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  • Product Name: Feprazone
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30748-29-9

30748-29-9 structure
30748-29-9 structure
  • Name: feprazone
  • Chemical Name: Feprazone
  • CAS Number: 30748-29-9
  • Molecular Formula: C20H20N2O2
  • Molecular Weight: 320.385
  • Catalog: API Antipyretic analgesics Non-steroidal anti-inflammatory drugs
  • Create Date: 2018-06-11 17:24:22
  • Modify Date: 2024-01-03 10:28:19
  • Feprazone (DA2370; Prenazone), an analogue of Phenylbutazone (HY-B0230), is a nonsteroidal anti-inflammatory agent with analgesic and antipyretic activities. Feprazone acts by inhibiting the activity of cyclooxygenase (COX)-2. Feprazone ameliorates free fatty acid (FFA)-induced oxidative stress by reducing the production of mitochondrial reactive oxygen species (ROS). Feprazone can decrease the expression of MMP-2 and MMP-9. Besides, Feprazone can suppress adipogenesis and increase lipolysis in differentiating 3 T3-L1 cells. Feprazone also can be used to research atherosclerosis and obesity[1][2][3].

Name Feprazone
Synonyms feprazone
Prenazone
da2370
analud
3,5-Pyrazolidinedione, 4-(3-methyl-2-buten-1-yl)-1,2-diphenyl-
methrazone
Grisona
MFCD00866063
3,5-Pyrazolidinedione, 4-(3-methyl-2-butenyl)-1,2-diphenyl-
4-Prenyl-1,2-diphenyl-3,5-pyrazolidindion
4-(3-Methyl-2-buten-1-yl)-1,2-diphenyl-3,5-pyrazolidinedione
4-(3-Methylbut-2-en-1-yl)-1,2-diphenylpyrazolidine-3,5-dione
Zepelin
EINECS 250-324-3
4-(b-Isoamylenyl)-1,2-diphenyl-3,5-pyrazolidinedione
Nilatin
Naloven
Tabrien
Description Feprazone (DA2370; Prenazone), an analogue of Phenylbutazone (HY-B0230), is a nonsteroidal anti-inflammatory agent with analgesic and antipyretic activities. Feprazone acts by inhibiting the activity of cyclooxygenase (COX)-2. Feprazone ameliorates free fatty acid (FFA)-induced oxidative stress by reducing the production of mitochondrial reactive oxygen species (ROS). Feprazone can decrease the expression of MMP-2 and MMP-9. Besides, Feprazone can suppress adipogenesis and increase lipolysis in differentiating 3 T3-L1 cells. Feprazone also can be used to research atherosclerosis and obesity[1][2][3].
Related Catalog
Target

COX, Reactive oxygen species, MMP[1]

In Vitro Feprazone (2.5-10 μM; 48 h) rescues cell viability of FFAs-stimulated human aortic endothelial cells (HAECs)[1]. Feprazone (5, 10 μM; 24 h) reduces ROS production in HAECs to only 2.4- and 1.6-fold at 5 and 10 μM, respectively, while 300 μM FFA increases ROS production by 3.4-fold; also decreases the mRNA expression and secretion of cytokines CCL5, IL-6, and IL-8, as well as MMP-2 and MMP-9[1]. Feprazone (5, 10 μM; 6 h) decreases TLR4 and MyD88 activities, as well as reduces the phosphorylation of p65 and subsequent activation of NF-κB[1]. Feprazone (30 and 60 μM; 7 days) suppresses the adipogenesis in differentiating 3 T3-L1 cells; reduced the triglyceride content and increased lipolysis during 3 T3-L1 adipogenesis[3]. Cell Viability Assay[1] Cell Line: HAECs (stimulated with 300 μM FFAs) Concentration: 2.5, 5 and 10 μM Incubation Time: 48 h Result: Rescued cell viability to 81 and 93% of baseline at 5 and 10 μM, while FFAs reduced the cell viability to 63% of baseline. RT-PCR[1] Cell Line: HAECs (stimulated with 300 μM FFAs) Concentration: 5 and 10 μM Incubation Time: 24 h Result: Decreased the mRNA expression and secretion of cytokines CCL5, IL-6, and IL-8 in a dose-dependent manner. Dose-dependently mitigated the VCAM-1 and ICAM-1 expression to only 1.7- and 1.8-fold, respectively, while FFA increased to 2.8- and 3.4-fold, respectively. Western Blot Analysis[1] Cell Line: HAECs (stimulated with 300 μM FFAs) Concentration: 5 and 10 μM Incubation Time: 6 h Result: Decreased TLR4 and MyD88 expression, as well as reduced the phosphorylation of p65 and subsequent activation of NF-κB.
In Vivo Significantly inhibited the adipocyte size, the visceral adipocyte tissue weights and the average bodyweights in HFD mice[3]. Animal Model: Male C57BL/6 N mice [high-fat diet (HFD) induced obesity model][3] Dosage: 75 mg/kg Administration: (no described in the research) Result: The visceral adipocyte tissue weights of mice in the control, HFD, and HFD + Feprazone groups were 0.38, 3.51, and 2.37 g, respectively. The average bodyweights of mice in the control, HFD, and HFD + Feprazone groups were 29.6, 41.3, and 34.1 g, respectively.
Density 1.2±0.1 g/cm3
Boiling Point 437.2±28.0 °C at 760 mmHg
Molecular Formula C20H20N2O2
Molecular Weight 320.385
Flash Point 178.7±16.4 °C
Exact Mass 320.152466
PSA 40.62000
LogP 3.41
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.600

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UQ8530000
CHEMICAL NAME :
3,5-Pyrazolidinedione, 1,2-diphenyl-4-(3-methyl-2-butenyl)-
CAS REGISTRY NUMBER :
30748-29-9
LAST UPDATED :
199612
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C20-H20-N2-O2
MOLECULAR WEIGHT :
320.42
WISWESSER LINE NOTATION :
T5VNNV EHJ BR& CR& E2UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1343 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,133,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
362 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,133,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
386 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 20,267,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1067 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,196,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
270 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,133,1979
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
374 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,133,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,196,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from stomach
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 33,233,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
18 gm/kg/30D-C
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Liver - changes in liver weight Related to Chronic Data - death
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 64,255,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
98820 mg/kg/26W-C
TOXIC EFFECTS :
Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 64,255,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6300 mg/kg/21D-I
TOXIC EFFECTS :
Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - death
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,226,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
16800 mg/kg/14W-I
TOXIC EFFECTS :
Cardiac - changes in heart weight Liver - changes in liver weight Kidney, Ureter, Bladder - other changes in urine composition
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,216,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
32400 mg/kg/30D-C
TOXIC EFFECTS :
Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - death
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 64,255,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
54750 mg/kg/1Y-C
TOXIC EFFECTS :
Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Liver - changes in liver weight
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 64,255,1982 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1320 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - delayed effects
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,149,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2640 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,149,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
180 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,164,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1620 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,164,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1560 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,149,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3120 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,149,1979
HS Code 2933990090
Precursor  0

DownStream  1

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%