SULFAMETER

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H12N4O3S
Molecular Weight	280.303
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CN=C(NS(=O)(=O)C2=CC=C(N)C=C2)N=C1

InChI

InChIKey=GPTONYMQFTZPKC-UHFFFAOYSA-N

InChI=1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

HIDE SMILES / InChI

Description
Sources: http://www.abcam.com/sulfameter-bayrena-ab143030.html
Curator's Comment: description was created based on several sources, including: http://www.sigmaaldrich.com/catalog/product/sigma/s0383?lang=es®ion=ES http://www.medchemexpress.com/sulfameter.html

Sulfametoxydiazine (INN) or sulfamethoxydiazine (USAN: sulfameter) is a long-acting sulfonamide antibacterial, shows bacteriostatic effects against Gram positive and Gram negative bacteria in vivo. It is used as a leprostatic agent and in the treatment of urinary tract infections. Orally active. Sulfonamides block the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfonamides are competitive inhibitors of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. Sulfameter is a dihydrofolate reductase (DHFR) inhibitor. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: http://www.abcam.com/sulfameter-bayrena-ab143030.html	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205 Sources: http://www.medchemexpress.com/sulfameter.html	Curative		Approved 8429	SULLA Approved Use Unknown Launch Date 1966

C_max

Value	Dose	Co-administered	Analyte	Population
44.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5072410/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETER plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1599 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5072410/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETER plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5072410/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETER plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
250 mg/kg 1 times / day steady, oral Recommended Dose: 250 mg/kg, 1 times / day Route: oral Route: steady Dose: 250 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/	unhealthy, adult n = 20 Health Status: unhealthy Condition: chronic urinary-tract infection Age Group: adult Sex: unknown Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/	Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/
500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/	unhealthy, adult n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/	Disc. AE: Nasal stuffiness, Edema lip... AEs leading to discontinuation/dose reduction: Nasal stuffiness (2 patients) Edema lip (1 patient) Leukopenia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/
2 g single, oral Studied dose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/468450/	healthy, adult n = 6 Health Status: healthy Age Group: adult Sex: unknown Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/468450/	Sources: https://pubmed.ncbi.nlm.nih.gov/468450/

