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4-Aminosalicylic Acid

HCID 4649
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Basic information

CAS
65-49-6
Standard SMILES
Nc1ccc(C(=O)O)c(O)c1
InChIKey
WUBBRNOQWQTFEX-UHFFFAOYSA-N
Molecular formula
C7H7NO3
Average molar mass
153.14 g/mol
Monoisotopic mass
153.04259309

Overview

4-aminosalicylic acid is an aminobenzoic acid that is salicylic acid substituted by an amino group at position 4. It has a role as an antitubercular agent. It is an aminobenzoic acid and a member of phenols. It is functionally related to a salicylic acid. It is a conjugate acid of a 4-aminosalicylate(1-).

Names & identifiers

Preferred name
4-Aminosalicylic Acid
IUPAC
4-amino-2-hydroxybenzoic acid
English name
4-Aminosalicylic acid
Molecular formula
C7H7NO3
Molecular weight
153.14

Names & synonyms

4-Aminosalicylic acid4-Amino-2-hydroxybenzoic acid65-49-6Aminosalicylic acidP-AMINOSALICYLIC ACIDParamycinParasalPaserParasalindonDeapasilApacilGabbropas
Show more names
PASPasa4-AsaSCHIFF REAGENTSCHIFF'S REAGENTApas
ParasalicilAminoparEntepasPamacylPasalonPasnodiaPasolacPropasa

Database identifiers

CAS
65-49-6
PubChem CID
4649
DTXSID
DTXSID2022591
ChEMBL
CHEMBL1169
ChEBI
CHEBI:27565
UNII
5B2658E0N2
EC Number
200-613-5
Nikkaji
J4.838K

Properties

Computed structural propertiesFilling in

XLogP
1.3
Topological polar surface area
83.6 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
11
Formal charge
0
Complexity
160

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Aminobenzoic Acids
Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

pHPH (SATURATED AQ SOLN): BETWEEN 3 & 3.7
SpringerMaterials PropertiesDiamagnetic susceptibility
LogP · 3 items

LogP= 1.32

1.6

0.87

OdorODORLESS, OR HAS SLIGHT ACETOUS ODOR
Color/Form · 4 items

MINUTE CRYSTALS FROM ALC

WHITE, OR NEARLY WHITE, BULKY POWDER

NEEDLES, PLATES FROM ALC-ETHER

A reddish-brown crystalline powder is obtained on recrystallization from ethanol-ether.

Solubility · 5 items

1 G SOL IN ABOUT 7 ML WATER; SLIGHTLY SOL IN ALC /CALCIUM SALT/

PH OF 1% SOLN: ABOUT 7; FREELY SOL IN WATER /POTASSIUM SALT/

For more Solubility (Complete) data for P-AMINOSALICYLIC ACID (7 total), please visit the HSDB record page.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (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.

Hazard information

Regulatory Information · 2 items

REACH registered substance: 4-aminosalicylic acid (EC: 200-613-5)

Benzoic acid, 4-amino-2-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzoic acid, 4-amino-2-hydroxy-: Environment tier I assessment
Hazards SummaryNot expected to increase congenital malformations based on animal studies; [REPROTOX] Oral LD50 (mouse) = 4000 mg/kg; [RTECS] An eye irritant; Targets the GI system and liver; [MSDSonline] See p-Aminosalicylic acid sodium salt dihydrate.
FDA Requirements · 1 item

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 amended; 21 U.S.C. 321-392).

Special Reports · 2 items

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 G; Drugs 37 (Jan): 73-86 (1989)]

Chemistry & industry

Pharmacology

ATC Code · 2 items

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding50-60%
Pharmacodynamics · 1 item

Aminosalicylic acid is an anti-mycobacterial agent used with other anti-tuberculosis drugs (most often isoniazid) for the treatment of all forms of active tuberculosis due to susceptible strains of tubercle bacilli. The two major considerations in the clinical pharmacology of aminosalicylic acid are the prompt production of a toxic inactive metabolite under acid conditions and the short serum half life of one hour for the free drug. Aminosalicylic acid is bacteriostatic against <i>Mycobacterium tuberculosis</i> (prevents the multiplying of bacteria without destroying them). It also inhibits the onset of bacterial resistance to streptomycin and isoniazid.

