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Compound Detail

CHEMBL1377

PROGUANIL
💊 Approved Drug
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💊 Approved Drug
CC(C)NC(=N)NC(=N)Nc1ccc(Cl)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1377
Name PROGUANIL
Phase Approved
Structure Type MOL
InChI Key SSOLNOMRVKKSON-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL747

Known Names

Chlorguanide Chloroguanide Proguanil
7
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
3
Known Names
4
Indications

Molecular Properties

253.7
MW (Da)
2.21
ALogP
2
HBA
5
HBD
83.8
PSA (Ų)
0.41
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2000
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product Prodrug
USAN Year 2000

Extended Properties

Molecular Formula C11H16ClN5
MW 253.74
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -0.85

Indications

Malaria Malaria, Falciparum Infections Gastroesophageal Reflux

ATC Classification

P01BB01
proguanil
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS
P01BB51
proguanil, combinations
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 7 meas. best 5.42
EC50 1 meas. best 5.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A549
CHEMBL392
 IC50 5.42 5.42 3800.0 1
Trace amine-associated receptor 1
CHEMBL4908
 EC50 5.27 5.27 5400.0 1
HCT-116
CHEMBL394
 IC50 5.08 5.08 8400.0 1
A2780
CHEMBL614004
 IC50 4.89 4.89 13000.0 1
UMUC3
CHEMBL612799
 IC50 4.79 4.79 16300.0 1
T-24
CHEMBL614774
 IC50 4.74 4.74 18400.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.44 4.44 36000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A549 IC50 = 3800.0 nM 5.42 Antiproliferative activity against human A549 cells assessed as reduction in cel... 31864776
Trace amine-associated receptor 1 EC50 = 5400.0 nM 5.27 Agonist activity at mouse TAAR1 expressed in HEK293 cells assessed as cAMP accum... 27823885
HCT-116 IC50 = 8400.0 nM 5.08 Antiproliferative activity against human HCT116 cells assessed as reduction in c... 31864776
A2780 IC50 = 13000.0 nM 4.89 Antiproliferative activity against human A2780 cells assessed as reduction in ce... 31864776
UMUC3 IC50 = 16300.0 nM 4.79 Antiproliferative activity against human UM-UC-3 cells assessed as reduction in ... 31864776
T-24 IC50 = 18400.0 nM 4.74 Antiproliferative activity against human T24 cells assessed as reduction in cell... 31864776
Plasmodium falciparum IC50 = 36000.0 nM 4.44 Antimicrobial activity against Plasmodium falciparum 20185316

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
31864776 10.1016/j.bmc.2019.115258 AMP-activated protein kinase, AMPK 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
27823885 10.1016/j.ejmech.2016.10.058 Trace amine-associated receptor 1 4
31864776 10.1016/j.bmc.2019.115258 UMUC3 3
31864776 10.1016/j.bmc.2019.115258 T-24 3
28477572 10.1016/j.ejmech.2017.04.070 Unchecked 3
20014752 10.1021/tx900326k Hepatotoxicity 3
31864776 10.1016/j.bmc.2019.115258 HCT-116 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
430476 10.1021/jm00190a006 Streptococcus mutans 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
31864776 10.1016/j.bmc.2019.115258 A2780 2
28477572 10.1016/j.ejmech.2017.04.070 Influenza A virus 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
28477572 10.1016/j.ejmech.2017.04.070 MDCK 2
31864776 10.1016/j.bmc.2019.115258 A549 2
28477572 10.1016/j.ejmech.2017.04.070 Coxsackievirus B4 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
15828818 10.1021/jm049683+ Plasmodium falciparum 2

Data from ChEMBL 36 via Core Engine