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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 of SULFAMETHOXYPYRIDAZINE

SMILES

COC1=CC=C(NS(=O)(=O)C2=CC=C(N)C=C2)N=N1

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
Molecular Formula C11H12N4O3S
Molecular Weight 280.303
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

1957
118
Targets

Targets

Primary TargetPharmacologyConditionPotency
bacterial dihydropteroate synthetase
2
Target ID: bacterial dihydropteroate synthetase
Inhibitor
8504
 0.017 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
Unknown

Approved Use

Unknown
Curative
Approved
8583
Unknown

Approved Use

Unknown
Preventing
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
38 h
OTHER
https://www.karger.com/Article/Abstract/414199
SULFAMETHOXYPYRIDAZINE unknown
Homo sapiens
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6.5%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/4981614/
SULFAMETHOXYPYRIDAZINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse 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
unhealthy, 5 - 15
Health Status: unhealthy
Age Group: 5 - 15
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/5939973
Disc. AE: Skin rash...
AEs leading to
discontinuation/dose reduction:
Skin rash (33%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/5939973
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
unhealthy, 68
Health Status: unhealthy
Age Group: 68
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/13526923
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
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
unhealthy, 89
Health Status: unhealthy
Age Group: 89
Sex: F
Sources:
https://www.nejm.org/doi/full/10.1056/NEJM196101052640111
Disc. AE: Exfoliative dermatitis...
AEs leading to
discontinuation/dose reduction:
Exfoliative dermatitis (grade 5)
Sources:
https://www.nejm.org/doi/full/10.1056/NEJM196101052640111
AEs

AEs

AESignificanceDosePopulation
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
unhealthy, 5 - 15
Health Status: unhealthy
Age Group: 5 - 15
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/5939973
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
unhealthy, 68
Health Status: unhealthy
Age Group: 68
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/13526923
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
unhealthy, 68
Health Status: unhealthy
Age Group: 68
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/13526923
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
unhealthy, 68
Health Status: unhealthy
Age Group: 68
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/13526923
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
unhealthy, 68
Health Status: unhealthy
Age Group: 68
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/13526923
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
unhealthy, 89
Health Status: unhealthy
Age Group: 89
Sex: F
Sources:
https://www.nejm.org/doi/full/10.1056/NEJM196101052640111
Sourcing

