SULFADIMETHOXINE SODIUM

First approved in 1958

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H13N4O4S.Na
Molecular Weight	332.311
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].COC1=NC(OC)=NC([N-]S(=O)(=O)C2=CC=C(N)C=C2)=C1

InChI

InChIKey=DQDZQHMCPDUUPC-UHFFFAOYSA-N

InChI=1S/C12H13N4O4S.Na/c1-19-11-7-10(14-12(15-11)20-2)16-21(17,18)9-5-3-8(13)4-6-9;/h3-7H,13H2,1-2H3;/q-1;+1

HIDE SMILES / InChI

Molecular Formula	C12H14N4O4S
Molecular Weight	310.329
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://drug.report/Sulfadimethoxine/
Curator's Comment: description was created based on several sources, including http://www.fda.gov/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm118359.htm; http://www.ema.europa.eu/docs/en_GB/document_library/Report/2013/02/WC500138474.pdf

Sulfadimethoxine is a sulfonamide antibacterial used to treat many infections including treatment of respiratory, urinary tract, enteric, and soft tissue infections. It is most frequently used in veterinary medicine, although it is approved in some countries for use in humans. Sulfadimethoxine inhibits bacterial synthesis of folic acid (pteroylglutamic acid) from para-aminobenzoic acid. Sulfadimethoxine is approved in Russia for use in humans, including children, and has been successfully used there for more than 35 years and is available as an over-the-counter drug manufactured by a number of Russian pharmaceutical companies. In USA and Europe sulfadimethoxine is approved in a veterinary medicinal products. ANADA was approved by FDA in US in 1997 as an Over the Counter medicine for treatment of bovine respiratory disease complex (shipping fever complex) and bacterial pneumonia associated with Pasteurella Spp. Sensitive to sulfadimethoxine; necrotic pododermatitis (foot rot) and calf diphtheria caused by Fusobacterium necrophorum (Sphaerophorus necrophorus) sensitive to sulfadimethoxine. Bioequivalence for this generic animal drug, Sulfadimethoxine Injection 40%, was established by demonstration of chemical equivalence to the pioneer product, Hoffmann-La Roche's Albon® Injection 40% (NADA 041-245).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Folate biosynthesis 3 Target ID: map00790 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23859210	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pneumonia associated with Pasteurella Spp. 2 Sources: http://www.fda.gov/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm118359.htm	Curative		Approved 8583	ANADA Approved Use For treatment of bovine respiratory disease complex (shipping fever complex) and bacterial pneumonia associated with Pasteurella Spp. sensitive to sulfadimethoxine; necrotic pododermatitis (foot rot) and calf diphtheria caused by Fusobacterium necrophorum (Sphaerophorus necrophorus) sensitive to sulfadimethoxine Launch Date 1997
Calf diphtheria 6 Sources: http://www.fda.gov/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm118359.htm	Curative		Approved 8583	ANADA Approved Use For treatment of bovine respiratory disease complex (shipping fever complex) and bacterial pneumonia associated with Pasteurella Spp. sensitive to sulfadimethoxine; necrotic pododermatitis (foot rot) and calf diphtheria caused by Fusobacterium necrophorum (Sphaerophorus necrophorus) sensitive to sulfadimethoxine Launch Date 1997

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt196895561			SULFADIMETHOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
7% EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt196895561			SULFADIMETHOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
500 mg 2 times / day multiple, oral Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4228868	unhealthy, 20 Health Status: unhealthy Age Group: 20 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/4228868	Disc. AE: Cholestatic jaundice... AEs leading to discontinuation/dose reduction: Cholestatic jaundice (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/4228868
500 mg 1 times / day multiple, oral Studied dose Dose: 500 mg, 1 times / day Route: oral Route: multiple Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5325539	unhealthy Health Status: unhealthy Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/5325539	Sources: https://pubmed.ncbi.nlm.nih.gov/5325539

AEs

AE	Significance	Dose	Population
Cholestatic jaundice	mild Disc. AE	500 mg 2 times / day multiple, oral Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4228868	unhealthy, 20 Health Status: unhealthy Age Group: 20 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/4228868

