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

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 of SULFADIMETHOXINE

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

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

8.5812478E11
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

8.5812478E11
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
Activity of sulfadimethoxine against cryptosporidiosis in dairy calves.
1992 Jun
In vitro hepatobiotransformation of sulphadimethoxine in laying hens.
2001 Apr
Pharmacokinetics of sulfadimethoxine and sulfamethoxazole in combination with trimethoprim after oral single- and multiple-dose administration to healthy pigs.
2001 Aug
High-performance liquid chromatographic procedure for routine residue monitoring of seven sulfonamides in milk.
2001 Dec
Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry.
2002 Apr 5
Penetration of drug resistance in Escherichia coli isolated from laboratory animals.
2002 Dec
Sulphadimethoxine and Azolla filiculoides Lam.: a model for drug remediation.
2002 Jul
Self-assembled hydrogel nanoparticles responsive to tumor extracellular pH from pullulan derivative/sulfonamide conjugate: characterization, aggregation, and adriamycin release in vitro.
2002 May
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.
2003 Jun
pH-dependent elution profiles of selected proteins in HPLC having a stationary phase modified with pH-sensitive sulfonamide polymers.
2004
Validation of a confirmatory method for the determination of sulphonamides in muscle according to the European Union regulation 2002/657/EC.
2004 Apr 2
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
Acute columnaris infection in channel catfish, Ictalurus punctatus (Rafinesque): efficacy of practical treatments for warmwater aquaculture ponds.
2004 Jan
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
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
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
Effects of sodium chlorate on antibiotic resistance in Escherichia coli O157:H7.
2004 Spring
[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
Nephrotic syndrome associated with administration of sulfadimethoxine/ormetoprim in a dobermann.
2005 May
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2005 Sep-Oct
Sex-specific regional brain bilirubin content in hyperbilirubinemic Gunn rat pups.
2006
Characterization of bacterial susceptibility isolates in sixteen dairy farms in Taiwan.
2006 Dec
Sulfadimethoxine degradation kinetics in manure as affected by initial concentration, moisture, and temperature.
2006 Nov-Dec
Occurrence of sulfonamide antimicrobials in private water wells in Washington County, Idaho, USA.
2006 Sep
Performance of blue-yellow screening test for antimicrobial detection in ovine milk.
2007 Dec
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
Determination of residues of sulphonamide in eggs and laying hens.
2007 Jul
Use of sulfadimethoxine in intensive calf farming: evaluation of transfer to stable manure and soil.
2007 Jun
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
Cytotoxicity is predicted by unbound and not total bilirubin concentration.
2007 Nov
Efficacy of eleven antimicrobials against a gregarine parasite (Apicomplexa: Protozoa).
2007 Nov 12
[Simultaneous determination of nine sulfonamide residues in milk using solid phase extraction and high performance liquid chromatography].
2007 Sep
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 15:02:36 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:36 UTC 2023
Record UNII
30CPC5LDEX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFADIMETHOXINE
GREEN BOOK   INN   JAN   MART.   MI   USP   USP-RS   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
WHO-VATC QJ01EQ59
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 556.640
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 520.2220B
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
WHO-VATC QP51AG02
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
WHO-VATC QJ01EW09
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 520.2220C
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
WHO-VATC QJ01EQ09
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
WHO-ATC J01ED01
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 520.2220D
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 520.2220A
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 522.2220
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 520.2220E
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
NCI_THESAURUS C29739
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
CFR 21 CFR 520.2220F
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
Code System Code Type Description
SMS_ID
100000083246
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
CHEBI
32161
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PRIMARY
RXCUI
10172
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PRIMARY RxNorm
ECHA (EC/EINECS)
204-523-7
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PRIMARY
ChEMBL
CHEMBL62193
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
NSC
757860
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
RS_ITEM_NUM
1626001
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PRIMARY
INN
840
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PRIMARY
EPA CompTox
DTXSID1023607
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PRIMARY
WIKIPEDIA
SULFADIMETHOXINE
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
DAILYMED
30CPC5LDEX
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PRIMARY
EVMPD
SUB10698MIG
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PRIMARY
DRUG BANK
DB06150
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PRIMARY
FDA UNII
30CPC5LDEX
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
NSC
683544
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PRIMARY
CAS
122-11-2
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
DRUG CENTRAL
2501
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
MESH
D013412
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PRIMARY
MERCK INDEX
m10307
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C76975
Created by admin on Fri Dec 15 15:02:36 UTC 2023 , Edited by admin on Fri Dec 15 15:02:36 UTC 2023
PRIMARY
PUBCHEM
5323
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PRIMARY
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