Propyphenazone (4-Isopropylantipyrine)
(Synonyms: 异丙安替比林; 4-Isopropylantipyrine; Isopropylphenazone) 目录号 : GC33876
Propyphenazone(4-Isopropylantipyrine, Isopropyrine), an analgesic and antipyretic agent, is a selective cyclooxygenase-2 inhibitor with anti-inflammatory activity.
Cas No.:479-92-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Propyphenazone(4-Isopropylantipyrine, Isopropyrine), an analgesic and antipyretic agent, is a selective cyclooxygenase-2 inhibitor with anti-inflammatory activity.
| Cas No. | 479-92-5 | SDF | |
| 别名 | 异丙安替比林; 4-Isopropylantipyrine; Isopropylphenazone | ||
| Canonical SMILES | O=C1N(C2=CC=CC=C2)N(C)C(C)=C1C(C)C | ||
| 分子式 | C14H18N2O | 分子量 | 230.31 |
| 溶解度 | DMSO : ≥ 2.6 mg/mL (11.29 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.342 mL | 21.7099 mL | 43.4197 mL |
| 5 mM | 0.8684 mL | 4.342 mL | 8.6839 mL |
| 10 mM | 0.4342 mL | 2.171 mL | 4.342 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
11C-labeled 4-Isopropylantipyrine: preparation and biological evaluation as a blood flow tracer in positron emission tomography (PET)
J Med Chem 1985 Sep;28(9):1325-8.PMID:3875726DOI:10.1021/jm00147a036.
Radiolabeled 4-Isopropylantipyrine (1) has been synthesized and evaluated as a tracer for the measurement of cerebral blood flow (CBF). Methylation of 4-isopropyl-3-methyl-1-phenylpyrazol-5-one (2) with [14C]methyl iodide in acetonitrile gave [14C]-1 in radiochemical yields of 10-20%. Its blood-brain partition coefficient in rats was determined to be 0.62 +/- 0.03 (mean +/- SE). Autoradiographic determination of regional cerebral blood flow under normal flow conditions indicated that [14 C]-1 gives results essentially identical with those obtained with the widely used tracer [14C]-4-iodoantipyrine ( [14C]-IAP). Studies performed in high-flow states indicated that [14C]-1 is not more diffusion limited than [14C]-IAP. A rapid synthesis was therefore developed for the preparation of [11C]-1. Radiochemical yields were increased to 40-50% when the alkylation of 2 with [11C]methyl iodide was performed in dimethyl sulfoxide using solid potassium hydroxide as a base. Since the 11C-labeled compound can easily be produced in large quantities and since the tracer is not diffusion limited at flow rates commonly observed in normal and most pathological states in man, [11C]-4-isopropylantipyrine will be used for in vivo studies of CBF using positron emission tomography.
Formation of the knee joint after prenatal Propyphenazone (isopropylantipyrine) administration
Cells Tissues Organs 2002;171(2-3):145-51.PMID:12097837DOI:10.1159/000063708.
Cyclooxygenase (COX) inhibitors could produce cartilage toxicity as well as delayed skeleton formation when administrated during pregnancy. The purpose of this experiment was to determine the effect of a nonselective COX inhibitor, Propyphenazone (isopropylantipyrine), on the development of the knee joint in rats. The drug was administered orally in Tween 80 water suspension once a day on days 8-14 of gestation in three doses: R1: 2.1 mg/kg, R2: 21.0 mg/kg and R3: 210.0 mg/kg. Two control groups were formed: untreated control (K) and Tween 80-treated (T) animals. Fetuses were delivered by cesarean section on day 21 of gestation and examined macroscopically for external malformations. The knee joints of two fetuses of each litter were sectioned in situ or paraffin-embedded. The slides were examined microscopically. The remaining fetuses were stained using the Alcian blue and red S alizarin skeleton double-staining method. Reduced alizarin staining in bones from the knee joint, and wider epiphysial cartilage was seen in 2 of 53 examined fetuses (3.77%) exposed prenatally to the highest dose of Propyphenazone. The extra sesamoid cartilage, located close to the lateral epicondyle of the femur, was absent in 10 cases in group T (15.87%), 9 cases in group K (15.00%), 8 cases in group R1 (12.50%), 9 cases in group R2 (14.75%) and 9 cases in group R3 (14.28%). Similarly sesamoid cartilage close to the middle epicondyle was seen in one fetus from group K (1.66%) and in one fetus from group R2 (1.63%). No histological changes were observed. Based on obtained results, it could be concluded that Propyphenazone did not delay the formation of the knee joint.
Kinetics and metabolism of pyrazolones (Propyphenazone, aminopyrine and dipyrone)
Br J Clin Pharmacol 1980 Oct;10 Suppl 2(Suppl 2):299S-308S.PMID:7002187DOI:10.1111/j.1365-2125.1980.tb01813.x.
