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4-Aminosalicylsure
PAS · 4-AMINO-2-HYDROXYBENZOIC ACID · AMINOSALICYLIC ACID · Pasa · 4-Asa · SCHIFF REAGENT · SCHIFF'S REAGENT · P-AMINOSALICYLIC ACID
Identifikatoren & physikalische Daten
| CAS No. | 65-49-6 |
|---|---|
| Summenformel | C7H7NO3 |
| Durchschnittliche Molmasse | 153,14 g/mol |
| Monoisotopische Masse | 153,04259308 g/mol |
| SMILES | Nc1ccc(C(=O)O)c(O)c1 |
| InChIKey | WUBBRNOQWQTFEX-UHFFFAOYSA-N |
| PubChem CID | 4649 |
| ChEMBL | CHEMBL1169 |
| ChEBI | CHEBI:27565 |
| EC No. | 200-613-5 |
| DTXSID | DTXSID2022591 |
| Lokaler Name | 4-Aminosalicylsure |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 83,6 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 160 |
| Stoffklassen | Nitrogen Compounds -> Aminobenzoic Acids |
| Arzneimittel | Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15 |
| pH | PH (SATURATED AQ SOLN): BETWEEN 3 & 3.73.5 (1g/l, H2O, 20℃) |
| SpringerMaterials Properties | Diamagnetic susceptibility |
| LogP (Verteilungskoeffizient) | LogP= 1.321.6 |
| Geruch | ODORLESS, OR HAS SLIGHT ACETOUS ODOR |
| Color/Form | MINUTE CRYSTALS FROM ALCWHITE, OR NEARLY WHITE, BULKY POWDERNEEDLES, PLATES FROM ALC-ETHERA reddish-brown crystalline powder is obtained on recrystallization from ethanol-ether. |
| Löslichkeit | 1 G SOL IN ABOUT 7 ML WATERSLIGHTLY SOL IN ALC /CALCIUM SALT/PH OF 1% SOLN: ABOUT 7FREELY SOL IN WATER /POTASSIUM SALT/For more Solubility (Complete) data for P-AMINOSALICYLIC ACID (7 total), please visit the HSDB record page.SOL IN DILUTE NITRIC ACID & DILUTE SODIUM HYDROXIDEVirtually insoluble in benzene, choroform, or carbon tetrachloride1.69g/l2 g/L (20 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-infective AgentsAntitubercular AgentsFDA approved drugs -> Active ingredient |
| Schmelzpunkt | 150-151 °C, with effervescenceNEEDLES FROM ALCMP: 115 °C /ETHYL ESTER/150.5 °C135-145 °C (lit.) |
| Dampfdruck | 0.000004 [mmHg] |
| Physical Description | White or nearly white solidAffected by light and air[Hawley] Beige powder[MSDSonline] |
| Siedepunkt | 276.03°C (rough estimate) |
| Dichte | 1.3585 (rough estimate) |
| Brechungsindex | 1.5500 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 3.25(at 25℃) |
| Farbe | Colorless |
| Merck | 14,477 |
| BRN | 473071 |
| Specific Activity | 17.6-26.4nmol/min·mg |
| BCS Class | 4/2 |
| Stabilität | Hygroscopic |
| Hauptanwendungen | peptide synthesis |
| InChI | 1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11) |
| InChIKey | WUBBRNOQWQTFEX-UHFFFAOYSA-N |
| SMILES | Nc1ccc(C(O)=O)c(O)c1 |
| CAS Datenbank | 65-49-6(CAS DataBase Reference) |
| NIST chemische Informationen | Aminosalicylic acid(65-49-6) |
| EPA chemische Informationen | 4-Aminosalicylic acid (65-49-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (43.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/25234Benzoic acid, 4-amino-2-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzoic acid, 4-amino-2-hydroxy-: Environment tier I assessment |
| Gefahrenübersicht | Not expected to increase congenital malformations based on animal studies[REPROTOX] Oral LD50 (mouse) = 4000 mg/kg[RTECS] An eye irritantTargets the GI system and liver[MSDSonline] See p-Aminosalicylic acid sodium salt dihydrate. |
| FDA-Anforderungen | Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392). |
| Special Reports | A review of the literature on the clinical experience, tolerance and toxicity of mesalamine (5-aminosalicylic acid), aminosalicylic acid (4-aminosalicylic acid) and newer mesalamine based drugs for the treatment of chronic inflammatory bowel disease is presented.[Jarnerot GDrugs 37 (Jan): 73-86 (1989)]The initial therapy and retreatment of pulmonary tuberculosis as well as various complicating factors that may affect treatment decisions are presented. Chemotherapeutic agents used in the treatment of tuberculosis and their dosage regiments are mentioned including isoniazid, ethambutol, rifampin, pyrazinamide, ethionamide, cycloserine, streptomycin, kanamycin, aminosalicylate (aminosalicylic acid), and capreomycin.[Spagnolo SVDrug Therapy 15 (Nov): 91-92, 97-100 (1985)] |
| Hazard Classes and Categories | Skin Irrit. 2 (43.5%) |
| Lagerbedingungen | Store below 90 °C (104 °F), unless otherwise specified by manufacturer. Store in tight, light resistant containers. |
| Entsorgungsverfahren | 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. |
