SULFAMERAZINE

US Previously Marketed

First approved in 1943

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H12N4O2S
Molecular Weight	264.304
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1

InChI

InChIKey=QPPBRPIAZZHUNT-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C11H12N4O2S
Molecular Weight	264.304
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1921061/pdf/canmedaj00982-0002.pdf | http://new.dhh.louisiana.gov/assets/oph/Center-PHCH/Center-CH/infectious-epi/VetInfo/VetAntibioResSen/LADDL/AntimicrobialClasses/sulfonamides/Sulfonamides.pdf

Sulfamerazine is a sulfonamide antibiotic, which acts by inhibiting folic acid synthesis in bacterias. The primary target of sulfamerazine is believed to be dihydropteroate synthetase. Sulfamerazine (in comination with Sulfadiazine and Sulfamethazine) was used in the US under different names, including the earliest brand of Neotrizine. Nowdays, the drugs containing sulfamerazine are no longer available for use in humans in the US, however, they may be prescribed for veterinary purposes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: http://new.dhh.louisiana.gov/assets/oph/Center-PHCH/Center-CH/infectious-epi/VetInfo/VetAntibioResSen/LADDL/AntimicrobialClasses/sulfonamides/Sulfonamides.pdf	Inhibitor 8504		0.078 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1921061/pdf/canmedaj00982-0002.pdf	Curative		Approved 8583	NEOTRIZINE Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
37.61 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8486092/	60 mg/kg single, intravenous dose: 60 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		SULFAMERAZINE plasma	Bos taurus population: HEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2023.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8486092/	60 mg/kg single, intravenous dose: 60 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		SULFAMERAZINE plasma	Bos taurus population: HEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8486092/	60 mg/kg single, intravenous dose: 60 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		SULFAMERAZINE plasma	Bos taurus population: HEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
6 g multiple, oral Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy Health Status: unhealthy Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	Other AEs: Renal calculus, Rash... Other AEs: Renal calculus (4 patients) Rash (2 patients) Conjunctivitis (2 patients) Fever (2 patients) Sources: https://jamanetwork.com/journals/jama/article-abstract/268209

AEs

AE	Significance	Dose	Population
Conjunctivitis	2 patients	6 g multiple, oral Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy Health Status: unhealthy Sources: https://jamanetwork.com/journals/jama/article-abstract/268209
Fever	2 patients	6 g multiple, oral Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy Health Status: unhealthy Sources: https://jamanetwork.com/journals/jama/article-abstract/268209
Rash	2 patients	6 g multiple, oral Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy Health Status: unhealthy Sources: https://jamanetwork.com/journals/jama/article-abstract/268209
Renal calculus	4 patients	6 g multiple, oral Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy Health Status: unhealthy Sources: https://jamanetwork.com/journals/jama/article-abstract/268209

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B1 14 CYP2B 16 CYP1A1 132 CYP2E1 1060 CYP4A 20 CYP3A 227

Drug as perpetrator

Target	Modality	Activity
CYP1A1 272	inhibitor 4027 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP2B 41	inhibitor 4027 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP2B1 41	inhibitor 4027 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP2E1 1146	inhibitor 4027 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP3A 317	inhibitor 4027 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP4A 34	inhibitor 4027 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:102130	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:102130
ChemicalBook	CB0693512	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0693512
eMolecules	474306	https://www.emolecules.com/cgi-bin/more?vid=474306
MolPort	MolPort-001-783-537	https://www.molport.com/shop/molecule-link/MolPort-001-783-537
Selleck Chemicals	sulfamerazine	http://www.selleckchem.com/products/sulfamerazine.html
ZINC	ZINC000000057501	http://zinc15.docking.org/substances/ZINC000000057501

