Banner
targets (1) carriers (1)
for drugs
Identification
Name Sulfamerazine
Accession Number DB01581
Type small molecule
Groups approved
Description

A sulfanilamide that is used as an antibacterial agent. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Anti-Infective Agents
  • Sulfonamides
CAS number 127-79-7
Weight Average: 264.304
Monoisotopic: 264.068096338
Chemical Formula C11H12N4O2S
InChI Key InChIKey=QPPBRPIAZZHUNT-UHFFFAOYSA-N
InChI
InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
Plain Text
IUPAC Name
4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide
SMILES
CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1
Plain Text
Mass Spec show (8.36 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzenesulfonamides
  • Sulfanilamides
Substructures
  • Sulfonyls
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Benzenesulfonamides
  • Pyrimidines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Sulfanilamides
  • Sulfonamides
  • Imines
  • Cyanamides
  • Anilines
Pharmacology
Indication A sulfanilamide that is used as an antibacterial agent. It can be used to treat bronchitis, prostatitis and urinary tract infections.
Pharmacodynamics Sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis in bacteria.
Mechanism of action Sulfamerazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.
Absorption Rapidly absorbed following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Sulfamerazine may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 236 °C PhysProp
water solubility 202 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 0.14 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 3.04e-01 g/l ALOGPS
logP 0.44 ALOGPS
logP 0.52 ChemAxon
logS -2.9 ALOGPS
pKa (strongest acidic) 6.99 ChemAxon
pKa (strongest basic) 2.01 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 97.97 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 68.79 ChemAxon
polarizability 26.51 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 5325 Link_out
PubChem Substance 46505036 Link_out
ChemSpider 5134 Link_out
ChEBI 102130 Link_out
ChEMBL 102130 Link_out
Therapeutic Targets Database DAP001240 Link_out
PharmGKB PA164776842 Link_out
Wikipedia http://en.wikipedia.org/wiki/Sulfamerazine Link_out
ATC Codes
  • J01ED07
  • D06BA06
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (72.7 KB)
Interactions
Drug Interactions
Drug Interaction
Chlorpropamide Sulfonamide/sulfonylurea: possible hypoglycemia
Methotrexate The sulfamide increases the toxicity of methotrexate
Food Interactions
  • Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
Targets

1. Dihydropteroate synthase

Pharmacological action: yes
Actions: inhibitor

DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide

Organism class: bacterial
UniProt ID: P0AC13 Link_out
Gene: folP
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hong YL, Hossler PA, Calhoun DH, Meshnick SR: Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother. 1995 Aug;39(8):1756-63. Pubmed
  2. Friaza V, Morilla R, Respaldiza N, de la Horra C, Calderon EJ: Pneumocystis jiroveci dihydropteroate synthase gene mutations among colonized individuals and Pneumocystis pneumonia patients from Spain. Postgrad Med. 2010 Nov;122(6):24-8. Pubmed
  3. Thijssen HH: A simplified radioassay method of dihydropteroate synthetase activity in Escherichia coli and its application for an inhibition study of p-aminobenzoi acid derivatives. Anal Biochem. 1973 Jun;53(2):579-85. Pubmed
Carriers

1. Serum albumin

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. Pubmed
  2. Angelakou A, Valsami G, Koupparis M, Macheras P: Use of 1-anilino-8-napthalenesulphonate as an ion probe for the potentiometric study of the binding of sulphonamides to bovine serum albumin and plasma. J Pharm Pharmacol. 1993 May;45(5):434-8. Pubmed
Comments
Drug created on August 29, 2007 08:53 / Updated on February 08, 2013 16:20