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1397-89-3

Basic Information
CAS No.: 1397-89-3
Name: Amphotericin B
Molecular Structure:
Molecular Structure of 1397-89-3 (Amphotericin B)
Formula: C47H73NO17
Molecular Weight: 924.21
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;
EINECS: 215-742-2
Density: 1.34 g/cm3
Melting Point: >170 °C
Boiling Point: 1140.4 °C at 760 mmHg
Flash Point: 643.5 °C
Solubility: <0.1 g/100 mL at 21 °C in water
Appearance: crystalline yellow solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39-45-36
Transport Information: UN 1759 8
PSA: 319.61000
LogP: 1.41200
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
1112349-87-7

amphotericin B methyl pivalate

1397-89-3

AmBisome

Conditions
ConditionsYield
With water In dimethyl sulfoxide at 37℃; pH=7; Phosphate buffer; Enzymatic reaction;
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

1397-89-3

AmBisome

127970-81-4

3′-N-Fmoc-AmB

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 20℃; for 18h;100%
With pyridine In methanol; N,N-dimethyl-formamide at 23℃; for 4h;99%
With pyridine In methanol; N,N-dimethyl-formamide at 20℃; for 12h;95%
135544-68-2

N-(allyloxycarbonyloxy)succinimide

1397-89-3

AmBisome

C51H77NO19

Conditions
ConditionsYield
With pyridine In methanol; N,N-dimethyl-formamide at 23℃; for 16h; Inert atmosphere;100%
In methanol; N,N-dimethyl-formamide at 23℃; for 16h;100%
With pyridine In methanol; N,N-dimethyl-formamide at 23℃; Inert atmosphere;99%
135544-68-2

N-(allyloxycarbonyloxy)succinimide

1397-89-3

AmBisome

C50H75NO19

Conditions
ConditionsYield
With pyridine In methanol; N,N-dimethyl-formamide99%
1397-89-3

AmBisome

4023-02-3

1H-pyrazole-1-carboximidamide hydrochloride

1033521-39-9

guanidine-AmB

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;97%
1397-89-3

AmBisome

amphotericin B

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dimethyl sulfoxide at 23 - 25℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Darkness;97%
1397-89-3

AmBisome

100-46-9

benzylamine

amphotericin B N-benzylamide

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃;95.5%
With triethylamine In N,N-dimethyl acetamide at 20℃; Inert atmosphere;
3731-52-0

3-Aminomethylpyridine

1397-89-3

AmBisome

amphotericin B 3-pyridylamide

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃; Darkness; Inert atmosphere;95.09%
1631-25-0

N-cyclohexylmaleimide

1397-89-3

AmBisome

N-(N-cyclohexylsuccinimidyl)-amphotericin B

Conditions
ConditionsYield
Michael Addition;94.6%
1397-89-3

AmBisome

amphotericin B N-(D)-methoxytryptophanamide

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃;93.85%
18783-53-4

O-tert-Butyl-D-serine

1397-89-3

AmBisome

N-(O-tert-butyl-D-seryl)amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide93.3%
1206-49-1

N-(2,6-dimethylphenyl)maleimide

1397-89-3

AmBisome

N-(N-2,6-dimethylphenylsuccinimidyl)-amphotericin B

Conditions
ConditionsYield
Michael Addition;92.2%
O,O'-bis(4-formylphenylcarbonyl)poly(ethylene)glycol, Mw 20000 (of polyethylene glycol chain)

O,O'-bis(4-formylphenylcarbonyl)poly(ethylene)glycol, Mw 20000 (of polyethylene glycol chain)

1397-89-3

AmBisome

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

Conditions
ConditionsYield
With 4 A molecular sieve; trimethyl orthoformate In N,N-dimethyl-formamide at 20℃;92%
51-45-6

histamine

1397-89-3

AmBisome

amphotericin B N-histaminamide

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere; Darkness;92%
1397-89-3

AmBisome

156775-78-9

1-(2-tert-butylphenyl)-1H-pyrrole-2,5-dione

1513872-40-6

N-(N-2-tert-butylphenylsuccinimidyl)-amphotericin B

Conditions
ConditionsYield
Michael Addition;91.9%
2566-34-9

2-(methylamino)isobutyric acid

1397-89-3

AmBisome

N-(N-methyl-α-methylalanyl)amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide91.1%
55862-98-1

