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Etodolac

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Name

Etodolac

EINECS 629-689-1
CAS No. 41340-25-4 Density 1.193 g/cm3
PSA 62.32000 LogP 3.38300
Solubility 40mg/L(37 oC) Melting Point 145-148 °C
Formula C17H21NO3 Boiling Point 507.9 °C at 760 mmHg
Molecular Weight 287.359 Flash Point 260.9 °C
Transport Information UN 3249 Appearance crystalline solid
Safety 22-36-45-26-36/37 Risk Codes 23/24/25-40-36-25-36/37/38
Molecular Structure Molecular Structure of 41340-25-4 (Etodolac) Hazard Symbols ToxicT, IrritantXi
Synonyms

(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid;1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid;Prestwick_209;Pyrano(3,4-b)indole-1-acetic acid, 1,8-diethyl-1,3,4,9-tetrahydro-;Lodine;Lodine (TN);Ultradol;{Pyrano[3,} 4-b]indole-1-acetic acid, 1,8-diethyl-1,3,4,9-tetrahydro-;{1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic} acid;Etodolacum [INN-Latin];1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid;Etodolaco [INN-Spanish];Pyrano(3,4-b)indole-1-acetic acid, 1,3,4,9-tetrahydro-1,8-diethyl-;Pyrano[3,4-b]indole-1-acetic acid,1,8-diethyl-1,3,4,9-tetrahydro-;Etodolac (JAN/USP);Etodolic acid;AY 24236;Etodolac Acid;

Article Data 11

Etodolac Synthetic route

41340-36-7

7-ethyl-2-(1H-indol-3-yl)ethan-1-ol

4949-44-4

ethyl propanoylacetate

41340-25-4

etodolac

Conditions
ConditionsYield
(i) TsOH, benzene, (ii) aq. NaOH, EtOH; Multistep reaction;

2,2-Dimethyl-propionic acid 2-(1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetoxymethyl ester

A

2,2-Dimethyl-propionic acid 2-((S)-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetoxymethyl ester

B

41340-25-4

etodolac

Conditions
ConditionsYield
With Lipase QL In di-isopropyl ether; water for 192h; Product distribution; Ambient temperature; various lipase enzymes;
87226-41-3

(R)-etodolac

41340-25-4

etodolac

Conditions
ConditionsYield
With tin(IV) chloride In tetrahydrofuran; dichloromethane for 4h; Heating / reflux;
sulfuric acid In isopropyl alcohol at 20℃; for 23h; Product distribution / selectivity;
87226-41-3

(R)-etodolac

87249-11-4

(S)-etodolac

41340-25-4

etodolac

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at 20℃; for 2h;
Stage #1: (R)-etodolac; (S)-etodolac In dichloromethane at 20℃; for 2h;
Stage #2: With sodium hydroxide; formic acid at 0℃; for 1h; pH=5;
87249-11-4

(S)-etodolac

41340-25-4

etodolac

Conditions
ConditionsYield
sulfuric acid In isopropyl alcohol at 20℃; for 4 - 18h; Product distribution / selectivity;
boron trifluoride diethyl etherate In isopropyl alcohol at 20℃; for 15h; Product distribution / selectivity;
41340-36-7

7-ethyl-2-(1H-indol-3-yl)ethan-1-ol

30414-53-0

methyl propanoyl acetate

41340-25-4

etodolac

Conditions
ConditionsYield
With sulfuric acid In methanol Pictet-Spengler Synthesis;
41340-25-4

etodolac

200880-25-7

(+/-)-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)ethanol

Conditions
ConditionsYield
With LiAlH4 In tetrahydrofuran; hexane; ethyl acetate98%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h;92%
58885-58-8

N-tert-butoxycarbonyl-3-aminopropanol

41340-25-4

etodolac

Boc-aminopropanol-etodolac

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;96%
528-43-8

Magnolol

41340-25-4

etodolac

5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;90%
With dmap In dichloromethane at 25 - 30℃;90%
64-19-7

acetic acid

41340-25-4

etodolac

2-(dimethylamino)ethyl 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetamide acetate

