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HCID 4075생성일: 2026년 10월 26일

5-아미노셀릭일 산

메살라민 · 5-아미노셀릭일산 · MESALAZINE · MESALAMINE · 5-ASA · 5-AMINO-2-HYDROXYBENZOIC ACID · Asacol · rowasa

https://huagongshe.com/ko/chemical/4075

5-아미노셀릭일 산 분자 구조식

식별자 및 물리적 특성

CAS No.89-57-6
분자식C7H7NO3
평균 분자량153.14 g/mol
단동위원소 질량153.04259308 g/mol
SMILESNc1ccc(O)c(C(=O)O)c1
InChIKeyKBOPZPXVLCULAV-UHFFFAOYSA-N
PubChem CID4075
ChEMBLCHEMBL704
ChEBICHEBI:6775
EC No.201-919-1
DTXSIDDTXSID5024506
현지명5-아미노셀릭일 산

화학 및 물리적 성질

XLogP1.3
극성 표면적83.6
수소 결합 공여자 수3
수소 결합 수용자 수4
회전 가능 결합 수1
무거운 원자 수11
형식 전하0
복잡도160
물질 분류Other Uses -> Pharmaceuticals
의약품Pharmaceuticals -> Metabolite of SulfasalazinePharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP(분배 계수)1.20.48
Color/FormWhite to pinkish crystals
용해도less than 1 mg/mL at 70 °F (NTP, 1992)Slightly soluble in water, alcoholmore soluble in hot watersoluble in hydrochloric acidInsoluble in ethanol1.22e+01 g/L디메틸설폭사이드에 용해됩니다.
Human DrugsBreast FeedingLactationMilk, HumanGastrointestinal AgentsAnti-Inflammatory Agents, Non-SteroidalFDA approved drugs -> Active ingredientPharmaceuticalsAnti-inflammatory medicines
녹는점536 °F (decomposes) (NTP, 1992)260-280 °C283 °C275-280 °C (dec.) (lit.)
증기압0.00000006 [mmHg]0Pa at 25℃
Physical Description5-aminosalicylic acid appears as odorless white to pinkish crystals or purplish-tan powder. Aqueous solutions acidic (pH approximately 4.1 at 0.8 mg/L water). (NTP, 1992)White to pinkish solid[Merck Index] Purplish tan solid[NTP] Powder[Alfa Aesar MSDS]
Stability/Shelf LifeMesalamine is unstable in the presence of water and light, since oxidation and, to a lesser extent, light-catalyzed degradation of the drug occur.
Dissociation ConstantsMesalamine's production and use in the manufacture of light-sensitive paper, azo and sulfur dyes and as a gastrointestinal medication may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 6.1X10-8 mm Hg at 25 °C indicates mesalamine will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase mesalamine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is estimated to be 18 hrs. Particulate-phase mesalamine will be removed from the atmosphere by wet or dry deposition. Mesalamine does contain chromophores that absorb at wavelengths >290 nm and therefore may be expected to be susceptible to direct photolysis by sunlight. If released to soil, mesalamine is expected to have very high mobility based upon an estimated Koc of 10. Estimated pKa values of 2.09, 5.26 and 13.64 indicate that this compound will dissociate to the zwitterion form in the environment. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 5.0X10-12 atm-cu m/mole. Mesalamine is considered completely biodegradable under anaerobic conditions as was indicated by 95.6% methane production following acclimation. If released into water, mesalamine is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to mesalamine may occur through inhalation and dermal contact with this compound at workplaces where mesalamine is produced or used. Use data indicate that the general population may be exposed to mesalamine via dermal contact with products containing this compound as well as via ingestion following administration of drugs containing mesalamine, a gastrointestinal anti-inflammatory. (SRC)
Collision Cross Section127.8 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID5024506]134.7 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]122.58 Ų [M+H-H2O]+ [CCS Type: TW
끓는 점276.03°C (rough estimate)
밀도1.3585 (rough estimate)
굴절률1.5500 (estimate)
인화점279-281°C
저장 조건2-8°C
pKa(산도 계수)2.74, 5.84(at 25℃)
물리적 상태플레이크 크리스탈
색상미색에서 회색까지
pH4.0-4.1 (0.8g/l, H2O, 20℃)
용해도21°C에서 <0.1g/100mL
Merck14,5904
BRN2090421
헨리 상수2.0×106 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class4
안정성안정적인. 산, 산 무수물, 산 염화물, 클로로포르메이트, 강산화제와 호환되지 않습니다.
주요 응용세제, 염색약, 대장암 예방, 염증성 장 질환 치료, 자가면역 질환, 위장관 염증, 케모카인 매개 질환, 점막 조직 질환, 수면 장애, 직장항문통증, 궤양성 대장염
InChI1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
InChIKeyKBOPZPXVLCULAV-UHFFFAOYSA-N
SMILESNc1ccc(O)c(c1)C(O)=O
LogP(분배 계수)0.98 at 25℃
NISTMesalamine(89-57-6)
EPABenzoic acid, 5-amino-2-hydroxy- (89-57-6)

화학적 성질

Off-White to pink crystals, melting point about 280 ℃ (decomposition). Soluble in hydrochloric acid, slightly soluble in hot water, and slightly bath in cold water or ethanol. In the manufacture of light-sensitive paper, azo and sulfur dyes.