Mechanism of Action · 3 items

There are two mechanisms responsible for aminosalicylic acid's bacteriostatic action against <i>Mycobacterium tuberculosis</i>. Firstly, aminosalicylic acid inhibits folic acid synthesis (without potentiation with antifolic compounds). The binding of para-aminobenzoic acid to pteridine synthetase acts as the first step in folic acid synthesis. Aminosalicylic acid binds pteridine synthetase with greater affinity than para-aminobenzoic acid, effectively inhibiting the synthesis of folic acid. As bacteria are unable to use external sources of folic acid, cell growth and multiplication slows. Secondly, aminosalicylic acid may inhibit the synthesis of the cell wall component, mycobactin, thus reducing iron uptake by <i>M. tuberculosis</i>.

The antimicrobial activity of aminosalicylic acid is highly specific, and microorganisms other than Mycobacterium tuberculosis are unaffected. Most nontuberculous mycobacteria are not inhibited by the drug.

Aminosalicyclic acid is a structural analog of paraaminobenzoic acid, and its mechanism of action appears to be very similar to that of the sulfonamides. Since the sulfonamides are ineffective against Mycobacterium tuberculosis, and aminosalicyclic is inactive against sulfonamide susceptible bacteria, it is probable that the enzymes responsible for folate biosynthesis in various microorganisms may be quite exacting in their capacity to distinguish various analogs from the true metabolite.

Related reactions

96 records
New reaction record
HRID 18440 reaction equation
HRID 18440As reactantuspto-grants-2010_06
HRID 71535 reaction equation
HRID 71535As reactantuspto-grants-2014_09
HRID 76646 reaction equation
HRID 76646As reactantuspto-grants-2014_09
HRID 98090 reaction equation
HRID 98090As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 101517 reaction equation
HRID 101517As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 107654 reaction equation
HRID 107654As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 136213 reaction equation
HRID 136213As productTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 162068 reaction equation
HRID 162068As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Compound notes

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SOL IN DILUTE NITRIC ACID & DILUTE SODIUM HYDROXIDE

Virtually insoluble in benzene, choroform, or carbon tetrachloride

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-infective Agents; Antitubercular Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 3 items

150-151 °C, with effervescence

NEEDLES FROM ALC; MP: 115 °C /ETHYL ESTER/

150.5 °C

Vapor Pressure0.000004 [mmHg]
Physical Description · 2 items

White or nearly white solid; Affected by light and air; [Hawley] Beige powder; [MSDSonline]

Solid

Physicochemical properties

Melting point
135 · 135-145 °C (lit.)
Boiling point
276.03 °C · 276.03°C (rough estimate)
Density
1.3585 · 1.3585 (rough estimate)
refractive index
1.55 · 1.5500 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
1.69 g/l · 1.69g/l
form
Powder
pka
3.25 · 3.25(at 25℃)
color
Colorless
PH
3.5 · 3.5 (1g/l, H2O, 20℃)
Water Solubility
2 g/L · 2 g/L (20 ºC)
Merck
14 · 14,477
BRN
473071 · 473071
Specific Activity
17.6 · 17.6-26.4nmol/min·mg
BCS Class
4 · 4/2
Stability
Hygroscopic
Major Application
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 DataBase Reference
65 · 65-49-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
5 B2658E0N2 · 5B2658E0N2
ATC code
4 AA01 · J04AA01
NIST Chemistry Reference
Aminosalicylic acid(65-49-6)
EPA Substance Registry System
4 · 4-Aminosalicylic acid (65-49-6)
UNSPSC Code
41116121 · 41116121
NACRES
47 · NA.47
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319-H335-H315
Precautionary statements
264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P405-P501a-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,Xi,T
Risk Statements
22 · 22-36-36/37/38-45-35-61
Safety Statements
26 · 26-37/39-45-53-36-36/37/39
RIDADR
1789 · UN 1789 8/PG 3
WGK Germany
2 · 2
RTECS
1225000 · VO1225000
TSCA
TSCA listed
HS Code
29225000 · 29225000
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
65 · 65-49-6(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in mice: 4 g/kg (Bavin)
REACH Registrations
Active

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 SV; Drug Therapy 15 (Nov): 91-92, 97-100 (1985)]

Hazard Classes and CategoriesSkin Irrit. 2 (43.5%)

Safety & protection

Storage ConditionsStore below 90 °C (104 °F), unless otherwise specified by manufacturer. Store in tight, light resistant containers.
Disposal Methods · 1 item

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.

Toxicology

Interactions · 5 items

...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.

