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Compound Detail

CHEMBL55

PENTAMIDINE
💊 Approved Drug
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💊 Approved Drug
N=C(N)c1ccc(OCCCCCOc2ccc(C(=N)N)cc2)cc1

Basic Information

ChEMBL ID CHEMBL55
Name PENTAMIDINE
Phase Approved
Structure Type MOL
InChI Key XDRYMKDFEDOLFX-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

GNF-Pf-3680 MB 800 FREE BASE MB-800 MB-800 (AS ISETHIONATE) MB-800 FREE BASE Mp-601205 NSC-9921 Pentacarinat Pentam 300 Pentamidina Pentamidine RP 2512 FREE BASE +2 more
78
Targets
558
Activities
4
Assay Types
5
PK Parameters
20
Publications
14
Known Names
11
Indications

Molecular Properties

340.4
MW (Da)
2.88
ALogP
4
HBA
4
HBD
118.2
PSA (Ų)
0.30
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1984
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral Topical

Flags

Natural Product
USAN Stem -amidine
USAN Year 2007

Extended Properties

Molecular Formula C19H24N4O2
MW 340.43
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.14

Indications

Infections Colorectal Neoplasms Diabetes Mellitus, Type 1 Leishmaniasis Lymphoma, AIDS-Related Melanoma Trypanosomiasis Carcinoma, Hepatocellular Hodgkin Disease Kidney Diseases Pancreatic Neoplasms

