이부프로펜

이부프로펜
이부프로펜 구조식 이미지
카스 번호:
15687-27-1
한글명:
이부프로펜
동의어(한글):
이부프로펜
상품명:
Ibuprofen
동의어(영문):
buluofen;Advil;Buprofen;rufen;Dolgit;Nurofen;2-(p-Isobutylphenyl)propionic acid;[A-METHYL-4-ISOBUTYL]PHENYLACETIC ACID;ALPHA-METHYL-4-(ISOBUTYL)PHENYLACETIC ACID;[2R,(-)]-2-[4-(2-Methylpropyl)phenyl]propanoic acid
CBNumber:
CB4336930
분자식:
C13H18O2
포뮬러 무게:
206.28
MOL 파일:
15687-27-1.mol

이부프로펜 속성

녹는점
77-78 °C
끓는 점
157 °C (4 mmHg)
알파
[α]D20 -1~+1°(c=1,C2H5OH)
밀도
1.0364 (rough estimate)
굴절률
1.5500 (estimate)
인화점
9℃
저장 조건
2-8°C
용해도
물에는 거의 녹지 않으며, 아세톤, 메탄올, 염화메틸렌에는 잘 녹습니다. 알칼리 수산화물과 탄산염의 묽은 용액에 용해됩니다.
산도 계수 (pKa)
pKa 4.45± 0.04(H2O,t = 25±0.5,I=0.15(KCl))(Approximate)
물리적 상태
결정성 분말
색상
흰색에서 황백색까지
수용성
불용성
Merck
14,4881
BCS Class
2
안정성
안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
InChIKey
HEFNNWSXXWATRW-UHFFFAOYSA-N
LogP
3.970
CAS 데이터베이스
15687-27-1(CAS DataBase Reference)
NIST
Ibuprofen(15687-27-1)
EPA
Benzeneacetic acid, .alpha.-methyl-4-(2-methylpropyl)- (15687-27-1)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn
위험 카페고리 넘버 22-63-51/53-39/23/24/25-23/24/25-11
안전지침서 36-61-36/37-45-16-7
HS 번호 29163920
유해 물질 데이터 15687-27-1(Hazardous Substances Data)
독성 LD50 in male mice, rats (mg/kg): 495, 626 i.p.; 1255, 1050 orally (Orzalesi)
기존화학 물질 KE-21458
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 GHS hazard pictograms P264, P270, P301+P312, P330, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고 GHS hazard pictograms
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P301+P312 삼켜서 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
NFPA 704
1
2 0

이부프로펜 MSDS


2-(4-Isobutylphenyl)-propionic acid

이부프로펜 C화학적 특성, 용도, 생산

화학적 성질

Colourless, Crystalline Solid

역사

Ibuprofen was developed while searching for an alternative pain reliever to aspirin in the 1950s. It and related compounds were synthesized in 1961 by Stewart Adams, John Nicholson, and Colin Burrows who were working for the Boots Pure Drug Company in Great Britain. Adams and Nicholson filed for a British patent on ibuprofen in 1962 and obtained the patent in 1964; subsequent patents were obtained in the United States. The patent of Adams and Nicholson was for the invention of phenylalkane derivatives of the form shown in Figure 49.1, where R1 could be various alkyl groups, R2 was hydrogen or methyl, and X was COOH or COOR, with R being alkyl or aminoalkyl groups. The first clinical trials for ibuprofen were started in 1966. Ibuprofen was introduced under the trade name Brufen in 1969 in Great Britain. It was introduced in the United States in 1974. Ibuprofen was initially off ered by prescription, but it became available in over-the-counter medications in the 1980s.

용도

A common goal in the development of pain and inflammation medicines has been the creation of compounds that have the ability to treat inflammation, fever, and pain without disrupting other physiological functions. General pain relievers, such as aspirin and ibuprofen, inhibit both COX-1 and COX-2. A medication's specificaction toward COX-1 versus COX-2 determines the potential for adverse side effects. Medications with greater specificity toward COX-1 will have greater potential for producing adverse side effects. By deactivating COX-1, nonselective pain relievers increase the chance of undesirable side effects, especially digestive problems such as stomach ulcers and gastrointestinal bleeding. COX-2 inhibitors, such as Vioxx and Celebrex, selectively deactivate COX-2 and do not aff ect COX-1 at prescribed dosages. COX-2 inhibitors are widely prescribed for arthritis and pain relief. In 2004, the Food and Drug Administration (FDA) announced that an increased risk of heart attack and stroke was associated with certain COX-2 inhibitors. This led to warning labels and voluntary removal of products from the market by drug producers; for example, Merck took Vioxx off the market in 2004. Although ibuprofen inhibits both COX-1 and COX-2, it has several times the specificity toward COX-2 compared to aspirin, producing fewer gastrointestinal side effects.