Adverse EffectsOccupational 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 · 3 items

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 · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Aminosalicylic acid

vMOST-DILI-concern

5

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Non-Human Toxicity Excerpts · 2 items

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
EPA Human Health Benchmarks for Pharmaceuticals · 6 items

Aminosalicylic acid

279.7

1183.4

The adult dosage of four grams (one packet) three times per day should be given by sprinkling on apple sauce or yogurt or by swirling in the glass to suspend the granules in an acidic drink such as tomato or orange juice.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 12000 mg/day, Lowest Therapeutic Dose (LTD): 150.0 mg/kg-day, and Screening Dose: 0.1 mg/kg-day.

1-Jun-10

Regulatory information

FDA Requirements · 1 item

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 amended; 21 U.S.C. 321-392).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
VO1225000
ridadr
UN 1789 8/PG 3
hs_code
29225000
Toxicity
LD50 orally in mice: 4 g/kg (Bavin)
risk_code
22-36-36/37/38-45-35-61
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi,T
safety_code
26-37/39-45-53-36-36/37/39
Storage Class
11 - Combustible Solids
Hazard statements
H319-H335-H315
REACH Registrations
Active
Precautionary statements
P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P405-P501a-P305+P351+P338
Hazardous Substances Data
65-49-6(Hazardous Substances Data)
Biological Half-LifeThe drug has a half life of about 1 hour, and concentrations in plasma are negligible within 4 to 5 hours after a single conventional dose.
Metabolism/Metabolites · 6 items

Hepatic.

ACETYLATION IS MAJOR ROUTE FOR INACTIVATION OF MANY DRUGS SUCH AS ... P-AMINOSALICYLIC ACID... ENZYMES WHICH CATALYSE THESE REACTIONS, ACETYL COENZYME A:N-ACETYLTRANSFERASES (EC2.3.1.5), ARE LOCATED IN LIVER CYTOSOL.

WHEN ADMIN ORALLY TO MAN IT IS RAPIDLY ABSORBED, & IS EXCRETED IN URINE AS UNCHANGED P-AMINOSALICYLIC ACID & AS ACETYL GLUCURONYL, GLYCYL & GLUTAMINYL CONJUGATES.

YIELDS 5-AMINO-2-CARBOXYPHENYL-BETA-D-GLUCURONIDE IN MAN. 4-AMINOCATECHOL IN PSEUDOMONAS. 4-AMINOSALICYLOYLGLUTAMINE & 4-AMINOSALICYLOYLGLYCINE IN MAN. /TABLE/

Blood from tuberculosis patients was cultured before, during, and after withdrawal of therapy involving five different drug combinations if isoniazid, thiacetazone, p-aminosalicyclic acid, and streptomycin. The approaches used to detect DNA damage were chromosome aberrations and sister chromatid exchanges (SCEs). A total of 179 subjects were analyzed. In combo these drugs showed synergistic, additive, and antagonistic effects, though they were found to be nonclastogenic individually. Four of the drug combinations, isoniazid plus thiacetazone, isoniazid plus p-aminosalicyclic acid, isoniazid plus thiacetazone plus streptomycin, and isoniazid plus p-aminosalicyclic acid plus streptomycin, induced a significant incr in the frequency of aberrations, whereas isoniazid plus streptomycin did not induce aberrations. In fact, streptomycin appeared to reduce the frequency of aberrations. SCEs were incr in only two patients: one treated with isoniazid plus thiacetazone and the other with isoniazid plus p-aminosalicyclic acid. The frequency of aberrations after withdrawal of therapy was decr; it was slightly higher than the controls, though it was insignificant. The return to normalcy could be due to elimination of damaged cells or the repair of DNA in lymphocytes. Though the drug-induced aberrations do not persist after withdrawal of therapy, the chromosome damaging combo of drugs should be used with caution, because the possibility of meiotic chromosome damage in germ cells (during therapy), which might be passed on to the next generation, cannot be ruled out.

For more Metabolism/Metabolites (Complete) data for P-AMINOSALICYLIC ACID (9 total), please visit the HSDB record page.

MeSH Pharmacological Classification · 1 item

Drugs used in the treatment of tuberculosis. They are divided into two main classes: first-line agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and second-line drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy.

