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Amphotericin B

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Name

Amphotericin B

EINECS 215-742-2
CAS No. 1397-89-3 Density 1.34 g/cm3
PSA 319.61000 LogP 1.41200
Solubility <0.1 g/100 mL at 21 °C in water Melting Point >170 °C
Formula C47H73NO17 Boiling Point 1140.4 °C at 760 mmHg
Molecular Weight 924.093 Flash Point 643.5 °C
Transport Information UN 1759 8 Appearance crystalline yellow solid
Safety 26-36/37/39-45-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 1397-89-3 (Amphotericin B) Hazard Symbols IrritantXi
Synonyms

Fungizone;Amphozone;component of Mysteclin-F;Mysteclin-F;33-((3-amino-3,6-dideoxyhexopyranosyl)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;IAB;Amphotericin B (JP14/USP);Amphotericin B (U.S. FDA Approved);AmphotericcinB;

Article Data 9

Amphotericin B Synthetic route

36148-89-7

amphotericin B methyl ester

1397-89-3

AmBisome

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water at 25℃; for 1h;80%
4-formylphenylcarbonyl-terminated poly(ethylene glycol)-poly[Nε-(4-formylphenyl-carbonyl)-L-lysine] amphotericin B Schiff's base, block copolymer, Mw = 26700, Mw/Mn = 1.11

4-formylphenylcarbonyl-terminated poly(ethylene glycol)-poly[Nε-(4-formylphenyl-carbonyl)-L-lysine] amphotericin B Schiff's base, block copolymer, Mw = 26700, Mw/Mn = 1.11

1397-89-3

AmBisome

Conditions
ConditionsYield
With water In phosphate buffer at 37℃; pH=5.5; Kinetics;

N-(4-carboxybenzylidene)amphotericin B

1397-89-3

AmBisome

Conditions
ConditionsYield
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis;
poly(ethylene glycol), Mw 10000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2

poly(ethylene glycol), Mw 10000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2

1397-89-3

AmBisome

Conditions
ConditionsYield
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis;
poly(ethylene glycol), Mw 20000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis-(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2

poly(ethylene glycol), Mw 20000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis-(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2

1397-89-3

AmBisome

Conditions
ConditionsYield
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis;
O-methylpoly(ethylene glycol), Mw 5000 (of polyethylene glycol chain), conjugated with amphotericin B through O'-(1,4-C6H4-CH=)-linker

O-methylpoly(ethylene glycol), Mw 5000 (of polyethylene glycol chain), conjugated with amphotericin B through O'-(1,4-C6H4-CH=)-linker

1397-89-3

AmBisome

Conditions
ConditionsYield
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis;
O-methylpoly(ethylene glycol), Mw 5000 (of polyethylene glycol chain), conjugated with amphotericin B through O'-(1,4-CH2CH2NHCOC6H4C=)-linker

O-methylpoly(ethylene glycol), Mw 5000 (of polyethylene glycol chain), conjugated with amphotericin B through O'-(1,4-CH2CH2NHCOC6H4C=)-linker

1397-89-3

AmBisome

Conditions
ConditionsYield
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis;
O-methylpoly(ethylene glycol), Mw 5000 (of polyethylene glycol chain), conjugated with amphotericin B through O'-(1,4-C(O)C6H4-C=)-linker

O-methylpoly(ethylene glycol), Mw 5000 (of polyethylene glycol chain), conjugated with amphotericin B through O'-(1,4-C(O)C6H4-C=)-linker

1397-89-3

AmBisome

Conditions
ConditionsYield
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis;

C55H85NO17

1397-89-3

AmBisome

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) CSA; 2.) H2O / 1.) MeOH, 25 deg C, 2 h; 2.) MeOH, 25 deg C, 4 h
2: 80 percent / LiOH / tetrahydrofuran; H2O / 1 h / 25 °C
View Scheme

