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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 4614作成日：2026年10月27日

オキサプロジン

4,5-ジフェニルオキサゾール-2-プロピオン酸 · オロサルジン · 4,5-ジフェニル-2-オキサゾールプロピオン酸 · 3-(4,5-ジフェニルオキサゾール-2-イル)プロパン酸 · オキシアシドン · オキサチリン · アルセロジン · イナミジン

https://huagongshe.com/ja/chemical/4614

オキサプロジン の分子構造式

識別子と物理属性

CAS No.21256-18-8
分子式C18H15NO3
平均分子量293.3 g/mol
単同位体質量293.10519334 g/mol
SMILESO=C(O)CCc1nc(-c2ccccc2)c(-c2ccccc2)o1
InChIKeyOFPXSFXSNFPTHF-UHFFFAOYSA-N
PubChem CID4614
ChEMBLCHEMBL1071
ChEBICHEBI:7822
EC No.244-296-1
DTXSIDDTXSID1045118
現地名オキサプロジン

化学・物理的性質

XLogP4.2
極性表面積63.3
水素結合供与体数1
水素結合受容体数4
回転可能結合数5
重原子数22
形式電荷0
複雑度361
LogP（分配係数）4.19log Kow = 4.193.7
Color/FormCrystals from methanol
溶解度InsolubleSlightly soluble in alcohol. Insoluble in water3.25e-02 g/LDMSOに可溶4mg/L(37℃)
DecompositionWhen heated to decomposition it emits toxic fumes of /Nitrogen oxide/.
融点158-159 °C160.5 to 161.5 °C158 - 159 °C154 °C
Physical DescriptionSolid
Dissociation Constants4.3pKa = 4.3
Collision Cross Section169.7 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]176 Ų [M+Na]+ [CCS Type: TW160.98 Ų [M+H-H2O]+ [CCS Type: TW168.56 Ų [M+H]+ [CCS Type: TW
沸点435.17°C (rough estimate)
密度1.2278 (rough estimate)
屈折率1.5100 (estimate)
貯蔵条件2-8°C
pKa（酸解離定数）4.3(at 25℃)
外観・状態個体
色メタノールからの結晶
Merck14,6924
BCS Class2
安定性-20°C の DMSO 溶液で最大 3 か月間保存できます。
主な用途医薬品（低分子化合物）
InChI1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)
InChIKeyOFPXSFXSNFPTHF-UHFFFAOYSA-N
SMILESOC(=O)CCc1nc(-c2ccccc2)c(o1)-c3ccccc3
CAS データベース21256-18-8(CAS DataBase Reference)
EPAの化学物質情報2-Oxazolepropanoic acid, 4,5-diphenyl- (21256-18-8)

化学的特性

White Solid

安全性と法規制

GHS 分類WarningH302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H411 (25%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]H412 (25%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]H413 (25%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
FDA 要件The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl oxaprozin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Hazard Classes and CategoriesAcute Tox. 4 (25%)Skin Irrit. 2 (25%)Eye Irrit. 2 (25%)Aquatic Chronic 2 (25%)Aquatic Chronic 4 (25%)
保管条件Store below 30 °C (86 °F), preferably between 15 and 30 °C (59 and 86 °F), in a tight, light-resistant container, unless otherwise specified by manufacturer. Note: Protect unit-dose packages from light.
処分方法SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

用途

用途

プロピオン酸系化合物です。 シクロオキシゲナーゼ（COX）を阻害し、プ ロスタグランジン生合成抑制作用を示します。

説明

Oxaprozin is a non-steroidal antiinflammatory agent indicated for use in various forms of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. A long T1/2 allows once/twice daily dosing. Structurally it is somewhat unique, being a 3- substituted, rather than a 2-substituted propionic acid.

使用

Oxaprozin is an anti-inflammatory drug. Oxaprozin was comparable to Aspirin (A687780).

一般的な説明

Oxaprozin, 4,5-diphenyl-2-oxazolepropionic acid (Daypro),differs from the other members of this group in being anarylpropionic acid derivative. It shares the same propertiesand side effects of other members in this group. It is indicatedfor the short- and long-term management of OA andRA, administered as a once-daily dose of 600- to 1,200-mgdose because of its long duration of action.