1 Propyphenazone 220 mg was administered orally to volunteers. Maximum plasma concentrations between 1.5 microgram/ml and 3.5 micrograms/ml were found 30 min later. After comparable doses plasma concentrations in dog and rabbit were lower. The distribution volumes were 2 l/kg. 2 The major metabolic route of Propyphenazone is demethylation. The main urinary metabolite is the enolglucuronide of N-(2)-demethylpropyphenazone. 3 Aminopyrine is rapidly and almost completely absorbed after oral administration. Maximum plasma concentrations of 10 microgram/ml are reached 1.5 h after a 500 mg dose. The biological half-life is 2-3 h, the relative distribution volume 60% on average, and binding to plasma proteins approximately 15%. 4 Unchanged aminopyrine is only excreted in small quantities. The major routes of metabolism are demethylation (4-methylaminoantipyrine and 4-aminoantipyrine) and acylation (4-acetyl and 4-formylaminoantipyrine). There are other biotransformation products. 5 After oral administration of [14C]-dipyrone 480 mg the maximum serum concentration of 13.4 +/- 0.8 microgram/ml occurred at 1-1.5 hours. 6 Dipyrone was not detectable in serum or urine. Four of seven metabolites were identified, and were identical with the main metabolites of aminopyrine.
Pyrazolone derivatives
Drugs 1986;32 Suppl 4:60-70.PMID:3552586DOI:10.2165/00003495-198600324-00006.
In many countries, the pyrazolone derivatives, which include dipyrone, antipyrine, aminopyrine and Propyphenazone, are widely used analgesics. Dipyrone, the most widely used pyrazolone, has been the most studied. The pyrazolidine derivatives, phenylbutazone and oxyphenbutazone, which are not generally used for analgesia since they differ from the pyrazolones in terms of efficacy and tolerance, are not discussed in this article. Dipyrone is an inhibitor of cyclo-oxygenase but, unlike aspirin, its effect is rapidly reversible. The inhibition of prostaglandin biosynthesis contributes to the analgesic activity of the pyrazolone derivatives. Peak plasma concentrations of the pyrazolone derivatives generally occur 1 to 1.5 hours after oral administration. Half-lives vary from 1 to 2 hours with Propyphenazone, to about 7 hours with dipyrone (2 hours for the active metabolite of dipyrone, 4-methylaminoantipyrine, MAA). Half-life of antipyrine varies considerably between individuals (5 to 35 hours). Unlike the NSAIDs generally, the pyrazolone derivatives antipyrine, aminopyrine and Propyphenazone are minimally bound to plasma proteins. The pyrazolones undergo extensive biotransformation, aminopyrine and dipyrone being converted to active metabolites. Dipyrone is the only drug for which results of recent double-blind trials are available. Oral dipyrone has been shown to be more effective than an equal dose of aspirin or paracetamol in alleviating postoperative pain, and intravenous dipyrone 2.5g was similar in efficacy to pethidine 50 mg. In patients with acute ureteral or biliary colic, dipyrone 2.5g intravenously was similar in efficacy to indomethacin 50 mg or pethidine 50 mg. The most frequently reported side effects of the pyrazolone derivatives are skin rashes. Gastrointestinal side effects are rare. Blood dyscrasias, mostly associated with aminopyrine, have received wide attention in the medical literature, but their true incidence with dipyrone is considerably lower than the often quoted incidence for amidopyrine reported more than 30 years ago.
Somatic and skeleton development of rat foetuses following in-utero exposure to isopropylantipyrine (Propyphenazone) during the second trimester of gestation
Folia Morphol (Warsz) 2000;59(4):317-22.PMID:11107705doi
Isopropylantipyrine (IPA, Propyphenazone) is a pyrazolone derivative, widely used as an antipyretic and analgesic drug. The aim of the study was to evaluate the influence of Propyphenazone on rat development. IPA was administered to pregnant rats from day 8 to day 14 of pregnancy once a day, orally by a stomach tube at doses of 2.10 (R1), 21.0 (R2), and 210.0 mg/kg/day (R3). The dams were sacrificed on day 21 of gestation and corpora luteum, implants, resorptions, and live foetuses were counted. The weight of foetuses and placentas, the length of foetuses and their tails were checked. The foetuses were fixed in alcohol and skeletons were stained with alizarin. There was a statistical difference in body length in R1, R2 and numbers of subcutaneous ecchymose in R1. External and skeletal examination of the foetuses revealed no evidence of teratogenesis. It can be concluded that IPA has no harmful effects on the prenatal development of the rat offspring at doses used in the present study.