C55H83N3O17

1397-89-3

AmBisome

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / HS(CH2)3SH, Et3N / methanol / 24 h / 25 °C
2: 1.) CSA; 2.) H2O / 1.) MeOH, 25 deg C, 2 h; 2.) MeOH, 25 deg C, 4 h
3: 80 percent / LiOH / tetrahydrofuran; H2O / 1 h / 25 °C
View Scheme

Amphotericin B Specification

The Amphotericin B, with the CAS registry number 1397-89-3,is also known as 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; Fungizone. It belongs to the product categories of Antifungal;Carbohydrates & Derivatives;Chiral Reagents. This chemical's molecular formula is C47H73NO17 and molecular weight is 924.08.Its EINECS number is 215-742-2. What's more,Its systematic name is Amphotericin B.It is a Crystalline Yellow Solid which is stable,incompatible with strong oxidizing agents,but may be light sensitive. It is a kind of polyene antifungal drugs,Isolated from Streptomyces culture.

Physical properties about Amphotericin B are:
(1)ACD/LogP:  1.164; (2)# of Rule of 5 Violations:  3; (3)ACD/LogD (pH 5.5):  -1.34; (4)ACD/LogD (pH 7.4):  -1.41; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  1.00; (8)ACD/KOC (pH 7.4):  1.00; (9)#H bond acceptors:  18; (10)#H bond donors:  13; (11)#Freely Rotating Bonds:  14; (12)Index of Refraction:  1.614; (13)Molar Refractivity:  240.249 cm3; (14)Molar Volume:  689.435 cm3; (15)Surface Tension:  71.6880035400391 dyne/cm; (16)Density:  1.34 g/cm3; (17)Flash Point:  643.47 °C; (18)Enthalpy of Vaporization:  189.982 kJ/mol; (19)Boiling Point:  1140.365 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)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)Std. 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;
(3)Std. InChIKey:APKFDSVGJQXUKY-INPOYWNPSA-N.

Safety Information of Amphotericin B:
The Amphotericin B is irritating to eyes, respiratory system and skin and harmful if swallowed.But there is limited evidence of a carcinogenic effect.It is toxic by inhalation, in contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. When you use it ,wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) .

The toxicity data of Amphotericin B as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 6mg/kg (6mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES Biokhimiya Vol. 43, Pg. 2043, 1978.
infant TDLo intravenous 15mg/kg/4D-I (15mg/kg)   Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 371, 1990.
infant TDLo intravenous 15mg/kg/4D-I (15mg/kg)   Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 371, 1990.
man LDLo intravenous 164ug/kg/5H-I (0.164mg/kg) CARDIAC: OTHER CHANGES Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 547, 1983.
mouse LD unreported > 50mg/kg (50mg/kg)   Journal of Antibiotics. Vol. 24, Pg. 561, 1971.
mouse LD12 oral 280mg/kg (280mg/kg)   British UK Patent Application. Vol. #2067993,
mouse LD50 intramuscular > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
mouse LD50 intraperitoneal 27740ug/kg (27.74mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 1200ug/kg (1.2mg/kg)   Pharmacy International. Vol. 6, Pg. 164, 1985.
rabbit LDLo intravenous 5mg/kg (5mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics Annual. Vol. 5, Pg. 53, 1957/1958.
rat LD50 intramuscular > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
rat LD50 intravenous 1600ug/kg (1.6mg/kg)   Journal of Antimicrobial Chemotherapy. Vol. 28(Suppl,
rat LD50 oral > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
women LDLo intravenous 22mg/kg/4D-I (22mg/kg) BLOOD: LEUKOPENIA Southern Medical Journal. Vol. 76, Pg. 409, 1983.
women TDLo intravenous 20ug/kg (0.02mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES New England Journal of Medicine. Vol. 315, Pg. 836, 1986.
women TDLo intravenous 1mg/kg/1H-C (1mg/kg) CARDIAC: PULSE RATE Lancet. Vol. 341, Pg. 372, 1993.

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