SULFADIMETHOXINE

US Previously Marketed

First approved in 1958

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H14N4O4S
Molecular Weight	310.329
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ZZORFUFYDOWNEF-UHFFFAOYSA-N

InChI=1S/C12H14N4O4S/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,(H,14,15,16)

HIDE SMILES / InChI

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
Effects of sodium chlorate on antibiotic resistance in Escherichia coli O157:H7.	2004 Spring	15992263
The jaundiced gunn rat model of auditory neuropathy/dyssynchrony.	2005 Dec	16369161
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
Confirmation of sulfamethazine, sulfathiazole, and sulfadimethoxine residues in condensed milk and soft-cheese products by liquid chromatography/tandem mass spectrometry.	2005 May-Jun	16001847
[Determination of residual sulfonamides in meat by high performance liquid chromatography with solid-phase extraction].	2005 Nov	16498995
Determination of pKa values by capillary zone electrophoresis with a dynamic coating procedure.	2005 Nov	16342805
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
Evaluation of changes in antimicrobial susceptibility patterns of Pasteurella multocida subsp multocida isolates from pigs in Spain in 1987-1988 and 2003-2004.	2006 Apr	16579760
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
Characterization of bacterial susceptibility isolates in sixteen dairy farms in Taiwan.	2006 Dec	17106089
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
Degradation kinetics of manure-derived sulfadimethoxine in amended soil.	2006 Jan 11	16390193
Oxidation of sulfonamides, macrolides, and carbadox with free chlorine and monochloramine.	2006 Jul	16790259
Calculated in vivo free bilirubin levels in the central nervous system of Gunn rat pups.	2006 Jul	16690957
Absence of in vivo genotoxic potential and tumor initiation activity of kojic acid in the rat thyroid.	2006 May 15	16603304
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
Occurrence of sulfonamide antimicrobials in private water wells in Washington County, Idaho, USA.	2006 Sep	16497355
Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction.	2006 Sep 22	16828782
Observational study of hepatic cytochrome P-450 protein expression and activity in summer flounder (Paralichtys dentatus) after combination ormetoprim-sulfadimethoxine treatment.	2007	17728539
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
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
Depression of T cell-mediated immunity reduces sulfadimethoxine-induced capsular inflammation and inhibits associated development of invasive thyroid follicular cell carcinomas in rats.	2007 Mar	17270018
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
Efficacy of eleven antimicrobials against a gregarine parasite (Apicomplexa: Protozoa).	2007 Nov 12	17997852
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
Antimicrobial susceptibility of Shiga toxin-producing Escherichia coli isolated from organic dairy farms, conventional dairy farms, and county fairs in Minnesota.	2007 Summer	17600485
Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan.	2008 Aug	17961277
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

Name

Type

Language

SULFADIMETHOXINE

Official Name

English

SULFADIMETHOXINE [MI]

Common Name

English

N(SUP 1)-(2,6-DIMETHOXY-4-PYRIMIDINYL)SULFANILAMIDE

Systematic Name

English

SULFADIMETHOXINE [MART.]

Common Name

English

SULFADIMETHOXINE [USP-RS]

Common Name

English

NSC-683544

Code

English

SULFADIMETHOXINE [JAN]

Common Name

English

sulfadimethoxine [INN]

Common Name

English

SULPHADIMETHOXINE

Common Name

English

SULFADIMETHOXINE [GREEN BOOK]

Common Name

English

SULFADIMETHOXINE [USP IMPURITY]

Common Name

English

BENZENESULFONAMIDE, 4-AMINO-N-(2,6-DIMETHOXY-4-PYRIMIDINYL)-

Systematic Name

English

SULFADIMETHOXINE [USP MONOGRAPH]

Common Name

English

Sulfadimethoxine [WHO-DD]

Common Name

English

NSC-757860

Code

English

Classification Tree Code System Code

CFR

21 CFR 520.2220