CAS 70374-39-9|Lorcam|Safem|Lorcam (TN)|CLTX|CTX|(3E)-6-chloro-3-[hydroxy(pyridin-2-ylamino)methylidene]-2-methyl-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione|Xafon|XEFO|Xefocam|(3E)-6-...

General Information

Structure

Molecular Formula

C₁₃H₁₀ClN₃O₄S₂

Molecular Mass

371.8192

Exact Mass

370.9801255

Charge

InChI

InChI=1S/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/h2-6,19H,1H3,(H,15,16)/b13-10+

InChIKey

OXROWJKCGCOJDO-JLHYYAGUSA-N

Canonic Smiles

Clc1sc2c(c1)S(=O)(=O)N(/C(=C(\Nc1ccccn1)/O)/C2=O)C

Isomeric Smiles

Clc1sc2c(S(=O)(=O)N(/C(=C(/O)\Nc3ncccc3)/C2=O)C)c1

Calculated Properties

JChem

Acid pKa

6.8801155

H Acceptors

H Donor

LogD (pH = 5.5)

1.89714

LogD (pH = 7.4)

1.350553

Log P

1.9918677

Molar Refractivity

97.0238

Polarizability

33.356422

Polar Surface Area

99.6

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.53

LOG S

-3.91

Solubility (Water)

4.61e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Brand Name

XafonLorcam

Synonyms

Lornoxicamum [inn-latin]Lorcam (TN)CLTXXefocamSafemCTXXEFOchlortenoxicamAcabelTelosLorcamLornoxicamumTaigalorLornoxicam

IUPAC Traditional name

(3E)-6-chloro-3-[hydroxy(pyridin-2-ylamino)methylidene]-2-methyl-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione

IUPAC name

(3E)-6-chloro-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione

Names and Identifiers

Registration numbers

PubChem SID

16096788899443271

PubChem CID

546900315282204

CAS Number

70374-39-9

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.62 [BIOBYTE STARLIST (2009)]

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB06725

Drug Groups

approved

Description

Lornoxicam (chlortenoxicam) is a new nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class with analgesic, anti-inflammatory and antipyretic properties. Lornoxicam differs from other oxicam compounds in its potent inhibition of prostaglandin biosynthesis, a property that explains the particularly pronounced efficacy of the drug. Lornoxicam is approved for use in Japan.

Indication

For the treatment of acute mild to moderate pain, as well as pain and inflammation of the joints caused by certain types of rheumatic diseases.

Pharmacology

Lornoxicam is a non-steroidal anti-inflammatory drug (NSAID) that belongs to the oxicam class. As with other NSAIDS, lornoxicam is a potent inhibitor of the cyclooxgenase enzymes, which are responsible for catalyzing the formation of prostaglandins (act as messenger molecules in the process of inflammation) and thromboxane from arachidonic acid. Unlike some NSAIDS, lornoxicam's inhibition of cyclooxygenase does not lead to an increase in leukotriene formation, meaning that arachidonic acid is not moved to the 5-lipoxygenase cascade, resulting in the minimization of the risk of adverse events.

Affected Organisms

Humans and other mammals

Biotransformation

Lornoxicam is metabolized completely by cyp 2C9 with the principal metabolite being 5'-hydroxy-lornoxicam and only negligible amounts of intact lornoxicam are excreted unchanged in the urine. Approximately 2/3 of the drug is eliminated via the liver and 1/3 via the kidneys in the active form.

Absorption

Lornoxicam is absorbed rapidly and almost completely from the GI tract (90-100%).

Half Life

3-5 hours

Protein Binding

Lornoxicam is 99% bound to plasma proteins (almost exlusively to serum albumin).

References

• Balfour JA, Fitton A, 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. [Pubmed]

• Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. [Pubmed]

• Radhofer-Welte S, Rabasseda X: Lornoxicam, a new potent NSAID with an improved tolerability profile. Drugs Today (Barc). 2000 Jan;36(1):55-76. [Pubmed]

• Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. [Pubmed]

• Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [Pubmed]

• Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. [Pubmed]

• Pruss TP, Stroissnig H, Radhofer-Welte S, Wendtlandt W, Mehdi N, Takacs F, Fellier H: Overview of the pharmacological properties, pharmacokinetics and animal safety assessment of lornoxicam. Postgrad Med J. 1990;66 Suppl 4:S18-21. [Pubmed]

• Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. [Pubmed]

External Links

• [Wikipedia]

Molecule Details

References

PubChem Literature

From Data Sources

• Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. Pubmed

• Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. Pubmed

• Radhofer-Welte S, Rabasseda X: Lornoxicam, a new potent NSAID with an improved tolerability profile. Drugs Today (Barc). 2000 Jan;36(1):55-76. Pubmed

• Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. Pubmed

• Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. Pubmed

• Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Brand Name

• Synonyms

• IUPAC Traditional name

• IUPAC name

Registration numbers

• PubChem SID

• PubChem CID

• CAS Number

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Brand Name

XafonLorcam

Synonyms

Lornoxicamum [inn-latin]Lorcam (TN)CLTXXefocamSafemCTXXEFOchlortenoxicamAcabelTelosLorcamLornoxicamumTaigalorLornoxicam

IUPAC Traditional name

(3E)-6-chloro-3-[hydroxy(pyridin-2-ylamino)methylidene]-2-methyl-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione

IUPAC name

(3E)-6-chloro-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione

PubChem SID

16096788899443271

PubChem CID

546900315282204

CAS Number

70374-39-9

Physical Property

Hydrophobicity(logP)

2.62 [BIOBYTE STARLIST (2009)]

DrugBank

DB06725

Drug Groups

approved

Description

Indication

For the treatment of acute mild to moderate pain, as well as pain and inflammation of the joints caused by certain types of rheumatic diseases.

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

Lornoxicam is absorbed rapidly and almost completely from the GI tract (90-100%).

Half Life

3-5 hours

Protein Binding

Lornoxicam is 99% bound to plasma proteins (almost exlusively to serum albumin).

References

• Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. [Pubmed]

• Radhofer-Welte S, Rabasseda X: Lornoxicam, a new potent NSAID with an improved tolerability profile. Drugs Today (Barc). 2000 Jan;36(1):55-76. [Pubmed]

• Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. [Pubmed]

• Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [Pubmed]

• Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. [Pubmed]

• Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. [Pubmed]

External Links

• [Wikipedia]

From Data Sources

• Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. Pubmed

• Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. Pubmed

• Radhofer-Welte S, Rabasseda X: Lornoxicam, a new potent NSAID with an improved tolerability profile. Drugs Today (Barc). 2000 Jan;36(1):55-76. Pubmed

• Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. Pubmed

• Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. Pubmed

• Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. Pubmed

Molecule

ID:4456