안전 및 규제

GHS 분류This chemical does not meet GHS hazard criteria for 0.5% (1 of 195) of reports.WarningH315 (81.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 195 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보Status: Active Update: 01-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5887Mesalazine: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보IMAP assessments - Benzoic acid, 5-amino-2-hydroxy-: Environment tier I assessment
화재 위험Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
건강 유해성SYMPTOMS: Symptoms of exposure to this compound include acute intolerance syndrome characterized by cramping, acute abdominal pain and discomfort, and bloody diarrhea. It may also cause headache, rash, gas (flatulence), nausea, flu, tiredness, weakness, malaise, fatigue, cold, sore throat, leg pain, joint pain, dizziness, bloating, back pain, hemorrhoids, itching, rectal pain, constipation, hair loss, peripheral edema, urinary burning, rectal soreness and burning, asthenia and insomnia. Other symptoms include fever, gastrointestinal problems, anorexia, epigastric pain, skin eruptions of various types, agranulocytosis, leukopenia, eosinophilia, lymphocytosis, atypical mononucleosis syndrome, thrombocytopenia and acute hemolytic anemia. Symptoms of exposure to a related compound include pruritus, erythematous macular or bullous eruptions, acidosis, hypokalemia, crystalluria, vomiting, hepatic necrosis, leukocytosis, laryngeal edema, methemoglobinemia and thyroid suppression. Other symptoms include allergic reactions, gastrointestinal irritation and prolonged prothrombin times.
유해성 요약Cardiac effects, renal toxicity, and pulmonary toxicity have been reported in patients taking this drugRenal toxicity observed in experimental animals[HSDB] Occupational asthma confirmed by broncho-provocation testing in a pharmaceutical worker[Malo] No developmental toxicity observed in rats dosed up to 400 mg/kg/day during gestationThe preponderance of evidence suggests normal pregnancy outcomes in humans from therapeutic use throughout pregnancyDoes not appear to have the same effects on male fertility as sulfasalazine (abnormal semen parameters and infertility)[REPROTOX] May cause photosensitivity, cholestatic jaundice, diarrhea, dermatitis, agranulocytosis, muscle weakness, acute tubular necrosis, changes in structure or function of endocrine pancreas, focal lung fibrosis, and eosinophilia following oral administration in humans[RTECS] A skin and strong eye irritant[Alfa Aesar MSDS]
FDA 요건The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl mesalamine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
반응성 그룹Acids, Carboxylic
Reactivity Profile5-AMINOSALICYLIC ACID is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers. (NTP, 1992)
Air and Water ReactionsSensitive to moisture. Water insoluble.
Hazard Classes and CategoriesSkin Irrit. 2 (81.5%)
소화Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
응급 처치EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
보관 조건Commercially available oral mesalamine delayed-release tablets should be stored at a controlled room temperature of 20-25 °C, while the commercially available oral extended-release capsules should be stored at 25 °C but may be exposed to temperatures ranging from 15-30 °C.
비화재 누출 대응SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
처리 방법SRP: 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.
Personal Protective Equipment (PPE)RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
상호 작용Omeprazole may increase gastrointestinal pHconcurrent use may result in an increase in the absorption of mesalamine.Acidification of the colonic lumen by lactulose may impair release of mesalamine from delayed- or extended-release formulations.
HepatotoxicityIn large registration trials of various forms of mesalamine, serum enzyme elevations were no more common with the products than with placebo therapy and were less common than with sulfasalazine. In these large studies, there were no reported instances of clinically apparent liver injury. Since approval and wide scale usage, however, there have been isolated reports of acute and chronic liver injury with jaundice attributed to mesalamine therapy. Clinically apparent liver injury is estimated to occur at an incidence of 3.2 cases per million prescriptions. Several patterns of injury have been reported, including asymptomatic and mild elevations in serum ALT levels, mild hepatitis accompanying a hypersensitivity reaction within a few days or weeks of starting (sometimes following a similar reaction to sulfasalazine), drug fever with accompanying serum enzyme elevations or mild hepatitis, and more typically, idiosyncratic cholestatic or hepatocellular liver injury (Cases 1 and 2), which typically arises after 1 to 6 months of treatment and is not accompanied by signs of hypersensitivity (rash, fever, eosinophilia). Most cases of liver injury with jaundice have been mild-to-moderate in severity and resolve rapidly upon stopping. In cases with hypersensitivity reactions, corticosteroid therapy is often used and appears to speed recovery. There have been no convincing reports of fatal acute liver injury, chronic hepatitis or vanishing bile duct syndrome attributable to mesalamine.
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that mesalamine is expected to have very high mobility in soil(SRC). Volatilization of mesalamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.0X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Mesalamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.1X10-8 mm Hg(SRC), determined from a fragment constant method(4). Mesalamine is considered completely biodegradable under anaerobic conditions, as was indicated by 95.6% methane production following acclimation(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that mesalamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.0X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.98(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Mesalamine is considered completely biodegradable under anaerobic conditions, as was indicated by 95.6% methane production following acclimation(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mesalamine, which has an estimated vapor pressure of 6.1X10-8 mm Hg at tt °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase mesalamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 18 hrs(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Mesalamine does contain chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(4).
유해 작용Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.Patients tolerate most 5-ASA formulations. However, adverse effects may include nausea, gastrointestinal upset, abdominal pain, headaches, nasopharyngitis, rash, arthralgias, agranulocytosis, aplastic anemia, myalgias, bone marrow suppression, oligospermia, hematuria, and cholestatic hepatitis. Renal impairment, including interstitial nephritis, nephrotic syndrome, and renal failure, can be seen and must be carefully monitored before initiating treatment and during treatment.