AEs

AE	Significance	Dose	Population
Edema lip	1 patient Disc. AE	500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/	unhealthy, adult n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/
Leukopenia	1 patient Disc. AE	500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/	unhealthy, adult n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/
Nasal stuffiness	2 patients Disc. AE	500 mg/kg 1 times / day steady, oral Recommended Dose: 500 mg/kg, 1 times / day Route: oral Route: steady Dose: 500 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/	unhealthy, adult n = 43 Health Status: unhealthy Condition: pustular acne vulgaris Age Group: adult Sex: unknown Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/4246303/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY565548	https://www.001chemical.com/chem/651-06-9
3B Scientific (Wuhan) Corp	3B3-003585	http://www.3bsc.com/index/pro_info.php?id=25476
AA Blocks	AA00IBDG	http://www.aablocks.com/goods/Goods/detail?id=AA00IBDG
AHH Chemical co.,ltd	MT-17238	http://www.ahhchemical.com/product/MT-17238.html
AK Scientific, Inc. (AKSCI)	K058	http://www.aksci.com/item_detail.php?cat=K058
Aaron Chemicals	AR00IC58	http://www.aaronchem.com/651-06-9
AbMole Bioscience	M5977	http://www.abmole.com/products/sulfameter.html
Acadechem	ACDS-028478	http://www.acadechemical.com/product/103177
Achemo Scientific Limited	AC-16807	http://www.achemo.com/product_view.asp?ID=6697
Achemtek	0104-008679	http://www.achemtek.com/651-06-9
Active Biopharma	ABP000630	http://www.activebiopharma.com/651-06-9
Alfa Chemistry	AP651069	https://reagents.alfa-chemistry.com/product/sulfameter-cas-651-06-9-14638.html
Allbio Pharm Co., Ltd	AD02699	http://www.allbiopharm.com/product/n/AD02699
Angene	AGN-PC-07Y4WB	http://www.angenechemical.com/productshow/AGN-PC-07Y4WB.html
ApexBio Technology	B2038	http://www.apexbt.com/sulfameter.html
Ark Pharm	AK126667	http://www.arkpharminc.com/products/651-06-9.html
AstaTech, Inc.	23101	http://www.astatechinc.com/CPSResult.php?CRNO=26842
BLD Pharm	BD13105	http://www.bldpharm.com/products/651-06-9.html
BioCrick	BCC4855	http://www.biocrick.com/Sulfameter-BCC4855.html
BioSynth	W-104807	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-104807.html
CSNpharm	CSN11047	https://www.csnpharm.com/products/sulfameter.html
Chem Scene	CS-2158	http://www.chemscene.com/651-06-9.html
ChemMol	30107605	http://www.chemmol.com/chemmol/30107605.html
ChemMol	49428489	http://www.chemmol.com/chemmol/49428489.html
ChemMol	99124934	http://www.chemmol.com/chemmol/99124934.html
Chemenu	CM110211	http://www.chemenu.com/products/CM110211
Chemspace	CSSB00000027250	https://chem-space.com/CSSB00000027250
Clearsynth	CS-T-42915	https://www.clearsynth.com/en/CST42915.html
DC Chemicals	DCAPI1294	http://www.dcchemicals.com//product_show-Sulfameter_Bayrena_.html
Debye Scientific	DB-054761	http://www.debyesci.com/cas_651-06-9.html
Enamine	Z1522567176	https://www.enaminestore.com/catalog/Z1522567176
Finetech	FT-0632748	http://www.finetechnology-ind.com/prod/detail/pub/651-06-9.html
Glentham Life Sciences	GA7394	http://www.glentham.com/products/product/GA7394/
Hairui	HR136088	http://www.hairuichem.com/en/product/651-06-9.html
LGC Standards	DRE-C16995150	https://www.lgcstandards.com/US/en/p/DRE-C16995150
LGC Standards	LGCFOR1942.00	https://www.lgcstandards.com/US/en/p/LGCFOR1942.00
LGC Standards	MM1942.00	https://www.lgcstandards.com/US/en/p/MM1942.00
Lab Network	LN00194872	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00194872
MedChem Express	HY-B0213	https://www.medchemexpress.com/sulfameter.html
Molcore	MC565548	https://www.molcore.com/product/651-06-9
MuseChem	A000416	https://www.musechem.com/product/A000416.html
OChem	5216	http://www.ocheminc.com/index.php?act=psearch&pid=51S069
Oakwood	322073	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=195750&ExtHyperLink=1
Selleck Chemicals	S1618	http://www.selleckchem.com/products/Sulfameter(Bayrena).html
Sigma-Aldrich	46834_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/46834?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	S0383_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/s0383?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S012821	http://www.sinfoobiotech.com/product/1016219
Smolecule	S544117	http://www.smolecule.com/products/s544117
THE BioTek	bt-285521	https://www.thebiotek.com/product/inhibitors/bt-285521
Yuhao Chemical	XJ1226	http://www.chemyuhao.com/651-06-9.html
abcr GmbH	AB449507	http://www.abcr.com/shop/en/AB449507
mcule	MCULE-7934329522	https://mcule.com/MCULE-7934329522/