Indications

Ibuprofen (Advil, Motrin) is used as an analgesic and antipyretic as well as a treatment for rheumatoid arthritis and degenerative joint disease. The most frequently observed side effects are nausea, heartburn, epigastric pain, rash, and dizziness. Incidence of GI side effects is lower than with indomethacin.Visual changes and cross-sensitivity to aspirin have been reported. Ibuprofen inhibits COX-1 and COX-2 about equally. It decreases platelet aggregation, but the duration is shorter and the effect quantitatively lower than with aspirin. Ibuprofen prolongs bleeding times toward high normal value and should be used with caution in patients who have coagulation deficits or are receiving anticoagulant therapy.

정의

ChEBI: A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(2-methylpropyl)phenyl group.

World Health Organization (WHO)

Ibuprofen, a non-steroidal anti-inflammatory agent, was introduced in 1969. It was approved for sale without prescription in packages containing no more than 400 mg, in the United Kingdom in 1983. This action was followed by the USA, Canada and several European countries. Since this time reports of suspected adverse effects have increased. Most of these relate to gastrointestinal disturbances, hypersensitivity reactions but aseptic meningitis, skin rashes and renal damage have been recorded.

일반 설명

Ibuprofen, 2-(4-isobutylphenyl)propionic acid (Motrin,Advil, Nuprin), was introduced into clinical practice followingextensive clinical trials. It appears to have comparableefficacy to aspirin in the treatment of RA, but with a lowerincidence of side effects. It has also been approved for usein the treatment of primary dysmenorrhea, which is thoughtto be caused by an excessive concentration of PGs and endoperoxides. However, a recent study indicates that concurrentuse of ibuprofen and aspirin may actually interferewith the cardioprotective effects of aspirin, at least in patientswith established cardiovascular disease. This is becauseibuprofen can reversibly bind to the platelet COX-1isozymes, thereby blocking aspirin’s ability to inhibit TXA2synthesis in platelets.

Pharmacokinetics

Ibuprofen is rapidly absorbed on oral administration, with peak plasma levels being generally attained within 2 hours and a duration of action of less than 6 hours. As with most of these acidic NSAIDs, ibuprofen (pKa = 4.4) is extensively bound to plasma proteins (99%) and will interact with other acidic drugs that are protein bound.

Clinical Use

Ibuprofen is indicated for the relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis, the relief of mild to moderate pain, the reduction of fever, and the treatment of dysmenorrhea.

환경귀착

Ibuprofen has a high water solubility and low volatility, which suggest a high mobility in the aquatic environment. This makes it a commonly detected chemical of the pharmaceutical and personal care products (PPCPs) in the environment. It is not as persistent, however, as many other chemicals. Ibuprofen undergoes photodegradation with exposure to direct and indirect sunlight, although degradation products can have effects on aquatic environments.

신진 대사

Metabolism occurs rapidly, and the drug is nearly completely excreted in the urine as unchanged drug and oxidative metabolites within 24 hours following administration. Metabolism by CYP2C9 (90%) and CYP2C19 (10%) involves primarily ω-, and ω1-, and ω2-oxidation of the p-isobutyl side chain, followed by alcohol oxidation of the primary alcohol resulting from ω–oxidation to the corresponding carboxylic acid. All metabolites are inactive. When ibuprofen is administered as the individual enantiomers, the major metabolite isolated is the S-(+)-enantiomer whatever the configuration of the starting enantiomer. Interestingly, the R-(–)-enantiomer is inverted to the S-(+)-enantiomer in vivo via an acetyl–coenzyme A intermediate, accounting for the observation that the two enantiomers are bioequivalent in vivo. This is a metabolic phenomenon that also has been observed for other arylpropionic acids, such as ketoprofen, benoxaprofen, fenoprofen, and naproxen.

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