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MedKoo Cat#: 328903 | Name: Feprazone
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Description:

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

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

Chemical Structure

Feprazone
Feprazone
CAS#30748-29-9

Theoretical Analysis

MedKoo Cat#: 328903

Name: Feprazone

CAS#: 30748-29-9

Chemical Formula: C20H20N2O2

Exact Mass: 320.1525

Molecular Weight: 320.39

Elemental Analysis: C, 74.98; H, 6.29; N, 8.74; O, 9.99

Price and Availability

Size Price Availability Quantity
25mg USD 285.00 2 Weeks
50mg USD 500.00 2 Weeks
100mg USD 850.00 2 Weeks
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Related CAS #
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Synonym
Feprazone; Prenazone; Fenilprenazone; Phenylprenazone; DA-2370; DA 2370; DA2370;
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
Product Data
Product Data
Instruction
View handling instruction
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/
Solvent mg/mL 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
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 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.
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. Erratum in: ACS Omega. 2022 Feb 15;7(8):7430. 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. 4: Song M, Meng L, Liu X, Yang Y. Feprazone Prevents Free Fatty Acid (FFA)-Induced Endothelial Inflammation by Mitigating the Activation of the TLR4/MyD88/NF-κB Pathway. ACS Omega. 2021 Feb 9;6(7):4850-4856. doi: 10.1021/acsomega.0c05826. PMID: 33644593; PMCID: PMC7905947. 5: Huang Z, Lan J, Gao X. Correction to "Feprazone Mitigates IL-1β-Induced Cellular Senescence in Chondrocytes". ACS Omega. 2022 Feb 15;7(8):7430. doi: 10.1021/acsomega.2c00749. Erratum for: ACS Omega. 2021 Mar 31;6(14):9442-9448. PMID: 35252733; PMCID: PMC8892662. 6: Haslock I, Burkinshaw L, Berry DJ, Donovan B, Wright V. Some studies of feprazone. Rheumatol Rehabil. 1976 May;15(2):81-6. doi: 10.1093/rheumatology/15.2.81. PMID: 132695. 7: Cusano F, Luciano S, Iannazzone S, Adamo F. Contact dermatitis from feprazone. Contact Dermatitis. 1993 Feb;28(2):109. doi: 10.1111/j.1600-0536.1993.tb03353.x. PMID: 8458203. 8: 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. doi: 10.1185/03007997709115289. PMID: 338255. 9: 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. doi: 10.1136/ard.34.2.190. PMID: 1094965; PMCID: PMC1006371. 10: Berry D, Parke DV. The disposition of feprazone and its hydroxylated metabolite in human volunteers. Xenobiotica. 1988 Jul;18(7):857-68. doi: 10.3109/00498258809041724. PMID: 3176523. 11: 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. doi: 10.1002/jbt.2570050103. PMID: 2402005. 12: Harkness AJ, Burry HC, Grahame R. A trial of feprazone in ankylosing spondylitis. Rheumatol Rehabil. 1977 Aug;16(3):158-61. doi: 10.1093/rheumatology/16.3.158. PMID: 333540. 13: 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. doi: 10.3109/00498259309059434. PMID: 8310707. 14: Wiggins J, Scott DL. Hepatic injury following feprazone therapy. Rheumatol Rehabil. 1981 Feb 1;20(1):44-5. doi: 10.1093/rheumatology/20.1.44. PMID: 6452677. 15: Harris PG. Miscellaneous rheumatological conditions treated in monitored- release studies with feprazone. J Int Med Res. 1981;9(4):248-52. doi: 10.1177/030006058100900402. PMID: 6973494. 16: 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. doi: 10.1002/j.1552-4604.1982.tb02695.x. PMID: 7130431. 17: Berry DJ, Parke DV. The micro gas-liquid chromatographic analysis of 4-(3',3'-dimethylallyl)-1,2-diphenylpyrazolidine-3,5-dione (feprazone) in human biosamples. J Pharm Biomed Anal. 1988;6(5):493-501. doi: 10.1016/0731-7085(88)80016-5. PMID: 16867395. 18: Koyama T, Izawa Y, Wada H, Makita T, Hashimoto Y, Enomoto M. Toxicological aspects of feprazone, a new nonsteroidal anti-inflammatory drug. Toxicol Appl Pharmacol. 1982 Jun 30;64(2):255-70. doi: 10.1016/0041-008x(82)90222-8. PMID: 7123554. 19: 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. doi: 10.1007/BF00870999. PMID: 3780819. 20: Sturrock R, Isaacs A, Hart FD. Feprazone compared with indomethacin in the management of rheumatoid arthritis. Practitioner. 1975 Jul;215(1285):94-7. PMID: 1103113.