SULFAMETHOXYPYRIDAZINE

First approved in 1957

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=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)C=C1

InChI

InChIKey=VLYWMPOKSSWJAL-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/13783165
Curator's Comment: description was created based on several sources, including DOI: 10.1002/0471238961.1921120606152505.a01 http://www.ncbi.nlm.nih.gov/pubmed/7486915

Sulfamethoxypyridazine is a sulfonamide antibacterial with a broad spector of activity. It acts by inhibiting the enzyme dihydropteroate synthetase (DHPS), required for the synthesis of nucleic acids and microbial cells.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial dihydropteroate synthetase 2 Target ID: bacterial dihydropteroate synthetase Sources: http://www.ncbi.nlm.nih.gov/pubmed/7486915	Inhibitor 8297		0.017 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205 Sources: http://www.ncbi.nlm.nih.gov/pubmed/13783165	Curative	Approved 8429	Unknown Approved Use Unknown
Bronchopneumonia 4 Sources: http://www.ncbi.nlm.nih.gov/pubmed/13767473	Curative	Approved 8429	Unknown Approved Use Unknown
Rheumatic fever 6 Sources: http://www.ncbi.nlm.nih.gov/pubmed/5939973	Preventing	Preclinical	Unknown Approved Use Unknown
Dermatitis herpetiformis 9 Sources: http://www.ncbi.nlm.nih.gov/pubmed/13842251	Primary	Preclinical	Unknown Approved Use Unknown
Herpes gestationis 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/13842251	Primary	Preclinical	Unknown Approved Use Unknown
Linear IgA disease 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2692691	Primary	Preclinical	Unknown Approved Use Unknown
Cicatricial pemphigoid 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2692691	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.75 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6081878/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETHOXYPYRIDAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
0.85 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6081878/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		SULFAMETHOXYPYRIDAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
38 h OTHER https://www.karger.com/Article/Abstract/414199			SULFAMETHOXYPYRIDAZINE unknown	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
6.5% REVIEW https://pubmed.ncbi.nlm.nih.gov/4981614/			SULFAMETHOXYPYRIDAZINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
3 g 1 times / week multiple, oral Highest studied dose Dose: 3 g, 1 times / week Route: oral Route: multiple Dose: 3 g, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/5939973 Page: p.507	unhealthy, 5 - 15 n = 6 Health Status: unhealthy Condition: Rheumatic fever Age Group: 5 - 15 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/5939973 Page: p.507	Disc. AE: Skin rash... AEs leading to discontinuation/dose reduction: Skin rash (33%) Sources: https://pubmed.ncbi.nlm.nih.gov/5939973 Page: p.507
1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688	unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688	Disc. AE: Skin rash, Itching... AEs leading to discontinuation/dose reduction: Skin rash (severe) Itching (severe) Hepatitis (acute) Fever Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688
0.5 g 1 times / day multiple, oral Studied dose Dose: 0.5 g, 1 times / day Route: oral Route: multiple Dose: 0.5 g, 1 times / day Sources: https://www.nejm.org/doi/full/10.1056/NEJM196101052640111 Page: p.40	unhealthy, 89 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 89 Sex: F Population Size: 1 Sources: https://www.nejm.org/doi/full/10.1056/NEJM196101052640111 Page: p.40	Disc. AE: Exfoliative dermatitis... AEs leading to discontinuation/dose reduction: Exfoliative dermatitis (grade 5) Sources: https://www.nejm.org/doi/full/10.1056/NEJM196101052640111 Page: p.40

AEs

AE	Significance	Dose	Population
Skin rash	33% Disc. AE	3 g 1 times / week multiple, oral Highest studied dose Dose: 3 g, 1 times / week Route: oral Route: multiple Dose: 3 g, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/5939973 Page: p.507	unhealthy, 5 - 15 n = 6 Health Status: unhealthy Condition: Rheumatic fever Age Group: 5 - 15 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/5939973 Page: p.507
Fever	Disc. AE	1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688	unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688
Hepatitis	acute Disc. AE	1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688	unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688
Itching	severe Disc. AE	1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688	unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688
Skin rash	severe Disc. AE	1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688	unhealthy, 68 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 68 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13526923 Page: p.688
Exfoliative dermatitis	grade 5 Disc. AE	0.5 g 1 times / day multiple, oral Studied dose Dose: 0.5 g, 1 times / day Route: oral Route: multiple Dose: 0.5 g, 1 times / day Sources: https://www.nejm.org/doi/full/10.1056/NEJM196101052640111 Page: p.40	unhealthy, 89 n = 1 Health Status: unhealthy Condition: Urinary-tract infection Age Group: 89 Sex: F Population Size: 1 Sources: https://www.nejm.org/doi/full/10.1056/NEJM196101052640111 Page: p.40

