Feprazone
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Hodoodo CAT#: H328903

CAS#: 30748-29-9

Description: Feprazone, also known as Prenazone and DA-2370, is a pyrazolone anti-inflammatory agent used for joint and muscular pain.


Chemical Structure

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Feprazone
CAS# 30748-29-9

Theoretical Analysis

Hodoodo Cat#: H328903
Name: Feprazone
CAS#: 30748-29-9
Chemical Formula: C20H20N2O2
Exact Mass: 320.15
Molecular Weight: 320.392
Elemental Analysis: C, 74.98; H, 6.29; N, 8.74; O, 9.99

Price and Availability

Size Price Availability Quantity
25mg USD 285 2 Weeks
50mg USD 500 2 Weeks
100mg USD 850 2 Weeks
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Synonym: Feprazone; DA-2370; DA 2370; DA2370; Prenazone

IUPAC/Chemical Name: 4-(3-methylbut-2-en-1-yl)-1,2-diphenylpyrazolidine-3,5-dione

InChi Key: RBBWCVQDXDFISW-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H20N2O2/c1-15(2)13-14-18-19(23)21(16-9-5-3-6-10-16)22(20(18)24)17-11-7-4-8-12-17/h3-13,18H,14H2,1-2H3

SMILES Code: O=C(C1C/C=C(C)\C)N(C2=CC=CC=C2)N(C3=CC=CC=C3)C1=O

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:

Biological target: A COX-2 inhibitor.
In vitro activity: As shown in Figure 1, significantly elevated positive SA-β-Gal staining was observed in the chondrocytes stimulated with IL-1β but it was dramatically suppressed by treatment with Feprazone in a dose-dependent manner. For further confirmation, the telomerase activity in the treated chondrocytes was evaluated. As shown in Figure 2, the telomerase activities in the control, IL-1β, IL-1β + 10 μM Feprazone, and IL-1β + 20 μM Feprazone were 21.8, 12.5, 16.7, and 19.2 IU/L, respectively. These data indicate that the cell senescence induced by IL-1β was alleviated by Feprazone. Reference: ACS Omega. 2021 Apr 13; 6(14): 9442–9448. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8047674/
In vivo activity: As shown in Figure 7A,B, according to the images of HE staining on adipocyte tissues, compared to the control, the adipocyte size was significantly elevated in the HFD mice but was greatly inhibited by the administration of Feprazone. Reference: ACS Omega. 2021 Mar 16; 6(10): 6674–6680. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7970497/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 25.0 78.03
DMF 25.0 78.03
Ethanol 50.0 156.06
PBS (pH 7.2) 0.5 1.56
Water 1.0 3.12

Preparing Stock Solutions

The following data is based on the product molecular weight 320.39 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. Huang Z, Lan J, Gao X. Feprazone Mitigates IL-1β-Induced Cellular Senescence in Chondrocytes. ACS Omega. 2021 Mar 31;6(14):9442-9448. doi: 10.1021/acsomega.0c06066. PMID: 33869924; PMCID: PMC8047674. 2. Xiong X, Liu L, Xu F, Wu X, Yin Z, Dong Y, Qian P. Feprazone Ameliorates TNF-α-Induced Loss of Aggrecan via Inhibition of the SOX-4/ADAMTS-5 Signaling Pathway. ACS Omega. 2021 Mar 12;6(11):7638-7645. doi: 10.1021/acsomega.0c06212. PMID: 33778274; PMCID: PMC7992146. 3. Che L, Ren B, Jia Y, Dong Y, Wang Y, Shan J, Wang Y. Feprazone Displays Antiadipogenesis and Antiobesity Capacities in in Vitro 3 T3-L1 Cells and in Vivo Mice. ACS Omega. 2021 Mar 7;6(10):6674-6680. doi: 10.1021/acsomega.0c05470. PMID: 33748580; PMCID: PMC7970497.
In vitro protocol: 1. Huang Z, Lan J, Gao X. Feprazone Mitigates IL-1β-Induced Cellular Senescence in Chondrocytes. ACS Omega. 2021 Mar 31;6(14):9442-9448. doi: 10.1021/acsomega.0c06066. PMID: 33869924; PMCID: PMC8047674. 2. Xiong X, Liu L, Xu F, Wu X, Yin Z, Dong Y, Qian P. Feprazone Ameliorates TNF-α-Induced Loss of Aggrecan via Inhibition of the SOX-4/ADAMTS-5 Signaling Pathway. ACS Omega. 2021 Mar 12;6(11):7638-7645. doi: 10.1021/acsomega.0c06212. PMID: 33778274; PMCID: PMC7992146.
In vivo protocol: 1. Che L, Ren B, Jia Y, Dong Y, Wang Y, Shan J, Wang Y. Feprazone Displays Antiadipogenesis and Antiobesity Capacities in in Vitro 3 T3-L1 Cells and in Vivo Mice. ACS Omega. 2021 Mar 7;6(10):6674-6680. doi: 10.1021/acsomega.0c05470. PMID: 33748580; PMCID: PMC7970497.

