U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=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
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
114
Targets

Targets

Primary TargetPharmacologyConditionPotency
bacterial dihydropteroate synthetase
2
Target ID: bacterial dihydropteroate synthetase
Inhibitor
8297
 0.017 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
Unknown

Approved Use

Unknown
Curative
Approved
8429
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
0.75 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
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
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

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
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

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
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

PubMed

TitleDatePubMed
In vitro activity of antimicrobial agents against mycobacteria.
1988
Drugs as allergens: detection and combining site specificities of IgE antibodies to sulfamethoxazole.
1988 Dec
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.
1995 Aug
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.
1996 Apr
Evaluation of sulfa drugs against recombinant Pneumocystis carinii dihydropteroate synthetase and in vivo.
1996 Sep-Oct
Simultaneous determination of binary mixtures of trimethoprim and sulfamethoxazole or sulphamethoxypyridazine by the bivariate calibration spectrophotometric method.
2002 Aug 22
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.
2002 Jun
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.
2003 Jun
Determination of some sulfonamides and trimethoprim in chicken, fish muscle and eggs by liquid chromatography-tandem mass spectrometry.
2004 Apr-Jun
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
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
Possible association between different congenital abnormalities and use of different sulfonamides during pregnancy.
2004 Jun
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection.
2004 Sep 8
Sulfamethoxypyridazine-responsive pemphigoid nodularis: a report of two cases.
2005 Aug
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].
2005 Jul
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2005 Sep-Oct
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
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.
2006 Jun 28
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
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
Determination of sulfonamides in selected Malaysian swine wastewater by high-performance liquid chromatography.
2006 Sep 15
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.
2007
Monoclonal antibody-based fluorescence polarization immunoassay for sulfamethoxypyridazine and sulfachloropyridazine.
2007 Aug 22
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.
2007 Aug 3
Development of a group-specific immunoassay for sulfonamides. Application to bee honey analysis.
2007 Feb 15
An in vivo evaluation of the induction of abnormal sperm morphology by sulphamethoxypyridazine: pyrimethamine (Metakelfin).
2007 Jan 1
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
Development of an enzyme-linked immunosorbent assay for seven sulfonamide residues and investigation of matrix effects from different food samples.
2007 Mar 21
Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms.
2007 Mar 28
Rapid simultaneous determination of 14 sulfonamides in wastewater by liquid chromatography tandem mass spectrometry.
2007 Oct
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].
2007 Sep
[Use of soybean peroxidase for the enzyme immunoassay of sulfamethoxipyridazine in milk].
2007 Sep-Oct
Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan.
2008 Aug
Immunochemical assays for direct sulfonamide antibiotic detection in milk and hair samples using antibody derivatized magnetic nanoparticles.
2008 Feb 13
Therapeutic effect of a novel oxazolidinone, DA-7867, in BALB/c mice infected with Nocardia brasiliensis.
2008 Sep 10
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.
2008 Sep 26
Degradation and elimination of various sulfonamides during anaerobic fermentation: a promising step on the way to sustainable pharmacy?
2009 Apr 1
Determination of ten sulphonamides in egg by liquid chromatography-tandem mass spectrometry.
2009 Apr 1
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
Assessment of antimicrobial usage and residues in commercial chicken eggs from smallholder poultry keepers in Morogoro municipality, Tanzania.
2010 Aug
Antibiotic immunosensing: determination of sulfathiazole in water and honey.
2010 Jun 15
Development and validation of a pressurised liquid extraction liquid chromatography-electrospray-tandem mass spectrometry method for beta-lactams and sulfonamides in animal feed.
2010 Jun 25
Advantages of soybean peroxidase over horseradish peroxidase as the enzyme label in chemiluminescent enzyme-linked immunosorbent assay of sulfamethoxypyridazine.
2010 Mar 24
[Enzyme immunoassay for determination of sulfamethoxypyridazine in honey].
2010 Mar-Apr
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 Oct 1
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 Sat Dec 16 04:48:04 UTC 2023
Edited
by admin
on Sat Dec 16 04:48:04 UTC 2023
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
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
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
WHO-VATC QJ01EW15
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
WHO-ATC J01ED05
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
WHO-VATC QJ01EQ15
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
Code System Code Type Description
NSC
757875
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
WIKIPEDIA
SULFAMETHOXYPYRIDAZINE
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
CHEBI
102516
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHOXYPYRIDAZINE
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
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 Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
CAS
80-35-3
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
INN
780
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
ChEMBL
CHEMBL268869
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
MESH
D013421
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
MERCK INDEX
m10321
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C80795
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
DRUG CENTRAL
2515
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
SMS_ID
100000083251
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
PUBCHEM
5330
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
FDA UNII
T034E4NS2Z
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
RXCUI
10181
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY RxNorm
EVMPD
SUB10712MIG
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
DRUG BANK
DB13773
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID5023611
Created by admin on Sat Dec 16 04:48:04 UTC 2023 , Edited by admin on Sat Dec 16 04:48:04 UTC 2023
PRIMARY
Related Record Type Details
Structure of SODIUM SULFAPYRIDAZINE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of SULFAMETHOXYPYRIDAZINE
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