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

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

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 8297		0.078 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1921061/pdf/canmedaj00982-0002.pdf	Curative		Approved 8429	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 (starting) Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy n = 35 Health Status: unhealthy Population Size: 35 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 (starting) Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy n = 35 Health Status: unhealthy Population Size: 35 Sources: https://jamanetwork.com/journals/jama/article-abstract/268209
Fever	2 patients	6 g multiple, oral (starting) Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy n = 35 Health Status: unhealthy Population Size: 35 Sources: https://jamanetwork.com/journals/jama/article-abstract/268209
Rash	2 patients	6 g multiple, oral (starting) Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy n = 35 Health Status: unhealthy Population Size: 35 Sources: https://jamanetwork.com/journals/jama/article-abstract/268209
Renal calculus	4 patients	6 g multiple, oral (starting) Highest studied dose Dose: 6 g Route: oral Route: multiple Dose: 6 g Sources: https://jamanetwork.com/journals/jama/article-abstract/268209	unhealthy n = 35 Health Status: unhealthy Population Size: 35 Sources: https://jamanetwork.com/journals/jama/article-abstract/268209

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B1 14 CYP2B 15 CYP1A1 110 CYP2E1 882 CYP4A 19 CYP3A 214

Drug as perpetrator

Target	Modality	Activity
CYP1A1 218	inhibitor 3277 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP2B 40	inhibitor 3277 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP2B1 41	inhibitor 3277 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP2E1 970	inhibitor 3277 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP3A 298	inhibitor 3277 Sources: http://biosciencediscovery.com/Vol%202%20No2/Dandge.pdf Page: 3.0	yes
CYP4A 33	inhibitor 3277 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
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
eMolecules	474306	https://www.emolecules.com/cgi-bin/more?vid=474306