Absorption, Distribution and Excretion · 5 items

BIOAVAILABILITY STUDIES ON P-AMINOSALICYLIC ACID & ITS SALTS IN 12 SUBJECTS. COLORIMETRIC ASSAY INDICATED THAT PEAK BLOOD LEVELS OCCURRED @ 0.5, 0.75, 1.5, & 3 HR FOR SODIUM, POTASSIUM, & CALCIUM SALTS & P-AMINOSALICYLIC ACID, RESPECTIVELY.

URINE EXCRETION DATA SHOWED ABSORPTION TO BE ESSENTIALLY COMPLETE ALTHOUGH RATES OF ABSORPTION DIFFERED.

Aminosalicyclic acid is readily absorbed from the gastrointestinal tract. A single oral dose of 4 g of the free acid produces maximal concentrations in plasma of about 75 ug/ml within 1.5 to 2 hours. The sodium salt is absorbed even more rapidly. The drug appears to be distributed throughout the total body water and reaches high concentrations in pleural fluid and caseous tissue. However, values in CSF are low, perhaps because of active outward transport.

Over 80% of the drug is excreted in the urine; more than 50% is in the form of the acetylated compound. The largest portion of the remainder is made up of the free acid.

For more Absorption, Distribution and Excretion (Complete) data for P-AMINOSALICYLIC ACID (8 total), please visit the HSDB record page.

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 5 items

Used as an industrial preservative, a chemical intermediate, and an antitubercular drug; [HSDB]

Industrial preservative.

Used as a chemical intermediate for the synthesis of bromopride; metoclopramide; xipamide

MEDICATION (VET)

MEDICATION

Methods of Manufacturing · 2 items

PREPD BY HEATING M-AMINOPHENOL WITH AMMONIUM CARBONATE OR POTASSIUM BISCARBONATE IN SOLN UNDER PRESSURE. PREPN FROM SODIUM P-AMINOSALICYLATE.

Derivation: From m-aminophenol and potassium bicarbonate, soluble under pressure.

Formulations/Preparations · 2 items

USP

Available commercially as the free acid and as the sodium dihydrate salt.

General Manufacturing InformationBenzoic acid, 4-amino-2-hydroxy-: ACTIVE
Applications · 4 items

UsesIntended for use in Sigma Periodic Acid Staining Procedure, 395. Kit is intended for use with blood, bone marrow, tissue touch preparations or routine tissue sections. It is used for staining glycoproteins in polyacrylamide gels. Schiff's reagent is also sometimes used to dye organic tissues. It is been widely used for detection of a certain functional group in chemical solutions.

Usesantimycobacterial 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.

UsesAn antibiotic used to treat tuberculosis.

General Description4-Aminosalicylic acid occurs as a white to yellowish white crystalline solid that darkens on exposure to light or air. It is slightly soluble in water but more soluble in alcohol. Alkali metal salts and the nitric acid salt are soluble in water, but the salts of hydrochloric acid and sulfuric acid are not. The acid undergoes decarboxylation when heated. An aqueous solution has a pH of approximately 3.2. PAS is administered orally in the form of the sodium salt, usually in tablet or capsule form. Symptoms of gastrointestinal irritation are common with both the acid and the sodium salt. Various enteric-coated dosage forms have been used in an attempt to overcome this disadvantage. Other forms that are claimed to improve gastrointestinal tolerance include the calcium salt, the phenyl ester, and a combination with an anion exchange resin (Rezi-PAS). An antacid such as aluminum hydroxide is frequently prescribed. The oral absorption of PAS is rapid and nearly complete, and it is widely distributed into most of the body fluids and tissues, with the exception of the CSF, in which levels are significantly lower.It is excreted primarily in the urine as both unchanged drug and metabolites.

Upstream & downstream products

Upstream raw materials

2,4-DINITROPHENYLACETIC ACID1-Butyl nitriteSodium sulfideSodium sulfite4-Nitrosalicylic acidCarbon dioxidePotassium hydroxide solutionSodium MethoxideMETHYL 2,4-DINITROPHENYLACETATENitric acidEsterified product3-Aminophenol2-CyanophenolPhenylacetic acidAmmonium carbonateP-AMINOSALICYLIC ACID SODIUM SALT

Downstream products

4-Chlorosalicylic acidMethyl 4-acetamido-2-methoxybenzoateoptical plastics based on coplymer of diene macromoleculeMETHYL 4-ACETAMIDO-2-HYDROXYBENZOATE2-hydroxy-4-(4-pyridyl)benzoic acidPhenyl-4-aminosalicylate

Additional notes

DefinitionChEBI: An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.