Basic information
- Standard SMILES
Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1- InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N- Molecular formula
- C10H10N4O2S
- Average molar mass
- 250.28 g/mol
- Monoisotopic mass
- 250.05244656
Overview
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.
Names & identifiers
- Preferred name
- Sulfadiazine
- IUPAC
- 4-amino-N-pyrimidin-2-ylbenzenesulfonamide
- English name
- Sulfadiazine
- Molecular formula
- C10H10N4O2S
- Molecular weight
- 250.28
Names & synonyms
Show more names
Database identifiers
- CAS
68-35-9- PubChem CID
- 5215
- DTXSID
DTXSID7044130- ChEMBL
CHEMBL439- ChEBI
CHEBI:9328- UNII
- 0N7609K889
- EC Number
- 200-685-8
- Nikkaji
- J1.418D
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 327
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics (Sulfonamide)
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP
-0.2
-0.04
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Anti-infective medicines
Animal Drugs
Active Ingredients (Sulfadiazine) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section
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]+
Physicochemical properties
- Melting point
- 253 °C · 253 °C (dec.) (lit.)
- Boiling point
- 512.6 · 512.6±52.0 °C(Predicted)
- Density
- 1.378 · 1.3780 (rough estimate)
- refractive index
- 1.644 · 1.6440 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in dimethyl sulfoxide.
- pka
- 2.21 · pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain)
- form
- powder
- color
- white
- Water Solubility
- 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 DataBase Reference
- 68 · 68-35-9(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 N7609K889 · 0N7609K889
- ATC code
- 1 EC02 · J01EC02
- NIST Chemistry Reference
- Sulfadiazine(68-35-9)
- EPA Substance Registry System
- 4 · Benzenesulfonamide, 4-amino-N-2-pyrimidinyl- (68-35-9)
- UNSPSC Code
- 51283908 · 51283908
- NACRES
- 85 · NA.85
- Protein binding
- 20 · 20-55%
- Excreted unchanged in urine
- 80 % · 80%
- Volume of distribution
- 0.29 · 0.29(L/kg)
- Biological half-life
- 17 · 17 / Prolonged
- Symbol(GHS)
- 7 · GHS07,GHS08,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H361d-H362-H411
- Precautionary statements
- 202 · P202-P260-P263-P273-P301+P312-P308+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-42/43-43-42
- Safety Statements
- 26 · 26-36
- RIDADR
- 3249 · 3249
- WGK Germany
- 3 · 3
- RTECS
- 1925000 · WP1925000
- F
- 10 · 10
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29335990 · 29335990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Repr. 2
- Toxicity
- 50 oral · LD50 oral in mouse: 1500mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Regulatory Information
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
Toxicology
Hepatotoxicity
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.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Sulfadiazine
vLess-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- WP1925000
- ridadr
- 3249
- hs_code
- 29335990
- Toxicity
- LD50 oral in mouse: 1500mg/kg
- risk_code
- 22-36/37/38-42/43-43-42
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- hazard_class
- 6.1(b)
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H302-H361d-H362-H411
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Repr. 2
- Precautionary statements
- P202-P260-P263-P273-P301+P312-P308+P313
Chemistry & industry
Pharmacology
ATC Code
J01EC02
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J01EC02
Pharmacodynamics
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
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.
FDA Pharmacological Classification
0N7609K889
SULFADIAZINE
Established Pharmacologic Class [EPC] - Sulfonamide Antibacterial
Chemical Structure [CS] - Sulfonamides
Sulfadiazine is a Sulfonamide Antibacterial.
SULFADIAZINE
MeSH Pharmacological Classification
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.
Uses & manufacturing
Use Classification
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
Applications
UsesIt is excellent kinds of sulfa drugs with strong antibacterial activity, good efficacy, rapid absorption, slow excretion rate and high plasma concentration. It is clinically used for treating upper respiratory tract infection, Meningococcal meningitis, otitis media, boils carbuncle, puerperal fever, urinary tract infections and acute dysentery and so on. It is a sulfa-type drug which is used for the treatment of infection caused by hemolytic streptococcus, pneumococcus, meningococcis, Neisseria gonorrhea, and E. coli. It is a sulfa drug with antibacterial effect and convergence effect.
UsesIt 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.
UsesSulfonamide antibacterial.
UsesDMSO soluble potent immunosuppressant, neuroprotective neuroregenerative, in vitro T cell proliferation blocker. disrupts calcineurin-mediated signal transduction in T lymphocytes
General DescriptionSulfadiazine’s plasma half-life is 17 hours. It is a white,odorless crystalline powder soluble in water to the extentof 1:8,100 at 37°C and 1:13,000 at 25°C, in human serumto the extent of 1:620 at 37°C, and sparingly soluble in alcoholand acetone. It is readily soluble in dilute mineralacids and bases. Its pKa is 6.3.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.
Related reactions
Linked notes
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