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Sulfadiazin

Sulfadiazine

HCID 5215
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Grundinformationen

CAS
68-35-9
Standard-SMILES
Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1
InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N
Summenformel
C10H10N4O2S
Durchschnittliche Molmasse
250,28 g/mol
Monoisotopische Masse
250,05244656

Überblick

Sulfadiazine is a sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position. It has a role as an antimicrobial agent, an antiinfective agent, a xenobiotic, a coccidiostat, an antiprotozoal drug, an EC 2.5.1.15 (dihydropteroate synthase) inhibitor, an EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor, an environmental contaminant and a drug allergen. It is a sulfonamide, a member of pyrimidines, a substituted aniline and a sulfonamide antibiotic. It is functionally related to a sulfanilamide. It is a conjugate acid of a sulfadiazinate.

Namen und Bezeichner

Bevorzugter Name
Sulfadiazine
IUPAC
4-amino-N-pyrimidin-2-ylbenzenesulfonamide
Lokaler Name
Sulfadiazin
Englischer Name
Sulfadiazine
Summenformel
C10H10N4O2S
Molmasse
250.28

Namen und Synonyme

sulfadiazine68-35-9SulphadiazineSulfapyrimidineSulfadiazinAdiazineCoco-Diazine2-SulfanilamidopyrimidineSulfolexBenzenesulfonamide, 4-amino-N-2-pyrimidinyl-2-Sulfanilylaminopyrimidine4-amino-N-pyrimidin-2-ylbenzenesulfonamide
Weitere Namen anzeigen
Sulfadiazine,(S)SulfadiazeneDiazinSulfoseTerfonylDiazoloneNeotrizinesuldadiazine
N(1)-2-pyrimidylsulfanilamideN(sup 1)-2-Pyrimidinylsulfanilamide4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamideN(1)-2-pyrimidinylsulfanilamide4-AMINO-N-2-PYRIMIDINYLBENZENESULFONAMIDEDTXSID7044130CHEBI:9328NSC35600

Datenbank-Bezeichner

CAS
68-35-9
PubChem CID
5215
DTXSID
DTXSID7044130
ChEMBL

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-0,1
Polarare Oberfläche (TPSA)
106 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
3
Schwere Atome
17
Formalladung
0
Komplexität
327

Experimentelle und physikochemische Eigenschaften

Drugs · 4 Einträge

Pharmaceuticals -> Antibiotics (Sulfonamide)

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

SpringerMaterials PropertiesFusion temperature
LogP · 2 Einträge

-0.2

-0.04

Solubility6.01e-01 g/L
Human Drugs · 3 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Anti-infective medicines

Animal Drugs · 3 Einträge

Active Ingredients (Sulfadiazine) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Physical DescriptionSolid
Dissociation Constants6.36

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 1.2% (2 of 171) of reports.

Danger

H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P233, P260, P261, P263, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 171 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Status: Active Update: 23-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17511

Sulphadiazine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (98.2%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Sulfadiazine, like other sulfonamides, causes a characteristic idiosyncratic liver injury which has features of drug-allergy or hypersensitivity. The typical onset is sudden development of fever and rash followed by jaundice within a few days or weeks of starting the medication. The pattern of injury is typically mixed, although fatal cases are often hepatocellular and prolonged cholestatic cases have also been described. Eosinophilia or atypical lymphocytosis are also common and the clinical pattern can be considered a part of DRESS syndrome (drug rash with eosinophilia and systemic symptoms). Cases of Stevens Johnson syndrome due to sulfadiazine have also been described. Sulfonamides such as sulfadiazine have been linked to many cases of acute liver failure and as a class, the sulfonamides still rank in the top 5 to 10 causes of drug induced, idiosyncratic fulminant hepatic failure. However, most cases of sulfonamide induced liver injury resolve rapidly, usually within 2 to 4 weeks unless cholestasis is severe. Onset of injury is more rapid with rechallenge and can appear within a day or reexposure. Patients with hepatic injury due to sulfadiazine may have a history of previous exposure to the drug without injury. Sulfonamides such as sulfadiazine can also cause mild and transient ALT elevations that do not progress to jaundice or more severe liver injury either alone or as a part of a generalized hypersensitivity reaction. Sulfonamides have also been linked to hepatic granulomas.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

J01EC02

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J01EC02

Pharmacodynamics · 1 Eintrag

Sulfadiazine 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

Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Metabolism/MetabolitesSulfadiazine has known human metabolites that include Sulfadiazine hydroxylamine.
FDA Pharmacological Classification · 6 Einträge

0N7609K889

SULFADIAZINE

Established Pharmacologic Class [EPC] - Sulfonamide Antibacterial

Chemical Structure [CS] - Sulfonamides

Sulfadiazine is a Sulfonamide Antibacterial.

