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Compound Detail

CHEMBL1109

SULFAPHENAZOLE
💊 Approved Drug
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💊 Approved Drug
Nc1ccc(S(=O)(=O)Nc2ccnn2-c2ccccc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1109
Name SULFAPHENAZOLE
Phase Approved
Structure Type MOL
InChI Key QWCJHSGMANYXCW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

NSC-757859 Orisulf Sulfabid Sulfafenazol Sulfaphenazol Sulfaphenazole
3
Targets
61
Activities
2
Assay Types
3
PK Parameters
20
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

314.4
MW (Da)
2.26
ALogP
5
HBA
2
HBD
90.0
PSA (Ų)
0.72
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem sulfa-

Extended Properties

Molecular Formula C15H14N4O2S
MW 314.37
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -1.89

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial dihydropteroate synthase inhibitor INHIBITOR Dihydropteroate synthase ✓ ✓

Indications

Bacterial Infections Eye Infections

ATC Classification

J01ED08
sulfaphenazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AB05
sulfafenazol
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 59 meas. best 7.1
Ki 2 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 2C9
CHEMBL3397
 IC50 7.1 6.322 80.0 55
Cytochrome P450 2C9
CHEMBL3397
 Ki 6.7 6.5 200.0 2
Mycobacterium tuberculosis variant bovis
CHEMBL613086
 IC50 5.0 5.0 10000.0 1
Cytochrome P450 2C18
CHEMBL2408
 IC50 4.22 4.22 60000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Inhibition 83.0 % Homo sapiens
Inhibition 82.0 % Homo sapiens
Inhibition 75.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 2C9 IC50 = 80.0 nM 7.1 Inhibition of CYP2C9 (unknown origin) using luciferin tagged substrate preincuba... 26355532
Cytochrome P450 2C9 IC50 = 140.0 nM 6.85 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate inc... 35609303
Cytochrome P450 2C9 IC50 = 180.0 nM 6.75 Inhibition of recombinant CYP2C9 (unknown origin) using 7-methoxy-4-trifluoromet... 24793360
Cytochrome P450 2C9 IC50 = 180.0 nM 6.75 Inhibition of CYP2C9 in human liver microsome 25082126
Cytochrome P450 2C9 IC50 = 180.0 nM 6.75 Inhibition of human recombinant CYP2C9 using MFC as substrate incubated for 40 m... 27105029
Cytochrome P450 2C9 IC50 = 200.0 nM 6.7 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Cytochrome P450 2C9 Ki = 200.0 nM 6.7 Binding affinity measured on human cytochrome P450 2C9 (CYP2C9) enzyme 10956186
Cytochrome P450 2C9 IC50 = 205.0 nM 6.69 Inhibition of CYP2C9 in human liver microsomes using tolbutamide as substrate af... 28337324
Cytochrome P450 2C9 IC50 = 210.0 nM 6.68 Extracellular Cytochrome P450 Inhibition Assay: Specific aspects of the incubati... -
Cytochrome P450 2C9 IC50 = 245.0 nM 6.61 Inhibition of CYP2C9 in human liver microsomes using tolbutamide as substrate an... 35834906
Cytochrome P450 2C9 IC50 = 245.0 nM 6.61 Inhibition of CYP2C9 in human liver microsomes using tolbutamide as substrate by... 36846364
Cytochrome P450 2C9 IC50 = 250.0 nM 6.6 Inhibition of human CYP2C9 18324762
Cytochrome P450 2C9 IC50 = 250.0 nM 6.6 Inhibition of human CYP2C9 21189020
Cytochrome P450 2C9 IC50 = 258.0 nM 6.59 Inhibition of CYP2C9 (unknown origin) 37982711
Cytochrome P450 2C9 IC50 = 270.0 nM 6.57 Fluorescent High Throughput P450 Assay: The interaction of SC12 with cytochrome ... -
Cytochrome P450 2C9 IC50 = 270.0 nM 6.57 Fluorescent High Throughput P450 Assays: The interaction of SC12 with cytochrome... -
Cytochrome P450 2C9 IC50 = 270.0 nM 6.57 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre... 39041662
Cytochrome P450 2C9 IC50 = 280.0 nM 6.55 Inhibition of human CYP2C9 by fluorescence method 31693857
Cytochrome P450 2C9 IC50 = 318.0 nM 6.5 Inhibition of human recombinant CYP2C9 expressed in insect microsomes 18672861
Cytochrome P450 2C9 IC50 = 318.0 nM 6.5 Inhibition of human recombinant CYP2C9 expressed in baculovirus-infected insect ... 18763754

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
- 10.6019/CHEMBL5303304 U2OS 9
- 10.6019/CHEMBL5303304 HEK-293T 5
- 10.6019/CHEMBL5303304 Fibroblast 4
- 10.6019/CHEMBL3637782 No relevant target 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.1039/C4MD00196F ADMET 3
- 10.6019/CHEMBL3637782 Mycobacterium tuberculosis H37Rv 3
39041662 10.1021/acs.jmedchem.4c00483 Cytochrome P450 2C9 2
22931300 10.1021/tx300075j Liver microsomes 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
33705901 10.1016/j.bmcl.2021.127924 Mycobacterium tuberculosis 2
24974340 10.1016/j.bmcl.2014.06.026 Cytochrome P450 2C9 2
33705901 10.1016/j.bmcl.2021.127924 Cytochrome P450 2C9 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
34415148 10.1021/acs.jmedchem.1c00271 Cytochrome P450 2C9 2
37499291 10.1016/j.ejmech.2023.115671 Cytochrome P450 2C9 1
18763754 10.1021/jm800683c Cytochrome P450 2C9 1

Data from ChEMBL 36 via Core Engine