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이부프로펜

이부프로펜
이부프로펜 구조식 이미지
카스 번호:
15687-27-1
한글명:
이부프로펜
동의어(한글):
이부프로펜
상품명:
Ibuprofen
동의어(영문):
Adran;Advil;IP-82;rufen;rufin;Andran;Bluton;Brufen;Dolgin;Dolgit
CBNumber:
CB4336930
분자식:
C13H18O2
포뮬러 무게:
206.28
MOL 파일:
15687-27-1.mol

이부프로펜 속성

녹는점
77-78 °C
알파
[α]D20 -1~+1°(c=1,C2H5OH)
끓는 점
157 °C (4 mmHg)
밀도
1.0364 (rough estimate)
굴절률
1.5500 (estimate)
인화점
9℃
저장 조건
2-8°C
용해도
Practically insoluble in water, freely soluble in acetone, in methanol and in methylene chloride. It dissolves in dilute solutions of alkali hydroxides and carbonates.
산도 계수 (pKa)
pKa 4.45± 0.04(H2O,t = 25±0.5,I=0.15(KCl))(Approximate)
물리적 상태
Crystalline Powder
색상
white to off-white
수용성
insoluble
Merck
14,4881
안정성
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
HEFNNWSXXWATRW-UHFFFAOYSA-N
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):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
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.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P311 의료기관(의사)의 진찰을 받으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

이부프로펜 MSDS


2-(4-Isobutylphenyl)-propionic acid

이부프로펜 C화학적 특성, 용도, 생산

개요

Ibuprofen is a white, crystalline anti-infl ammatory drug used in numerous medications. It is the active ingredient marketed under various trade names including Advil, Motrin, and Nurofen. Ibuprofen is a nonsteroidal anti-infl ammatory drug (NSAID) used as a pain reliever (analgesic), fever reducer (antipyretic), and inflammation reducer. Infl ammation is a general physiological response to tissue damage characterized by swelling, pain, and heat.
Ibuprofen works by inhibiting the enzyme cyclooxygenase (COX), which in turn interferes with the synthesis of prostaglandins. COX exists as several coenzyme forms that are similar in structure: COX-1, COX-2, COX-3; ibuprofen is a nonselective inhibitor of both COX-1 and COX-2. COX-1 is continually produced in mammalian cells throughout the body in response to physiological stimuli. It is responsible for the production of prostaglandins, which get their name because it was originally believed they were synthesized in the prostate gland. In fact, prostaglandins are synthesized throughout the body and act like hormones by stimulating action in target cells. Prostaglandins, which are fatty acid compounds consisting of a 20-carbon chain including a 5 carbon ring, are involved in numerous physiological processes including renal function, blood clotting, and stomach mucus production. COX-2 is synthesized only in specifi c parts of the body (kidneys, brain, trachea) as needed and is therefore called an induced enzyme. COX-2 produces prostaglandins in response to tissue damage and infl ammation. Infl ammatory prostaglandins produce swelling, pain, and fever.

화학적 성질

Colourless, Crystalline Solid

Originator

Brufen,Boots,UK,1969

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.

용도

A selective cyclooxygenase inhibitor (IC50=14.9uM). Inhibits PGH synthase-1 and PGH synthase-2 with comparable potency

용도

Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory.

용도

Antibiotic

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.

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.

Manufacturing Process

Isobutylbenzene is first acetylated to give isobutylacetophenone. 4-ibutylacetophenone (40 g), sulfur (11 g) and morpholine (30 ml) were refluxed for 16 hours, cooled, acetic acid (170 ml) and concentrated hydrochloric acid (280 ml) were added and the mixture was refluxed for a further 7 hours. The mixture was concentrated in vacuo to remove acetic acid and the concentrate was diluted with water.
The oil which separated was isolated with ether, the ethereal solution was extracted with aqueous sodium carbonate and this extract was acidified with hydrochloric acid. The oil was isolated with ether, evaporated to dryness and the residue was esterified by refluxing with ethanol (100 ml) and concentrated sulfuric acid (3 ml) for 5 hours. The excess alcohol was distilled off, the residue was diluted with water, and the oil which separated was isolated with ether. The ethereal solution was washed with sodium carbonate solution; then with water and was dried. The ether was evaporated off and the oil was distilled to give ethyl 4-i-butylphenylacetate.
Sodium ethoxide from sodium (3.67 g) in absolute alcohol (64 ml) was added over 20 minutes with stirring to a mixture of ethyl 4-i-butylphenylacetate (28.14 g) and ethyl carbonate (102 ml) at 100°C. The reaction flask was fitted with a Fenske column through which alcohol and then ethyl carbonate distilled. After 1 hour when the still head reached 124°C heating was discontinued. Glacial acetic acid (12 ml) and water (50 ml) was added to the stirred ice-cooled mixture and the ester isolated in ether, washed with sodium carbonate solution, water and distilled to give ethyl 4-i-butylphenylmalonate.
Ethyl 4-i-butylphenylmalonate (27.53 g) in absolute alcohol (25 ml) was added with stirring to a solution of sodium ethoxide From sodium (2.17 g) in absolute alcohol (75 ml). Ethyl iodide (15 ml) was added and the mixture refluxed for 2% hours, the alcohol distilled and the residue diluted with water, extracted with ether, washed with sodium bisulfite, water, and evaporated to dryness.
The residual oil was stirred and refluxed with sodium hydroxide (75 ml of 5 N), water (45 ml) and 95% ethanol (120 ml). Within a few minutes a sodium salt separated and after 1 hour the solid was collected, washed with ethanol, dissolved in hot water and acidified with dilute hydrochloric acid to give the methyl malonic acid which was collected and dried in vacuo MP 177° to 180°C (dec.).
The malonic acid (9 g) was heated to 210° to 220°C in an oil bath for 20 minutes until decarboxylation had ceased. The propionic acid was cooled and recrystallized from light petroleum (BP 60° to 80°C). Two further recrystallizations from the same solvent gave colorless prisms of 2-(4- isobutylphenyl)propionicacid MP 75° to 77.5°C. (The procedure was reported in US Patent 3,228,831.)

