Identification
- Summary
Sulfametopyrazine is an antibiotic used in the treatment or prevention of bacterial infections and malaria.
- Generic Name
- Sulfametopyrazine
- DrugBank Accession Number
- DB00664
- Background
Long-acting plasma-bound sulfonamide used for respiratory and urinary tract infections and also for malaria.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Sulfametopyrazine (DB00664)
- Weight
- Average: 280.303
Monoisotopic: 280.06301096 - Chemical Formula
- C11H12N4O3S
- Synonyms
- Solfametopirazina
- Sulfalene
- Sulfaleno
- Sulfalenum
- Sulfamethopyrazine
- External IDs
- AS-18908
- NSC-110433
- WR 4629
Pharmacology
- Indication
For the treatment of urinary tract infection and chronic bronchitis.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to prevent Plasmodium infections Combination Product in combination with: Pyrimethamine (DB00205) •••••••••••• •••••• •••••••• ••••••••• •••••• Used in combination to treat Plasmodium infections Combination Product in combination with: Pyrimethamine (DB00205) •••••••••••• •••••• •••••••• ••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Sulfametopyrazine 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
Sulfametopyrazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. Para-aminobenzoic acid (PABA), a substrate of the enzyme is prevented from binding. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Target Actions Organism ADihydropteroate synthetase inhibitorPlasmodium 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
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfametopyrazine. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfametopyrazine. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfametopyrazine. Alogliptin The therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfametopyrazine. Benzylpenicillin Sulfametopyrazine may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Kelfizina
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image METAKELFIN Sulfametopyrazine (500 mg) + Pyrimethamine (25 mg) Tablet Oral Pfizer Italia S.R.L. 2014-07-08 2021-06-04 Italy 
METAKELFIN Sulfametopyrazine (200 mg/mL) + Pyrimethamine (10 mg/mL) Solution / drops Oral Pfizer Italia S.R.L. 2014-07-08 2021-06-04 Italy
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- J01ED — Long-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Benzene Derivatives
- Benzenesulfonamides
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Long-Acting Antibacterial Sulfonamides
- Sulfanilamides
- Sulfonamides
- Sulfonamides and trimethoprim
- Sulfones
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonamides
- Direct Parent
- Benzenesulfonamides
- Alternative Parents
- Benzenesulfonyl compounds / Methoxypyrazines / Aniline and substituted anilines / Alkyl aryl ethers / Imidolactams / Sulfonyls / Organosulfonic acids and derivatives / Heteroaromatic compounds / Azacyclic compounds / Primary amines show 3 more
- Substituents
- Alkyl aryl ether / Amine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Ether / Heteroaromatic compound / Hydrocarbon derivative show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrazines, sulfonamide, sulfonamide antibiotic (CHEBI:32162)
- Affected organisms
- Gram negative, positive bacteria and plasmodium
Chemical Identifiers
- UNII
- T6BL4ZC15G
- CAS number
- 152-47-6
- InChI Key
- KXRZBTAEDBELFD-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
- IUPAC Name
- 4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide
- SMILES
- COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014802
- KEGG Drug
- D01216
- KEGG Compound
- C12616
- PubChem Compound
- 9047
- PubChem Substance
- 46505111
- ChemSpider
- 8695
- 10175
- ChEBI
- 32162
- ChEMBL
- CHEMBL1525826
- ZINC
- ZINC000000002097
- Therapeutic Targets Database
- DAP001199
- PharmGKB
- PA164747038
- Wikipedia
- Sulfalene
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Tablet Tablet Solution / drops Oral Tablet Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 176 °C PhysProp water solubility 4030 mg/L Not Available logP 0.70 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.406 mg/mL ALOGPS logP 0.41 ALOGPS logP 0.23 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 5.91 Chemaxon pKa (Strongest Basic) 1.98 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 107.2 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 70.37 m3·mol-1 Chemaxon Polarizability 27.12 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9797 Blood Brain Barrier + 0.6436 Caco-2 permeable - 0.5125 P-glycoprotein substrate Non-substrate 0.748 P-glycoprotein inhibitor I Non-inhibitor 0.8708 P-glycoprotein inhibitor II Non-inhibitor 0.9728 Renal organic cation transporter Non-inhibitor 0.9066 CYP450 2C9 substrate Non-substrate 0.6554 CYP450 2D6 substrate Non-substrate 0.8908 CYP450 3A4 substrate Non-substrate 0.7127 CYP450 1A2 substrate Non-inhibitor 0.8964 CYP450 2C9 inhibitor Non-inhibitor 0.831 CYP450 2D6 inhibitor Non-inhibitor 0.9467 CYP450 2C19 inhibitor Non-inhibitor 0.8826 CYP450 3A4 inhibitor Non-inhibitor 0.8952 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6424 Ames test Non AMES toxic 0.7455 Carcinogenicity Non-carcinogens 0.8527 Biodegradation Not ready biodegradable 0.9973 Rat acute toxicity 1.9789 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9669 hERG inhibition (predictor II) Non-inhibitor 0.7806
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-05ec-8950000000-e07820181c0d509b6744 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0290000000-24e142763c47cd247be0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6r-0970000000-bf2d1035c7d18bf219b1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0910000000-50abd80da5d7f386882d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0900000000-0bcac65a7338af060967 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-07do-9440000000-89111416c198a27ead07 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-052e-3900000000-7fe4ce0917d648d5d78a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.1714009 predictedDarkChem Lite v0.1.0 [M-H]- 169.5038009 predictedDarkChem Lite v0.1.0 [M-H]- 162.44022 predictedDeepCCS 1.0 (2019) [M+H]+ 172.6443009 predictedDarkChem Lite v0.1.0 [M+H]+ 170.9468009 predictedDarkChem Lite v0.1.0 [M+H]+ 164.79822 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.4786009 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.0342009 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.89134 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:53