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Oxaceprol

Alias: AHP 200; Jonctum; Oxaceprol
Cat No.:V26999 Purity: ≥98%
Oxaceprol (N-Acetyl-L-hydroxyproline) is an orally bioactive L-proline analogue with significant anti~inflammatory activity.
Oxaceprol
Oxaceprol Chemical Structure CAS No.: 33996-33-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25g
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Product Description
Oxaceprol (N-Acetyl-L-hydroxyproline) is an orally bioactive L-proline analogue with significant anti~inflammatory activity. Oxaceprol is widely utilized in the research on osteoarthritis and rheumatoid arthritis.
Oxaceprol (CAS#: 33996-33-7), also known as N-Acetyl-L-hydroxyproline, is an orally active L-proline derivative with significant anti-inflammatory activity. With a molecular formula of C7H11NO4 and a molecular weight of 173.17, Oxaceprol is a modified proline analog that acts by modulating cytokine production and inhibiting leukocyte infiltration. It is commonly used for the research of osteoarthritis and rheumatoid arthritis. Oxaceprol inhibits inflammatory cell infiltration and bone damage in the adjuvant-injected paw. At 6 mg/kg/day for 7 days, it significantly reduces both the surface area and wet weight of cotton pellet granulomas, being slightly less effective than indomethacin (3 mg/kg). Oxaceprol (6–54 mg/kg/day) given therapeutically had no effect on the primary paw oedema response, but inhibits secondary lesions in the ears and tail. The compound is for research use only and is not for human therapeutic use.
Biological Activity I Assay Protocols (From Reference)
Targets
Oxaceprol does not have a single defined molecular target. It is an L-proline derivative that acts by modulating cytokine production and inhibiting leukocyte infiltration. The compound's anti-inflammatory activity is attributed to its ability to modulate inflammatory cell infiltration and bone damage. Oxaceprol is an amino acid derivative that may interact with various cellular targets and pathways involved in inflammation. It is commonly used for the research of osteoarthritis and rheumatoid arthritis. The compound's mechanism of action involves the inhibition of leukocyte infiltration and modulation of cytokine production, which are key processes in the pathogenesis of inflammatory joint diseases.
ln Vitro
Oxaceprol demonstrates significant anti-inflammatory activity in vivo. It inhibits inflammatory cell infiltration and bone damage in the adjuvant-injected paw. At 6 mg/kg/day for 7 days, it significantly reduces both the surface area and wet weight of cotton pellet granulomas. Oxaceprol (6–54 mg/kg/day) given therapeutically had no effect on the primary paw oedema response, but inhibits secondary lesions in the ears and tail. The compound's anti-inflammatory effects are comparable to indomethacin, though slightly less effective. Oxaceprol is commonly used for the research of osteoarthritis and rheumatoid arthritis.
ln Vivo
The surface area and wet weight of cotton ball granuloma can be greatly reduced by oxapropanol at a dose of 6 mg/kg each day for 7 days. Its effectiveness is somewhat greater than that of indomethacin at 3 mg/kg. Oxapropanol, when administered therapeutically (6–54 mg/kg/day), suppresses subsequent lesions in the ears and tail but has no effect on the main paw edema response [3]. While oxapropanol greatly reduces neutrophil infiltration into the joints of rats suffering from adjuvant arthritis, it has no effect on prostaglandin generation in vitro [4].
Oxaceprol has been studied in vivo in animal models of inflammation and arthritis. The compound is administered orally at doses determined by preclinical studies. In the cotton pellet granuloma model, Oxaceprol at 6 mg/kg/day for 7 days significantly reduces granuloma formation. In adjuvant-induced arthritis models, Oxaceprol (6–54 mg/kg/day) inhibits secondary lesions in the ears and tail. The compound's anti-inflammatory effects on paw oedema and bone damage have been evaluated. Sample sizes typically range from 6-10 animals per group. Clinical studies have been conducted for osteoarthritis and rheumatoid arthritis.
Enzyme Assay
Oxaceprol does not have established receptor binding or enzyme inhibition assay protocols. Its anti-inflammatory activity is assessed by measuring its effects on inflammatory cell infiltration, cytokine production, and tissue damage. Inflammatory cell infiltration is assessed by histopathological analysis. Cytokine production is measured by ELISA. Tissue damage is assessed by measuring paw oedema, granuloma formation, and bone erosion. Physical properties: molecular weight 173.17 g/mol; molecular formula C7H11NO4; CAS name: (4R)-1-Acetyl-4-hydroxy-L-proline; melting point 74-76°C; solubility: DMSO: ≥100 mg/mL (577.47 mM).
Cell Assay
Cellular activity of Oxaceprol is evaluated in immune cells and synovial cells. Cells are cultured in appropriate media at 37°C with 5% CO₂ and treated with Oxaceprol at various concentrations. Cytokine production (e.g., TNF-α, IL-6) is measured by ELISA. Leukocyte infiltration is assessed in chemotaxis assays. Cell viability is assessed using MTT or LDH assays. Each experiment includes vehicle controls and appropriate positive controls (e.g., indomethacin) to validate the assay systems.
Animal Protocol
Animal/Disease Models: Male SD (SD (Sprague-Dawley)) rat [3].
Doses: 18, 50 or 150 mg/kg.
Route of Administration: Administer daily for 15 days.
Experimental Results: The inhibitory effect on hyperalgesia was comparable to that of indomethacin.
In vivo efficacy of Oxaceprol is evaluated in animal models of osteoarthritis and rheumatoid arthritis. The compound is administered orally at doses determined by preclinical studies. In the cotton pellet granuloma model, Oxaceprol at 6 mg/kg/day for 7 days reduces granuloma formation. In adjuvant-induced arthritis models, Oxaceprol (6–54 mg/kg/day) inhibits secondary lesions. Paw oedema is measured by plethysmometry. Bone damage is assessed by radiological and histopathological analysis. Sample sizes typically range from 6-10 animals per group.
ADME/Pharmacokinetics
Molecular Weight: 173.17. Formula: C7H11NO4. CAS No.: 33996-33-7. CAS Name: (4R)-1-Acetyl-4-hydroxy-L-proline. Synonyms: N-Acetyl-L-hydroxyproline. Appearance: Crystals from moist ethyl acetate or acetone. Melting Point: 74-76°C. Solubility: DMSO: ≥100 mg/mL (577.47 mM). Storage: Powder at -20°C for 3 years; 4°C for 2 years; In solvent at -80°C for 2 years; -20°C for 1 year. Oxaceprol is an orally active L-proline derivative with anti-inflammatory activity.
Toxicity/Toxicokinetics
No comprehensive toxicology data are publicly available for Oxaceprol. The compound is intended for research use only and has not undergone full preclinical toxicology evaluation required for clinical development. In animal studies, the compound is generally well-tolerated at the doses tested (6-54 mg/kg/day). Standard toxicity studies would include acute toxicity assessment in rodents, repeated dose toxicity studies (14-day and 28-day), and genotoxicity screening (Ames test, micronucleus assay). The compound is for research use only and not for human therapeutic use.
References

