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

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 of SULFADIMETHOXINE SODIUM

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
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

Curator's Comment: Sulfadimethoxine (madribon) was developed in the late 1950s. # Roche Laboratories, Division of Hoffman-La Roche Inc

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
SULFADIMETHOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7%
SULFADIMETHOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

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

AEs

AESignificanceDosePopulation
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: Page: p.344, 345
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Acne
Age Group: 20
Sex: F
Population Size: 1
Sources: Page: p.344, 345
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.
1991 Nov-Dec
High-performance liquid chromatographic procedure for routine residue monitoring of seven sulfonamides in milk.
2001 Dec
Effect of hypothermia on bilirubin-induced alterations in brain cell membrane function and energy metabolism in newborn piglets.
2001 Dec 20
Sulfadimethoxine and rhodamine B as oral biomarkers for European badgers (Meles meles).
2002 Apr
Sulphonamide residues in eggs following drug administration via the drinking water.
2002 Apr
Sulphadimethoxine and Azolla filiculoides Lam.: a model for drug remediation.
2002 Jul
Comparison of ion-pairing and ion-suppressing liquid chromatographic methods for the determination of pyrimethamine and ormetoprim in chicken feed.
2002 Jul
Disposition of sulfadimethoxine in male llamas (Llama glama) after single intravenous and oral administrations.
2003 Mar
Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC.
2004 Apr 2
Evaluation of antimicrobial agents for veterinary use in the ecotoxicity test using microalgae.
2004 Dec
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
Application of shielded column liquid chromatography for determination of sulfamonomethoxine, sulfadimethoxine, and their N4-acetyl metabolites in milk.
2004 Feb 27
Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.
2004 Jul
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.
2004 Jul-Aug
Idiosyncratic toxicity associated with potentiated sulfonamides in the dog.
2004 Jun
[Determination of the residues of five sulfa drugs in eel by HPLC].
2004 Mar
Intramolecular isobaric fragmentation: a curiosity of accurate mass analysis of sulfadimethoxine in pond water.
2004 Mar 1
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
Specificity of co-promoting effects of caffeine on thyroid carcinogenesis in rats pretreated with N-bis(2-hydroxypropyl)nitrosamine.
2004 May-Jun
Pharmacokinetics of quinacrine in the treatment of prion disease.
2004 Nov 29
Intestinal microflora in 45 crows in Ueno Zoo and the in vitro susceptibilities of 29 Escherichia coli isolates to 14 antimicrobial agents.
2004 Oct
Comparative efficacy of enrofloxacin, oxytetracycline, and sulfadimethoxine for the control of morbidity and mortality caused by Escherichia coli in broiler chickens.
2004 Sep
Determination of sulfonamide residues in the tissues of food animals using automated precolumn derivatization and liquid chromatography with fluorescence detection.
2004 Sep-Oct
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
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].
2005 Jul
Effect of selective cyclooxygenase-2 inhibitors on heart rate in healthy young men.
2005 Jun 15
Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups: identification of an SO2 extrusion photoproduct.
2005 May 15
Determination of pKa values by capillary zone electrophoresis with a dynamic coating procedure.
2005 Nov
Actinomyces naeslundii infection in an African hedgehog (Atelerix albiventris) with mandibular osteomyelitis and cellulitis.
2005 Oct 8
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
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
Degradation kinetics of manure-derived sulfadimethoxine in amended soil.
2006 Jan 11
Calculated in vivo free bilirubin levels in the central nervous system of Gunn rat pups.
2006 Jul
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
Observational study of hepatic cytochrome P-450 protein expression and activity in summer flounder (Paralichtys dentatus) after combination ormetoprim-sulfadimethoxine treatment.
2007
Minocycline blocks acute bilirubin-induced neurological dysfunction in jaundiced Gunn rats.
2007
Aquatic toxicity of acetaminophen, carbamazepine, cimetidine, diltiazem and six major sulfonamides, and their potential ecological risks in Korea.
2007 Apr
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.
2007 Dec
Validation of an analytical method to determine sulfamides in kidney by HPLC-DAD and PARAFAC2 with first-order derivative chromatograms.
2007 Mar 28
Cytotoxicity is predicted by unbound and not total bilirubin concentration.
2007 Nov
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].
2007 Sep
Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan.
2008 Aug
Diagnosis and treatment of Eimeria macusaniensis in an adult alpaca with signs of colic.
2009 Mar
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: ANADA, a generic product and the pioneer product Albon have identical indications for use in cattle.
25 mg/lb initial dose of ANADA followed by 12.5 mg/lb for maintenance doses every 24 hours.
Route of Administration: Intravenous
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
USP   WHO-DD  
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
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
Code System Code Type Description
FDA UNII
49DG2B481W
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY
PUBCHEM
13384041
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY
SMS_ID
300000023743
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY
NCI_THESAURUS
C76976
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL62193
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY
RXCUI
1306121
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m10307
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY Merck Index
CAS
1037-50-9
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY
DAILYMED
49DG2B481W
Created by admin on Fri Dec 15 15:50:44 GMT 2023 , Edited by admin on Fri Dec 15 15:50:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID50858735
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PRIMARY
DRUG BANK
DBSALT000956
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PRIMARY
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