CAS No.1397-89-3,Amphotericin B Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	1397-89-3
Name:	Amphotericin B
Article Data:	9
Cas Database

Formula:	C₄₇H₇₃NO₁₇
Molecular Weight:	924.093
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:	Xi
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

Conditions	Yield
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

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

: N-(4-carboxybenzylidene)amphotericin B

: 1397-89-3
AmBisome

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C55H85NO17

: 1397-89-3
AmBisome

Conditions

Conditions	Yield
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

Conditions	Yield
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

Raw Materials

36148-89-7

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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.