sterile water: 20 mg/mL as a stock solution. Stock solutions should be stored at −20?#x00b0;C. Stable at 37?#x00b0;C for 3 days. | <0.1 g/100 mL at 21 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BU2625000
CHEMICAL NAME :
Amphotericin B
CAS REGISTRY NUMBER :
1397-89-3
BEILSTEIN REFERENCE NO. :
0078342
LAST UPDATED :
199612
DATA ITEMS CITED :
33
MOLECULAR FORMULA :
C47-H73-N-O17
MOLECULAR WEIGHT :
924.21
WISWESSER LINE NOTATION :
T6-36- A AO RVO A&U C&U E&U G&U I&U K&U M&UTJ CVQ DQ FQ HQ JQ KQ NQ PQ T1 U1 VQ W1 O&O- BT6OT

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
22 mg/kg/4D-I
TOXIC EFFECTS :
Blood - leukopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
20 ug/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
164 ug/kg/5H-I
TOXIC EFFECTS :
Cardiac - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
15 mg/kg/4D-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - changes in potassium Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1 mg/kg/1H-C
TOXIC EFFECTS :
Cardiac - pulse rate
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
27740 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
6 mg/kg
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
490 mg/kg/14W-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
55 mg/kg/13W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
37 mg/kg/30D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
5500 ug/kg
SEX/DURATION :
female 6-16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
20 mg/kg
SEX/DURATION :
male 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

MUTATION DATA

TEST SYSTEM :
Rodent - rabbit
DOSE/DURATION :
20 mg/kg/11D
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 7,13,1964 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84491 No. of Facilities: 561 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 6392 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84491 No. of Facilities: 386 (estimated) No. of Industries: 2 No. of Occupations: 10 No. of Employees: 15048 (estimated) No. of Female Employees: 12218 (estimated)
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H335
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant
Risk Phrases R36/37/38
Safety Phrases S26-S36/37/39-S45-S36
RIDADR UN 1759 8/PG 3
WGK Germany 3
RTECS BU2625000
Packaging Group III
Hazard Class 6.1(b)
Precursor  2

DownStream  0


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