相互作用Prolonged concurrent use of acetaminophen with a nonsteroidal anti-inflammatory drug may increase the risk of adverse renal effectsit is recommended that patients be under close medical supervision while receiving such combined therapy. /Nonsteroidal anti-inflammatory drugs/Concurrent use /of alcohol or oral glucocorticoid or corticosteroids or chronic therapeutic use of corticotropin or potassium supplements/ with a nonsteroidal anti-inflammatory drug may increase the risk of gastrointestinal side effects, including ulceration or hemorrhagehowever, concurrent use with a glucocorticoid or corticotropin in the treatment of arthritis may provide additional therapeutic benefit and permit reduction of glucocorticoid or corticotropin dosage. /Nonsteroidal anti-inflammatory drugs/Increased monitoring of the response to an antihypertensive agent may be advisable when /oxaprozin/ is used concurrently because ... oxaprozin has been shown to reduce or reverse the effects of antihypertensives, possibly by inhibiting renal prostaglandin synthesis and/or by causing sodium and fluid retention.Nonsteroidal anti-inflammatory drugs may increase the hypoglycemic effect of these medications /oral antidiabetic agents or insulin/ because prostaglandins are directly involved in regulatory mechanisms of glucose metabolism and possibly because of displacement of the oral antidiabetics from serum proteinsdosage adjustments of the antidiabetic agent may be necessary... caution with concurrent use is recommended. /Nonsteroidal anti-inflammatory drugs/For more Interactions (Complete) data for OXAPROZIN (8 total), please visit the HSDB record page.
HepatotoxicityProspective studies show that up to 15% of patients taking oxaprozin chronically experience at least transient serum aminotransferase elevations. These usually resolve even with drug continuation. Marked aminotransferase elevations (>3 fold elevated) occur in approximately 1% of patients.Clinically apparent liver injury with jaundice from oxaprozin is rare, estimated to occur in 1 in 10,000 to 1 in 20,000 new users each year. Oxaprozin is rarely listed in large surveys of cases of drug induced liver injury perhaps because it is infrequently used in comparison to other NSAIDs. The usual clinical presentation of oxaprozin induced liver injury is an acute hepatitis-like picture arising 2 to 8 weeks after starting the medication (Case 1). The pattern of injury is typically hepatocellular, but mixed hepatocellular-cholestatic cases have been described. Symptoms may include allergic manifestations such as fever, rash, arthralgias and facial edema. Autoantibody formation is rare. Liver biopsy findings are hepatocellular necrosis with prominent periportal and lobular eosinophilic infiltration suggestive of drug induced acute hepatitis. Recovery may be delayed for several days, but is usually complete within one to two months. At least one case of acute liver failure attributed to oxaprozin has been published.Likelihood score: C (probable rare cause of clinically apparent liver injury).
Milk Concentrations... Oxaprozin is expected to be excreted in human milk based on its physical-chemical propertieshowever, the amount of oxaprozin excreted in breast milk has not been evaluated.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ No patient experienced either an accidental or intentional overdosage of daypro in the clinical trials of the drug. Symptoms following acute overdose with other NSAIDs are usually limited to lethargy, drowsiness, nausea, vomiting, and epigastric pain and are generally reversible with supportive care. Gastrointestinal bleeding and coma have occurred following NSAID overdose. Hypertension, acute renal failure, and respiratory depression are rare. Anaphylactoid reactions have been reported with therapeutic ingestion of NSAIDs, and may occur following an overdose./CASE REPORTS/ A 41-year-old white woman was admitted to the hospital with malaise, anorexia, and right upper quadrant pain. The patient was found to have severe jaundice with liver enzyme elevation. Laboratory test results for potential etiologies were negative, except for the use of oxaprozin for the preceding six weeks. Diagnosis of drug-induced hepatotoxicity was made by liver biopsy. The patient's symptoms resolved and liver enzymes normalized after oxaprozin was discontinued./CASE REPORTS/ A 56-year-old woman was admitted with fulminant hepatic failure. Work-up for potential etiologies was negative except for the use of oxaprozin for the preceding two months. Results of premortem liver biopsy were consistent with drug-induced hepatic injury similar to that previously reported with diclofenac. ... Elevations in hepatic transaminase concentrations and now fulminant hepatic failure have been shown to occur with oxaprozin, as previously seen with other nonsteroidal antiinflammatory drugs (NSAIDs). Transaminitis is a known adverse effect of NSAID use, but is usually mild and reversible with discontinuation of drug. Transaminitis may be more likely to occur in the elderly, in patients receiving concurrent potentially hepatotoxic medications, and possibly with the newer long-acting NSAIDs. The existence of fulminant hepatitis, although rare, supports the need for monitoring liver function enzymes during NSAID therapy./CASE REPORTS/ Pseudoporphyria is a diagnosis that is used when porphyria-like clinical lesions arise in the setting of normal porphyrin levels. This condition was first described in the 1960s and was initially related