Identification
- Generic Name
- Sulfaphenazole
- DrugBank Accession Number
- DB06729
- Background
Sulfaphenazole is a sulfonamide antibacterial.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Sulfaphenazole (DB06729)
- Weight
- Average: 314.362
Monoisotopic: 314.083746402 - Chemical Formula
- C15H14N4O2S
- Synonyms
- 1-phenyl-5-sulfanilamidopyrazole
- 3-(p-aminobenzenesulfonamido)-2-phenylpyrazole
- 5-sulfanilamido-1-phenylpyrazole
- N'-(1-phenylpyrazol-5-yl)sulfanilamide
- N(1)-(1-phenylpyrazol-5-yl)sulfanilamide
- Sulfafenazol
- Sulfafenazolo
- Sulfaphénazol
- Sulfaphenazole
- Sulfaphenazolum
- Sulphaphenazole
Pharmacology
- Indication
For the treatment bacterial infections.
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Not Available
- Mechanism of action
Sulfaphenazole is a sulfonamide antibacterial. In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis. As such, the microorganism will be "starved" of folate and die.
Target Actions Organism ADihydropteroate synthase inhibitorEscherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Sulfaphenazole. Acebutolol The metabolism of Acebutolol can be decreased when combined with Sulfaphenazole. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Sulfaphenazole. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Sulfaphenazole. Acetohexamide The metabolism of Acetohexamide can be decreased when combined with Sulfaphenazole. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Sulfaphenazole. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfaphenazole. Almotriptan The metabolism of Almotriptan can be decreased when combined with Sulfaphenazole. Alogliptin The metabolism of Alogliptin can be decreased when combined with Sulfaphenazole. Alosetron The metabolism of Alosetron can be decreased when combined with Sulfaphenazole. 
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- 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
- Sulfabid
Categories
- ATC Codes
- S01AB05 — SulfafenazolJ01ED08 — Sulfaphenazole
- J01ED — Long-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors (strong)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Intermediate-Acting Antibacterial Sulfonamides
- Long-Acting Antibacterial Sulfonamides
- Ophthalmologicals
- Pyrazoles
- Sensory Organs
- Sulfanilamides
- Sulfonamides
- Sulfonamides and trimethoprim
- Sulfones
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Pyrazoles
- Direct Parent
- Phenylpyrazoles
- Alternative Parents
- Aminobenzenesulfonamides / Benzenesulfonyl compounds / Aniline and substituted anilines / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organic oxides show 1 more
- Substituents
- Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Heteroaromatic compound show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrazoles, substituted aniline, sulfonamide, primary amino compound, sulfonamide antibiotic (CHEBI:77780)
- Affected organisms
- Gram negative and gram positive bacteria
Chemical Identifiers
- UNII
- 0J8L4V3F81
- CAS number
- 526-08-9
- InChI Key
- QWCJHSGMANYXCW-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2
- IUPAC Name
- 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-sulfonamide
- SMILES
- NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015667
- KEGG Drug
- D01954
- PubChem Compound
- 5335
- PubChem Substance
- 99443275
- ChemSpider
- 5144
- BindingDB
- 50090677
- ChEBI
- 77780
- ChEMBL
- CHEMBL1109
- ZINC
- ZINC000000057490
- PharmGKB
- PA130231310
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sulfaphenazole
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 181 °C PhysProp water solubility 1500 mg/L (at 25 °C) MERCK (1989) logP 1.52 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.278 mg/mL ALOGPS logP 1.59 ALOGPS logP 1.81 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 6.82 ChemAxon pKa (Strongest Basic) 2.44 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 90.01 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 85.21 m3·mol-1 ChemAxon Polarizability 31.82 Å3 ChemAxon Number of Rings 3 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 + 1.0 Blood Brain Barrier + 0.9466 Caco-2 permeable + 0.5558 P-glycoprotein substrate Non-substrate 0.8991 P-glycoprotein inhibitor I Non-inhibitor 0.8958 P-glycoprotein inhibitor II Non-inhibitor 0.7623 Renal organic cation transporter Non-inhibitor 0.8586 CYP450 2C9 substrate Non-substrate 0.7047 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7386 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.6159 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6835 Ames test Non AMES toxic 0.7824 Carcinogenicity Non-carcinogens 0.8409 Biodegradation Not ready biodegradable 0.9925 Rat acute toxicity 2.1884 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9548 hERG inhibition (predictor II) Non-inhibitor 0.8109
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
- Gene Name
- folP
- Uniprot ID
- P0AC13
- Uniprot Name
- Dihydropteroate synthase
- Molecular Weight
- 30614.855 Da
References
- Hong YL, Hossler PA, Calhoun DH, Meshnick SR: Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother. 1995 Aug;39(8):1756-63. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- Kiang TK, Ho PC, Anari MR, Tong V, Abbott FS, Chang TK: Contribution of CYP2C9, CYP2A6, and CYP2B6 to valproic acid metabolism in hepatic microsomes from individuals with the CYP2C9*1/*1 genotype. Toxicol Sci. 2006 Dec;94(2):261-71. doi: 10.1093/toxsci/kfl096. Epub 2006 Aug 31. [Article]
- Rehmel JL, Eckstein JA, Farid NA, Heim JB, Kasper SC, Kurihara A, Wrighton SA, Ring BJ: Interactions of two major metabolites of prasugrel, a thienopyridine antiplatelet agent, with the cytochromes P450. Drug Metab Dispos. 2006 Apr;34(4):600-7. doi: 10.1124/dmd.105.007989. Epub 2006 Jan 13. [Article]
- Sai Y, Dai R, Yang TJ, Krausz KW, Gonzalez FJ, Gelboin HV, Shou M: Assessment of specificity of eight chemical inhibitors using cDNA-expressed cytochromes P450. Xenobiotica. 2000 Apr;30(4):327-43. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- 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
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Yoshimoto K, Echizen H, Chiba K, Tani M, Ishizaki T: Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers--N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol. 1995 Apr;39(4):421-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Spracklin DK, Thummel KE, Kharasch ED: Human reductive halothane metabolism in vitro is catalyzed by cytochrome P450 2A6 and 3A4. Drug Metab Dispos. 1996 Sep;24(9):976-83. [Article]
- Sai Y, Dai R, Yang TJ, Krausz KW, Gonzalez FJ, Gelboin HV, Shou M: Assessment of specificity of eight chemical inhibitors using cDNA-expressed cytochromes P450. Xenobiotica. 2000 Apr;30(4):327-43. [Article]
Drug created at August 18, 2010 20:44 / Updated at February 21, 2021 18:52