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)

HIDE SMILES / InChI

Molecular Formula	C13H10ClN3O4S2
Molecular Weight	371.819
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Pharmacokinetics of lornoxicam in man.	1990	2284217
Overview of the pharmacological properties, pharmacokinetics and animal safety assessment of lornoxicam.	1990	2284216
Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents.	1994 Feb	8162655
Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam.	1996	8857077
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
Clinical pharmacokinetics of lornoxicam. A short half-life oxicam.	1998 Jun	9646006
Analgesic efficacy and safety of lornoxicam quick-release formulation compared with diclofenac potassium: randomised, double-blind trial in acute low back pain.	2006	17163260
Toxicogenomic biomarkers for renal papillary injury in rats.	2013 Jan 7	23142791
Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis.	2014	24152722

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:06 UTC 2023` Edited by `admin` on `Fri Dec 15 15:06:06 UTC 2023`
Record UNII	ER09126G7A
Record Status	`Validated (UNII)`
Record Version

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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