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70374-39-9

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70374-39-9 Usage

Description

Lornoxicam, also known as Xefo, is a non-steroidal anti-inflammatory drug (NSAID) that belongs to the oxicam class. It possesses analgesic, anti-inflammatory, and antipyretic properties, making it effective for treating various types of acute mild to moderate pain resulting from inflammatory diseases of the joints, osteoarthritis, surgery, sciatica, and rheumatic diseases. Lornoxicam potently inhibits prostaglandin biosynthesis, exhibiting highly pronounced efficacy. Although its exact mechanism is not fully understood, it is known to inhibit prostaglandin and thromboxane synthesis by targeting both COX-1 and COX-2 enzymes, leading to a reduction in inflammation, pain, fever, and swelling.

Uses

Used in Pharmaceutical Industry:
Lornoxicam is used as an analgesic, anti-inflammatory, and antipyretic agent for the management of various types of acute mild to moderate pain, including that resulting from inflammatory diseases of the joints, osteoarthritis, surgery, sciatica, and rheumatic diseases.
Used in Pain Management:
Lornoxicam is used as a pain reliever for postoperative pain, as it is as effective as morphine, meperidine, and tramadol in providing relief.
Used in Arthritis Treatment:
Lornoxicam is used as an anti-inflammatory agent for the treatment of osteoarthritis and rheumatoid arthritis, helping to alleviate symptoms and improve joint function.
Used in Melanin Binding Studies:
Lornoxicam has been utilized in melanin binding studies with cassette dosing and rapid equilibrium dialysis inserts, providing insights into its interaction with melanin.
Used in Migraine Treatment:
Lornoxicam has been found to have inhibitory effects on spinal nocicceptive processing, presumably via the release of endogenous opioids, making it a potential candidate for migraine treatment.

References

https://www.drugbank.ca/drugs/DB06725 https://en.wikipedia.org/wiki/Lornoxicam

Originator

Nycomed Amersham (Norway)

Indications

Lornoxicam is a non-steroidal anti-inflammatory drug (NSAID) that is used as a painkiller (analgesic). A high level of pain relief is experienced by about 45% of those with moderate to severe postoperative dental pain after a single dose of lornoxicam 8 mg, compared to about 10% with placebo. This is comparable to the proportion experiencing the same level of pain relief with ibuprofen 200 to 400 mg. Adverse events were generally mild and did not differ from placebo in these singe dose studies. There were insufficient data to assess duration of action, but it is likely to be similar to ibuprofen 200 mg.

in vitro

studies on intact human cells showed that lornoxicam intensively inhibit cox-1 and cox-2 with the lowest ic50 among a large panel of nsaids tested. similar findings were obtained in the whole blood for cox-1/-2. in addition lornoxicam suppressed no formation in a dose-dependently manner with an ic50 of 65 μm. [2]

in vivo

in vivo studies found that lornoxicam was as effective as comparative nsaids and that 8 mg lornoxicam was more effective than 10 mg morphine as a pain-reliever after oral surgery. orally administration of lornoxicam at 16-24 mg daily was more effective than tramadol at 300 mg daily in pain-alleviating after knee surgery. compared to naproxen, lornoxicam showed higher therapeutic potency and lower gastrointestinal toxicity. this was probably due to the short half-life of lornoxicam as compared to the other oxicams. [3]

IC 50

a potent cox-1 and cox-2 inhibitor with ic50 values of 5 nm and 8 nm, respectively.

references

[1]balfour ja, fitton a and barradell lb. lornoxicam, a review of its pharmacology and therapeutic potential in the management of painful and inflammatory conditions. drugs. 1996 apr; 51(4): 639-57.[2]berg j, fellier h, christoph t, grarup j and stimmeder d. the analgesic nsaid lornoxicam inhibits cyclooxygenase (cox)-1/-2, inducible nitric oxide synthase (inos), and the formation of interleukin (il)-6 in vitro. inflamm res. 1999 jul; 48(7): 369-79.[3]radhofer-welte s and rabasseda x. lornoxicam, a new potent nsaid with an improved tolerability profile. drugs today (barc). 2000 jan; 36(1): 55-76.[4]sharma a, pingle a, and baliga vp. lornoxicam efficacy in acute pain (leap) trial. j indian med assoc. 2008 dec; 106(12): 811-3.