PubMed

Title	Date	PubMed
Anticryptosporidial activity is associated with specific sulfonamides in immunosuppressed rats.	1991 Apr	2010856
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.	1996 Apr	8849260
Hydrogen bonding in sulfonamides.	2001 Dec	11745765
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.	2003 Jun	12739095
Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy.	2004 Jun	15198720
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005 Jul	16250451
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Complementary use of model-free and modelistic methods in the analysis of solid-state kinetics.	2005 May 26	16852219
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.	2006 Jun 28	16786990
Development of an immunochromatographic lateral-flow test strip for rapid detection of sulfonamides in eggs and chicken muscles.	2007 Mar 21	17316015
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
ELISA for sulfonamides and its application for screening in water contamination.	2008 Aug 13	18616276
Characterization of integrons-mediated antimicrobial resistance among Escherichia coli strains isolated from bovine mastitis.	2008 Feb 5	17897793
Desolvation kinetics of sulfameter solvates.	2008 Jun	17975809
[Simultaneous determination of sulfonamides and fluoroquinolones residues in chicken by high performance liquid chromatography-electrospray tandem mass spectrometry].	2008 May	18724674
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.	2008 Sep 26	18723177
On-line coupling of dynamic microwave-assisted extraction to solid-phase extraction for the determination of sulfonamide antibiotics in soil.	2009 Aug 26	19646585
[Investigation of sulfonamides and tetracyclines antibiotics in soils from various vegetable fields].	2009 Jun 15	19662865
Analysis of sulfonamides in environmental water samples based on magnetic mixed hemimicelles solid-phase extraction coupled with HPLC-UV detection.	2009 Nov	19836824
Fast and selective extraction of sulfonamides from honey based on magnetic molecularly imprinted polymer.	2009 Nov 11	19817457
Determination of 76 pharmaceutical drugs by liquid chromatography-tandem mass spectrometry in slaughterhouse wastewater.	2009 Nov 20	19825501
A new and simple method to determine trace levels of sulfonamides in honey by high performance liquid chromatography with fluorescence detection.	2009 Oct 23	19505691
N-(4,6-Dimethyl-pyrimidin-2-yl)-4-(oxolan-2-ylamino)benzene-sulfonamide.	2009 Oct 28	21578440
Determination of sulfonamides in soil samples based on alumina-coated magnetite nanoparticles as adsorbents.	2010 Apr 30	20417329
Gene expression signature-based screening identifies new broadly effective influenza a antivirals.	2010 Oct 4	20957181

Patents

Sample Use Guides

In Vivo Use Guide

Loading dose first-day only (single dose): 1500 mg (3 tablets) Daily maintenance (single dose at 24 hour intervals): 500 mg (1 tablet).

Route of Administration: Oral

In Vitro Use Guide

Titrations of antibacterial activity were carried out by making twofold serial dilutions dilutions of plasma or serum and adding an equal volume (0.5 ml.) of a 10-5 dilution of an overnight culture of a strain of Escherichia coli which had been isolated from the peritoneal fluid of a patient with peritonitis and which was consistently sensitive to 0.30 mg. of sulfamethoxydiazine per 100 ml. of broth. Study of antibacterial titers showed that at 1: 64 the sulfonamide concentrations varied from 7 to 14 mg. per 100 ml

Name

Type

Language

SULFAMETER

Official Name

English

N(SUP 1)-(5-METHOXY-2-PYRIMIDINYL)SULFANILAMIDE

Systematic Name

English

ULTRAX

Brand Name

English

AHR-857

Code

English

SULFAMETHOXYDIAZINE

Common Name

English

SH-613

Code

English

SULFAMETER [MI]

Common Name

English

SULFAMETER [USAN]

Common Name

English

Sulfametoxydiazine [WHO-DD]

Common Name

English

BENZENESULFONAMIDE, 4-AMINO-N-(5-METHOXY-2-PYRIMIDINYL)-

Systematic Name

English

SULFAMETHOXYPYRIMIDINE

Common Name

English

BAY-5400

Code

English

SULFAMETOXYDIAZINE

Official Name

English

sulfametoxydiazine [INN]

Common Name

English

SULFAMETER [ORANGE BOOK]

Common Name

English

NSC-757874

Code

English

NSC-683528

Code

English

SULLA

Brand Name

English

Classification Tree Code System Code

WHO-ATC

J01ED04