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Identification
NameSulfamoxole
Accession NumberDB08798
TypeSmall Molecule
GroupsApproved
DescriptionSulfamoxole is a sulfonamide antibacterial.
Structure
Thumb
Synonyms
2-(P-Aminobenzenesulfonamido)-4,5-dimethyloxazole
2-(P-Aminobenzolsulfonamido)-4,5-dimethyloxazol
4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide
4,5-Dimethyl-2-sulfanilamidooxazole
N(Sup 1)-(4,5-dimethyl-2-oxazolyl)sulfanilamide
N1-(4,5-Dimethyl-2-oxazolyl)sulfanilamide
Oxasulfa
P-Aminobenzenesulfonyl-2-amino-4,5-dimethyloxazole
Sulfadimethyloxazole
Sulfamoxol
Sulfamoxolum
Sulphamoxole
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
SulfmidilNot Available
SulfunoNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIHGG82XE020
CAS number729-99-7
WeightAverage: 267.304
Monoisotopic: 267.067761987
Chemical FormulaC11H13N3O3S
InChI KeyCYFLXLSBHQBMFT-UHFFFAOYSA-N
InChI
InChI=1S/C11H13N3O3S/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6H,12H2,1-2H3,(H,13,14)
IUPAC Name
4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide
SMILES
CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1
Pharmacology
IndicationFor the treatment of bacterial infection.
Structured Indications Not Available
PharmacodynamicsSulfamoxole is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Mechanism of actionSulfamoxole is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
TargetKindPharmacological actionActionsOrganismUniProt ID
Dihydropteroate synthetaseProteinyes
inhibitor
Plasmodium falciparumQ27738 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity Oral Rat LD50: > 12500 mg/kg; Intravenous Mouse LD50: 1 g/kg
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe metabolism of Sulfamoxole can be decreased when combined with Abiraterone.Approved
AmiodaroneThe metabolism of Sulfamoxole can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe metabolism of Sulfamoxole can be increased when combined with Aprepitant.Approved, Investigational
CapecitabineThe metabolism of Sulfamoxole can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Sulfamoxole can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Sulfamoxole can be increased when it is combined with Ceritinib.Approved
CholecalciferolThe metabolism of Sulfamoxole can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
ClotrimazoleThe metabolism of Sulfamoxole can be decreased when combined with Clotrimazole.Approved, Vet Approved
CyclosporineThe metabolism of Sulfamoxole can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Sulfamoxole can be decreased when it is combined with Dabrafenib.Approved
DelavirdineThe metabolism of Sulfamoxole can be decreased when combined with Delavirdine.Approved
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfamoxole.Approved
EfavirenzThe metabolism of Sulfamoxole can be decreased when combined with Efavirenz.Approved, Investigational
EtravirineThe metabolism of Sulfamoxole can be decreased when combined with Etravirine.Approved
FloxuridineThe metabolism of Sulfamoxole can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Sulfamoxole can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Sulfamoxole can be decreased when combined with Fluorouracil.Approved
FluvastatinThe metabolism of Sulfamoxole can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Sulfamoxole can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe metabolism of Sulfamoxole can be increased when combined with Fosphenytoin.Approved
GemfibrozilThe metabolism of Sulfamoxole can be decreased when combined with Gemfibrozil.Approved
IndinavirThe metabolism of Sulfamoxole can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Sulfamoxole can be decreased when combined with Irbesartan.Approved, Investigational
KetoconazoleThe metabolism of Sulfamoxole can be decreased when combined with Ketoconazole.Approved, Investigational
LeflunomideThe metabolism of Sulfamoxole can be decreased when combined with Leflunomide.Approved, Investigational
LosartanThe metabolism of Sulfamoxole can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Sulfamoxole can be decreased when combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Sulfamoxole can be decreased when it is combined with Lumacaftor.Approved
MecamylamineThe risk or severity of adverse effects can be increased when Sulfamoxole is combined with Mecamylamine.Approved
MifepristoneThe serum concentration of Sulfamoxole can be increased when it is combined with Mifepristone.Approved, Investigational
NicardipineThe metabolism of Sulfamoxole can be decreased when combined with Nicardipine.Approved
