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Compound Detail

CHEMBL585

TRIAMTERENE
💊 Approved Drug
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💊 Approved Drug
Nc1nc(N)c2nc(-c3ccccc3)c(N)nc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL585
Name TRIAMTERENE
Phase Approved
Structure Type MOL
InChI Key FNYLWPVRPXGIIP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Dyrenium Dytac NSC-639359 NSC-77625 SK&F 8542 SK&F-8542 SK-8542 Triamterene Triamterene component of dyazide Triamterene component of maxzide Triamtereno
10
Targets
90
Activities
2
Assay Types
7
PK Parameters
20
Publications
11
Known Names
13
Indications
1
Mechanisms

Molecular Properties

253.3
MW (Da)
0.83
ALogP
7
HBA
3
HBD
129.6
PSA (Ų)
0.59
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1963

Extended Properties

Molecular Formula C12H11N7
MW 253.27
Aromatic Rings 3
Heavy Atoms 19
NP-Likeness -0.43

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Amiloride-sensitive sodium channel, ENaC blocker BLOCKER Amiloride-sensitive sodium channel, ENaC ✓ ✓

Indications

Cardiovascular Diseases Edema Heart Failure Hyperaldosteronism Hypertension Liver Cirrhosis Nephrotic Syndrome Toxemia Atherosclerosis Coronary Disease Death, Sudden, Cardiac Diabetes Mellitus, Type 2 Hypercholesterolemia

ATC Classification

C03DB02
triamterene
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Drug Warnings

Black Box Warning
metabolic toxicity
Country: United States

Activity Summary

IC50 88 meas. best 6.09
Ki 2 meas. best 5.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.09 6.09 807.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.0 4.7005 1000.0 75
Unchecked
CHEMBL612545
 Ki 5.92 5.92 1200.0 1
Pteridine reductase 1
CHEMBL6194
 Ki 5.47 5.47 3400.0 1
Caspase-1
CHEMBL4801
 IC50 5.44 5.44 3663.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 5.34 5.34 4613.0 1
Cathepsin G
CHEMBL4071
 IC50 5.13 5.13 7413.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.07 5.07 8530.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.0 5.0 10000.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.66 4.66 21680.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.64 4.64 22740.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 63.0 mL.min-1.kg-1 Homo sapiens
CL 63.0 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
F 51.0 % Homo sapiens
Fu 0.42 - Homo sapiens
MRT 3.4 hr Homo sapiens
T1/2 4.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 807.0 nM 6.09 PUBCHEM_BIOASSAY: Luminescent dose response cell-based high throughput screening... -
Plasmodium falciparum IC50 = 1000.0 nM 6.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Unchecked Ki = 1200.0 nM 5.92 Inhibition of Trypanosoma brucei recombinant PTR1 19916554
Plasmodium falciparum IC50 = 1995.26 nM 5.7 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 2200.0 nM 5.66 Antiplasmodial activity against Plasmodium falciparum 3D7 harboring polymorphic ... 19734910
Plasmodium falciparum IC50 = 2190.0 nM 5.66 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3294.0 nM 5.48 Antiplasmodial activity against Plasmodium falciparum JON after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3294.0 nM 5.48 Antiplasmodial activity against Plasmodium falciparum JON after 72 hrs by SYBR g... 19734910
Pteridine reductase 1 Ki = 3400.0 nM 5.47 Inhibition of Leishmania major recombinant PTR1 19916554
Plasmodium falciparum IC50 = 3540.0 nM 5.45 Antiplasmodial activity against Plasmodium falciparum QF5 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3540.0 nM 5.45 Antiplasmodial activity against Plasmodium falciparum QF5 after 72 hrs by SYBR g... 19734910
Caspase-1 IC50 = 3663.0 nM 5.44 DRUGMATRIX: Protease, Caspase 1 enzyme inhibition (substrate: Ac-YVAD-AMC) -
Plasmodium falciparum IC50 = 4000.0 nM 5.4 Antiplasmodial activity against transgenic Plasmodium falciparum Dd2 pDT harbori... 19734910
Plasmodium falciparum IC50 = 4263.0 nM 5.37 Antiplasmodial activity against Plasmodium falciparum JC3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 4263.0 nM 5.37 Antiplasmodial activity against Plasmodium falciparum JC3 after 72 hrs by SYBR g... 19734910
Tyrosine-protein kinase JAK2 IC50 = 4613.0 nM 5.34 PUBCHEM_BIOASSAY: Luminescent counterscreen for inhibitors of the Janus kinase 2... -
Plasmodium falciparum IC50 = 5191.0 nM 5.29 Antiplasmodial activity against Plasmodium falciparum KA6 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 5110.0 nM 5.29 Antiplasmodial activity against Plasmodium falciparum JF11 after 72 hrs by SYBR ... 19734910
Plasmodium falciparum IC50 = 5191.0 nM 5.29 Antiplasmodial activity against Plasmodium falciparum KA6 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1423
- 10.6019/CHEMBL3885881 Rattus norvegicus 202
19734910 10.1038/nchembio.215 Plasmodium falciparum 78
1433206 10.1021/jm00100a001 Rattus norvegicus 48
2724291 10.1021/jm00126a003 Rattus norvegicus 24
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
1433206 10.1021/jm00100a001 ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
874960 10.1021/jm00216a021 Rattus norvegicus 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 5
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 5
11602674 - ATP-dependent translocase ABCB1 5
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 5
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 5
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
18426954 10.1124/dmd.108.020479 ADMET 4
1560438 10.1021/jm00085a012 Rattus norvegicus 4

Data from ChEMBL 36 via Core Engine