1-(2,4,6-trimethylphenyl)pyrrole-2,5-dione

1397-89-3

AmBisome

1513872-37-1

N-(N-2,4,6-trimethylphenylsuccinimidyl)-amphotericin B

Conditions
ConditionsYield
Michael Addition;89.9%
Stage #1: AmBisome With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: 1-(2,4,6-trimethylphenyl)pyrrole-2,5-dione In N,N-dimethyl-formamide at 20℃;
30 mg

Fmoc-Glu(OtBu)-OH

1397-89-3

AmBisome

1513872-70-2

N-(N-methyl-Oγ-tert-butyl-L-glutamyl)amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide89.9%
1397-89-3

AmBisome

46277-44-5

1-[(pyridin-4-yl)methyl]pyrrole-2,5-dione

N-{N-[(2-pyridin-4-yl)-methyl]succinimidyl}-amphotericin B

Conditions
ConditionsYield
Michael Addition;89.7%
1397-89-3

AmBisome

64960-75-4

(2R)-2-amino-4-tert-butoxy-4-oxobutanoic acid

1513872-71-3

N-(Oβ-tert-butyl-D-aspartyl)amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide88.4%
1631-26-1

1-benzyl-1H-pyrrole-2,5-dione

1397-89-3

AmBisome

1513872-38-2

N-(N-benzylsuccinimidyl)-amphotericin B

Conditions
ConditionsYield
Michael Addition;88%
26371-07-3

1-piperidinepropionic acid

1397-89-3

AmBisome

N-[(3-piperidin-1-yl)propionyl]amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide87.9%
97731-02-7

(R)-2'-fluorophenylalanine

1397-89-3

AmBisome

N-(2-fluoro-D-phenylalanyl)amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide87.6%
875-74-1

(R)-phenylglycine

1397-89-3

AmBisome

N-D-phenylglycyl-amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide87%
4-formylphenylcarbonyl-terminated poly(ethylene glycol)-poly[Nε-(4-formylphenyl-carbonyl)-L-lysine], block copolymer, Mw = 15500, Mw/Mn = 1.18

4-formylphenylcarbonyl-terminated poly(ethylene glycol)-poly[Nε-(4-formylphenyl-carbonyl)-L-lysine], block copolymer, Mw = 15500, Mw/Mn = 1.18

1397-89-3

AmBisome

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

Conditions
ConditionsYield
With 4 A molecular sieve; trimethyl orthoformate86%
O-methyl-O'-(4-formylphenylcarbonyl)poly(ethylene)glycol, Mw 5000 (of polyethylene glycol chain)

O-methyl-O'-(4-formylphenylcarbonyl)poly(ethylene)glycol, Mw 5000 (of polyethylene glycol chain)

1397-89-3

AmBisome

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

Conditions
ConditionsYield
With 4 A molecular sieve; trimethyl orthoformate In N,N-dimethyl-formamide at 20℃;86%
1021027-70-2

1-[3-(N,N-dimethylamino)-2,2-dimethylpropyl]-pyrrole-2,5-dione

1397-89-3

AmBisome

1513872-43-9

N-{N-[3-(N,N-dimethylamino)-2,2-dimethylpropyl]-succinimidyl}-amphotericin B

Conditions
ConditionsYield
Michael Addition;85.5%

2-methyl-3-(pyridin-3-yl)propanoic acid

1397-89-3

AmBisome

1513872-72-4

N-[β-(pyridine-1-yl)-D-alanyl]amphotericin B

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide85.3%
1397-89-3

AmBisome

125697-63-4

6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid 2,5-dioxopyrrolidin-1-yl ester

942412-22-8

N-(Fmoc-6-aminohexanoyl)-amphotericin B

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide for 20h;85%
1397-89-3

AmBisome

619-66-9

4-Carboxybenzaldehyde

N-(4-carboxybenzylidene)amphotericin B

Conditions
ConditionsYield
With 4 A molecular sieve; trimethyl orthoformate In dimethyl sulfoxide at 25℃; for 48h;84%
O,O'-bis(4-formylphenylcarbonyl)poly(ethylene)glycol, Mw 10000 (of polyethylene glycol chain)

O,O'-bis(4-formylphenylcarbonyl)poly(ethylene)glycol, Mw 10000 (of polyethylene glycol chain)

1397-89-3

AmBisome

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

Conditions
ConditionsYield
With 4 A molecular sieve; trimethyl orthoformate In N,N-dimethyl-formamide at 20℃;83%
Raw Materials
36148-89-7
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  • Casno:

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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.