PubMed

Title	Date	PubMed
Calorimetric investigation of solvent-mediated transformation of sulfamerazine polymorphism.	2010-01	19718749
A confirmatory method for the simultaneous extraction, separation, identification and quantification of Tetracycline, Sulphonamide, Trimethoprim and Dapsone residues in muscle by ultra-high-performance liquid chromatography-tandem mass spectrometry according to Commission Decision 2002/657/EC.	2009-11-13	19586630
A new and simple method to determine trace levels of sulfonamides in honey by high performance liquid chromatography with fluorescence detection.	2009-10-23	19505691
Chitosan membranes modified by contact with poly(acrylic acid).	2009-09-08	19555925
Hollow fiber supported ionic liquid membrane microextraction for determination of sulfonamides in environmental water samples by high-performance liquid chromatography.	2009-08-28	19632683
The first bioreversible prodrug of metformin with improved lipophilicity and enhanced intestinal absorption.	2009-07-23	19522462
[Investigation of sulfonamides and tetracyclines antibiotics in soils from various vegetable fields].	2009-06-15	19662865
Determination of sulfonamide residues in water samples by in-line solid-phase extraction-capillary electrophoresis.	2009-04-10	19232622
Degradation and elimination of various sulfonamides during anaerobic fermentation: a promising step on the way to sustainable pharmacy?	2009-04-01	19452918
Determination of ten sulphonamides in egg by liquid chromatography-tandem mass spectrometry.	2009-04-01	19286032
Development and validation of a confirmatory method for the determination of sulphonamides in milk by liquid chromatography with diode array detection.	2009-04-01	19286007
Purification of nine sulfonamides from chicken tissues by immunoaffinity chromatography using two monoclonal antibodies.	2009-02-11	19202813
Synthesis of 4'-substituted cordycepins via benzenesulfenylation at the 4'-position as a key step.	2009	19749279
Occurrence and elimination of antibiotics at four sewage treatment plants in Japan and their effects on bacterial ammonia oxidation.	2009	19237773
Theoretical 14N nuclear quadrupole resonance parameters for sulfa drugs: sulfamerazine and sulfathiazole.	2008-10	18603459
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.	2008-09-26	18723177
[Development of a fluorescence polarization immunoassay for sulfamerazine].	2008-07	18844174
Analysis of sulfamerazine in pond water and several fishes by high-performance liquid chromatography using molecularly imprinted solid-phase extraction.	2008-07	18496678
Intramolecular nonbonded S...N interaction in rabeprazole.	2008-06	18520084
Stable-form screening: overcoming trace impurities that inhibit solution-mediated phase transformation to the stable polymorph of sulfamerazine.	2008-06	17879974
Simultaneous determination of sulphamerazine, sulphamethazine and sulphadiazine in honey and chicken muscle by a new monoclonal antibody-based fluorescence polarisation immunoassay.	2008-05	18473212
Application of matrix solid-phase dispersion and high-performance liquid chromatography for determination of sulfonamides in honey.	2008-04-02	18376605
Application of liquid-liquid-liquid microextraction and high-performance liquid-chromatography for the determination of sulfonamides in water.	2008-03-31	18331856
Optimization of a FIA system with amperometric detection by means of a desirability function: determination of sulfadiazine, sulfamethazine and sulfamerazine in milk.	2008-03-15	18371879
Validation of a Biacore method for screening eight sulfonamides in milk and porcine muscle tissues according to European decision 2002/657/EC.	2008-01-17	18196645
Regioselective hydroxysulfenylation of alpha,beta-unsaturated imines: enhanced stability of an intermediate radical.	2008	18553331
Preparation, characterization and in vivo conversion of new water-soluble sulfenamide prodrugs of carbamazepine.	2007-12-01	17928225
Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 1. N-alkoxysulfenate derivatives.	2007-11-14	17941694
Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS.	2007-11	17960854
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.	2007-11	17868178
Free-radical-induced oxidative and reductive degradation of sulfa drugs in water: absolute kinetics and efficiencies of hydroxyl radical and hydrated electron reactions.	2007-09-20	17715905
Comparison of benzene, nitrobenzene, and dinitrobenzene 2-arylsulfenylpyrroles.	2007-09-14	17705533
[Simultaneous determination of seven sulfonamides and metronidazole and chloramphenicol in cosmetics by high performance liquid chromatography].	2007-09	18161331
A sensitive spectrophotometric method for the determination of sulfonamides in pharmaceutical preparations.	2007-09	17878112
Determination of sulfonamides in milk after precolumn derivatisation by micellar liquid chromatography.	2007-06-19	17543601
Simple and rapid determination of sulfonamides in milk using Ether-type column liquid chromatography.	2007-06-15	19071760
Trace determination of sulfonamides residues in meat with a combination of solid-phase microextraction and liquid chromatography-mass spectrometry.	2007-05-15	19071729
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007-05-04	17474530
Synthesis and evaluation of galactofuranosyl N,N-dialkyl sulfenamides and sulfonamides as antimycobacterial agents.	2007-04-15	17303419
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007-03-22	17373466
Proteins protect lipid membranes from oxidation by thiyl radicals.	2007-03-15	17306209
Rapid determination of sulfonamides in milk samples using fluorescence spectroscopy and class modeling with n-way partial least squares.	2007-03-07	17386685
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].	2007-03	17580695
Reactions of sulfenic acid with 2-mercaptoethanol: a mechanism for the inhibition of gastric (H+-K+)-adenosine triphosphate by omeprazole.	2007-01	16998872
Catalytic enantio- and diastereoselective formation of beta-sultones: ring-strained precursors for enantioenriched beta-hydroxysulfonyl derivatives.	2007	17330913
Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water.	2006-10	16991204
Synthesis, characterization, and biotoxicity of N N donor sulphonamide imine silicon(IV) complexes.	2006	17496998
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection.	2004-09-08	18969572
Voltammetric detection of sulfonamides at a poly(3-methylthiophene) electrode.	2002-09-12	18968788
Quantitative determination of sulfonamide in meat by liquid chromatography-electrospray-mass spectrometry.	2001-12-24	18968466

