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Sulfapyridin

Sulfapyridine

HCID 5336
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Grundinformationen

CAS
144-83-2
Standard-SMILES
Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1
InChIKey
GECHUMIMRBOMGK-UHFFFAOYSA-N
Summenformel
C11H11N3O2S
Durchschnittliche Molmasse
249,29 g/mol
Monoisotopische Masse
249,05719778

Überblick

Sulfapyridine appears as odorless or almost odorless white or yellowish-white crystalline powder. Very slightly bitter taste. Aqueous solution is neutral. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Sulfapyridine
IUPAC
4-amino-N-pyridin-2-ylbenzenesulfonamide
Lokaler Name
Sulfapyridin
Englischer Name
Sulfapyridine
Summenformel
C11H11N3O2S
Molmasse
249.29

Namen und Synonyme

sulfapyridine144-83-2Sulphapyridine2-Sulfapyridine2-SulfanilamidopyridinePiridazolSulfidineDagenanSulfidinStreptosilpyridineCoccoclasePlurazol
Weitere Namen anzeigen
SulfapyridinTHAP114-AMINO-N-[2-PYRIDYL]BENZENE SULFONAMIDE2-hydroxybenzenecarboxylic acid (salicylic acid)RoninA-499m+b693TrianonAdiplon
PyriamidPyridazolEubasin2-SulfanilylaminopyridineEubasinumRelbapiridinaSeptipulmonThioseptal

Datenbank-Bezeichner

CAS
144-83-2
PubChem CID
5336
DTXSID
DTXSID3026067
ChEMBL
CHEMBL700
ChEBI
CHEBI:132842
UNII
Y5V2N1KE8U
EC Number
205-642-7

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0
Polarare Oberfläche (TPSA)
93,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
3
Schwere Atome
17
Formalladung
0
Komplexität
331

Experimentelle und physikochemische Eigenschaften

Drugs · 5 Einträge

Pharmaceuticals -> Metabolite of Sulfasalazine

Pharmaceuticals -> Antibiotics (Sulfonamide)

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

SpringerMaterials PropertiesFusion temperature
LogP · 2 Einträge

0.9

0.35

Solubility · 3 Einträge

less than 1 mg/mL at 72 °F (NTP, 1992)

2.35e-01 g/L

33.1 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point · 2 Einträge

376 to 379 °F (NTP, 1992)

192 °C

Physical Description · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 12% (6 of 50) of reports.

Danger

H300 (72%): Fatal if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P264, P270, P272, P273, P280, P301+P316, P302+P352, P308+P316, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

REACH registered substance: Sulfapyridine (EC: 205-642-7)

Sulfapyridine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-2-pyridinyl-: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound include fever, rash, agranulocytosis, deposition of crystals in the urinary tract with consequent hematuria or anuria, nausea, vomiting, cyanosis, sensitization and, rarely, granulocytopenia. Other symptoms include acute transient myopia, conjunctivitis, keratitis, disturbances of the optic nerve and retina, temporary impairment of depth perception, swelling of the eyelids, photophobia, lacrimation, Stevens-Johnson syndrome, Lyell syndrome, amblyopia, central scotoma and optic neuritis, usually with papilledema. It can induce crystalluria.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingApproximately 50% bound to plasma proteins.
Pharmacodynamics · 1 Eintrag

Sulfapyridine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of <i>p</i>-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.

Mechanism of Action · 1 Eintrag

Sulfapyridine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid by means of processing the substrate para-aminobenzoic acid (PABA). Dihydropteroate synthetase activity is vital in the synthesis of folate, and folate is required for cells to make nucleic acids, such as DNA or RNA. So if DNA molecules cannot be built, the cell cannot divide.

Biological Half-Life6-14 hours.
Metabolism/Metabolites · 2 Einträge

Hepatic.

Sulfapyridine has known human metabolites that include Sulfapyridine, N-acetyl.

