SULFADIMETHOXINE SODIUM

US Previously Marketed

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=CC([N-]S(=O)(=O)C2=CC=C(N)C=C2)=NC(OC)=N1

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	Na
Molecular Weight	22.9898
Charge	1
Count

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

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

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 8297

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 8429	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 8429	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 Page: p.344, 345	unhealthy, 20 n = 1 Health Status: unhealthy Condition: Acne Age Group: 20 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4228868 Page: p.344, 345	Disc. AE: Cholestatic jaundice... AEs leading to discontinuation/dose reduction: Cholestatic jaundice (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/4228868 Page: p.344, 345
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 Page: p.230	unhealthy n = 24 Health Status: unhealthy Condition: Urinary tract infections\| Pyuria\| Pyelonephritis\| Cystitis Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/5325539 Page: p.230	Sources: https://pubmed.ncbi.nlm.nih.gov/5325539 Page: p.230

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 Page: p.344, 345	unhealthy, 20 n = 1 Health Status: unhealthy Condition: Acne Age Group: 20 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4228868 Page: p.344, 345

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-036287	http://www.3bsc.com/index/pro_info.php?id=58318
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
Aaron Chemicals	AR00HAUY	http://www.aaronchem.com/1037-50-9
Achemtek	0104-023973	http://www.achemtek.com/1037-50-9
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
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
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
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
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
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
Molcore	MC503532	https://www.molcore.com/product/1037-50-9
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
abcr GmbH	AB251954	http://www.abcr.de/shop/en/AB251954
eNovation Chemicals	D128662	https://www.enovationchem.com/ProductDetails.asp?ProductID=D128662
eNovation Chemicals	D961680	https://www.enovationchem.com/ProductDetails.asp?ProductID=D961680

PubMed

Title	Date	PubMed
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.	1991 Nov-Dec	1818183
Activity of sulfadimethoxine against cryptosporidiosis in dairy calves.	1992 Jun	1597803
Sulfadimethoxine and rhodamine B as oral biomarkers for European badgers (Meles meles).	2002 Apr	12038137
Sulphonamide residues in eggs following drug administration via the drinking water.	2002 Apr	11962695
Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry.	2002 Apr 5	12064522
Penetration of drug resistance in Escherichia coli isolated from laboratory animals.	2002 Dec	12520107
Characterization of a Cu(II) complex of sulfadimethoxine.	2003 Feb 1	12620693
Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC.	2004 Apr 2	15065772
Pharmacokinetics of sulfadimethoxine and ormetoprim in a 5:1 ratio following intraperitoneal and oral administration, in the hybrid striped bass (Morone chrysops x Morone saxitalis).	2004 Feb	14995959
Acute columnaris infection in channel catfish, Ictalurus punctatus (Rafinesque): efficacy of practical treatments for warmwater aquaculture ponds.	2004 Jan	14986936
Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.	2004 Jul	15346776
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.	2004 Jul-Aug	15254115
Idiosyncratic toxicity associated with potentiated sulfonamides in the dog.	2004 Jun	15189298
Sequential analysis of development of invasive thyroid follicular cell carcinomas in inflamed capsular regions of rats treated with sulfadimethoxine after N-bis(2-hydroxypropyl)nitrosamine-initiation.	2004 Mar-Apr	15200161
Specificity of co-promoting effects of caffeine on thyroid carcinogenesis in rats pretreated with N-bis(2-hydroxypropyl)nitrosamine.	2004 May-Jun	15204976
Intestinal microflora in 45 crows in Ueno Zoo and the in vitro susceptibilities of 29 Escherichia coli isolates to 14 antimicrobial agents.	2004 Oct	15528866
Comparative efficacy of enrofloxacin, oxytetracycline, and sulfadimethoxine for the control of morbidity and mortality caused by Escherichia coli in broiler chickens.	2004 Sep	15529991
Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection.	2004 Sep-Oct	15493686
Effects of sodium chlorate on antibiotic resistance in Escherichia coli O157:H7.	2004 Spring	15992263
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 Dec 2	16298184
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005 Jul	16250451
Effect of selective cyclooxygenase-2 inhibitors on heart rate in healthy young men.	2005 Jun 15	15950593
Actinomyces naeslundii infection in an African hedgehog (Atelerix albiventris) with mandibular osteomyelitis and cellulitis.	2005 Oct 8	16215248
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Sex-specific regional brain bilirubin content in hyperbilirubinemic Gunn rat pups.	2006	16534185
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
Biliverdin-induced brainstem auditory evoked potential abnormalities in the jaundiced Gunn rat.	2006 Aug 30	16828065
Oxidation of sulfonamide antimicrobials by ferrate(VI) [Fe(VI)O4(2-)].	2006 Dec 1	17180970
Prevalence and characterization of Escherichia coli O157 isolates from Minnesota dairy farms and county fairs.	2006 Feb	16496562
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 Jan	16367917
Oxidation of sulfonamides, macrolides, and carbadox with free chlorine and monochloramine.	2006 Jul	16790259
Sulfadimethoxine degradation kinetics in manure as affected by initial concentration, moisture, and temperature.	2006 Nov-Dec	17071885
Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water.	2006 Oct	16991204
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
Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods.	2006 Oct 27	16879830
Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction.	2006 Sep 22	16828782
Aquatic toxicity of acetaminophen, carbamazepine, cimetidine, diltiazem and six major sulfonamides, and their potential ecological risks in Korea.	2007 Apr	17223195
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.	2007 Dec	18024727
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
Determination of residues of sulphonamide in eggs and laying hens.	2007 Jul	17545104
Use of sulfadimethoxine in intensive calf farming: evaluation of transfer to stable manure and soil.	2007 Jun	17368507
Development of an immunochromatographic lateral-flow test strip for rapid detection of sulfonamides in eggs and chicken muscles.	2007 Mar 21	17316015
Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms.	2007 Mar 28	17386777
Determination of 10 sulfonamide residues in meat samples by liquid chromatography with ultraviolet detection.	2007 Mar-Apr	17474530
Cytotoxicity is predicted by unbound and not total bilirubin concentration.	2007 Nov	18049372
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
Organic solvents-free technique for determining sulfadimethoxine and its metabolites in chicken meat.	2007 Nov 16	17936765
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].	2007 Sep	18161327
Diagnosis and treatment of Eimeria macusaniensis in an adult alpaca with signs of colic.	2009 Mar	18036857

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 `Fri Dec 15 15:50:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:50:44 GMT 2023`
Record UNII	49DG2B481W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFADIMETHOXINE SODIUM

Common Name

English

DI-METHOX

Brand 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