NAV

Sulfaphenazole

Identification

Generic Name
Sulfaphenazole
DrugBank Accession Number
DB06729
Background

Sulfaphenazole is a sulfonamide antibacterial.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
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
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Pharmacology

Indication

For the treatment bacterial infections.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
ADihydropteroate synthase
inhibitor
Escherichia 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
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Sulfaphenazole.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfaphenazole.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Sulfaphenazole.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Sulfaphenazole.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Sulfaphenazole.
Food Interactions
Not Available

Products

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International/Other Brands
Sulfabid

Categories

ATC Codes
S01AB05 — SulfafenazolJ01ED08 — SulfaphenazoleG01AE10 — Combinations of sulfonamides
Drug Categories
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
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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)181 °CPhysProp
water solubility1500 mg/L (at 25 °C)MERCK (1989)
logP1.52HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.278 mg/mLALOGPS
logP1.59ALOGPS
logP1.81Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)6.82Chemaxon
pKa (Strongest Basic)2.44Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area90.01 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity85.21 m3·mol-1Chemaxon
Polarizability31.82 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9466
Caco-2 permeable+0.5558
P-glycoprotein substrateNon-substrate0.8991
P-glycoprotein inhibitor INon-inhibitor0.8958
P-glycoprotein inhibitor IINon-inhibitor0.7623
Renal organic cation transporterNon-inhibitor0.8586
CYP450 2C9 substrateNon-substrate0.7047
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7386
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.6159
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6835
Ames testNon AMES toxic0.7824
CarcinogenicityNon-carcinogens0.8409
BiodegradationNot ready biodegradable0.9925
Rat acute toxicity2.1884 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9548
hERG inhibition (predictor II)Non-inhibitor0.8109
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-MSsplash10-0bu0-5950000000-0cc1951df9ab2bdd4675
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0309000000-a7a9b7f135e2e1a8b56a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066r-0609000000-ee0bfd3285d8d6440ff5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-ec6ba76bcd99c7a7ee28
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-07vl-9640000000-97f231fb4875715d8a8b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0019000000-65c0217bcf4e8042b7f0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014m-6930000000-953309e9c9886e530964
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.521459
predicted
DarkChem Lite v0.1.0
[M-H]-182.760859
predicted
DarkChem Lite v0.1.0
[M-H]-168.05432
predicted
DeepCCS 1.0 (2019)
[M+H]+183.266559
predicted
DarkChem Lite v0.1.0
[M+H]+183.442959
predicted
DarkChem Lite v0.1.0
[M+H]+170.41231
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.471959
predicted
DarkChem Lite v0.1.0
[M+Na]+182.775659
predicted
DarkChem Lite v0.1.0
[M+Na]+177.18582
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydropteroate synthase
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
  1. 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

Details1. Cytochrome P450 2B6
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
  1. 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]
Details2. Cytochrome P450 2C8
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
  1. 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]
Details3. Cytochrome P450 2D6
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
  1. 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]
  2. 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]
Details4. Cytochrome P450 2C9
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
  1. 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]
  2. 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]
  3. 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]
  4. Flockhart Table of Drug Interactions [Link]

Drug created at August 18, 2010 20:44 / Updated at November 30, 2023 01:44