Oxaceprol (BAT-008134)

Oxaceprol derived from L-proline, inhibiting inflammatory cell infiltration and bone damage in the adjuvant-injected paw.

Category
Cyclic Amino Acids
Catalog number
BAT-008134
CAS number
33996-33-7
Molecular Formula
C7H11NO4
Molecular Weight
173.17
Oxaceprol
IUPAC Name
(2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acid
Synonyms
trans-1-Acetyl-4-hydroxy-L-proline;N-Acetyl-L-hydroxyproline; Oxaceprol; Jonctum; AHP 200; AHP-200; AHP200; Oxaceprolum; Tejuntivo; EINECS 251-780-6;
Appearance
White powder
Purity
≥98%
Density
1.439 g/cm3
Melting Point
132-133ºC (dec.)
Boiling Point
442.1ºC at 760 mmHg
Storage
Store at RT.
Solubility
Soluble in DMSO
Application
An anti-inflammatory drug used in the treatment of osteoarthritis.
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
InChI Key
BAPRUDZDYCKSOQ-RITPCOANSA-N
Canonical SMILES
CC(=O)N1CC(CC1C(=O)O)O
1.[Autoradiography studies of the effect of oxaceprol on the metabolism of joint cartilage in vitro and in vivo].
Kalbhen DA, Kalkert B. Z Rheumatol. 1987 May-Jun;46(3):136-42.
Using the radiolabelled precursors (3H-Glucosamine, 3H-proline) and a new procedure of quantitative microautoradiography we investigated the influence of N-acetyl-L-hydroxyproline (Oxaceprol) on anabolic processes in joint cartilage tissue of hens. After in vitro incubation, Oxaceprol stimulated the uptake of 3H-glucosamine and 3H-proline in chondrocytes and enhanced the incorporation of 3H-proline into the macromolecular structures of the cartilage matrix. Also, after in vivo intra-articular injection of Oxaceprol into the knee joints we could demonstrate a significant increase of intracellular glucosamine uptake. Because in our micro-autoradiographic detection method low molecular substances are excluded, the higher rate of precursor incorporation into cells and matrix can be interpreted as a stimulation of proteoglycan and collagen synthesis.
2.Oxaceprol, an atypical inhibitor of inflammation, reduces leukocyte adherence in mouse antigen-induced arthritis.
Veihelmann A1, Hofbauer A, Refior HJ, Messmer K. Acta Orthop Scand. 2001 Jun;72(3):293-8.
Oxaceprol (N-acetyl-L-hydroxyproline), an atypical inhibitor of inflammation, is an established drug forjoint disease without serious side-effects. Recent studies have emphasized that oxaceprol has an effect on the microcirculation. Since the exact mechanism of action remains unclear, the aim of our study was to investigate the leukocyte-endothelial cell interactions in oxaceprol-treated mice with antigen-induced arthritis (AiA) using intravital microscopy. In our study, Balb/c mice were allocated to 4 groups (n 7, 8, 8, 8): 2 control groups with saline or oxaceprol and 2 groups of arthritic animals which received saline or oxaceprol (100 mg/kg twice a day intraperitoneally). The severity of arthritis was quantified by the transverse knee joint diameter. For the intravital fluorescence microscopy measurements on day 10 after inducing arthritis, the patella tendon was partily resected to visualize the intraarticular synovial tissue of the knee joint.
3.Topical effects of N-acetyl-L-hydroxyproline on ceramide synthesis and alleviation of pruritus.
Hashizume E1, Nakano T, Kamimura A, Morishita K. Clin Cosmet Investig Dermatol. 2013;6:43-9. doi: 10.2147/CCID.S39370. Epub 2013 Feb 12.
PURPOSE: N-acetyl-l-hydroxyproline (AHYP) is an acetylated form of l-hydroxyproline that is used to treat skin ulcers and porphyria cutanea tarda. Its other biological and physiological effects on the skin have not been elucidated. We investigated the effects of AHYP on the skin-barrier function, focusing on ceramide synthesis and the effects of topical AHYP on atopic dermatitis.
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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