SULFADIAZINE

MeSH Pharmacological Classification · 3 Einträge

Zugehörige Reaktionen

36
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 3696
HRID 3696als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 94566
HRID 94566als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 156477
HRID 156477als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 213337
HRID 213337als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 365062
HRID 365062als Produktuspto-grants-1986_08
Reaktionsgleichung von HRID 489948
HRID 489948als Eduktuspto-grants-2005_12
Reaktionsgleichung von HRID 583483
HRID 583483als Eduktuspto-grants-1999_07
Reaktionsgleichung von HRID 697622
HRID 697622als EduktTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
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Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
CHEMBL439
ChEBI
CHEBI:9328
UNII
0N7609K889
EC Number
200-685-8
Nikkaji
J1.418D
Collision Cross Section · 5 Einträge

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

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

148.7 Ų [M+H]+ [CCS Type: TW]

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

151.96 Ų [M+H]+

Physikochemische Eigenschaften

Schmelzpunkt
253 °C · 253 °C (dec.) (lit.)
Siedepunkt
512.6 · 512.6±52.0 °C(Predicted)
Dichte
1.378 · 1.3780 (rough estimate)
Brechungsindex
1.644 · 1.6440 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
Soluble in dimethyl sulfoxide.
pka
2.21 · pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain)
Aggregatzustand
powder
Farbe
white
Wasserlöslichkeit
67.13 mg/L · 67.13mg/L(25 ºC)
Merck
14 · 14,8903
BRN
6733588 · 6733588
BCS Class
4 · 4/3
Major Application
clinical testing
InChI
1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N
SMILES
Nc1ccc(cc1)S(=O)(=O)Nc2ncccn2
CAS Datenbank
68 · 68-35-9(CAS DataBase Reference)
NIST chemische Informationen
Sulfadiazine(68-35-9)
EPA chemische Informationen
4 · Benzenesulfonamide, 4-amino-N-2-pyrimidinyl- (68-35-9)
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Sulfadiazine

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

F
10
wgk
3
tsca
TSCA listed
ridadr
3249
hs_code
29335990
RTECS-Nr.
WP1925000
risk_code
22-36/37/38-42/43-43-42
Toxizität
LD50 oral in mouse: 1500mg/kg
hazard_code
Xn,Xi
safety_code
26-36
hazard_class
6.1(b)
packing_group
III
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2Repr. 2

Substances that are destructive to protozoans.

Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals.

Substances that inhibit the growth or reproduction of BACTERIA.

Absorption, Distribution and ExcretionSulfadiazine is excreted largely in the urine.
Cellular LocationsMembrane

Verwendung und Herstellung

UsesUse (kg) in Switzerland (2009): >250
Use Classification · 3 Einträge

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals -> Antiinfectives for systemic use -> Antibacterials for systemic use -> Sulfonamides and trimethoprims -> Intermediate-acting sulfonamides -> Antibiotics

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

General Manufacturing InformationBenzenesulfonamide, 4-amino-N-2-pyrimidinyl-: ACTIVE
Anwendungen · 1 Eintrag

VerwendenIt is used in the form of silver salts (sulfadiazine silver) as an external antibacterial agent, primarily for treating burns. It is believed that the presence of the silver ion in the molecule facilitates increased antimicrobial and wound-healing action.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

ThiaminEthylvinyletherEthanolN,N-DimethylformamidProp-2-in-1-olDiethylamin, in wässriger LösungCalciumacetylidNatriummethanolatPhosphorige Säure-trichloridSulfaguanidin4-NitrobenzolsulfonylchloridPyrimidin-2-ylamin

Nachgelagerte Produkte

2-Chloro-N-{4-[(pyrimidin-2-ylamino)sulfonyl]phenyl}acetamide2-chloro-5-nitro-N-[4-(pyrimidin-2-ylsulfamoyl)phenyl]benzamide

Ergänzende Hinweise

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