OXACEPROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C7H11NO4
Molecular Weight	173.1665
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI

InChIKey=BAPRUDZDYCKSOQ-RITPCOANSA-N

InChI=1S/C7H11NO4/c1-4(9)8-3-5(10)2-6(8)7(11)12/h5-6,10H,2-3H2,1H3,(H,11,12)/t5-,6+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C7H11NO4
Molecular Weight	173.1665
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10791619 | https://www.ncbi.nlm.nih.gov/pubmed/10423160

Oxaceprol, a structural analog of hydroxyproline, has been used for several years for the treatment of osteoarthritis and rheumatoid arthritis, showing good gastrointestinal safety, particularly in comparison with NSAIDs. It was shown that oxaceprol does not inhibit the synthesis of prostaglandins in vitro, but acts predominantly by inhibiting leukocyte adhesion and migration, thus inhibiting inflammation at an early stage and helps in pain relief.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
leukocyte cell-cell adhesion 1 Target ID: GO:0007159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10423160	Inhibitor 8504
leukocyte migration 1 Target ID: GO:0050900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10423160	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10791619	Palliative		Approved 8583	Unknown Approved Use Unknown
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10423160	Palliative		Approved 8583	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
1200 mg 1 times / day steady-state, oral Studied dose Dose: 1200 mg, 1 times / day Route: oral Route: steady-state Dose: 1200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17417987/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17417987/	Sources: https://pubmed.ncbi.nlm.nih.gov/17417987/
200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	Other AEs: Gastrointestinal disorder, Gastrointestinal fullness... Other AEs: Gastrointestinal disorder (2 patients) Gastrointestinal fullness (2 patients) Nausea (1 pt) Diarrhoea (3 patients) Exanthema (2 patients) Migraine (1 pt) Pain (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/

AEs

AE	Significance	Dose	Population
Migraine	1 pt	200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/
Nausea	1 pt	200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/
Pain	1 pt	200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/
Exanthema	2 patients	200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/
Gastrointestinal disorder	2 patients	200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/
Gastrointestinal fullness	2 patients	200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/
Diarrhoea	3 patients	200 mg 3 times / day steady-state, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: steady-state Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10088941/

PubMed

Title	Date	PubMed
Oxaceprol, an atypical inhibitor of inflammation, reduces leukocyte adherence in mouse antigen-induced arthritis.	2001-06	11480608
Oxaceprol is a well-tolerated therapy for osteoarthritis with efficacy equivalent to diclofenac.	2000	10791619
Antirheumatic agents and leukocyte recruitment. New light on the mechanism of action of oxaceprol.	1999-07-15	10423160
Oxaceprol is as effective as diclofenac in the therapy of osteoarthritis of the knee and hip.	1999	10088941

Patents

Sample Use Guides

In Vivo Use Guide

for 21 days with 400 mg t.i.d. oxaceprol

Route of Administration: Oral

In Vitro Use Guide

It was studied the effect of oxaceprol on the synthesis and degradation of proteoglycans and proteins by calf articular cartilage explants. The effect was observed at concentrations 10(-6) M to 10(-9) M, i.e. at 170 ng to 170 pg of the oxaceprol per ml of culture media, respectively. However, no significant effect was seen at concentrations 10(-4) M (17 micrograms/ml) to 10(-8) M (1.7 ng/ml) on the protein and proteoglycan catabolism.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:07 GMT 2025`
Record UNII	Q0XV76B96L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXACEPROL

Official Name

English

ACETYL HYDROXYPROLINE

Preferred Name

English

N-ACETYLHYDROXYPROLINE

Systematic Name

English

N-ACETYL-L-HYDROXYPROLINE

Systematic Name

English

JONCTUM

Brand Name

English

Oxaceprol [WHO-DD]

Common Name

English

oxaceprol [INN]

Common Name

English

OXACEPROL [MART.]

Common Name

English

OXACEPROL [MI]

Common Name

English

(-)-1-ACETYL-4-HYDROXY-L-PROLINE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QM01AX24