상표명

Abbifen;Abuprohm;Abu-tab;Aches-n-pain;Acril;Actifen;Actiprofen;Actren;Addaprin;Advil 200 mg;Advil cold & sinus;Agisan;Aktren;Aldospray;Algiasdin;Algifor;Algisan;Algofer;Altior;Amersol;Anadin ibuprofen;Analgesico;Analgil;Analgyl;Anco;Antalgil;Antiflam;Antiruggen;Apsifen;Artofen;Artren;Artril;Artrofen;Bayer select ibuprofen pain reliever;Benflogin;Betagesic;Betaprofen;Brofen 200 mg;Brofen 400 mg;Brufert;Brufort;Buborone;Bufedon;Bufigen;Burana;Cesra;Children's advil;Children's motrin;Codafen continus;Contraneural;Contrneural;Cuisialigil;Cunil;Cuprofen;Dansida;Dentigoa forte;Dignoflex;Dimetap sinus;Dimidon;Dismenodl n;Dolgirit;Dolocyl;Dolo-dolgit;Dologesic;Dolo-neos;Dolo-puren;Doltibil;Dolven;Donjust-b;Dorival;Dristan sinus;Duradyne;Dura-ibu;Duralbuprofen;Dysdolen;Ecoprofen;Ediluna;Esprenit;Excedrin ib;Exidol;Exneural;Femafen;Femapirin;Femidol;Fenalgic;Fenlong;Genpril;Guildprofen;Halprin;Ibenon;Ibol;Ibosure;Ibruthalal;Ibu-attritin;Ibucasen;Ibu-cream;Ibufac;Ibufen tablets;Ibufen-l;Ibufug;Ibugel;Ibugesic;Ibuhexal;Ibular;Ibulav;Ibuleve;Ibulgan;Ibumetin;Ibuphlogont;Ibupirac;Ibuprin;Ibuprofen 200;Ibuprohm;Ibu-slow;Ibusure;Ibu-tab;Ibutad;Ibutid;Ibutop;Ibuvivimed;Ibux;Imben;Inabrin;Incefal;Inflam;Inoven;Inza;Iproben;Irfen;Isdol;Isisfen;Junifen;Kalma;Kos;Lacondan;Librofem;Librofen;Lidifen;Lisi-budol;Mediprofen;Melfen;Menado ibuprofen usp;Midol 200 advanced pain formula;Midol ib;Migrafen;Minadol;Moment;Motrin ib;Narfen;Neobrofen;Neobrufen;Nerofen;Niapren;Novaprin;Novogent;Novoprofen;Nu-ibuprofen;Optifen;Opturem;Pacifene;Padudent;Paxofen;Pfeil;Phor pain;Posodolor;Prontalgin;Recudik;Relcofen;Rheufen;Rimafen;Saleto-600;Seclodin;Sedaspray;Serviprofen;Sine-aid ib;Solufen;Spedifen;Stadasan;Superior pain medicine;Supreme pain medicine;Supren;Suspren;Tabalon;Tempil;Tendar;Trauma-dolgit;Ultraprin;Valprin.

Therapeutic Function

Antiinflammatory

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.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 31, p. 3139, 1983 DOI: 10.1248/cpb.31.3139
The Journal of Organic Chemistry, 52, p. 287, 1987 DOI: 10.1021/jo00378a027

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.

Chemical Synthesis

Ibuprofen, 2-(4-iso-butylphenyl)propionic acid (3.2.23), can be synthesized by various methods [88–98]. The simplest way to synthesize ibuprofen is by the acylation of iso-butylbenzol by acetyl chloride. The resulting iso-butylbenzophenone (3.2.21) is reacted with sodium cyanide, giving oxynitrile (3.2.22), which upon reaction with hydroiodic acid in the presence of phosphorus is converted into 2-(4-iso-butylphenyl)propionic acid (3.2.23), which subsequently undergoes phases of dehydration, reduction, and hydrolysis.
CB4336930-1.jpg
Another way to synthesize ibuprofen consists of the chloromethylation of iso-butylbenzene, giving 4-iso-butylbenzylchloride (3.2.24). This product is reacted with sodium cyanide, making 4-iso-butylbenzyl cyanide (3.2.25), which is alkylated in the presence of sodium amide by methyl iodide into 2-(4-iso-butylbenzyl)propionitrile (3.2.26). Hydrolysis of the resulting product in the presence of a base produces ibuprofen (3.2.23).
CB4336930-2.jpg

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.

Toxicity evaluation

The mechanisms of ibuprofen-induced toxicity have not been clearly defined. Acute renal failure is postulated to result from decreased production of intrarenal prostaglandins via inhibition of the cyclooxygenase pathway. In turn, this will decrease the renal blood flow and glomerular filtration rate. Ibuprofen also interferes with prostaglandin synthesis in the gastrointestinal system, which can contribute to its irritating effect on the mucosa of the gastrointestinal tract. Anion gap metabolic acidosis is likely caused by elevated lactate due to hypotension and hypoperfusion and also due to ibuprofen and its metabolites, which are all weak acids. Seizures have been reported in large ibuprofen overdoses, but the mechanism of toxicity remains unknown. In massive overdoses, ibuprofen is thought to have cellular toxicity disrupting mitochondrial energy processes causing the formation of lactic acid.

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