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| CAS No.: | 41340-25-4 |
|---|---|
| Name: | Etodolac |
| Molecular Structure: | |
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|
|
| Formula: | C17H21NO3 |
| Molecular Weight: | 287.359 |
| 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; |
| EINECS: | 629-689-1 |
| Density: | 1.193 g/cm3 |
| Melting Point: | 145-148 °C |
| Boiling Point: | 507.9 °C at 760 mmHg |
| Flash Point: | 260.9 °C |
| Solubility: | 40mg/L(37 oC) |
| Appearance: | crystalline solid |
| Hazard Symbols: |
 T,  Xi
|
| Risk Codes: | 23/24/25-40-36-25-36/37/38 |
| Safety: | 22-36-45-26-36/37 |
| Transport Information: | UN 3249 |
| PSA: | 62.32000 |
| LogP: | 3.38300 |
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| Conditions | Yield |
|---|---|
| (i) TsOH, benzene, (ii) aq. NaOH, EtOH; Multistep reaction; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With tin(IV) chloride In tetrahydrofuran; dichloromethane for 4h; Heating / reflux; | |
| sulfuric acid In isopropyl alcohol at 20℃; for 23h; Product distribution / selectivity; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With LiAlH4 In tetrahydrofuran; hexane; ethyl acetate | 98% |
| With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h; | 92% |
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
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Chemistry
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/cm3
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
Uses
Etodolac (CAS NO.41340-25-4) is a non-steroidal anti-inflammatory drug (NSAID). It is used to anti-inflammatory.
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.
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. |
Safety Profile
Hazard Codes: 
T, 
Xi
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
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).