LORNOXICAM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10ClN3O4S2
Molecular Weight	371.819
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(C(=O)NC2=CC=CC=N2)=C(O)C3=C(C=C(Cl)S3)S1(=O)=O

InChI

InChIKey=WLHQHAUOOXYABV-UHFFFAOYSA-N

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/h2-6,18H,1H3,(H,15,16,19)

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Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Xefo_30/WC500009083.pdf
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB06725

Lornoxicam (Xefo®) is a nonsteroidal anti-inflammatory drug of the oxicam class with analgesic, anti-inflammatory and antipyretic properties. It differs from other oxicam compounds in its potent inhibition of prostaglandin biosynthesis, a property that explains the particularly pronounced efficacy of the drug. The inhibition of the cyclooxygenase enzymes (COX-1 and COX-2) by lornoxicam (Xefo®) leads to desensitisation of peripheral nociceptors and consequently inhibition of inflammation. A central effect on nociception which seems to be independent of anti-inflammatory effects has also been suggested.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Xefo_30/WC500009083.pdf	Inhibitor 8297		0.003 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Xefo_30/WC500009083.pdf	Inhibitor 8297		0.008 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Xefo_30/WC500009083.pdf	Primary	Approved 8429	XEFO Approved Use Short-term relief of acute mild to moderate pain. Symptomatic relief of pain and inflammation in osteoarthritis. Symptomatic relief of pain and inflammation in rheumatoid arthritis.
Osteoarthritis 157 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Xefo_30/WC500009083.pdf	Palliative	Approved 8429	XEFO Approved Use Short-term relief of acute mild to moderate pain. Symptomatic relief of pain and inflammation in osteoarthritis. Symptomatic relief of pain and inflammation in rheumatoid arthritis.
Rheumatoid arthritis 316 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Xefo_30/WC500009083.pdf	Palliative	Approved 8429	XEFO Approved Use Short-term relief of acute mild to moderate pain. Symptomatic relief of pain and inflammation in osteoarthritis. Symptomatic relief of pain and inflammation in rheumatoid arthritis.

PubMed

Title	Date	PubMed
Lornoxicam. A review of its pharmacology and therapeutic potential in the management of painful and inflammatory conditions.	1996 Apr	8706598
Introduction: mechanism of action of NSAIDs.	1996 Apr	8630629
Lornoxicam, a new potent NSAID with an improved tolerability profile.	2000 Jan	12879104

Patents

Sample Use Guides

In Vivo Use Guide

Pain: 8-16 mg lornoxicam (Xefo®) daily divided into 2 or 3 doses. Maximum recommended daily dose is 16 mg. Osteoarthritis and Rheumatoid arthritis: Initial recommended dose is 12 mg lornoxicam (Xefo®) daily divided into 2 or 3 doses. Maintenance dose should not exceed 16 mg lornoxicam daily.

Route of Administration: Oral

In Vitro Use Guide

In HEL/Mono Mac 6 human cells, lornoxicam showed a balanced inhibition of COX-1/-2 exhibiting the lowest IC50 (0.003 microM/0.008 microM) of the large panel of non steroidal antiinflammatory drugs tested. Similar results were obtained in the whole blood for COX-1/-2 (IC50 values of 0.13 microM for both isoenzymes). NO formation was dose-dependently inhibited by lornoxicam (IC50 of 65 microM) whereas piroxicam, diclofenac, ibuprofen, ketorolac and naproxen inhibited the NO formation markedly less. In stimulated human monocytic cells (THP-1), lornoxicam showed a marked inhibition of IL-6 formation (IC50 54 microM) while the formation ofTNF-alpha, IL-1beta and IL-8 was only moderately affected.

Name

Type

Language

LORNOXICAM

Official Name

English

LORCAM

Brand Name

English

RO 13-9297

Code

English

lornoxicam [INN]

Common Name

English

RO-13-9297

Code

English

LORNOXICAM [USAN]

Common Name

English

LORNOXICAM [JAN]

Common Name

English

CTX

Code

English

NSC-759620

Code

English

RO-139297

Code

English

LORNOXICAM [MI]

Common Name

English

LORNOXICAM [MART.]

Common Name

English

Lornoxicam [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM01AC05