MedKoo Cat#: 596277 | Name: Oxaceprol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxaceprol is an antirheumatic Agent.

Chemical Structure

Oxaceprol
Oxaceprol
CAS#33996-33-7

Theoretical Analysis

MedKoo Cat#: 596277

Name: Oxaceprol

CAS#: 33996-33-7

Chemical Formula: C7H11NO4

Exact Mass: 173.0688

Molecular Weight: 173.17

Elemental Analysis: C, 48.55; H, 6.40; N, 8.09; O, 36.96

Price and Availability

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10g USD 310.00
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Synonym
Oxaceprol; Jonctum; AHP 200; AHP-200; AHP200; Oxaceprolum; Tejuntivo; EINECS 251-780-6;
IUPAC/Chemical Name
(2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acid
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
SMILES Code
O=C(O)[C@H]1N(C(C)=O)C[C@H](O)C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Oxaceprol (N-Acetyl-L-hydroxyproline), an orally active derivative of L-proline, possesses distinct anti-inflammatory activity.
In vitro activity:
TBD
In vivo activity:
In adjuvant arthritic rats, oxaceprol (6-54 mg/kg/day p.o.) given therapeutically had no effect on the primary paw oedema response, but inhibited secondary lesions in the ears and tail. Histologically, oxaceprol markedly inhibited inflammatory cell infiltration and bone damage in the adjuvant-injected paw. In contrast to indomethacin, oxaceprol was more effective at inhibiting periarticular soft tissue inflammation but did not affect cartilage breakdown in this model. Reference: Pharmacol Res. 1996 Jun;33(6):367-73. https://pubmed.ncbi.nlm.nih.gov/8971960/
Solvent mg/mL mM
Solubility
DMSO 67.0 386.91
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 173.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Pawar HS, Francis NK, Hota T, Peter N, Mitra A. Comparative evaluation of therapeutic efficacy of intra-articular oxaceprol with conventional modalities in osteoarthritis animal model. Clin Rheumatol. 2018 Aug;37(8):2195-2201. doi: 10.1007/s10067-018-4087-1. Epub 2018 Apr 10. PMID: 29637484. 2. Ionac M, Parnham MJ, Plauchithiu M, Brune K. Oxaceprol, an atypical inhibitor of inflammation and joint damage. Pharmacol Res. 1996 Jun;33(6):367-73. doi: 10.1006/phrs.1996.0051. PMID: 8971960.
In vitro protocol:
TBD
In vivo protocol:
1. Pawar HS, Francis NK, Hota T, Peter N, Mitra A. Comparative evaluation of therapeutic efficacy of intra-articular oxaceprol with conventional modalities in osteoarthritis animal model. Clin Rheumatol. 2018 Aug;37(8):2195-2201. doi: 10.1007/s10067-018-4087-1. Epub 2018 Apr 10. PMID: 29637484. 2. Ionac M, Parnham MJ, Plauchithiu M, Brune K. Oxaceprol, an atypical inhibitor of inflammation and joint damage. Pharmacol Res. 1996 Jun;33(6):367-73. doi: 10.1006/phrs.1996.0051. PMID: 8971960.
1: Pawar HS, Francis NK, Hota T, Peter N, Mitra A. Comparative evaluation of therapeutic efficacy of intra-articular oxaceprol with conventional modalities in osteoarthritis animal model. Clin Rheumatol. 2018 Apr 10. doi: 10.1007/s10067-018-4087-1. [Epub ahead of print] PubMed PMID: 29637484. 2: Bach TM, Hara R, Kino K, Ohtsu I, Yoshida N, Takagi H. Microbial production of N-acetyl cis-4-hydroxy-L-proline by coexpression of the Rhizobium L-proline cis-4-hydroxylase and the yeast N-acetyltransferase Mpr1. Appl Microbiol Biotechnol. 2013 Jan;97(1):247-57. doi: 10.1007/s00253-012-4204-z. Epub 2012 Jun 16. PubMed PMID: 22707053. 3: Hoa BT, Hibi T, Nasuno R, Matsuo G, Sasano Y, Takagi H. Production of N-acetyl cis-4-hydroxy-L-proline by the yeast N-acetyltransferase Mpr1. J Biosci Bioeng. 2012 Aug;114(2):160-5. doi: 10.1016/j.jbiosc.2012.03.014. Epub 2012 May 10. PubMed PMID: 22578594. 