Check Digit Verification of cas no

The CAS Registry Mumber 70374-39-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,0,3,7 and 4 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 70374-39:
(7*7)+(6*0)+(5*3)+(4*7)+(3*4)+(2*3)+(1*9)=119
119 % 10 = 9
So 70374-39-9 is a valid CAS Registry Number.
InChI:InChI=1/C13H10ClN3O4S2/c1-17-10(13(19)16-9-4-2-3-5-15-9)11(18)12-7(23(17,20)21)6-8(14)22-12/h2-6,18H,1H3,(H,15,16,19)

70374-39-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (L0239)  Lornoxicam  >98.0%(HPLC)(N)

  • 70374-39-9

  • 1g

  • 880.00CNY

  • Detail
  • TCI America

  • (L0239)  Lornoxicam  >98.0%(HPLC)(N)

  • 70374-39-9

  • 5g

  • 2,650.00CNY

  • Detail
  • Sigma

  • (SML0338)  Lornoxicam  ≥98% (HPLC)

  • 70374-39-9

  • SML0338-10MG

  • 803.79CNY

  • Detail
  • Sigma

  • (SML0338)  Lornoxicam  ≥98% (HPLC)

  • 70374-39-9

  • SML0338-50MG

  • 3,261.96CNY

  • Detail

70374-39-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name lornoxicam

1.2 Other means of identification

Product number -
Other names Safem

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:70374-39-9 SDS

70374-39-9Synthetic route

C14H14ClN3O5S2

C14H14ClN3O5S2

lornoxicam
70374-39-9

lornoxicam

Conditions
ConditionsYield
With sodium methylate for 2h; Reflux;87%
2-aminopyridine
504-29-0

2-aminopyridine

lornoxicam
70374-39-9

lornoxicam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 2 h / Large scale
1.2: 1 h / 20 °C / Large scale
2.1: triethylamine / ethyl acetate / 0 - 20 °C / Large scale
3.1: sodium methylate / 2 h / Reflux
View Scheme
lornoxicam
70374-39-9

lornoxicam

methanesulfonic acid
75-75-2

methanesulfonic acid

lornoxicam mesylate
1608472-15-6

lornoxicam mesylate

Conditions
ConditionsYield
In ethanol for 1h; Milling;96%
lornoxicam
70374-39-9

lornoxicam

cobalt(II) tetrafluoroborate hexahydrate
15684-35-2

cobalt(II) tetrafluoroborate hexahydrate

glycine
56-40-6

glycine

[Co(lornoxicam)2(glycine)]BF4

[Co(lornoxicam)2(glycine)]BF4

Conditions
ConditionsYield
In ethanol for 2h; Reflux;96%
piperazine
110-85-0

piperazine

lornoxicam
70374-39-9

lornoxicam

lornoxicam piperazinium salt

lornoxicam piperazinium salt

Conditions
ConditionsYield
In ethanol for 1h; Milling;95%
lornoxicam
70374-39-9

lornoxicam

chromium(III) chloride hexahydrate

chromium(III) chloride hexahydrate

glycine
56-40-6

glycine

[Cr(lornoxicam)2(glycine)]Cl2*3H2O

[Cr(lornoxicam)2(glycine)]Cl2*3H2O

Conditions
ConditionsYield
In ethanol for 2h; Reflux;95%
lornoxicam
70374-39-9

lornoxicam

iron(III) chloride hexahydrate

iron(III) chloride hexahydrate

glycine
56-40-6

glycine

[Fe(lornoxicam)(glycine)(H2O)2]Cl2*H2O

[Fe(lornoxicam)(glycine)(H2O)2]Cl2*H2O

Conditions
ConditionsYield
In ethanol for 2h; Reflux;95%
lornoxicam
70374-39-9

lornoxicam

lornoxicam hydrochloride

lornoxicam hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 0.75h; Milling;93%
lornoxicam
70374-39-9

lornoxicam

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

glycine
56-40-6

glycine

[Ni(lornoxicam)2(glycine)]Cl

[Ni(lornoxicam)2(glycine)]Cl

Conditions
ConditionsYield
In ethanol for 2h; Reflux;93%
lornoxicam
70374-39-9

lornoxicam

iron(II) tetrafluoroborate hexahydrate

iron(II) tetrafluoroborate hexahydrate

glycine
56-40-6

glycine

[Fe(lornoxicam)(glycine)(H2O)2]BF4*H2O

[Fe(lornoxicam)(glycine)(H2O)2]BF4*H2O

Conditions
ConditionsYield
In ethanol for 2h; Reflux;93%
lornoxicam
70374-39-9

lornoxicam

lornoxicam ammonium salt
1608472-18-9

lornoxicam ammonium salt

Conditions
ConditionsYield
With ammonium hydroxide In ethanol; water for 0.75h; Milling;92%
lornoxicam
70374-39-9