OmeprazoleThe metabolism of Sulfamoxole can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
PhenobarbitalThe metabolism of Sulfamoxole can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Sulfamoxole can be increased when combined with Phenytoin.Approved, Vet Approved
PrimidoneThe metabolism of Sulfamoxole can be increased when combined with Primidone.Approved, Vet Approved
PyrimethamineThe metabolism of Sulfamoxole can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinineThe metabolism of Sulfamoxole can be decreased when combined with Quinine.Approved
RifampicinThe metabolism of Sulfamoxole can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Sulfamoxole can be increased when combined with Rifapentine.Approved
SecobarbitalThe metabolism of Sulfamoxole can be increased when combined with Secobarbital.Approved, Vet Approved
SildenafilThe metabolism of Sulfamoxole can be decreased when combined with Sildenafil.Approved, Investigational
SorafenibThe metabolism of Sulfamoxole can be decreased when combined with Sorafenib.Approved, Investigational
SulfadiazineThe metabolism of Sulfamoxole can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Sulfamoxole can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Sulfamoxole can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TicagrelorThe metabolism of Sulfamoxole can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Sulfamoxole can be decreased when combined with Ticlopidine.Approved
TolbutamideThe metabolism of Sulfamoxole can be decreased when combined with Tolbutamide.Approved
TrimethoprimThe metabolism of Sulfamoxole can be decreased when combined with Trimethoprim.Approved, Vet Approved
Valproic AcidThe metabolism of Sulfamoxole can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Sulfamoxole can be decreased when combined with Valsartan.Approved, Investigational
VoriconazoleThe metabolism of Sulfamoxole can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Sulfamoxole can be decreased when combined with Zafirlukast.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. [PubMed:13888264 ]
External Links
ATC CodesJ01EE04J01EC03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (34.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.99
Blood Brain Barrier+0.8658
Caco-2 permeable-0.5783
P-glycoprotein substrateNon-substrate0.8973
P-glycoprotein inhibitor INon-inhibitor0.9293
P-glycoprotein inhibitor IINon-inhibitor0.959
Renal organic cation transporterNon-inhibitor0.9337
CYP450 2C9 substrateNon-substrate0.6623
CYP450 2D6 substrateNon-substrate0.8971
CYP450 3A4 substrateNon-substrate0.7834
CYP450 1A2 substrateNon-inhibitor0.9043
CYP450 2C9 inhibitorNon-inhibitor0.8433
CYP450 2D6 inhibitorNon-inhibitor0.9269
CYP450 2C19 inhibitorNon-inhibitor0.9104
CYP450 3A4 inhibitorNon-inhibitor0.9378
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7653
Ames testNon AMES toxic0.8674
CarcinogenicityNon-carcinogens0.8029
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity1.3610 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9396
hERG inhibition (predictor II)Non-inhibitor0.9361
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point193 °CPhysProp
water solubility1680 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.267 mg/mLALOGPS
logP1.04ALOGPS
logP0.59ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.81ChemAxon
pKa (Strongest Basic)1.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.22 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.51 m3·mol-1ChemAxon
Polarizability27.44 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Sulfonylaniline
  • Substituted aniline
  • 2,4,5-trisubstituted 1,3-oxazole
  • Aniline
  • Primary aromatic amine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Oxazole
  • Azole
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
yes
Actions
inhibitor
General Function:
Dihydropteroate synthase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q27738
Molecular Weight:
43370.845 Da
References
  1. Prabhu V, Lui H, King J: Arabidopsis dihydropteroate synthase: general properties and inhibition by reaction product and sulfonamides. Phytochemistry. 1997 May;45(1):23-7. [PubMed:9127492 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zweers-Zeilmaker WM, Horbach GJ, Witkamp RF: Differential inhibitory effects of phenytoin, diclofenac, phenylbutazone and a series of sulfonamides on hepatic cytochrome P4502C activity in vitro, and correlation with some molecular descriptors in the dwarf goat (Caprus hircus aegagrus). Xenobiotica. 1997 Aug;27(8):769-80. [PubMed:9293615 ]
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Drug created on October 14, 2010 13:40 / Updated on August 17, 2016 12:24