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Tenoxicam
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Name

Tenoxicam

 EINECS 620-500-8
CAS No. 59804-37-4 Density 1.675 g/cm3
PSA 136.22000 LogP 2.73420
Solubility 61.9mg/L(32 oC) Melting Point 209-213 °C
Formula C13H11N3O4S2 Boiling Point N/A
Molecular Weight 337.38 Flash Point N/A
Transport Information N/A Appearance yellow crystalline powder
Safety 36/37/39-45-36-26 Risk Codes 23/24/25-36/37/38
Molecular Structure Molecular Structure of 59804-37-4 (Tenoxicam) Hazard Symbols ToxicT,IrritantXi
Synonyms

Tenoxicam (JAN/USAN);Ro 12-0068/000;Tilcotil (TN);Tenoxicam [USAN:BAN:INN:JAN];2H-Thieno(2,3-e)-1,2-thiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide;Tenoxicamum [INN-Latin];(3Z)-3-[hydroxy-(pyridin-2-ylamino)methylidene]-4-methyl-5,5-dioxo-5$l^{6},9-dithia-4-azabicyclo[4.3.0]nona-7,10-dien-2-one;Ro 12-0068;Prestwick_849;4-Hydroxy-2-methyl-N-2-pyridinyl-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide;Tilcotil;Tenoxicam CP EP;4-Hydroxy-2-methyl-N-pyridin-2-yl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide-1,1-dioxide;

Article Data 8

Tenoxicam Synthetic route

106820-67-1

4-hydroxy-N-2-pyridyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

616-38-6

carbonic acid dimethyl ester

59804-37-4

tenoxicam

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 7h; Large scale;89%
504-29-0

2-aminopyridine

98827-44-2

methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide

616-38-6

carbonic acid dimethyl ester

59804-37-4

tenoxicam

Conditions
ConditionsYield
Stage #1: methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide; carbonic acid dimethyl ester With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 5h; Large scale;
Stage #2: 2-aminopyridine With potassium carbonate In N,N-dimethyl-formamide for 7h; Large scale;		83%
504-29-0

2-aminopyridine

59804-25-0

4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine,1,1-dioxide

59804-37-4

tenoxicam

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Concentration; Reflux;76.9%
In xylene for 7h; Heating;75%
59337-89-2

3-chlorothiophene-2-carboxylic acid

59804-37-4

tenoxicam

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 210 g / 1.) sodium bisulfite, NaOH, CuCl, 2.) KCl / H2O / 16 h / 143 °C
2: POCl3, PCl5 / 1.5 h / Heating
3: 95 percent / CHCl3 / 3 h / Heating
4: 71 percent / pyridine / 4 h / Ambient temperature
5: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating
6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h
7: 75 percent / xylene / 7 h / Heating
View Scheme
Multi-step reaction with 6 steps
1: 210 g / 1.) sodium bisulfite, NaOH, CuCl, 2.) KCl / H2O / 16 h / 143 °C
2: POCl3, PCl5 / 1.5 h / Heating
3: 95 percent / CHCl3 / 3 h / Heating
4: 84 percent / pyridine / 2 h / Ambient temperature
5: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min
6: 75 percent / xylene / 7 h / Heating
View Scheme
59337-92-7

2-(carbomethoxy)thiophene-3-sulfonyl chloride

59804-37-4

tenoxicam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 71 percent / pyridine / 4 h / Ambient temperature
2: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating
3: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h
4: 75 percent / xylene / 7 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 84 percent / pyridine / 2 h / Ambient temperature
2: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min
3: 75 percent / xylene / 7 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: water / 6 h / 20 °C / pH 7 - 8
2: sodium methylate / methanol / 2 h / Reflux
3: sodium hydroxide / methanol / 3 h / 20 °C
4: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
View Scheme
59337-91-6

3-chlorosulfonyl-thiophene-2-carboxylic acid chloride

59804-37-4

tenoxicam

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / CHCl3 / 3 h / Heating
2: 71 percent / pyridine / 4 h / Ambient temperature
3: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating
4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h
5: 75 percent / xylene / 7 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / CHCl3 / 3 h / Heating
2: 84 percent / pyridine / 2 h / Ambient temperature
3: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min
4: 75 percent / xylene / 7 h / Heating
View Scheme
98827-44-2

methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide

59804-37-4

tenoxicam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h
2: 75 percent / xylene / 7 h / Heating
View Scheme
106820-63-7

methyl 3-<<<(methoxcarbonyl)methyl>amino>sulfonyl>-2-thiophenecarboxylate

59804-37-4

tenoxicam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating
2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h
3: 75 percent / xylene / 7 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: sodium methylate / methanol / 2 h / Reflux
2: sodium hydroxide / methanol / 3 h / 20 °C
3: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
View Scheme
59804-24-9

methyl 3-<-N-methylamino>sulfonyl>-2-thiophenecarboxylate

59804-37-4

tenoxicam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min
2: 75 percent / xylene / 7 h / Heating
View Scheme

dibutylbis[4-(hydroxy-κO)-2-methyl-N-(pyridin-2-yl-κN)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxidato]tin

[Sn(C4H9)2(C6H2S2NCH3O3C(O)NC5H4N)]*0.5CH3OH

B

59804-37-4

tenoxicam

Conditions
ConditionsYield
In methanol; acetonitrile slow crystn. of soln.;
In chloroform-d1

Tenoxicam Chemical Properties

Molecular structure of Tenoxicam (CAS NO.59804-37-4) is:

Product Name: Tenoxicam
CAS Registry Number: 59804-37-4
IUPAC Name: (3E)-3-[hydroxy-(pyridin-2-ylamino)methylidene]-2-methyl-1,1-dioxothieno[2,3-e]thiazin-4-one
Molecular Weight: 337.37414 [g/mol]
Molecular Formula: C13H11N3O4S2
XLogP3-AA: 2.2
H-Bond Donor: 2
H-Bond Acceptor: 7
Melting Point: 209-2130 °C 
Surface Tension: 91.737 dyne/cm
Density: 1.675 g/cm3
Product Categories: Active Pharmaceutical Ingredients;Tenoxicam;Intermediates & Fine Chemicals;Pharmaceuticals;Fused Ring Systems;Lipid signaling

Tenoxicam Uses

 Tenoxicam (CAS NO.59804-37-4) is used to relieve swelling, inflammation,stiffness, and pain associated with rheumatoid arthritis, osteoarthritis, ankylosing spondylitis (a type of arthritis involving the spine), tendinitis (inflammation of a tendon), bursitis (inflammation of a bursa, a fluid-filled sac located around joints and near the bones), and periarthritis of the shoulders or hips (inflammation of tissues surrounding these joints).

Tenoxicam Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 128mg/kg (128mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 1030, 1987.
mouse LD50 intraperitoneal 446mg/kg (446mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,
mouse LD50 oral 297mg/kg (297mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,
mouse LD50 subcutaneous 449mg/kg (449mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,
rat LD50 intraperitoneal 234mg/kg (234mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,
rat LD50 oral 79mg/kg (79mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,
rat LD50 subcutaneous 186mg/kg (186mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,

Tenoxicam Safety Profile

Hazard Codes: ToxicT,IrritantXi
Risk Statements: 23/24/25-36/37/38 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37/39-45-36-26 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 2
RTECS: XJ9095060

Tenoxicam Specification

 Tenoxicam , its cas register number is 59804-37-4. It also can be called 4-Hydroxy-2-methyl-N-2-pyridinyl-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide ; Mobiflex ; Tilcotil .It is a yellow crystalline powder.

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