Conditions
ConditionsYield
Stage #1: N,N-dimethylethylenediamine; etodolac With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In acetonitrile at 20℃; for 3h;
Stage #2: acetic acid In ethyl acetate
89.4%

Etodolac Chemical Properties

Molecule structure of Etodolac (CAS NO.41340-25-4):

IUPAC Name: 2-(1,8-Diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetic acid 
Molecular Weight: 287.35354 g/mol
Molecular Formula: C17H21NO3 
Density: 1.193 g/cm
Melting Point:145-148 °C
Boiling Point: 507.9 °C at 760 mmHg 
Flash Point: 260.9 °C
Index of Refraction: 1.596
Molar Refractivity: 81.98 cm3
Molar Volume: 240.7 cm3
Surface Tension: 53.9 dyne/cm 
Enthalpy of Vaporization: 81.93 kJ/mol
Vapour Pressure: 3.88E-11 mmHg at 25 °C 
Storage Temp.: 2-8 °C
XLogP3-AA: 2.8
H-Bond Donor: 2
H-Bond Acceptor: 3
Rotatable Bond Count: 4
Exact Mass: 287.152144
MonoIsotopic Mass: 287.152144
Topological Polar Surface Area: 62.3
Heavy Atom Count: 21
Canonical SMILES: CCC1=CC=CC2=C1NC3=C2CCOC3(CC)CC(=O)O
InChI: InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,0-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
InChIKey: NNYBQONXHNTVIJ-UHFFFAOYSA-N
Product Categories: APIs; Intermediates & Fine Chemicals; Pharmaceuticals

Etodolac Uses

 Etodolac (CAS NO.41340-25-4) is a non-steroidal anti-inflammatory drug (NSAID). It is used to anti-inflammatory.

Etodolac Production

 Etodolac is manufactured by Shire under the trade name Lodine SR and by Meda Pharmaceuticals under the name Eccoxolac . Non-propriety etodolac is also available.

Etodolac Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral > 4gm/kg (4000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 40, Pg. 469, 1990.
mouse LD50 intraperitoneal 338mg/kg (338mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 40, Pg. 469, 1990.
mouse LD50 oral 593mg/kg (593mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 40, Pg. 469, 1990.
mouse LD50 subcutaneous 502mg/kg (502mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 40, Pg. 469, 1990.
rat LD50 intraperitoneal 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 40, Pg. 469, 1990.
rat LD50 oral 94mg/kg (94mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 40, Pg. 469, 1990.
rat LD50 subcutaneous 113mg/kg (113mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 40, Pg. 469, 1990.

Etodolac Safety Profile

Hazard Codes: ToxicT, IrritantXi
Risk Statements: 23/24/25-40-36-25-36/37/38 
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed. 
R40: Limited evidence of a carcinogenic effect. 
R36: Irritating to eyes. 
R25: Toxic if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-36-45-26-36/37 
S22: Do not breathe dust. 
S36: Wear suitable protective clothing.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37: Wear suitable protective clothing and gloves.
RIDADR: 3249
WGK Germany: 3
RTECS: UQ0360000
HazardClass: 6.1(b)
PackingGroup: III

Etodolac Specification

 Etodolac (CAS NO.41340-25-4) is also named as (+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid ; 1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid ; 1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid ; AY 24236 ; CCRIS 3923 ; Etodolaco ; Etodolaco [INN-Spanish] ; Etodolacum ; Etodolacum [INN-Latin] ; Etodolic acid ; Lodine ; Lodine XL ; NSC 282126 ; Pyrano(3,4-b)indole-1-acetic acid, 1,8-diethyl-1,3,4,9-tetrahydro-(+-)- ; UNII-2M36281008 ; Ultradol . Etodolac (CAS NO.41340-25-4) is crystalline solid. Etodolac belongs to a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs).

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