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1: Berry DJ, Crome P, Corless D, Parke DV. The pharmacokinetics of single oral doses of feprazone in healthy volunteers and elderly patients. Xenobiotica. 1991 Sep;21(9):1211-6. PubMed PMID: 1788989.

2: Spahn H, Mutschler E. The influence of aluminium hydroxide on the bioavailability of feprazone. Single dose study. Arzneimittelforschung. 1985;35(1):167-9. PubMed PMID: 4039147.

3: Meloni T, Forteleoni G, Serra M, Daniotti S, Negri L, Giuntini P, Canepa L, Gaetani GF. Feprazone: absence of hemolytic effects in glucose-6-phosphate dehydrogenase-deficient subjects. J Clin Pharmacol. 1982 Aug-Sep;22(8-9):418-20. PubMed PMID: 7130431.

4: Berry D, Parke DV. The disposition of feprazone and its hydroxylated metabolite in human volunteers. Xenobiotica. 1988 Jul;18(7):857-68. PubMed PMID: 3176523.

5: Berry DJ, Webley M, Grahame R, Goulding R, Gaetani M, Parke DV. Pharmacokinetics of single oral doses of feprazone in patients with rheumatoid arthritis or with impaired renal clearance. Xenobiotica. 1993 Nov;23(11):1231-40. PubMed PMID: 8310707.

6: Sturrock R, Isaacs A, Hart FD. Feprazone compared with indomethacin in the management of rheumatoid arthritis. Practitioner. 1975 Jul;215(1285):94-7. PubMed PMID: 1103113.

7: Bianchi G, Cerri B, Grasso S, Carazzi R, Dotti F, Ongari R, Cerrato O, Viara M. Safety and efficacy of feprazone for long-term treatment of rheumatoid arthritis and osteoarthritis. Clin Ther. 1981;3(5):349-55. PubMed PMID: 7471130.

8: Yamaguchi H, Kubo J, Sekine K, Naruchi T, Hashimoto Y, Kato R. Metabolites of feprazone in man. Drug Metab Dispos. 1979 Sep-Oct;7(5):340-4. PubMed PMID: 40778.

9: Smith JN, Ayrton AD, Chown J, Lewis DF, Ioannides C. Feprazone: an inducer of the P450 II B family of proteins in the rat. J Biochem Toxicol. 1990 Spring;5(1):9-12. PubMed PMID: 2402005.

10: Spahn H, Mutschler E. [Determination of feprazone and one of its metabolites in human plasma after high-performance liquid chromatographic or thin-layer chromatographic separation]. J Chromatogr. 1982 Oct 8;232(1):145-53. German. PubMed PMID: 7142323.

11: Crone M, Geimer R. [Results of an open study and a controlled comparative study of feprazone and naproxen in patients with rheumatoid arthritis or osteoarthrosis (author's transl)]. Wien Med Wochenschr. 1981 Dec 31;131(23-24):597-601. German. PubMed PMID: 7039147.

12: Bain LS, Lynch MP, Bruce GM. A double-blind trial of feprazone in osteoarthritis of the hip. Curr Med Res Opin. 1977;4(9):665-9. PubMed PMID: 338255.

13: Morita K, Shibata H, Ono T, Shimakawa H. Inducing effect of feprazone on hepatic drug-metabolizing enzymes in man. Eur J Clin Pharmacol. 1986;31(1):117-8. PubMed PMID: 3780819.

14: Fletcher MR, Loebl W, Scott JT. Feprazone, a new anti-inflammatory agent. Studies of potency and gastrointestinal tolerance. Ann Rheum Dis. 1975 Apr;34(2):190-4. PubMed PMID: 1094965; PubMed Central PMCID: PMC1006371.

15: Laurent MR, Berry D, Grahame R. Feprazone in osteoarthritis: comparison of twice and 3-times daily dosage regimens. Pharmatherapeutica. 1983;3(6):393-7. PubMed PMID: 6353430.