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-036287	http://www.3bsc.com/index/pro_info.php?id=58318
Aaron Chemicals	AR00HAUY	http://www.aaronchem.com/1037-50-9
abcr GmbH	AB251954	http://www.abcr.de/shop/en/AB251954
Achemtek	0104-023973	http://www.achemtek.com/1037-50-9
AHH Chemical co.,ltd	MT-58842	http://www.ahhchemical.com/product/MT-58842.html
AK Scientific, Inc. (AKSCI)	M933	http://www.aksci.com/item_detail.php?cat=M933
Alichem	89000446	http://www.alichem.com/en/products/1037-50-9.html
Ambinter	Amb22264695	http://www.ambinter.com/reference/22264695
Angel Pharmatech	AG333427	http://www.angelpharmatech.com/1037-50-9.html
Aurora Fine Chemicals LLC	A30.260.894	http://online.aurorafinechemicals.com/info?ID=A30.260.894
BioChemPartner	BCP15082	http://www.biochempartner.com/1037-50-9-BCP15082
BioSynth	W-108840	https://www.biosynth.com/products/biochemistry/other-biochemicals/products/W-108840.html
BLD Pharm	BD152146	http://www.bldpharm.com/products/1037-50-9.html
BOC Sciences	1037-50-9	https://www.bocsci.com/sulfadimethoxine-sodium-salt-cas-1037-50-9-item-358106.html
Chem Scene	CS-0014402	http://www.chemscene.com/1037-50-9.html
ChemMol	49429309	http://www.chemmol.com/chemmol/49429309.html
Chemspace	CSSB00000070610	https://chem-space.com/CSSB00000070610
Combi-Blocks	QE-9009	http://www.combi-blocks.com/cgi-bin/find.cgi?QE-9009
Debye Scientific	DB-040482	http://www.debyesci.com/cas_1037-50-9.html
eNovation Chemicals	D128662	https://www.enovationchem.com/ProductDetails.asp?ProductID=D128662
eNovation Chemicals	D961680	https://www.enovationchem.com/ProductDetails.asp?ProductID=D961680
Hairui	HR137624	http://www.hairuichem.com/en/product/1037-50-9.html
LGC Standards	LGCFOR1020.00	https://www.lgcstandards.com/US/en/p/LGCFOR1020.00
LGC Standards	MM1020.00	https://www.lgcstandards.com/US/en/p/MM1020.00
MedChem Express	HY-B0337A	https://www.medchemexpress.com/sulfadimethoxine-sodium.html
Molcore	MC503532	https://www.molcore.com/product/1037-50-9
MolPort	MolPort-021-783-035	https://www.molport.com/shop/molecule-link/MolPort-021-783-035
MolPort	MolPort-027-720-584	https://www.molport.com/shop/molecule-link/MolPort-027-720-584
Selleck Chemicals	S5096	http://www.selleckchem.com/products/sulfadiMethoxine-sodium.html
TCI (Tokyo Chemical Industry)	S0589	http://www.tcichemicals.com/eshop/en/us/commodity/S0589/index.html

