Panobinostat supplier | CasNO.404950-80-7

Name
Panobinostat
EINECS 803-814-1
CAS No. 404950-80-7
Article Data12
CAS DataBase
Density 1.241 g/cm³
Solubility
Melting Point 114-117?C
Formula C₂₁H₂₃N₃O₂
Boiling Point
Molecular Weight 349.433
Flash Point
Transport Information
Appearance Yellow solid
Safety 24/25
Risk Codes 22-36/37/38-20
Molecular Structure
Hazard Symbols
Synonyms LBH589;N-Hydroxy-3-[4-[2-(2-methyl-1H-indol-3-yl)ethylaminomethyl]phenyl]-2(E)-propenamide;
PSA 77.15000
LogP 4.10900

Synthetic route

: 441741-66-8
(E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
Stage #1: (E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride With sodium hydroxide In methanol at -15 - -10℃; for 0.166667h; Stage #2: With hydroxylamine hydrochloride In methanol at -15 - -10℃; for 3.66667h;	94.6%
With hydroxylamine; potassium hydroxide In methanol at 0℃; for 4h; Inert atmosphere;	73%
With sodium hydroxide; hydroxylamine hydrochloride In water at 0℃; for 6h;
Stage #1: (E)-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]acrylic acid methyl ester hydrochloride With hydroxylamine; sodium hydroxide In ethanol; water at 0℃; Stage #2: With hydrogenchloride In water

: 441741-65-7
(E)-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]acrylic acid methyl ester

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
With hyydroxylamine methanol; potassium hydroxide at 20℃; for 4h; Inert atmosphere;	62.5%
With hydroxylamine; potassium hydroxide In methanol at 20℃; for 6h;	62.5%

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-L-tartarate

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
pH = 6.8 buffer;

: 960058-93-9
(E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylic acid

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
Stage #1: (E)-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylic acid With hydroxylamine In methanol; water at -15 - 25℃; Stage #2: With hydrogenchloride In water pH=10.3 - 10.7;

: methyl (2E)-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoate hydrochloride

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; potassium hydroxide In propan-1-ol; ethylene glycol at -6℃;	77.0 g

: 2731-06-8
2-methyltryptamine

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 10 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / Inert atmosphere 3.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / Inert atmosphere 3.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme

: 100-63-0
phenylhydrazine

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 10 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: ethanol / 4.5 h / 35 - 40 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 2.2: 6 h / 0 °C / Inert atmosphere 3.1: hydroxylamine; potassium hydroxide / methanol / 6 h / 20 °C View Scheme

: 5891-21-4
5-chloro-2-pentanone

: 404950-80-7
panobinostat

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 10 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: ethanol / 4.5 h / 40 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: hyydroxylamine methanol; potassium hydroxide / 4 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: ethanol / 4.5 h / 35 - 40 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 2.2: 6 h / 0 °C / Inert atmosphere 3.1: hydroxylamine; potassium hydroxide / methanol / 6 h / 20 °C View Scheme

: 404950-80-7
panobinostat

: 75-75-2
methanesulfonic acid

: 960055-60-1
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide phosphate

Conditions

Conditions	Yield
In ethyl acetate at 50℃;	98.3%
In ethyl acetate at 50℃; Product distribution / selectivity;	98.3%
In ethyl acetate at 20 - 50℃; Product distribution / selectivity;
In ethyl acetate at 4 - 20℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 87-69-4
L-Tartaric acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-L-tartarate

Conditions

Conditions	Yield
In ethanol at 60℃; for 2h;	96.6%
In ethanol at 60℃; Product distribution / selectivity;	96.6%

: 404950-80-7
panobinostat

: 87-69-4
L-Tartaric acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-L-tartarate

Conditions

Conditions	Yield
In ethanol at 0 - 60℃; Product distribution / selectivity; Cooling with ice;	96.6%

: 404950-80-7
panobinostat

: 960055-52-1
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water	96.2%
With hydrogenchloride In ethanol; water at 60℃; Product distribution / selectivity;
With hydrogenchloride In ethyl acetate at 20℃; Product distribution / selectivity;

