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166663-25-8

Basic Information
CAS No.: 166663-25-8
Name: Anidulafungin
Article Data: 2
Molecular Structure:
Molecular Structure of 166663-25-8 (Anidulafungin)
Formula: C58H73N7O17
Molecular Weight: 1140.25
Synonyms: LY 303366;Ecalta;Eraxis;Anidulafungin;
EINECS: 658-060-4
Density: 1.47 g/cm3
Boiling Point: 1477 °C at 760 mmHg
Flash Point: 847 °C
PSA: 377.42000
LogP: 0.65480
Synthetic route

ECBN*HCl

1-({[4′′-(pentyloxy)-1,1′:4′,1′′-terphenyl-4-yl]carbonyl}oxy)-1H-1,2,3-benzotriazole

A

C82H95N7O19

B

C58H73N7O17

C

166663-25-8

Anidulafungin

Conditions
ConditionsYield
With potassium dihydrogenphosphate In water; acetone at 55℃; for 3h; Large scale;A n/a
B n/a
C 71%
158937-65-6

2,4,5-trichlorophenyl 4-(4'-pentyloxybiphenyl)benzoate

echinocandin B

166663-25-8

Anidulafungin

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature; Yield given;
619-44-3

methyl 4-iodobenzoate

166663-25-8

Anidulafungin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) sec-butyllithium, 2.) triisopropyl borate, 3.) K2CO3, tetrakis(triphenylphosphine)palladium(0)
2: 2 N aq. NaOH / dioxane / 17 h / Heating
3: dicyclohexylcarbodiimide / CH2Cl2 / Ambient temperature
4: dimethylformamide / Ambient temperature
View Scheme
63619-51-2

4-bromo-4'-pentyloxybiphenyl

166663-25-8

Anidulafungin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) sec-butyllithium, 2.) triisopropyl borate, 3.) K2CO3, tetrakis(triphenylphosphine)palladium(0)
2: 2 N aq. NaOH / dioxane / 17 h / Heating
3: dicyclohexylcarbodiimide / CH2Cl2 / Ambient temperature
4: dimethylformamide / Ambient temperature
View Scheme
158938-08-0

4′′-(pentyloxy)-1,1′:4′,1′′-terphenyl-4-carboxylic acid

166663-25-8

Anidulafungin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexylcarbodiimide / CH2Cl2 / Ambient temperature
2: dimethylformamide / Ambient temperature
View Scheme
158937-30-5

4′′-pentyloxy-[1,1':4',1′′-terphenyl]-4-carboxylic acid methyl ester

166663-25-8

Anidulafungin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2 N aq. NaOH / dioxane / 17 h / Heating
2: dicyclohexylcarbodiimide / CH2Cl2 / Ambient temperature
3: dimethylformamide / Ambient temperature
View Scheme
166663-25-8

Anidulafungin

179118-65-1

4''-pentyloxy-[1,1';4',1'']terphenyl-4-carboxylic acid {11,20,25-trihydroxy-3,15-bis-(1-hydroxy-ethyl)-6-[1-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl}-amide

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane for 24h; Ambient temperature;70%
2916-68-9

2-(Trimethylsilyl)ethanol

166663-25-8

Anidulafungin

185425-57-4

C63H85N7O17Si

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 3h; Ambient temperature;
80909-96-2

O-tosyl-3-tert-butoxycarbonylamino-1-propanol

166663-25-8

Anidulafungin

C61H80N8O17

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide
166663-25-8

Anidulafungin

nitro-anidulafugin

Conditions
ConditionsYield
With acetic acid; sodium nitrite
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    Product Name: Anidulafungin Synonyms: Anidulafungin;Echinocandin B, 1-(4R,5R)-4,5-dihydroxy-N2-4-(pentyloxy)1,1:4,1-terphenyl-4-ylcarbonyl-L-ornithine-;Anidulafungin(LY303366);Ecalta;Eraxis;LY 303366;LY 303366, Eraxis;1-[(4R,5R)-4,5-dihydroxy-N

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Specification

The Anidulafungin with CAS registry number 166663-25-8, belongs to the class of Antifungals. The IUPAC name is N-{(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydr o-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}-4''-(pentyloxy)-1,1':4',1''-terphenyl-4-carboxamide. In addition, the molecular formula is C58H73N7O17 and the molecular weight is 1140.24. And it is a cyclic hexapeptide echinocandin. It is an antifungal drug originally manufactured and submitted for FDA. This drug is safe to use in patients with any degree of hepatic or renal impairment. What's more, this chemical inhibits glucan synthase, which is important in the formation of β-(1,3)-D-glucan.

Physical properties about Anidulafungin are: (1)ACD/LogP: 4.343; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 4.34; (4)ACD/LogD (pH 7.4): 4.34; (5)ACD/BCF (pH 5.5): 1174.94; (6)ACD/BCF (pH 7.4): 1170.92; (7)ACD/KOC (pH 5.5): 5480.66; (8)ACD/KOC (pH 7.4): 5461.93; (9)#H bond acceptors: 24; (10)#H bond donors: 14; (11)#Freely Rotating Bonds: 23; (12)Index of Refraction: 1.688; (13)Molar Refractivity: 294.242 cm3; (14)Molar Volume: 771.385 cm3; (15)Polarizability: 116.647 10-24cm3; (16)Surface Tension: 88.3550033569336 dyne/cm; (17)Density: 1.478 g/cm3; (18)Flash Point: 847.048 °C; (19)Enthalpy of Vaporization: 237.592 kJ/mol; (20)Boiling Point: 1476.982 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4N7[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N5[C@H](C(=O)N[C@H](O)[C@H](O)C[C@H](NC(=O)c3ccc(c2ccc(c1ccc(OCCCCC)cc1)cc2)cc3)C(=O)N[C@H]4[C@H](O)C)[C@@H](O)[C@@H](C)C5)[C@H](O)C)[C@H](O)[C@@H](O)c6ccc(O)c c6)C[C@@H](O)C7
(2)InChI: InChI=1/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42-,43+,44-,45-,46-,47-,48-,49-,50-,54+/m0/s1
(3)InChIKey: JHVAMHSQVVQIOT-MFAJLEFUBR

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD oral > 1gm/kg (1000mg/kg)   Drugs of the Future. Vol. 19, Pg. 338, 1994.