PubMed

Title	Date	PubMed
Diagnosis and treatment of Eimeria macusaniensis in an adult alpaca with signs of colic.	2009-03	18036857
Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan.	2008-08	17961277
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.	2007-12	18024727
Organic solvents-free technique for determining sulfadimethoxine and its metabolites in chicken meat.	2007-11-16	17936765
Efficacy of eleven antimicrobials against a gregarine parasite (Apicomplexa: Protozoa).	2007-11-12	17997852
Cytotoxicity is predicted by unbound and not total bilirubin concentration.	2007-11	18049372
Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS.	2007-11	17960854
Determination of sulphonamides in animal tissues by high performance liquid chromatography with pre-column derivatization of 9-fluorenylmethyl chloroformate.	2007-11	17868178
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].	2007-09	18161327
Determination of residues of sulphonamide in eggs and laying hens.	2007-07	17545104
Use of sulfadimethoxine in intensive calf farming: evaluation of transfer to stable manure and soil.	2007-06	17368507
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007-05-04	17474530
Aquatic toxicity of acetaminophen, carbamazepine, cimetidine, diltiazem and six major sulfonamides, and their potential ecological risks in Korea.	2007-04	17223195
Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms.	2007-03-28	17386777
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	17373466
Development of an immunochromatographic lateral-flow test strip for rapid detection of sulfonamides in eggs and chicken muscles.	2007-03-21	17316015
Depression of T cell-mediated immunity reduces sulfadimethoxine-induced capsular inflammation and inhibits associated development of invasive thyroid follicular cell carcinomas in rats.	2007-03	17270018
Observational study of hepatic cytochrome P-450 protein expression and activity in summer flounder (Paralichtys dentatus) after combination ormetoprim-sulfadimethoxine treatment.	2007	17728539
Antimicrobial susceptibility of Shiga toxin-producing Escherichia coli isolated from organic dairy farms, conventional dairy farms, and county fairs in Minnesota.	2007	17600485
NMDA channel antagonist MK-801 does not protect against bilirubin neurotoxicity.	2007	17556843
Minocycline blocks acute bilirubin-induced neurological dysfunction in jaundiced Gunn rats.	2007	17556840
In-vitro antifungal activities of sulfa drugs against clinical isolates of Aspergillus and Cryptococcus species.	2007	17287722
Oxidation of sulfonamide antimicrobials by ferrate(VI) [Fe(VI)O4(2-)].	2006-12-01	17180970
Characterization of bacterial susceptibility isolates in sixteen dairy farms in Taiwan.	2006-12	17106089
Sulfadimethoxine degradation kinetics in manure as affected by initial concentration, moisture, and temperature.	2006-10-31	17071885
Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods.	2006-10-27	16879830
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	16822516
Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water.	2006-10	16991204
Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction.	2006-09-22	16828782
Occurrence of sulfonamide antimicrobials in private water wells in Washington County, Idaho, USA.	2006-09	16497355
Biliverdin-induced brainstem auditory evoked potential abnormalities in the jaundiced Gunn rat.	2006-08-30	16828065
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	16750659
Oxidation of sulfonamides, macrolides, and carbadox with free chlorine and monochloramine.	2006-07	16790259
Calculated in vivo free bilirubin levels in the central nervous system of Gunn rat pups.	2006-07	16690957
Absence of in vivo genotoxic potential and tumor initiation activity of kojic acid in the rat thyroid.	2006-05-15	16603304
Evaluation of changes in antimicrobial susceptibility patterns of Pasteurella multocida subsp multocida isolates from pigs in Spain in 1987-1988 and 2003-2004.	2006-04	16579760
Prevalence and characterization of Escherichia coli O157 isolates from Minnesota dairy farms and county fairs.	2006-02	16496562
Degradation kinetics of manure-derived sulfadimethoxine in amended soil.	2006-01-11	16390193
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2006-01-03	16385979
Comparison of enhancing effects of different goitrogen treatments in combination with beta-estradiol-3-benzoate for establishing a rat two-stage thyroid carcinogenesis model to detect modifying effects of estrogenic compounds.	2006-01	16367917
Sex-specific regional brain bilirubin content in hyperbilirubinemic Gunn rat pups.	2006	16534185
Simultaneous extraction and analysis of 11 tetracycline and sulfonamide antibiotics in influent and effluent domestic wastewater by solid-phase extraction and liquid chromatography-electrospray ionization tandem mass spectrometry.	2005-12-02	16298184
The jaundiced gunn rat model of auditory neuropathy/dyssynchrony.	2005-12	16369161
[Determination of residual sulfonamides in meat by high performance liquid chromatography with solid-phase extraction].	2005-11	16498995
Determination of pKa values by capillary zone electrophoresis with a dynamic coating procedure.	2005-11	16342805
Actinomyces naeslundii infection in an African hedgehog (Atelerix albiventris) with mandibular osteomyelitis and cellulitis.	2005-10-08	16215248
Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry.	2005-07-09	16001847
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005-07	16250451
Effects of sodium chlorate on antibiotic resistance in Escherichia coli O157:H7.	2004	15992263
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.	1991-11-01	1818183

Patents

Sample Use Guides

In Vivo Use Guide

25 mg/lb initial dose of ANADA followed by 12.5 mg/lb for maintenance doses every 24 hours.

Route of Administration: Intravenous

In Vitro Use Guide

Sulfadimethoxine MIC of <256 mg/ml was determined against Arcanobacterium pyogenes isolated from the lungs of white-tailed deer (Odocoileus virginianus) with pneumonia

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:10:42 GMT 2025` Edited by `admin` on `Mon Mar 31 18:10:42 GMT 2025`
Record UNII	49DG2B481W
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DI-METHOX

Preferred Name

English

SULFADIMETHOXINE SODIUM

Common Name

English

SULFADIMETHOXINE SODIUM SALT [MI]

Common Name

English

Sulfadimethoxine sodium [WHO-DD]

Common Name

English

SULFADIMETHOXINE SODIUM [USP MONOGRAPH]

Common Name

English

SODIUM SULFADIMETHOXINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29739