lornoxicam

copper(II) tetrafluroborate hexahydrate

copper(II) tetrafluroborate hexahydrate

glycine
56-40-6

glycine

[Cu(lornoxicam)2(glycine)]BF4*2H2O

[Cu(lornoxicam)2(glycine)]BF4*2H2O

Conditions
ConditionsYield
In ethanol for 2h; Reflux;91%
lornoxicam
70374-39-9

lornoxicam

dimethyltin oxide
2273-45-2

dimethyltin oxide

[SnMe2(lornoxicam)]

[SnMe2(lornoxicam)]

Conditions
ConditionsYield
In benzene Sn compd. added to soln. of ligand, refluxed for 7 h; evapd. in vac., chilled, triturated with Et2O, redissolved in Et2O (repeated twice), filtered, dried in vac. over silica gel, elem. anal.;90%
lornoxicam
70374-39-9

lornoxicam

manganese(II) chloride dihydrate

manganese(II) chloride dihydrate

glycine
56-40-6

glycine

[Mn(lornoxicam)2(glycine)]Cl*H2O

[Mn(lornoxicam)2(glycine)]Cl*H2O

Conditions
ConditionsYield
In ethanol for 2h; Reflux;89%
lornoxicam
70374-39-9

lornoxicam

zinc tetrafluoroborate

zinc tetrafluoroborate

glycine
56-40-6

glycine

[Zn(lornoxicam)2(glycine)]BF4*2H2O

[Zn(lornoxicam)2(glycine)]BF4*2H2O

Conditions
ConditionsYield
In ethanol for 2h; Reflux;87%
lornoxicam
70374-39-9

lornoxicam

N,N-dimethyl-γ-aminobutyric acid chloride hydrochloride

N,N-dimethyl-γ-aminobutyric acid chloride hydrochloride

6-chloro-4-(N,N-dimethylaminobutyryloxy)-2-methyl-N-2-pyridyl-2H-thieno[2,3-e][1,2]-thiazine-3-carboxamido-1,1-dioxide hydrochloride

6-chloro-4-(N,N-dimethylaminobutyryloxy)-2-methyl-N-2-pyridyl-2H-thieno[2,3-e][1,2]-thiazine-3-carboxamido-1,1-dioxide hydrochloride

Conditions
ConditionsYield
Stage #1: lornoxicam; N,N-dimethyl-γ-aminobutyric acid chloride hydrochloride With sodium hydrogencarbonate In water; acetone at 20℃; for 3h;
Stage #2: With hydrogenchloride
80.5%
lornoxicam
70374-39-9

lornoxicam

di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

[Sn(n-C4H9)2(lornoxicam)]

[Sn(n-C4H9)2(lornoxicam)]

Conditions
ConditionsYield
In benzene Sn compd. added to soln. of ligand, refluxed for 27 h; evapd. in vac., chilled, triturated with hexane, redissolved in Et2O (repeated twice), filtered, dried in vac. over silica gel, elem. anal.;66%
lornoxicam
70374-39-9

lornoxicam

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

6-chloro-2-methyl-4-palmitoyloxy-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

6-chloro-2-methyl-4-palmitoyloxy-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
With triethylamine In tetrachloromethane for 1.5h; Ambient temperature;45%
lornoxicam
70374-39-9

lornoxicam

(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

6-chloro-2-methyl-4-oleoyloxy-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

6-chloro-2-methyl-4-oleoyloxy-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
With triethylamine In tetrachloromethane for 1.5h; Ambient temperature;40%
lornoxicam
70374-39-9

lornoxicam

n-decanoyl chloride
112-13-0

n-decanoyl chloride

6-chloro-4-decanoyloxy-2-methyl-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

6-chloro-4-decanoyloxy-2-methyl-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 24h; Heating;35%
lornoxicam
70374-39-9

lornoxicam

phosgene
75-44-5

phosgene

C14H9Cl2N3O5S2

C14H9Cl2N3O5S2

Conditions
ConditionsYield
In N,N-dimethyl-formamide; toluene a) 5 deg C, 2 h, b) RT, 24 h;
lornoxicam
70374-39-9

lornoxicam

2-chloro-1,3-(dipalmitoyloxy)propane
169471-41-4

2-chloro-1,3-(dipalmitoyloxy)propane

6-chloro-2-methyl-4-<2-(1,3-dipalmitoyloxy)propyloxy>-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

