Identification

Name
Sulfamoxole
Accession Number
DB08798
Type
Small Molecule
Groups
Experimental
Description

Sulfamoxole 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
International/Other Brands
Sulfmidil / Sulfuno
Categories
UNII
HGG82XE020
CAS number
729-99-7
Weight
Average: 267.304
Monoisotopic: 267.067761987
Chemical Formula
C11H13N3O3S
InChI Key
CYFLXLSBHQBMFT-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

Indication

For the treatment of bacterial infection.

Pharmacodynamics

Sulfamoxole 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 action

Sulfamoxole 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.

TargetActionsOrganism
ADihydropteroate synthetase
inhibitor
Plasmodium falciparum
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral Rat LD50: > 12500 mg/kg; Intravenous Mouse LD50: 1 g/kg

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Sulfamoxole.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Sulfamoxole.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfamoxole.
AceclofenacThe metabolism of Aceclofenac can be decreased when combined with Sulfamoxole.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Sulfamoxole.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Sulfamoxole.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfamoxole.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Sulfamoxole.
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Sulfamoxole.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfamoxole.
Food Interactions
Not Available

References

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
Human Metabolome Database
HMDB0015688
KEGG Drug
D02516
PubChem Compound
12894
PubChem Substance
99445268
ChemSpider
12361
ChEBI
55548
ChEMBL
CHEMBL2105399
PharmGKB
PA165958417
Wikipedia
Sulfamoxole
ATC Codes
J01EE04 — Sulfamoxole and trimethoprimJ01EC03 — Sulfamoxole
MSDS
Download (34.3 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-3900000000-23eed4bc89bcf24079bd

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Aminobenzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / 2,4,5-trisubstituted oxazoles / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Oxacyclic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds
show 3 more
Substituents
Aminobenzenesulfonamide / Benzenesulfonyl group / 2,4,5-trisubstituted 1,3-oxazole / Aniline or substituted anilines / Organosulfonic acid amide / Azole / Oxazole / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, sulfonamide antibiotic, oxazole (CHEBI:55548)

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
Uniprot Name
Dihydropteroate synthetase
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
Inhibitor
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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]
  2. A Review on Drug Interactions in Oral Hypoglycemic Drugs by Mechanism of Cytochrome P450 Enzyme Inhibition [File]

Drug created on October 14, 2010 13:40 / Updated on November 02, 2018 06:54