PubMed

Title	Date	PubMed
High-performance liquid chromatographic procedure for routine residue monitoring of seven sulfonamides in milk.	2001 Dec	11769794
Hydrogen bonding in sulfonamides.	2001 Dec	11745765
Bendamustine monotherapy in advanced and refractory chronic lymphocytic leukemia.	2001 Jan	11206271
Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data.	2001 Sep	11745780
Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.	2002	11921244
Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.	2002 Mar	11880002
Two new cinnamic acid esters from Marine brown alga Spatoglossum variabile.	2002 Sep	12237559
In vitro susceptibility of Ornithobacterium rhinotracheale to several antimicrobial drugs.	2003 Apr-Jun	12887209
3-Aminophenol as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.	2003 Dec	14630242
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.	2003 Jun	12739095
Survey of residual tetracycline antibiotics and sulfa drugs in kidneys of diseased animals in the Aichi Prefecture, Japan (1995-1999).	2003 May-Jun	12852565
Linkage isomerism, structure, and reactivity studies of sulfenamide complexes of cobalt(III).	2004 Aug 23	15310212
[Hygienic forecasting and toxicologic evaluation of potential danger caused by new sulphenamide vulcanization accelerators].	2005	15822343
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005 Jul	16250451
A study of sulfamerazine single crystals using atomic force microscopy, transmission light microscopy, and Raman spectroscopy.	2005 Sep	16052565
Dispersive solid-phase extraction for the determination of sulfonamides in chicken muscle by liquid chromatography.	2005 Sep 16	16130722
Direct organocatalytic asymmetric alpha-sulfenylation of activated C-H bonds in lactones, lactams, and beta-dicarbonyl compounds.	2005 Sep 19	16035005
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Synthesis, characterization, and biotoxicity of N N donor sulphonamide imine silicon(IV) complexes.	2006	17496998
Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods.	2006 Oct 27	16879830
Catalytic enantio- and diastereoselective formation of beta-sultones: ring-strained precursors for enantioenriched beta-hydroxysulfonyl derivatives.	2007	17330913
Synthesis and evaluation of galactofuranosyl N,N-dialkyl sulfenamides and sulfonamides as antimycobacterial agents.	2007 Apr 15	17303419
Preparation, characterization and in vivo conversion of new water-soluble sulfenamide prodrugs of carbamazepine.	2007 Dec 1	17928225
Reactions of sulfenic acid with 2-mercaptoethanol: a mechanism for the inhibition of gastric (H+-K+)-adenosine triphosphate by omeprazole.	2007 Jan	16998872
Toxoplasma gondii: cross-immunity against the enteric cycle.	2007 Jan	16828745
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].	2007 Mar	17580695
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007 Mar-Apr	17474530
Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS.	2007 Nov	17960854
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.	2007 Nov	17868178
Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 1. N-alkoxysulfenate derivatives.	2007 Nov 14	17941694
Validation of a Biacore method for screening eight sulfonamides in milk and porcine muscle tissues according to European decision 2002/657/EC.	2007 Nov-Dec	18196645
[Simultaneous determination of seven sulfonamides and metronidazole and chloramphenicol in cosmetics by high performance liquid chromatography].	2007 Sep	18161331
[Development of a fluorescence polarization immunoassay for sulfamerazine].	2008 Jul	18844174
Analysis of sulfamerazine in pond water and several fishes by high-performance liquid chromatography using molecularly imprinted solid-phase extraction.	2008 Jul	18496678
Intramolecular nonbonded S...N interaction in rabeprazole.	2008 Jun	18520084
Application of liquid-liquid-liquid microextraction and high-performance liquid-chromatography for the determination of sulfonamides in water.	2008 Mar 31	18331856
Purification of nine sulfonamides from chicken tissues by immunoaffinity chromatography using two monoclonal antibodies.	2008 Nov-Dec	19202813
Theoretical 14N nuclear quadrupole resonance parameters for sulfa drugs: sulfamerazine and sulfathiazole.	2008 Oct	18603459
Occurrence and elimination of antibiotics at four sewage treatment plants in Japan and their effects on bacterial ammonia oxidation.	2009	19237773
Degradation and elimination of various sulfonamides during anaerobic fermentation: a promising step on the way to sustainable pharmacy?	2009 Apr 1	19452918
Development and validation of a confirmatory method for the determination of sulphonamides in milk by liquid chromatography with diode array detection.	2009 Apr 1	19286007
The first bioreversible prodrug of metformin with improved lipophilicity and enhanced intestinal absorption.	2009 Jul 23	19522462
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 Nov 13	19586630

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).

Name

Type

Language

SULFAMERAZINE

Official Name

English

SULFAMERAZINE COMPONENT OF NEOTRIZINE

Common Name

English

SULFAMERAZINE [VANDF]

Common Name

English

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

Systematic Name

English

SULFAMERAZINE COMPONENT OF SULFONAMIDES DUPLEX

Common 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

SULFAMERAZINE COMPONENT OF SULFOSE

Common Name

English

TERFONYL COMPONENT SULFAMERAZINE

Common Name

English

SULFAMERAZINE COMPONENT OF TERFONYL

Common Name

English

SULPHAMERAZINE

Common Name

English

SULFAMERAZINE [USP-RS]

Common Name

English

TRISULFAPYRIMIDINES (SULFAMERAZINE) [ORANGE BOOK]

Common Name

English

SULFAMERAZINE [EP MONOGRAPH]

Common Name

English

SULFAMERAZINE COMPONENT OF SULFALOID

Common Name

English

SULFAMERAZINE [MI]

Common Name

English

SULFALOID COMPONENT SULFAMERAZINE

Common Name

English

SULFAMERAZINE COMPONENT OF TRIPLE SULFOID

Common Name

English

SULFAMERAZINE [GREEN BOOK]

Common Name

English

SULFONAMIDES DUPLEX COMPONENT SULFAMERAZINE

Common Name

English

SULFAMERAZINE [MART.]

Common Name

English

LANTRISUL COMPONENT SULFAMERAZINE

Common Name

English

SULFAMERAZINE COMPONENT OF LANTRISUL

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