Milk ConcentrationsFollowing oral administration, low concentrations of mesalamine and higher concentrations of its metabolite, N-acetyl-5-aminosalicylic acid, have been detected in human breast milk. It is not known whether mesalamine or its metabolites are distributed into milk in humans following rectal administration.
독성 요약Signs and Symptoms of Overdose
Effluent ConcentrationsMesalamine was detected not quantified in municipal landfill waste(1). Mesalamine was not detected in munitions wastewater from a former ammunition plant in Stadtallendorf, Germany as part of study of nitroaromatic compounds in munition wastewater(2).
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of mesalamine can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that mesalamine is expected to have very high mobility in soil. A predicted Kd value of 1.37 calculated for sludge samples in the UK, suggests that adsorption to sludge is low(3). Estimated pKa values of 2.09, 5.26 and 13.64(4) indicate that this compound will dissociate to the zwitterion form in the environment(SRC).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Peripheral or generalized edema has been reported in about 1% of patients receiving the drug rectally. Pericarditis, manifested as chest pain, fever, and/or dyspnea, has occurred rarely in patients receiving rectal mesalamine. Evidence of pericarditis occurred within several days to weeks after initiation of rectal mesalamine therapy and resolved following discontinuance of the drug. In most patients, pericarditis recurred with mesalamine or olsalazine rechallenge. However, the risk of cross-sensitivity with sulfasalazine or other 5-aminosalicylic acid (mesalamine) prodrugs (e.g., olsalazine) currently is not known. Other evidence of pericarditis included pericardial friction rub, radiographic evidence of pleural effusion and/or cardiac enlargement with possible tamponade, echocardiographic evidence of pericardial effusion, and/or ECG abnormalities (e.g., ST- and T-wave changes and inferior Q waves suggestive of myocardial infarction, ST-segment depression). Although there appears to be an association between mesalamine use and the development of pericarditis in these patients, the mechanism is unknown and pericarditis also has been reported in patients with inflammatory bowel disease who were not receiving mesalamine. In some of these latter patients, pericarditis developed during sulfasalazine therapy and therefore, may have been secondary to the drug rather than to the underlying condition. The possibility of pericarditis should be considered in any patient who develops chest pain or dyspnea during mesalamine therapy. Discontinuance of therapy with the drug may be warranted in some such patients, while mesalamine rechallenge may be performed under careful clinical observation if there is a continued therapeutic need for the drug./SIGNS AND SYMPTOMS/ Ecchymosis, thrombocythemia, and thrombocytopenia have been reported in less than 1% of patients receiving oral mesalamine extended-release capsuleshowever, a causal relationship to the drug of these adverse effects has not been established. Adverse hematologic effects associated with preparations containing or being metabolized to mesalamine and reported in clinical studies, medical literature, or postmarketing reports include agranulocytosis, aplastic anemia, eosinophilia, leukopenia, anemia, and lymphadenopathy. In at least one patient receiving mesalamine rectal suppositories (500 mg every evening) for 7 months, leukopenia and thrombocytopenia occurred./CASE REPORTS/ We describe a case of a 25-yr-old woman with ulcerative colitis who developed marked thrombocytopenia during treatment and upon rechallenge with oral mesalamine. In contrast to its parent drug, sulfasalazine, which has often been reported to cause serious blood disorders, particularly agranulocytosis, mesalamine has rately been implicated as a cause of serious blood disorders. Although previous cases of hematological toxicity have been described in patients taking mesalamine, none of these patients were rechallenged in an effort to prove causality between 5-aminosalicyclic acid and the hematological abnormality as well as outrule the possible "autoimmune" contribution of inflammatory bowel disease to the hematological toxicity of these agents. This report demonstrates that mesalamine has the potential, like sulphasalazine, to cause marked thrombocytopenia in an idiosyncratic fashion. .../CASE REPORTS/ ... Two cases of biopsy-confirmed interstitial nephritis in patients being treated with 5-aminosalicylic acid /are reported/. Both had a trial of steroid therapy. One patient had partial recovery of renal function but the other patient was in chronic renal failure and likely was approaching the need for dialysis. Interstitial nephritis is an under-recognized complication of 5-aminosalicylic acid therapy. Early identification and withdrawal of this drug can lead to a partial or complete reversal of renal dysfunction.For more Human Toxicity Excerpts (Complete) data for MESALAMINE (18 total), please visit the HSDB record page.
Artificial Pollution SourcesMesalamine's production and use in the manufacture of light-sensitive paper, azo and sulfur dyes and as a gastrointestinal medication(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationANAEROBIC: Mesalamine, present at 250 mg/L, produced 95.6% methane following a lag phase of 65 days using 2-nitrophenol-adapted sludge in batch assays conducted in 120 ml glass serum flasks and is considered completely biodegradable under anaerobic conditions(1). Mesalamine was completely degraded by a mesophilic sludge in 30 days (mesophilic granular sludge from a full-scale UASB reactor treating chemical industry wastewater of Shell Nederland Chemie at Moerdijk, The Netherlands, VSS concn - 25.5 g/Lspecific aceticlastic activity - 0.3 COD/L/g VSS, 30 °C) following a 20-day lag period(2). It was also completely degraded using a mesophilic floccular sludge from a lab-scale UASB reactor treating cattle manure wastewater - VSS concn 20.5 g/Lspecific aceticlastic activity - 0.05 to 0.06 g COD/L/g VSS, so °Chowever, specific incubation and acclimation details were not provided(2). Degradation using a thermophilic sludge was 100% in 48 days following a 34 day lag period - full-scale CSTR reactor digesting primary and secondary sludges at Kur'yanovskaya municipal aeration station, Moscow, Russia - VSS concn 20.5 g/Lspecific aceticlastic activity 0.1 g COD/L g VSS, 55 °C(2).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)MesalaminevLess-DILI-concern7Adverse reactionsDOI:10.1016/j.drudis.2016.02.015
수질 위해 등급(WGK)2
TSCA 등재 상태TSCA listed
RTECS 번호VO1400000
독성LD50 orally in Rabbit: 2800 mg/kg LD50 dermal Rat > 5000 mg/kg
관세 코드29225000
위험 문구(R)36/37/38-52/53
위험 표시Xi
안전 문구(S)26-36-24/25-61-37/39
위험 등급IRRITANTEye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
기존화학 물질KE-01390
F 고인화성물질8-10-23
자연 발화 온도280 °C
저장 분류11 - Combustible Solids
유해 물질 데이터89-57-6(Hazardous Substances Data)