Sourcing

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

PubMed

TitleDatePubMed
Multiresidue analysis of sulfonamides in meat by supramolecular solvent microextraction, liquid chromatography and fluorescence detection and method validation according to the 2002/657/EC decision.
2010-10-01
Assessment of antimicrobial usage and residues in commercial chicken eggs from smallholder poultry keepers in Morogoro municipality, Tanzania.
2010-08
Development and validation of a pressurised liquid extraction liquid chromatography-electrospray-tandem mass spectrometry method for beta-lactams and sulfonamides in animal feed.
2010-06-25
Antibiotic immunosensing: determination of sulfathiazole in water and honey.
2010-06-15
Determination of some sulfonamides and trimethoprim in chicken, fish muscle and eggs by liquid chromatography-tandem mass spectrometry.
2010-05-04
[Enzyme immunoassay for determination of sulfamethoxypyridazine in honey].
2010-04-16
Advantages of soybean peroxidase over horseradish peroxidase as the enzyme label in chemiluminescent enzyme-linked immunosorbent assay of sulfamethoxypyridazine.
2010-03-24
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
Degradation and elimination of various sulfonamides during anaerobic fermentation: a promising step on the way to sustainable pharmacy?
2009-04-01
Determination of ten sulphonamides in egg by liquid chromatography-tandem mass spectrometry.
2009-04-01
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.
2008-09-26
Therapeutic effect of a novel oxazolidinone, DA-7867, in BALB/c mice infected with Nocardia brasiliensis.
2008-09-10
Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan.
2008-08
Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles.
2008-02-13
[Use of soybean peroxidase for the enzyme immunoassay of sulfamethoxipyridazine in milk].
2007-11-28
Rapid simultaneous determination of 14 sulfonamides in wastewater by liquid chromatography tandem mass spectrometry.
2007-10
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].
2007-09
Monoclonal antibody-based fluorescence polarization immunoassay for sulfamethoxypyridazine and sulfachloropyridazine.
2007-08-22
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.
2007-08-03
Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms.
2007-03-28
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
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.
2007-03-21
Development of a group-specific immunoassay for sulfonamides. Application to bee honey analysis.
2007-02-15
An in vivo evaluation of the induction of abnormal sperm morphology by sulphamethoxypyridazine: pyrimethamine (Metakelfin).
2007-01-01
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.
2007
Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry.
2006-10-13
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.
2006-09-15
Determination of sulfonamides in selected Malaysian swine wastewater by high-performance liquid chromatography.
2006-09-15
Multiresidue determination of sulfonamides in edible catfish, shrimp and salmon tissues by high-performance liquid chromatography with postcolumn derivatization and fluorescence detection.
2006-08-18
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.
2006-06-28
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2006-01-03
Sulfamethoxypyridazine-responsive pemphigoid nodularis: a report of two cases.
2005-08
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].
2005-07
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
Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection.
2004-08-20
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).
2004-08
Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy.
2004-06
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.
2003-06
Simultaneous determination of binary mixtures of trimethoprim and sulfamethoxazole or sulphamethoxypyridazine by the bivariate calibration spectrophotometric method.
2002-08-22
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.
2002-06
Evaluation of sulfa drugs against recombinant Pneumocystis carinii dihydropteroate synthetase and in vivo.
1996-09-01
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.
1996-04
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.
1995-08
Drugs as allergens: detection and combining site specificities of IgE antibodies to sulfamethoxazole.
1988-12
In vitro activity of antimicrobial agents against mycobacteria.
1988
Patents

Patents

US20070110685
2

Sample Use Guides

In Vivo Use Guide
Single weekly dose
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:23:40 GMT 2025
Edited
by admin
on Mon Mar 31 21:23:40 GMT 2025
Record UNII
T034E4NS2Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFAMETHOXYPYRIDAZINE
INN   MART.   MI   WHO-DD   WHO-IP  
INN  
Official Name English
LEDERKYN
Preferred 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
SULPHAMETHOXYPYRIDAZINE
Common Name English
RETASULPHINE
Common 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
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
WHO-VATC QJ01EW15
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
WHO-ATC J01ED05
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
WHO-VATC QJ01EQ15
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
Code System Code Type Description
NSC
757875
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
WIKIPEDIA
SULFAMETHOXYPYRIDAZINE
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
CHEBI
102516
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHOXYPYRIDAZINE
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY Description: A white or yellowish white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; sparingly soluble in ethanol (~750 g/l) TS; soluble in acetone R. Category: Antibacterial. Storage: Sulfamethoxypyridazine should be kept in a well-closed container, protected from light. Additional information: Sulfamethoxypyridazine becomes gradually coloured on exposure to light. Definition: Sulfamethoxypyridazine contains not less than 99.0% and not more than 101.0% of C11H12N4O3S, calculated with reference to the dried substance.
ECHA (EC/EINECS)
201-272-5
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
CAS
80-35-3
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
INN
780
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
ChEMBL
CHEMBL268869
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
MESH
D013421
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
MERCK INDEX
m10321
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C80795
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
DRUG CENTRAL
2515
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
SMS_ID
100000083251
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
PUBCHEM
5330
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
FDA UNII
T034E4NS2Z
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
RXCUI
10181
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY RxNorm
EVMPD
SUB10712MIG
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
DRUG BANK
DB13773
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023611
Created by admin on Mon Mar 31 21:23:40 GMT 2025 , Edited by admin on Mon Mar 31 21:23:40 GMT 2025
PRIMARY
Related Record Type Details
Structure of SODIUM SULFAPYRIDAZINE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of SULFAMETHOXYPYRIDAZINE
ACTIVE MOIETY
NIH
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