: 849585-22-4
LACTIC ACID

: 404950-80-7
panobinostat

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]acrylamide DL-lactate

Conditions

Conditions	Yield
In water at 60 - 90℃;	91%

: 404950-80-7
panobinostat

: 110-16-7
maleic acid

: 960055-57-6
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide maleate

Conditions

Conditions	Yield
In acetone at 45℃;	90.5%
In acetone at 0 - 45℃; Product distribution / selectivity; Cooling with ice;	90.5%
In isopropyl alcohol at 60℃; Product distribution / selectivity;
In acetone at 60℃; Product distribution / selectivity;
In isopropyl alcohol at 4 - 60℃; Product distribution / selectivity;

: 849585-22-4
LACTIC ACID

: 404950-80-7
panobinostat

: 960055-56-5
panobinostat lactate

Conditions

Conditions	Yield
In water; acetone at 0 - 20℃; Product distribution / selectivity; Cooling with ice;	86.2%
In isopropyl alcohol at 4℃; Product distribution / selectivity;

: 50-00-0
formaldehyd

: 404950-80-7
panobinostat

: (E)-N-hydroxy-3-(4-((methyl(2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)acrylamide

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride In methanol; dichloromethane at 20℃; for 3h; Inert atmosphere;	45%

: 404950-80-7
panobinostat

: (SP-4-2)-dichlorido(cyclohexane-1R,2R-diamine)-platinum(II)

: [PtII((1R,2R)-(–)-1,2-diaminocyclohexane)((E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide-2H)]

Conditions

Conditions	Yield
Stage #1: (SP-4-2)-dichlorido(cyclohexane-1R,2R-diamine)-platinum(II) With silver nitrate In water at 20℃; Darkness; Stage #2: panobinostat In water; N,N-dimethyl-formamide at 20℃; for 24h;	18%

: 404950-80-7
panobinostat

: 64-19-7
acetic acid

: 67-64-1
acetone

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide acetate acetone solvate

Conditions

Conditions	Yield
at 20℃;

...Expand

: 404950-80-7
panobinostat

: 64-19-7
acetic acid

: 960055-50-9
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide acetate

Conditions

Conditions	Yield
In isopropyl alcohol at 60℃; Product distribution / selectivity;
In ethyl acetate at 60℃; Product distribution / selectivity;
In acetone at 4 - 20℃; Product distribution / selectivity;
In acetone at 4 - 20℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 64-17-5
ethanol

: 65-85-0
benzoic acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide benzoate ethanol hemisolvate

Conditions

Conditions	Yield
In water at 20℃; Product distribution / selectivity;
at 20℃; Product distribution / selectivity;

...Expand

: 404950-80-7
panobinostat

: 67-63-0
isopropyl alcohol

: 65-85-0
benzoic acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide benzoate 2-propanol hemisolvate

Conditions

Conditions	Yield
In water at 20℃; Product distribution / selectivity;
at 20℃; Product distribution / selectivity;

...Expand

: 404950-80-7
panobinostat

: 65-85-0
benzoic acid

: 960055-51-0
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide benzoate

Conditions

Conditions	Yield
In acetone at 20℃;
In ethanol; water at 4 - 20℃; Product distribution / selectivity;
In ethanol; water at 4 - 20℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 77-92-9
citric acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemicitrate

Conditions

Conditions	Yield
In water; isopropyl alcohol at 60℃; Product distribution / selectivity;
In ethanol at 60℃; Product distribution / selectivity;
In water; acetone at 60℃; Product distribution / selectivity;
In acetone at 20 - 60℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 110-17-8
(2E)-but-2-enedioic acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-fumarate

Conditions

Conditions	Yield
In ethanol at 20℃;
In water; isopropyl alcohol at 20 - 60℃; Product distribution / selectivity;
In isopropyl alcohol at 20℃; Product distribution / selectivity;
In ethanol; water at 20 - 60℃; Product distribution / selectivity;
In ethanol at 4 - 20℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 490-79-9
2,5-dihydroxybenzoic acid.