4: Pavelka K. A comparison of the therapeutic efficacy of diclofenac in osteoarthritis: a systematic review of randomised controlled trials. Curr Med Res Opin. 2012 Jan;28(1):163-78. doi: 10.1185/03007995.2011.649848. Review. PubMed PMID: 22168216. 5: Gu J, Chen N, Ding G, Zhang Z. Determination of oxaceprol in rat plasma by LC-MS/MS and its application in a pharmacokinetic study. J Pharm Biomed Anal. 2011 Jan 5;54(1):173-8. doi: 10.1016/j.jpba.2010.08.011. Epub 2010 Aug 19. PubMed PMID: 20832228. 6: Aliev AE, Bhandal S, Courtier-Murias D. Quantum mechanical and NMR studies of ring puckering and cis/trans-rotameric interconversion in prolines and hydroxyprolines. J Phys Chem A. 2009 Oct 8;113(40):10858-65. doi: 10.1021/jp906006w. PubMed PMID: 19757781. 7: Clayton JJ. Nutraceuticals in the management of osteoarthritis. Orthopedics. 2007 Aug;30(8):624-9; quiz 630-1. Review. PubMed PMID: 17727018. 8: Krüger K, Klasser M, Mössinger J, Becker U. Oxaceprol--a randomised, placebo-controlled clinical study in osteoarthritis with a non-conventional non-steroidal anti-inflammatory drug. Clin Exp Rheumatol. 2007 Jan-Feb;25(1):29-34. PubMed PMID: 17417987. 9: Ponzio TA, Hatton GI. Adenosine postsynaptically modulates supraoptic neuronal excitability. J Neurophysiol. 2005 Jan;93(1):535-47. Epub 2004 Sep 8. PubMed PMID: 15356187. 10: Beyens MN, Guy C, Ratrema M, Ollagnier M. Prescription of drugs to pregnant women in France: the HIMAGE study. Therapie. 2003 Nov-Dec;58(6):505-11. PubMed PMID: 15058494. 11: Harris AG, Schropp A, Messmer K. [Oxaceprol reduced leukocyte adhesion and extravasation and preserves perfusion of tissue after ischemia/reperfusion]. Langenbecks Arch Chir Suppl Kongressbd. 1998;115(Suppl I):447-51. German. PubMed PMID: 14518294. 12: Witte S, Lasek R, Victor N. [Meta-analysis of the efficacy of adenosylmethionine and oxaceprol in the treatment of osteoarthritis]. Orthopade. 2002 Nov;31(11):1058-65. German. PubMed PMID: 12436324. 13: Veihelmann A, Hofbauer A, Refior HJ, Messmer K. Oxaceprol, an atypical inhibitor of inflammation, reduces leukocyte adherence in mouse antigen-induced arthritis. Acta Orthop Scand. 2001 Jun;72(3):293-8. PubMed PMID: 11480608. 14: Curatolo M, Bogduk N. Pharmacologic pain treatment of musculoskeletal disorders: current perspectives and future prospects. Clin J Pain. 2001 Mar;17(1):25-32. Review. PubMed PMID: 11289086. 15: Herrmann G, Steeger D, Klasser M, Wirbitzky J, Fürst M, Venbrocks R, Rohde H, Jungmichel D, Hildebrandt HD, Parnham MJ, Gimbel W, Dirschedl H. Oxaceprol is a well-tolerated therapy for osteoarthritis with efficacy equivalent to diclofenac. Clin Rheumatol. 2000;19(2):99-104. PubMed PMID: 10791619. 16: Parnham MJ. Antirheumatic agents and leukocyte recruitment. New light on the mechanism of action of oxaceprol. Biochem Pharmacol. 1999 Jul 15;58(2):209-15. Review. PubMed PMID: 10423160. 17: Bauer HW, Klasser M, von Hanstein KL, Rolinger H, Schladitz G, Henke HD, Gimbel W, Steinbach K. Oxaceprol is as effective as diclofenac in the therapy of osteoarthritis of the knee and hip. Clin Rheumatol. 1999;18(1):4-9. PubMed PMID: 10088941. 18: Villani P, Bouvenot G. [Assessment of the placebo effect of symptomatic slow-acting anti-arthritics]. Presse Med. 1998 Feb 7;27(5):211-4. Review. French. PubMed PMID: 9768015. 19: Harris A, Schropp A, Messmer K. Effects of oxaceprol on the microcirculation in ischemia/reperfusion injury. Eur J Med Res. 1998 Apr 8;3(4):182-8. PubMed PMID: 9533926. 20: Steinmeyer J, Kalbhen DA. The inhibitory effects of antirheumatic drugs on the activity of human leukocyte elastase and cathepsin G. Inflamm Res. 1996 Jul;45(7):324-9. PubMed PMID: 8841833.