[1]. Oxaceprol, an atypical inhibitor of inflammation and joint damage. Pharmacol Res, 1996 Jun, 33(6):367-73.

[2]. Comparative evaluation of therapeutic efficacy of intra-articular oxaceprol with conventional modalities in osteoarthritis animal model. Clin Rheumatol. 2018 Aug;37(8):2195-2201.

[3]. Oxaceprol, an atypical inhibitor of inflammation and joint damage. Pharmacol Res. 1996 Jun;33(6):367-73.

[4]. Antirheumatic agents and leukocyte recruitment. New light on the mechanism of action of oxaceprol. Biochem Pharmacol. 1999 Jul 15;58(2):209-15.

Additional Infomation
Oxaceprol is also known as N-Acetyl-L-hydroxyproline. Its CAS name is (4R)-1-Acetyl-4-hydroxy-L-proline. Oxaceprol is an orally active L-proline derivative with significant anti-inflammatory activity. It is commonly used for the research of osteoarthritis and rheumatoid arthritis. Oxaceprol inhibits inflammatory cell infiltration and bone damage. No clinical trials have been reported for this compound. Oxaceprol is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H11NO4
Molecular Weight
173.16
Exact Mass
173.068
CAS #
33996-33-7
PubChem CID
65784
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
442.1±45.0 °C at 760 mmHg
Melting Point
132-133 °C (dec.)(lit.)
Flash Point
221.2±28.7 °C
Vapour Pressure
0.0±2.4 mmHg at 25°C
Index of Refraction
1.561
LogP
-2.04
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
12
Complexity
216
Defined Atom Stereocenter Count
2
SMILES
CC(=O)N1C[C@@H](C[C@H]1C(=O)O)O
InChi Key
BAPRUDZDYCKSOQ-RITPCOANSA-N
InChi Code
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
Chemical Name
(2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acid
Synonyms
AHP 200; Jonctum; Oxaceprol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~577.47 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.44 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (14.44 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.7750 mL 28.8750 mL 57.7501 mL
5 mM 1.1550 mL 5.7750 mL 11.5500 mL
10 mM 0.5775 mL 2.8875 mL 5.7750 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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