to the use of certain antibiotic drugs. In 1985, pseudoporphyria was first attributed to the use of nonsteroidal antiinflammatory drugs (NSAIDs). ... six patients diagnosed with pseudoporphyria /are described/ ... The patients ranged in age from 27 to 59 years and had a female:male predominance of 2:1. The offending NSAID was DayPro (oxaprozin) for three of the patients, Relafen (nabumetone) for two of the patients, and Aleve (naproxen) for one patient. For each patient, histology and immunofluorescence was either consistent with the diagnosis of porphyria cutanea tarda or nonspecific, while serum, stool, and urine porphyrins did not support that diagnosis. Withdrawal of the offending agent provided relief from the clinical symptoms for each patient. None of our patients were rechallenged with the putative offending drug. However, prolonged avoidance has provided a sustained remission from symptoms in all six patients. Pseudoporphyria is a relatively rarely reported condition. Clinical suspicion with appropriate laboratory and histopathologic findings help to make this diagnosis, and exclude true porphyrias. Rechallenge with the offending drug to produce symptom relapse has been proposed to be helpful in confirming this diagnosis of exclusion. Since all 6 patients with drug-induced pseudoporphyria experienced resolution of their symptoms after discontinuing the offending agent, we propose that this clinical correlation alone is sufficient to confirm this diagnosis. ...For more Human Toxicity Excerpts (Complete) data for OXAPROZIN (7 total), please visit the HSDB record page.
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)OxaprozinvLess-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ An increased incidence of hepatic adenomas and carcinomas occurred in 2 year studies in male CD mice, but not in female CD mice or in rats, given oxaprozin. The significance of this species-specific finding is not known./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Fetal malformations occurred infrequently in rabbits receiving 7.5 to 30 mg/kg per day (doses within the usual human dose range). However, no teratogenicity occurred in mice or rats receiving 50 to 200 mg/kg (225 to 600 mg/sq m) per day./GENOTOXICITY/ No mutagenic activity was demonstrated in the Ames test, forward mutation testing in yeast and chinese hamster ovary cells, DNA repair testing in Chinese hamster ovary cells, micronucleus testing in mouse bone marrow, chromosomal aberration testing in human lymphocytes, or cell transformation testing in mouse fibroblasts.
Populations at Special RiskThe pharmacokinetics of oxaprozin have been investigated in patients with renal insufficiency. Oxaprozin's renal clearance decreased proportionally with creatinine clearance (CrCl), but since only about 5% of oxaprozin dose is excreted unchanged in the urine, the decrease in total body clearance becomes clinically important only in those subjects with highly decreased CrCl. Oxaprozin is not significantly removed from the blood in patients undergoing hemodialysis or continuous ambulatory peritoneal dialysis (CAPD) due to its high protein binding. Oxaprozin plasma protein binding may decrease in patients with severe renal deficiency. Dosage adjustment may be necessary in patients with renal insufficiency.Approximately 95% of oxaprozin is metabolized by the liver. However, patients with well-compensated cirrhosis do not require reduced doses of oxaprozin as compared to patients with normal hepatic function. Nevertheless, caution should be observed in patients with severe hepatic dysfunction.
Environmental Water ConcentrationsWhile data specific to oxaprozin were not located(SRC, 2008), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2). Studies have indicated that several polar pharmaceutically active compounds can leach through soils(1).
Antidote and Emergency TreatmentThere is no antidote. Vitamin K may be used for patients with elevated prothrombin time caused by hypoprothrombinemia. /Nonsteroidal anti-inflammatory drugs/Emergency and supportive measures: Maintain on open airway and assist ventilation if necessary. Administer supplemental oxygen. Treat seizures, coma, and hypotension if the occur. Antacids may be used for mild GI upset. Replace fluid losses with intravenous crystalloid solutions. /Nonsteroidal anti-inflammatory drugs/Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. /Nonsteroidal anti-inflammatory drugs/Nonsteroidal anti-inflammatory drugs are highly protein bound and extensively metabolized. Thus, hemodialysis, peritoneal dialyses, and forced diuresis are not likely to be effective. /Nonsteroidal anti-inflammatory drugs/
Effects During Pregnancy and Lactation◉ Summary of Use during LactationBecause there is no published experience with oxaprozin during breastfeeding, other agents are preferred, especially while nursing a newborn or preterm infant.◉ Effects in Breastfed InfantsRelevant published information was not found as of the revision date.◉ Effects on Lactation and Breastmilk
Non-Human Toxicity ValuesLD50 Dog ip 200 mg/kgLD50 Dog iv 124 mg/kgLD50 Mouse ip 376 mg/kgLD50 Mouse iv 93 mg/kgFor more Non-Human Toxicity Values (Complete) data for OXAPROZIN (10 total), please visit the HSDB record page.
水環境危害等級（WGK）3
RTECS 番号RP6990000
毒性TDLo orl-rbt: 39 mg/kg (female 6-18D post):TER IYKEDH 15,250,84
税関コード29349990
危険文句（R）20/21/22-36/37/38
危険表示Xn,Xi
hazard_noteIrritant
安全措置（S）24/25-36/37/39-36-26
貯蔵分類11 - Combustible Solids
有害物質データ21256-18-8(Hazardous Substances Data)