DrugBank: Sulfamerazine (DB01581)

targets (1) carriers (1)

Identification

Name

Sulfamerazine

Accession Number

DB01581

Type

small molecule

Groups

approved

Description

A sulfanilamide that is used as an antibacterial agent. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Brand names

Not Available

Brand name 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=CC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1

Plain Text

Mass Spec

show (8.4 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

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

Melting point

236 oC

Experimental Properties

Property	Value	Source
water solubility	0.202 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
logP	0.14 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
water solubility	3.04e-01 g/l	ALOGPS
logP	0.44	ALOGPS
logP	0.52	ChemAxon Molconvert
logS	-2.94	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	5	ChemAxon Molconvert
hydrogen donor count	2	ChemAxon Molconvert
polar surface area	97.97	ChemAxon Molconvert
rotatable bond count	2	ChemAxon Molconvert
refractivity	68.79	ChemAxon Molconvert
polarizability	26.51	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	5325
PubChem Substance	46505036
ChemSpider	5134
ChEBI	102130
ChEMBL	102130
Therapeutic Targets Database	DAP001240
PharmGKB	PA451541
Drug Product Database	0
Wikipedia	http://en.wikipedia.org/wiki/Sulfamerazine

ATC Codes

J01ED07
D06BA06

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (72.7 KB)

Interactions

Drug Interactions

Not Available

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 Gene: folP Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 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

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:

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
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
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 Gene: ALB Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. Pubmed 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

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

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. Pubmed
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 April 19, 2011 15:10

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.