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Compound Detail

CHEMBL439

SULFADIAZINE
💊 Approved Drug
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💊 Approved Drug
Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL439
Name SULFADIAZINE
Phase Approved
Structure Type MOL
InChI Key SEEPANYCNGTZFQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Coco-diazine Diazyl NSC-35600 Sulfadiazina Sulfadiazine Sulfadiazine (trisulfapyrimidines) Sulfadiazine (trisulfapyrimidines) component of neotrizine Sulfadiazine (trisulfapyrimidines) component of terfonyl Sulfadiazine component of lantrisul Sulfadiazine component of neotrizine Sulfadiazine component of sulfaloid Sulfadiazine component of sulfonamides duplex +5 more
10
Targets
20
Activities
1
Assay Types
10
PK Parameters
20
Publications
17
Known Names
7
Indications
1
Mechanisms

Molecular Properties

250.3
MW (Da)
0.86
ALogP
5
HBA
2
HBD
98.0
PSA (Ų)
0.79
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1941
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Stem sulfa-
USAN Year 1975

Extended Properties

Molecular Formula C10H10N4O2S
MW 250.28
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -1.65

Mechanism of Action

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

Indications

Bacterial Infections Malaria Chorioretinitis Toxoplasmosis, Congenital Burns Toxoplasmosis, Cerebral Osteomyelitis

ATC Classification

J01EC02
sulfadiazine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 20 meas. best 6.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL202
 IC50 6.89 6.89 130.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.84 5.84 1440.0 1
Escherichia coli
CHEMBL354
 IC50 4.92 4.92 12000.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.73 4.73 18450.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.69 4.545 20620.0 2
Aurora kinase A
CHEMBL4722
 IC50 4.68 4.68 21000.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.6 4.6 24870.0 1
Toxoplasma gondii
CHEMBL612888
 IC50 4.58 4.32 26050.0 3
ADMET
CHEMBL612558
 IC50 4.56 4.56 27300.0 1
Vero
CHEMBL391
 IC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.55 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 0.55 mL.min-1.kg-1 Homo sapiens
CL 0.55 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
F 100.0 % Homo sapiens
Fu 0.44 - Homo sapiens
Fu 0.44 - Homo sapiens
MRT 8.8 hr Homo sapiens
T1/2 7.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase IC50 = 130.0 nM 6.89 Inhibition of DHFR (unknown origin) 35685617
Plasmodium falciparum IC50 = 1440.0 nM 5.84 DNDI: Malaria in Vitro, 72 hour -
Escherichia coli IC50 = 12000.0 nM 4.92 Antibacterial activity against sensitive Escherichia coli ATCC 10536 assessed as... 137981
Trypanosoma brucei rhodesiense IC50 = 18450.0 nM 4.73 DNDI: HAT in Vitro, 72 hour -
NON-PROTEIN TARGET IC50 = 20620.0 nM 4.69 DNDI: Cytotoxicity in Vitro, 72 hour, in rat skeletal myoblast cells -
Aurora kinase A IC50 = 21000.0 nM 4.68 Inhibition of aurora kinase A 18457385
Trypanosoma cruzi IC50 = 24870.0 nM 4.6 DNDI: Chagas in Vitro, 96 hour -
Toxoplasma gondii IC50 = 26050.0 nM 4.58 Antiparasitic activity against Toxoplasma gondii infected in HFF cells assessed ... 34894691
ADMET IC50 = 27300.0 nM 4.56 Cytotoxicity against human CRL1634 cells after 48 hrs by MTT assay 20456959
NON-PROTEIN TARGET IC50 = 40120.0 nM 4.4 DNDI: Cytotoxicity in Vitro, 96 hour, in mouse macrophages (infected-amastigotes... -
Toxoplasma gondii IC50 = 41200.0 nM 4.38 Antitoxoplasma activity against wild type Toxoplasma gondii RH assessed as survi... 18563892
Vero IC50 = 90000.0 nM 4.05 Compound tested on vero cells infected with Toxoplasma gondii after 24 h 15863319
Toxoplasma gondii IC50 = 100000.0 nM 4.0 Compound tested on intracellular parasites Toxoplasma gondii in vero cells after... 15863319

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 252
16472241 10.2174/1570163043334794 Hepatotoxicity 18
18212105 10.1128/aac.01203-07 Toxoplasma gondii 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
36274280 10.1016/j.ejmech.2022.114812 ADMET 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
20456959 10.1016/j.bmc.2010.04.003 Toxoplasma gondii 8
17905587 10.1016/j.bmc.2007.09.025 Toxoplasma gondii 7
22365879 10.1016/j.ejmech.2012.01.060 Mycobacterium kansasii 6
19188396 10.1128/aac.00994-08 Neisseria meningitidis 6
36274280 10.1016/j.ejmech.2022.114812 Toxoplasma gondii 6
15055998 10.1021/jm030537y Unchecked 5
18563892 10.1021/jm800201s Toxoplasma gondii 5
15055998 10.1021/jm030537y Toxoplasma gondii 5
18563892 10.1021/jm800201s ADMET 4
14552772 10.1016/j.bmcl.2003.08.017 Bacillus subtilis 4
14552772 10.1016/j.bmcl.2003.08.017 Klebsiella pneumoniae 4
15603963 10.1016/j.bmcl.2004.10.076 Klebsiella pneumoniae 4

Data from ChEMBL 36 via Core Engine