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:102516	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:102516
ChemicalBook	CB1107025	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1107025
MolPort	MolPort-000-697-322	https://www.molport.com/shop/molecule-link/MolPort-000-697-322
ZINC	ZINC000000049141	http://zinc15.docking.org/substances/ZINC000000049141
eMolecules	631768	https://www.emolecules.com/cgi-bin/more?vid=631768

PubMed

Title	Date	PubMed
Drugs as allergens: detection and combining site specificities of IgE antibodies to sulfamethoxazole.	1988 Dec	3237218
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.	1995 Aug	7486915
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.	1996 Apr	8849260
Evaluation of sulfa drugs against recombinant Pneumocystis carinii dihydropteroate synthetase and in vivo.	1996 Sep-Oct	8822843
Simultaneous determination of binary mixtures of trimethoprim and sulfamethoxazole or sulphamethoxypyridazine by the bivariate calibration spectrophotometric method.	2002 Aug 22	12151067
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.	2002 Jun	12019133
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.	2003 Jun	12739095
Determination of some sulfonamides and trimethoprim in chicken, fish muscle and eggs by liquid chromatography-tandem mass spectrometry.	2004 Apr-Jun	20437390
Robustness of the extraction step when parallel factor analysis (PARAFAC) is used to quantify sulfonamides in kidney by high performance liquid chromatography-diode array detection (HPLC-DAD).	2004 Aug	15284923
Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection.	2004 Aug 20	15481463
Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy.	2004 Jun	15198720
Sulfamethoxypyridazine-responsive pemphigoid nodularis: a report of two cases.	2005 Aug	16021154
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005 Jul	16250451
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection.	2006 Aug 18	16750659
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.	2006 Jun 28	16786990
Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry.	2006 Oct 13	16822516
Multiwalled carbon nanotubes as sorbent for on-line coupling of solid-phase extraction to high-performance liquid chromatography for simultaneous determination of 10 sulfonamides in eggs and pork.	2006 Sep 15	16820156
Determination of sulfonamides in selected Malaysian swine wastewater by high-performance liquid chromatography.	2006 Sep 15	16806241
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.	2007	17287722
Monoclonal antibody-based fluorescence polarization immunoassay for sulfamethoxypyridazine and sulfachloropyridazine.	2007 Aug 22	17661485
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007 Aug 3	17433345
Development of a group-specific immunoassay for sulfonamides. Application to bee honey analysis.	2007 Feb 15	19071396
Simultaneous determination of 17 sulfonamides and the potentiators ormetoprim and trimethoprim in salmon muscle by liquid chromatography with tandem mass spectrometry detection.	2007 Jan-Feb	17373466
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.	2007 Mar 21	17300200
Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms.	2007 Mar 28	17386777
Rapid simultaneous determination of 14 sulfonamides in wastewater by liquid chromatography tandem mass spectrometry.	2007 Oct	17763515
[Use of soybean peroxidase for the enzyme immunoassay of sulfamethoxipyridazine in milk].	2007 Sep-Oct	18038682
Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan.	2008 Aug	17961277
Antibiotic immunosensing: determination of sulfathiazole in water and honey.	2010 Jun 15	20441943
Advantages of soybean peroxidase over horseradish peroxidase as the enzyme label in chemiluminescent enzyme-linked immunosorbent assay of sulfamethoxypyridazine.	2010 Mar 24	20175541

Patents

Sample Use Guides

In Vivo Use Guide

Single weekly dose

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

SULFAMETHOXYPYRIDAZINE

Official Name

English

SULFAMETHOXYPYRIDAZINE [WHO-IP]

Common Name

English

SULFAMETHOXYPYRIDAZINUM [WHO-IP LATIN]

Common Name

English

CL-13494

Code

English

SULFAMETHOXYPYRIDAZINE [MI]

Common Name

English

NSC-757875

Code

English

DEPOVERNIL

Common Name

English

RETASULPHINE

Common Name

English

LEDERKYN

Brand Name

English

SULFAMETHOXYPYRIDAZINE [MART.]

Common Name

English

sulfamethoxypyridazine [INN]

Common Name

English

Sulfamethoxypyridazine [WHO-DD]

Common Name

English

N(SUP 1)-(6-METHOXY-3-PYRIDAZINYL)SULFANILAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29739