용도

개요

5-Aminosalicylic acid (5-ASA), also known as mesalazine or mesalamine, is a metabolite and potential pharmacologically active component of sulphasalazine, a drug used in the treatment of Crohn’s disease and ulcerative colitis. However, the mechanism by which this drug works has not been established. In whole blood assays, 5-ASA proves to be a weak, non-selective inhibitor of both COX-1 and COX-2 with IC50 values of 410 and 61 μM, respectively. In ionophore-stimulated colonic mucosal cells, 1 mM 5-ASA does not inhibit prostaglandin E2 (PGE2) production, but does reduce leukotriene B4 (LTB4) synthesis approx. 50%. In ionophore-stimulated human leukocytes, 400 μM 5-ASA reduces LTB4 production approximately 20%. 5-ASA does not inhibit 15-hydroxy PGDH at concentrations up to 50 μM.

용도

5-Aminosalicylic acid is used in the preparation of gastrointestinal anti-inflammatory agents. It is a metabolite of sulfasalazine. It acts as a drug involved in the treatment of Crohn's disease and ulcerative colitis. Further, it is used to make dyes and light-sensitive papers.

일반 설명

Odorless white to pinkish crystals or purplish-tan powder. Aqueous solutions acidic (pH approximately 4.1 at 0.8 mg/L water) .

제조 및 합성 방법

제조 방법

Preparation by reduction of m-nitrobenzoic acid with Zn dust and HCl.