: 960055-55-4
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide gentisate

Conditions

Conditions	Yield
In ethanol; water at 60℃;
In ethanol; water at 4 - 60℃;

: 849585-22-4
LACTIC ACID

: 404950-80-7
panobinostat

: 960055-68-9
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide DL-lactate monohydrate

Conditions

Conditions	Yield
In isopropyl alcohol at 4 - 20℃; Product distribution / selectivity;
In acetone at 4 - 20℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 617-48-1
malic acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-malate

Conditions

Conditions	Yield
In ethanol; water at 20 - 60℃; Product distribution / selectivity;
In isopropyl alcohol at 60℃; Product distribution / selectivity;
In ethanol at 60℃; Product distribution / selectivity;
In ethanol; water at 4 - 60℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 141-82-2
malonic acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-malonate

Conditions

Conditions	Yield
In ethanol at 60℃; Product distribution / selectivity;
In isopropyl alcohol at 60℃; Product distribution / selectivity;
In acetone at 20 - 60℃; Product distribution / selectivity;
In isopropyl alcohol at 4 - 60℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 64-17-5
ethanol

: 86119-84-8, 7664-38-2
phosphoric acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide phosphate ethanol hemisolvate

Conditions

Conditions	Yield
at 20℃;

...Expand

: 404950-80-7
panobinostat

: 86119-84-8, 7664-38-2
phosphoric acid

: 67-63-0
isopropyl alcohol

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide phosphate isopropanol hemisolvate

Conditions

Conditions	Yield
at 20℃;

...Expand

: 404950-80-7
panobinostat

: 86119-84-8, 7664-38-2
phosphoric acid

: 960055-62-3
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide phosphate

Conditions

Conditions	Yield
In acetone at 20 - 60℃; Product distribution / selectivity;
In ethyl acetate at 20 - 60℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 802294-64-0
propionic acid

: 67-63-0
isopropyl alcohol

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide propionate isopropanol hemisolvate

Conditions

Conditions	Yield
at 60℃;

...Expand

: 404950-80-7
panobinostat

: 802294-64-0
propionic acid

: 960055-63-4
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide propionate

Conditions

Conditions	Yield
In acetone at 60℃; Product distribution / selectivity;
In ethyl acetate at 60℃; Product distribution / selectivity;
In isopropyl alcohol at 4 - 60℃; Product distribution / selectivity;

: 404950-80-7
panobinostat

: 67-63-0
isopropyl alcohol

: 1.5C3H8O*C21H23N3O2*H2O4S

Conditions

Conditions	Yield
With sulfuric acid at 60℃;

: 404950-80-7
panobinostat

: 960055-65-6
N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide sulfate

Conditions

Conditions	Yield
With sulfuric acid In ethyl acetate at 20℃;

: 404950-80-7
panobinostat

: 110-15-6
succinic acid

: N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide hemi-succinate

Conditions

Conditions	Yield
In ethanol; water at 60℃; Product distribution / selectivity;
In ethanol at 20 - 60℃; Product distribution / selectivity;
In ethanol; water at 4 - 60℃; Product distribution / selectivity;

Panobinostat Specification

The IUPAC name of Panobinostat is (E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide. With the CAS registry number 404950-80-7, it is also named as 2-Propenamide, N-hydroxy-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)-, (2E)-. The product's category is Intracellular Signaling. It is yellow solid which is soluble in DMSO and methanol.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.58; (4)ACD/LogD (pH 7.4): 1.63; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 3.42; (7)ACD/KOC (pH 5.5): 2.04; (8)ACD/KOC (pH 7.4): 22.9; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.682; (13)Molar Refractivity: 106.66 cm³; (14)Molar Volume: 281.4 cm³; (15)Polarizability: 42.28×10^-24 cm³; (16)Surface Tension: 58.2 dyne/cm; (17)Rotatable Bond Count: 7; (18)Tautomer Count: 3; (19)Exact Mass: 349.179027; (20)MonoIsotopic Mass: 349.179027; (21)Topological Polar Surface Area: 77.2; (22)Heavy Atom Count: 26; (23)Complexity: 474.

Uses of Panobinostat: It is an experimental drug developed by Novartis for the treatment of cancer. And it inhibits one or more of the histone deacetylase enzymes, a mechanism leading to apoptosis of malignant cells via multiple pathways.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(NO)\C=C\c1ccc(cc1)CNCCc3c2ccccc2nc3C
2. InChI:InChI=1/C21H23N3O2/c1-15-18(19-4-2-3-5-20(19)23-15)12-13-22-14-17-8-6-16(7-9-17)10-11-21(25)24-26/h2-11,22-23,26H,12-14H2,1H3,(H,24,25)/b11-10+

Product Name

Panobinostat

Synthetic route

Panobinostat Specification

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