Patents

Sample Use Guides

In Vivo Use Guide

Adults: 2 tablets (each tablets contains 167 mg Sulfamerazine, 167 mg Sulfadiazine and 167 mg Sulfamethazine) every 12 hours or an initial dose of 4 tablets followed by 2 tablets every 6 hours.

Route of Administration: Oral

In Vitro Use Guide

Sulfamerazine MIC50 values were >50 ug/ml (B. fragilis group), 6.4 ug/ml (Bacteroides sp.), 3.2 ug/ml (Fusobacterium sp.), 1.6 ug/ml (Clostridium sp.), 12.5 ug/ml (Anaerobic cocci) and 6.4 ug/ml (Non-spore-forming, gram-positive rods).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:35 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:35 GMT 2025`
Record UNII	UR1SAB295F
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SULFAMERAZINE

Official Name

English

LANTRISUL COMPONENT SULFAMERAZINE

Preferred Name

English

SULFAMERAZINE [VANDF]

Common Name

English

N(SUP 1)-(4-METHYL-2- PYRIMIDINYL)SULFANILAMIDE

Systematic Name

English

SULFOSE COMPONENT SULFAMERAZINE

Common Name

English

TRISULFAPYRIMIDINES (SULFAMERAZINE)

Common Name

English

BENZENESULFONAMIDE, 4-AMINO-N-(4-METHYL-2-PYRIMIDINYL)-

Systematic Name

English

sulfamerazine [INN]

Common Name

English

NSC-27259

Code

English

TRIPLE SULFOID COMPONENT SULFAMERAZINE

Common Name

English

SULFAMERAZINE [ORANGE BOOK]

Common Name

English

TERFONYL COMPONENT SULFAMERAZINE

Common Name

English

SULPHAMERAZINE

Common Name

English

SULFAMERAZINE [USP-RS]

Common Name

English

TRISULFAPYRIMIDINES (SULFAMERAZINE) [ORANGE BOOK]

Common Name

English

SULPHAMERAZINE

Common Name

English

SULFAMERAZINE [EP MONOGRAPH]

Common Name

English

SULFAMERAZINE [MI]

Common Name

English

SULFALOID COMPONENT SULFAMERAZINE

Common Name

English

SULFAMERAZINE [GREEN BOOK]

Common Name

English

SULFONAMIDES DUPLEX COMPONENT SULFAMERAZINE

Common Name

English

SULFAMERAZINE [MART.]

Common Name

English

Sulfamerazine [WHO-DD]

Common Name

English

SULFADIMIDINE IMPURITY A [EP IMPURITY]

Common Name

English

NEOTRIZINE COMPONENT SULFAMERAZINE

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 556.660