Activity Summary

IC50 415 meas. best 9.7
EC50 114 meas. best 9.96
Ki 23 meas. best 7.44
Kd 6 meas. best 6.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei brucei
CHEMBL612851
EC50 9.96 7.8397 0.1 38
Trypanosoma brucei
CHEMBL612849
IC50 9.7 7.7918 0.2 17
Trypanosoma brucei
CHEMBL612849
EC50 9.47 7.5997 0.3 30
Trypanosoma brucei rhodesiense
CHEMBL612348
EC50 9.22 9.22 0.6 1
Trypanosoma brucei gambiense
CHEMBL613768
EC50 9.15 8.4967 0.7 3
NON-PROTEIN TARGET
CHEMBL3879801
EC50 9.05 5.8557 0.9 7
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 9.0 8.3303 1.0 40
Trypanosoma brucei gambiense
CHEMBL613768
IC50 9.0 8.4 1.0 7
Trypanosoma brucei brucei
CHEMBL612851
IC50 8.85 8.1103 1.4 31
Leishmania donovani
CHEMBL367
IC50 8.72 5.4649 1.9 75
NON-PROTEIN TARGET
CHEMBL3879801
IC50 8.68 6.136 2.1 5
Trypanosoma cruzi
CHEMBL368
IC50 8.62 6.5075 2.4 8
Mus musculus
CHEMBL375
IC50 8.49 8.49 3.2 1
Plasmodium falciparum
CHEMBL364
IC50 8.19 7.3483 6.4 24
Leishmania amazonensis
CHEMBL612877
IC50 7.68 5.5394 21.0 31
Leishmania tarentolae
CHEMBL612915
IC50 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
Ki 7.44 5.89 36.0 7
A549
CHEMBL392
IC50 7.4 5.3175 40.0 4
L6
CHEMBL614793
IC50 7.33 4.8665 46.6 23
Leishmania braziliensis
CHEMBL612878
IC50 7.22 5.371 60.0 10
Leishmania infantum
CHEMBL612848
IC50 7.21 5.3475 62.0 4
Plasmodium falciparum
CHEMBL364
EC50 7.18 7.17 66.2 2
Pneumocystis carinii
CHEMBL613064
IC50 7.08 6.43 84.0 6
Unchecked
CHEMBL612545
Kd 6.92 6.07 120.0 3
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.66 6.66 220.0 1
Unchecked
CHEMBL612545
IC50 6.62 5.06 242.0 10
Leishmania major
CHEMBL612879
EC50 6.55 5.9225 280.0 4
Diamine oxidase [copper-containing]
CHEMBL2118
Ki 6.54 6.54 290.0 1
Protein tyrosine phosphatase type IVA 2
CHEMBL1075105
IC50 6.52 6.52 300.0 1
Protein tyrosine phosphatase type IVA 1
CHEMBL1075169
IC50 6.52 6.52 300.0 1
Protein tyrosine phosphatase type IVA 3
CHEMBL4162
IC50 6.52 5.02 300.0 3
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 6.39 5.8867 410.0 3
Leishmania amazonensis
CHEMBL612877
EC50 6.34 5.6575 460.0 4
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.33 6.33 468.0 1
Leishmania major
CHEMBL612879
IC50 6.33 5.3485 470.0 13
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.31 6.31 491.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.29 6.29 516.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.29 6.29 507.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 6.27 6.27 535.0 1
ADMET
CHEMBL612558
IC50 6.25 5.59 560.0 3
Glutamate NMDA receptor; GRIN1/GRIN2A
CHEMBL1907604
IC50 6.14 6.14 720.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
IC50 6.1 6.1 793.0 1
Leishmania guyanensis
CHEMBL612793
IC50 6.05 6.05 900.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 6.01 6.01 967.0 1
Protein S100-B
CHEMBL4300
Kd 6.0 6.0 1000.0 1
Leishmania mexicana
CHEMBL612880
IC50 6.0 5.2714 1000.0 7
J774.A1
CHEMBL614040
IC50 5.99 5.99 1030.0 1
Leishmania chagasi
CHEMBL612790
IC50 5.96 5.6667 1110.0 3
Suppressor of tumorigenicity 14 protein
CHEMBL3018
Ki 5.94 5.94 1160.0 1
Solute carrier family 22 member 2
CHEMBL1743122
IC50 5.92 5.92 1200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 74.0 mL.min-1.kg-1 Homo sapiens
Cmax 900.0 nM Homo sapiens
MRT 12.0 hr Homo sapiens
T1/2 25.0 hr Homo sapiens
T1/2 265.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei brucei EC50 = 0.11 nM 9.96 Trypanocidal activity against wild type bloodstream form of Trypanosoma brucei b... 26231081
Trypanosoma brucei IC50 = 0.2 nM 9.7 Antitrypanosomal activity against Trypanosoma brucei 38924701
Trypanosoma brucei EC50 = 0.34 nM 9.47 Antitrypanosomal activity against wildtype bloodstream Trypanosoma brucei Lister... 37729094
Trypanosoma brucei rhodesiense EC50 = 0.6 nM 9.22 Antitrypanosomal activity against bloodstream forms of wild type Trypanosoma bru... 23484493
Trypanosoma brucei gambiense EC50 = 0.7 nM 9.15 Antitrypanosomal activity against Trypanosoma brucei gambiense STIB930 after 70 ... 23484493
Trypanosoma brucei IC50 = 0.8 nM 9.1 In vitro inhibitory concentration against mice infected with Trypanosoma brucei ... 12620080
Trypanosoma brucei gambiense EC50 = 0.9 nM 9.05 Antitrypanosomal activity against Trypanosoma brucei gambiense DAL 898R after 70... 23484493
NON-PROTEIN TARGET EC50 = 0.9 nM 9.05 Antitrypanosomal activity against Trypanosoma brucei 427 bloodstream forms asses... 27788467
Trypanosoma brucei EC50 = 0.95 nM 9.02 Antimicrobial activity against Trypanosoma brucei 20439607
Trypanosoma brucei rhodesiense IC50 = 1.0 nM 9.0 Antitrypanosomal activity against Trypanosoma brucei rhodesiense IL-1501 assesse... 33369420
Trypanosoma brucei gambiense IC50 = 1.0 nM 9.0 Trypanocidal activity against Trypanosoma brucei gambiense 30774852
Trypanosoma brucei EC50 = 1.1 nM 8.96 Trypanocidal activity against bloodstream form of N-(4-(allyloxy)-3-(trifluorome... 23281892
Trypanosoma brucei rhodesiense IC50 = 1.3 nM 8.89 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei rhodesi... 21112788
Trypanosoma brucei brucei EC50 = 1.4 nM 8.85 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei ... 24900279
Trypanosoma brucei brucei IC50 = 1.4 nM 8.85 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei ... 31051403
Trypanosoma brucei gambiense IC50 = 1.5 nM 8.82 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei gambien... 31051403
Trypanosoma brucei IC50 = 1.55 nM 8.81 Antitrypanosomal activity against Trypanosoma brucei bloodstream form after 72 h... 30996791
Trypanosoma brucei brucei EC50 = 1.55 nM 8.81 Antitrypanosomal activity against Trypanosoma brucei brucei Lister 427 bloodstre... 27411733
Trypanosoma brucei brucei EC50 = 1.55 nM 8.81 Anti-parasitic activity against bloodstream form of Trypanosoma brucei brucei Li... 28064141
Trypanosoma brucei brucei IC50 = 1.6 nM 8.8 Antiparasitic activity against bloodstream form of Trypanosoma brucei brucei 427... 26322631

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
16472241 10.2174/1570163043334794 Hepatotoxicity 18
26296478 10.1016/j.bmcl.2015.08.017 Glutamate NMDA receptor 15
19786608 10.1128/aac.00803-09 Mycolicibacterium smegmatis 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
7381860 10.1021/jm00179a022 Mus musculus 10
336890 10.1021/jm00219a023 Trypanosoma brucei rhodesiense 9
- 10.1016/S0960-894X(97)00240-0 Glutamate NMDA receptor 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
16107157 10.1021/jm050177+ Mus musculus 8
321783 10.1021/jm00214a014 Trypanosoma brucei rhodesiense 8
19091566 10.1016/j.bmcl.2008.11.094 Leishmania donovani 7
29544150 10.1016/j.ejmech.2018.02.075 Trypanosoma brucei brucei 7
30677668 10.1016/j.ejmech.2018.12.050 Trypanosoma brucei 7
19620327 10.1128/aac.00225-09 Trypanosoma brucei rhodesiense 7
24858543 10.1016/j.ejmech.2014.05.037 Unchecked 7
28571825 10.1016/j.bmcl.2017.05.052 Trypanosoma brucei 7
24980054 10.1016/j.bmcl.2014.06.030 Leishmania donovani 6
17116678 10.1128/aac.01193-06 Leishmania donovani 6
- 10.1039/C3MD00097D Unchecked 6

Data from ChEMBL 36 via Core Engine