MeSH Pharmacological Classification · 2 Einträge

Zugehörige Reaktionen

9
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 122078
HRID 122078als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 214740
HRID 214740als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 840816
HRID 840816als Eduktuspto-grants-2002_04
Reaktionsgleichung von HRID 1248965
HRID 1248965als Eduktuspto-grants-1986_12
Reaktionsgleichung von HRID 1263962
HRID 1263962als Eduktuspto-grants-2003_04
Reaktionsgleichung von HRID 1391491
HRID 1391491als Eduktuspto-grants-2008_03
Reaktionsgleichung von HRID 1639484
HRID 1639484als Produktuspto-grants-2012_02
Reaktionsgleichung von HRID 1790179
HRID 1790179als Eduktuspto-grants-2006_07
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Nikkaji
J5.831I

Sulfapyridine appears as odorless or almost odorless white or yellowish-white crystalline powder. Very slightly bitter taste. Aqueous solution is neutral. (NTP, 1992)

Solid

Dissociation Constants8.43
Collision Cross Section · 6 Einträge

150.94 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

142.3 Ų [M+H]+ [CCS Type: TW]

150.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

163.9 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

151.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

156.54 Ų [M-H]-

Physikochemische Eigenschaften

Schmelzpunkt
191 · 191-193°C
Siedepunkt
473.5 · 473.5±51.0 °C(Predicted)
Dichte
1.322 · 1.3220 (rough estimate)
Brechungsindex
1.674 · 1.6740 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
8.48 · pKa 8.48(H2O t = 25 I = 0.05) (Uncertain)
Farbe
White to Off-White
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 22 ºC
Merck
14 · 14,8938
BRN
222065 · 222065
Stabilität
Stable. Combustible. Protect from light. Incompatible with strong oxidizing agents.
Major Application
forensics and toxicologypharmaceutical (small molecule)
InChI
1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14)
InChIKey
GECHUMIMRBOMGK-UHFFFAOYSA-N
SMILES
Nc1ccc(cc1)S(=O)(=O)Nc2ccccn2
CAS Datenbank
144 · 144-83-2(CAS DataBase Reference)
NIST chemische Informationen
Sulfapyridine(144-83-2)
EPA chemische Informationen
Sulfapyridine (144-83-2)
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity ProfileSULFAPYRIDINE is an amino acid. Slowly darkens on exposure to light (NTP, 1992). Soluble in both acidic and basic aqueous solutions
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 2 (72%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: 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. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing 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.

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Sicherheitsdaten

wgk
2
tsca
TSCA listed
hs_code
29350010
RTECS-Nr.
DA9625000
risk_code
36/37/38
Toxizität
LD50 orally in mice: 7.5 mg/g (Wien)
hazard_code
Xi
safety_code
22-24/25-36-26
hazard_class
IRRITANT
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Repr. 2

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Drugs used to treat or prevent skin disorders or for the routine care of skin.

Absorption, Distribution and ExcretionApproximately 60-80%
Cellular LocationsMembrane

Verwendung und Herstellung

UsesUse (kg) in Switzerland (2009): >1000
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
General Manufacturing InformationBenzenesulfonamide, 4-amino-N-2-pyridinyl-: ACTIVE
Anwendungen · 2 Einträge

BeschreibungSulfapyridine is a sulfonamide antibiotic with antibacterial and anti-inflammatory activities. It is also a metabolite of sulfasalazine formed through bacterial conversion in the colon. It is active against strains of Y. enterocolitica and Salmonella (MICs = 3.1-25 and 25-100 μg/ml, respectively), as well as S. aureus (MBC = 0.8 μM). It is an inhibitor of recombinant P. carinii dihydropteroate synthetase (DHPS; IC50 = 0.18 μM). Sulfapyridine scavenges peroxyl radicals in an oxygen radical absorbance capacity (ORAC) assay. It inhibits histamine release induced by compound 48/80 from isolated rat peritoneal mast cells in a dose-dependent manner. Sulfapyridine (1 μg/kg) also inhibits compound 48/80-induced systemic allergic reaction in rats. Formulations containing sulfapyridine have previously been used in the treatment of dermatological conditions and ulcerative colitis.

VerwendenUsed in treatment of dermatitis herpetiformis; antibacterial.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-Pyridylamin4-Nitro-N-2-pyridinyl-benzenesulphonamideDiazene, 1,2-diphenyl-, stereoisomer4-Chloro-N-(pyridin-2-yl)benzenesulfonamide4'-(2-Pyridylsulfamoyl)acetanilidSulfanilylfluoridN-AcetylsulfanilylchloridAcetanilidSulfanilamid

Nachgelagerte Produkte

Salazosulfapyridin

Ergänzende Hinweise

DefinitionChEBI: A sulfonamide consisting of pyridine with a 4-aminobenzenesulfonamido group at the 2-position.