6-chloro-2-methyl-4-<2-(1,3-dipalmitoyloxy)propyloxy>-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
With sodium hydride 1.) THF, 2.) THF, RT, 6 h; Yield given. Multistep reaction;
lornoxicam
70374-39-9

lornoxicam

C36H67ClO6

C36H67ClO6

4-<<2-(1,3-dipalmitoyloxy)propyl>carbonyloxy>-6-chloro-2-methyl-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

4-<<2-(1,3-dipalmitoyloxy)propyl>carbonyloxy>-6-chloro-2-methyl-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
In chloroform; toluene at 60℃; for 2h; Yield given;
lornoxicam
70374-39-9

lornoxicam

4-<<2-(1,3-dipalmitoyloxy)propyl>carbonyloxy>-6-chloro-2-methyl-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

4-<<2-(1,3-dipalmitoyloxy)propyl>carbonyloxy>-6-chloro-2-methyl-N-2-pyridinyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide; toluene / a) 5 deg C, 2 h, b) RT, 24 h
2: dimethylformamide / 6 h / 50 °C
View Scheme
lornoxicam
70374-39-9

lornoxicam

1-Chloroethyl ethyl carbonate
50893-36-2

1-Chloroethyl ethyl carbonate

6-chloro-4-(1-(ethoxycarbonyloxy)ethoxy)-2-methyl-N-(pyridin-2-yl)-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide

6-chloro-4-(1-(ethoxycarbonyloxy)ethoxy)-2-methyl-N-(pyridin-2-yl)-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
With sodium iodide; potassium carbonate In dichloromethane; water; acetone
lornoxicam
70374-39-9

lornoxicam

methanol
67-56-1

methanol

A

methyl 5-chloro-2-thiophenecarboxylate
35475-03-7

methyl 5-chloro-2-thiophenecarboxylate

B

N-methyl-N'-(pyridin-2-yl)oxalamide

N-methyl-N'-(pyridin-2-yl)oxalamide

C

N-methyl-N'-(pyridin-2-ylcarbamoyl)methanethioamide

N-methyl-N'-(pyridin-2-ylcarbamoyl)methanethioamide

D

5-chloro-N-methyl-3-oxothieno[2,3-d]-1,2-thiazole-1,1-dioxide

5-chloro-N-methyl-3-oxothieno[2,3-d]-1,2-thiazole-1,1-dioxide

E

methyl (pyridin-2-ylcarbamoyl)formate
54166-60-8

methyl (pyridin-2-ylcarbamoyl)formate

Conditions
ConditionsYield
for 7h; Irradiation;
lornoxicam
70374-39-9

lornoxicam

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C42H70O35*C13H10ClN3O4S2

C42H70O35*C13H10ClN3O4S2

Conditions
ConditionsYield
In ethanol; water for 24h; pH=2.5; pH-value;
lornoxicam
70374-39-9

lornoxicam

cyclomaltooctaose
17465-86-0

cyclomaltooctaose

C48H80O40*C13H10ClN3O4S2

C48H80O40*C13H10ClN3O4S2

Conditions
ConditionsYield
In ethanol; water for 24h; pH=2.5; pH-value;

70374-39-9Relevant articles and documents

Synthesis method of high-purity lornoxicam

-

Paragraph 0038-0062, (2021/10/11)

The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthesis method of high-purity lornoxicam. The method comprises the following steps: by taking 6-chloro-4-hydroxy-2-methyl-2-H-thieno [2, 3-e]-1, 2-thiazine carboxylic acid methyl ester-1, 1-dioxide and 2-aminopyridine as raw materials and xylene as a solvent, carrying out distillation reaction, condensing mixed gas obtained by the distillation reaction to obtain condensate, adsorbing methanol in the condensate by adopting a solid acid catalyst, and recycling the adsorbed condensate. According to the invention, the methanol generated by the reaction is distilled out so as to promote the reaction to proceed forwards, and then the methanol is absorbed under the catalysis of H2SO4/MxOy superacid solid acid, so that the xylene returned to the reaction system does not contain methanol, and the coking of the reaction is reduced so as to improve the product quality and yield; and the purity of the prepared lornoxicam is high and can reach 99.9% or above, the solvent amount is reduced, and the method is suitable for industrial production.

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