| Wechselwirkungen | ...PARA-AMINOSALICYLIC ACID.../INHIBITS METABOLISM OF CHLORAMPHENICOL/PENTOBARBITAL /SRP: CNS DEPRESSION/ IN MICE WAS ENHANCED AFTER PRE-TREATMENT WITH... P-AMINOSALICYLIC ACID. INCR /SRP: CNS DEPRESSION/ APPEARED TO BE DUE TO RELEASE OF PENTOBARBITAL FROM SERUM-PROTEIN BINDING, RESULTING IN HIGHER CEREBRAL CONCN...ADDITIVE & SYNERGISTIC WITH STREPTOMYCINS & ISONIAZID.Probenecid decreases the renal excretion of this agent.For more Interactions (Complete) data for P-AMINOSALICYLIC ACID (19 total), please visit the HSDB record page. |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Human Toxicity Excerpts | SEVERE THERAPEUTIC MISADVENTURES, ALTHOUGH RARE, HAVE INCL...HEPATITIS...METHEMOGLOBINEMIA...Adequate and well-controlled studies in humans have not been done. In one study, an increased malformation rate for ears and limbs, and hypospadias were reported in infants of patients taking aminosalicylates with other antitubercular medications. However, other studies have not found aminosalicylates to be teratogenic. /Aminosalicylates/The literature has been reviewed for contact dermatitis occurring to antituberculosis agents. Of the 12 known drugs, 6 (isoniazid, rifampicin, ethambutol, p-aminosalicylic acid, streptomycin and kanamycin) have been documented by patch test to cause this type of dermatitis in certain individuals. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Aminosalicylic acidvMOST-DILI-concern5Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Non-Human Toxicity Excerpts | An N-acetylation polymorphism is described that is expressed toward arylamine carcinogens in tumor target organs of an inbred rat model. High levels ... of arylamine carcinogen N-acetyltransferase activity were observed in kidney, colon, prostate and urinary bladder cytosols derived from Fischer (F-344) inbred rats ... Significantly lower ... levels of arylamine carcinogen N-acetyltransferase activity were observed for corresponding tissue cytosols derived from Wistar-Kyoto inbred rats. Intermediate levels of arylamine carcinogen N-acetyltransferase activity significantly different from both the parental strains were observed in F1 hybrids of the parental strains, consistent with codominant expression of two alleles at a single gene locus. The arylamine substrates exhibiting the acetylator phenotype-dependent N-acetyltransferase activities included ... p-aminosalicylic acid ... Highest levels of arylamine carcinogen N-acetyltransferase were expressed consistently in colon cytosol, but expression of the N-acetylation polymorphism toward arylamine carcinogens was observed in each (kidney, colon, prostate and urinary bladder) of the tumor target organs. The expression of the N-acetylation polymorphism in tumor target organs suggests that the inbred rat model will be useful in assessing the role of acetylator phenotype in arylamine-induced cancers of the colon and prostate.An overview is presented of a selected number of mono-aromatic derivatives and their short-term effects on hepatic fatty acid biosynthesis. The cmpd discussed in this paper are o-hydroxybenzoate ... m-hydroxybenzoate, p-hydroxybenzoate, benzoate, p-t-butylbenzoate, p-aminosalicylate, clofibrate, halofenate, alpha-cyano-4-hydroxycinnamate and benfluorex. All of these drugs inhibit fatty acid biosynthesis by isolated rat liver cells, albeit with different effectiveness. In contrast, the cmpd have differential effects on fatty acid esterification and oxidation by isolated hepatocytes. An attempt is made to describe in molecular terms the underlying mechanisms of the acute inhibitory effects of the mono-aromatic derivatives on hepatic lipogenesis. It is proposed that all of the drugs exert an inhibitory action at the level of acetyl-CoA carboxylase, the enzyme generally considered to catalyze the rate-limiting step in hepatic fatty acid synthesis. This inhibitory effect may be either direct, i.e. by an alteration of the enzyme's structure as a results of interaction between drug and enzyme, or indirect, i.e. through a drug-induced change in the cellular levels of allosteric effectors of acetyl-CoA carboxylase. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1789 8/PG 3 |
| Zollcode | 29225000 |
| RTECS-Nr. | VO1225000 |
| R-Sätze (R) | 22-36-36/37/38-45-35-61 |
| Toxizität | LD50 orally in mice: 4 g/kg (Bavin) |
| Gefahrensymbole | Xn,Xi,T |
| Sicherheitshinweise (S) | 26-37/39-45-53-36-36/37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 65-49-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
antimycobacterial antitubercular;NF-kB inhibitor.4-Aminosalicylic acid (p-aminosalicylic acid, PAS), an antituberculosis drug, is a model active pharmaceutical ingredient to study salt and cocrystal formation in a multiple hydrogen-bonding functionality molecule with carboxylic acid, amine, and phenol groups.It has also been used as a second line agent to sulfasalazine in people with inflammatory bowel disease such as ulcerative colitis and Crohn's disease.It is typically taken by mouth.