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Compound Detail

CHEMBL1201303

PYRVINIUM
💊 Approved Drug
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💊 Approved Drug
Cc1cc(/C=C/c2ccc3cc(N(C)C)ccc3[n+]2C)c(C)n1-c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201303
Name PYRVINIUM
Phase Approved
Structure Type MOL
InChI Key QMHSXPLYMTVAMK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Pyrvinium Pyrvinium (cation) Pyrvinium cation Pyrvinium hydroxide Pyrvinium ion Pyrvinum (base)
12
Targets
20
Activities
3
Assay Types
1
PK Parameters
20
Publications
6
Known Names
1
Indications

Molecular Properties

382.5
MW (Da)
5.31
ALogP
2
HBA
0
HBD
12.1
PSA (Ų)
0.44
QED
1
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 -ium; -vin-

Extended Properties

Molecular Formula C26H28N3+
MW 382.53
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -1.03

Indications

Helminthiasis

ATC Classification

P02CX01
pyrvinium
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTHELMINTICS

Activity Summary

IC50 16 meas. best 8.0
EC50 3 meas. best 7.37
Kd 1 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Casein kinase I isoform alpha
CHEMBL2793
 Kd 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 IC50 8.0 7.248 10.0 5
Programmed cell death protein 1/Programmed cell death 1 ligand 1
CHEMBL4523993
 IC50 7.53 6.025 29.7 2
HCT-116
CHEMBL394
 EC50 7.37 7.37 43.0 1
SW480
CHEMBL612544
 EC50 7.25 7.25 56.0 1
Androgen receptor
CHEMBL1871
 IC50 6.72 6.72 190.0 1
Cryptosporidium parvum
CHEMBL612855
 IC50 6.45 6.45 354.0 1
Molecular identity unknown
CHEMBL612546
 IC50 6.23 6.23 592.0 1
MCF-10A
CHEMBL614321
 EC50 6.1 6.1 800.0 1
Synaptojanin-1
CHEMBL4523136
 IC50 6.0 6.0 1000.0 2
Synaptojanin-2
CHEMBL4523129
 IC50 5.9 5.9 1250.0 3
Serine hydroxymethyltransferase, mitochondrial
CHEMBL4295747
 IC50 5.59 5.59 2570.4 1

Pharmacokinetic Data

Parameter Value Units Species
F 1.0 % Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Casein kinase I isoform alpha Kd = 1.0 nM 9.0 Binding affinity to CK1alpha (unknown origin) using casein as substrate by fluor... 33636537
Unchecked IC50 = 10.0 nM 8.0 Inhibition of Wnt/beta-catenin transactivation signalling in Wnt3a stimulated hu... 33636537
Unchecked IC50 = 10.0 nM 8.0 Inhibition of hedgehog signalling in mouse Shh Light II cells assessed as lucife... 33636537
Unchecked IC50 = 10.0 nM 8.0 Inhibition of Wnt signalling pathway in HEK293 cells assessed growth inhibition ... 33822624
Programmed cell death protein 1/Programmed cell death 1 ligand 1 IC50 = 29.66 nM 7.53 Inhibition of PD-1/PD-L1 (unknown origin) protein-protein interaction incubated ... 38665838
HCT-116 EC50 = 43.0 nM 7.37 Anticancer activity against human HCT-116 cells assessed as reduction in cell vi... 33445154
SW480 EC50 = 56.0 nM 7.25 Anticancer activity against human SW480 cells assessed as reduction in cell viab... 33445154
Androgen receptor IC50 = 190.0 nM 6.72 Antagonist activity at Androgen receptor in human LNCaP cells assessed as inhibi... 35786895
Cryptosporidium parvum IC50 = 354.0 nM 6.45 Antimicrobial activity against Cryptosporidium parvum infected in human HCT-8 ce... 18591280
Molecular identity unknown IC50 = 592.0 nM 6.23 Inhibition of beta-casein-dependent canonical Wnt3 pathway in human HEK293T cell... 22191557
Unchecked IC50 = 750.0 nM 6.12 Inhibition of Wnt3a activated Wnt/beta-catenin signaling (unknown origin) expres... 30605343
Unchecked IC50 = 750.0 nM 6.12 Inhibition of Wnt/beta-Catenin signaling (unknown origin) expressed in recombina... 31769984
MCF-10A EC50 = 800.0 nM 6.1 Inhibition of EGF-induced cell migration in human MCF10A cells incubated for 18 ... -
Synaptojanin-1 IC50 = 1000.0 nM 6.0 Inhibition of C-Myc/DDK-tagged human recombinant SYNJ1 expressed in HEK293T cell... -
Synaptojanin-1 IC50 = 1000.0 nM 6.0 Inhibition of C-Myc/DDK-tagged human recombinant SYNJ1 expressed in HEK293T cell... -
Synaptojanin-2 IC50 = 1250.0 nM 5.9 Inhibition of C-Myc/DDK-tagged human recombinant SYNJ2 expressed in HEK293T cell... -
Synaptojanin-2 IC50 = 1250.0 nM 5.9 Inhibition of C-Myc/DDK-tagged human recombinant SYNJ2 expressed in HEK293T cell... -
Synaptojanin-2 IC50 = 1250.0 nM 5.9 Inhibition of recombinant full length C-Myc/DDK-tagged human SYNJ2 expressed in ... -
Serine hydroxymethyltransferase, mitochondrial IC50 = 2570.4 nM 5.59 Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli B... -
Programmed cell death protein 1/Programmed cell death 1 ligand 1 IC50 = 30000.0 nM 4.52 Inhibition of PD-1/PD-L1 interaction (unknown origin) by HTRF assay 37196547

Literature References

PubMed DOI Target Context # Activities
18591280 10.1128/aac.00207-08 Cryptosporidium parvum 8
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
33636537 10.1016/j.ejmech.2021.113268 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37196547 10.1016/j.ejmech.2023.115465 Programmed cell death protein 1/Programmed cell death 1 ligand 1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
31769984 10.1021/acs.jmedchem.9b01252 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
18591280 10.1128/aac.00207-08 HCT-8 2
33636537 10.1016/j.ejmech.2021.113268 Casein kinase I isoform alpha 1

Data from ChEMBL 36 via Core Engine