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Compound Detail

CHEMBL19224

PAPAVERINE
🧪 Phase III
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🧪 Phase III
COc1ccc(Cc2nccc3cc(OC)c(OC)cc23)cc1OC

Basic Information

ChEMBL ID CHEMBL19224
Name PAPAVERINE
Phase Phase III
Structure Type MOL
InChI Key XQYZDYMELSJDRZ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

NSC-136630 Papaverine Papaverinum
30
Targets
69
Activities
3
Assay Types
8
PK Parameters
20
Publications
3
Known Names
7
Indications

Molecular Properties

339.4
MW (Da)
3.86
ALogP
5
HBA
0
HBD
49.8
PSA (Ų)
0.68
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -verine

Extended Properties

Molecular Formula C20H21NO4
MW 339.39
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 0.12

Indications

Digestive System Diseases Erectile Dysfunction Gastroenteritis Prostatic Neoplasms, Castration-Resistant Carcinoma, Non-Small-Cell Lung Lung Neoplasms Prostatic Hyperplasia

ATC Classification

A03AD01
papaverine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
G04BE02
papaverine
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: UROLOGICALS
G04BE52
papaverine, combinations
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: UROLOGICALS

Activity Summary

IC50 65 meas. best 10.23
Ki 3 meas. best 7.77
Kd 1 meas. best 4.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Ileum
CHEMBL613633
IC50 10.23 8.086 0.1 5
Unchecked
CHEMBL612545
Ki 7.77 7.77 17.0 1
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
CHEMBL4409
IC50 7.77 7.2681 17.0 16
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
CHEMBL6140
IC50 7.44 7.44 36.0 4
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A
CHEMBL241
IC50 6.55 6.255 284.0 4
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A
CHEMBL241
Ki 6.55 6.55 279.0 1
Uterus
CHEMBL4296544
IC50 6.38 6.38 420.0 1
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B
CHEMBL290
Ki 6.38 6.38 417.0 1
Unchecked
CHEMBL612545
IC50 6.26 5.86 550.0 5
Phosphodiesterase 3A
CHEMBL3061
IC50 6.21 6.21 620.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 6.12 6.12 762.0 1
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B
CHEMBL290
IC50 5.99 5.99 1030.0 1
SARS-CoV-2
CHEMBL4303835
IC50 5.96 5.96 1100.0 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
IC50 5.85 5.85 1400.0 1
Rattus norvegicus
CHEMBL376
IC50 5.81 5.81 1550.0 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
IC50 5.8 5.8 1600.0 1
Phosphodiesterase 4A
CHEMBL3333
IC50 5.77 5.77 1700.0 1
Parainfluenza virus 5
CHEMBL5209661
IC50 5.7 5.7 2000.0 1
Influenza B virus
CHEMBL613129
IC50 5.7 5.7 2000.0 2
Influenza A virus
CHEMBL613740
IC50 5.7 5.7 2000.0 4
cGMP-dependent 3',5'-cyclic phosphodiesterase
CHEMBL2652
IC50 5.64 5.205 2300.0 2
Serine hydroxymethyltransferase, mitochondrial
CHEMBL4295747
IC50 5.57 5.57 2691.5 1
Ileum
CHEMBL613680
IC50 5.37 5.37 4230.0 1
Phosphodiesterase; PDE3 & PDE4
CHEMBL2095153
IC50 5.18 5.18 6600.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.14 5.14 7244.4 1
Phosphodiesterase 1
CHEMBL2097166
IC50 5.06 5.06 8800.0 1
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
IC50 5.06 5.06 8800.0 1
Phosphodiesterase 1
CHEMBL2095150
IC50 5.05 4.86 9000.0 2
Phosphodiesterase 1
CHEMBL2111322
IC50 4.92 4.8 12000.0 2
Intestine
CHEMBL613634
Kd 4.8 4.8 15848.9 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.64 4.64 23130.0 1
Acetylcholinesterase
CHEMBL4078
IC50 4.61 4.61 24300.0 1
Acetylcholinesterase
CHEMBL220
IC50 4.61 4.61 24330.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
Fu 0.073 - Homo sapiens
Fu 0.073 - Homo sapiens
MRT 1.4 hr Homo sapiens
T1/2 1.8 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Ileum IC50 = 0.059 nM 10.23 Antispasmodic activity in rat ileum assessed as inhibition of spontaneous contra... -
Ileum IC50 = 6.2 nM 8.21 Antispasmodic activity in rat ileum assessed as inhibition of histamine-induced ... -
Ileum IC50 = 7.07 nM 8.15 Antispasmodic activity in rat ileum assessed as inhibition of acetylcholine-indu... -
Ileum IC50 = 9.44 nM 8.03 Antispasmodic activity in rat ileum assessed as inhibition of barium chloride-in... -
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 17.0 nM 7.77 Inhibition of human PDE10A expressed in Sf9 cells using [3H]cAMP by scintillatio... 21087867
Unchecked Ki = 17.0 nM 7.77 Inhibition of rat recombinant PDE10A transfected in Sf9 cells by SPA 17228859
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 21.0 nM 7.68 Inhibition of human recombinant PDE10A assessed as reduction in hydrolysis of [3... 21705115
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Competitive inhibition of rat recombinant PDE10A by scintillation proximity assa... 26597534
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Inhibition of PDE10A (unknown origin) 34042442
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Inhibition of PDE10A (unknown origin) 31235264
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Inhibition of recombinant rat PDE10A expressed in Sf9 cells using cGMP/cAMP as s... 30952590
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Inhibition of recombinant rat PDE10A expressed in Sf9 insect cells using cGMP or... 29574203
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Binding affinity to PDE10A (unknown origin) 25592707
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Inhibition of PDE10A (unknown origin) 24721831
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Inhibition of human recombinant full length PDE10A using cAMP as substrate prein... 22321214
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 36.0 nM 7.44 Inhibition of rat PDE10A 21705115
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 38.0 nM 7.42 Inhibition of human recombinant PDE10A using cAMP as substrate incubated for 20 ... 33022582
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 40.0 nM 7.4 Inhibition of PDE10A 22834877
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 56.9 nM 7.25 Inhibition of human recombinant PDE10A expressed in baculovirus-SF21 cell system... 20450197
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 76.0 nM 7.12 Inhibition of human recombinant PDE10A expressed in baculovirus-SF21 cell system... 20450197

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1395
- 10.6019/CHEMBL3885881 Rattus norvegicus 143
- 10.5281/zenodo.13943903 ADMET 83
31158845 10.1038/s41586-019-1291-3 ADMET 60
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
31035240 10.1016/j.ejmech.2019.04.020 cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A 6
- 10.1007/s00044-011-9601-9 Ileum 5
8411013 10.1021/jm00072a016 Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
10576697 10.1016/s0960-894x(99)00569-7 Rattus norvegicus 4
33970631 10.1021/acs.jmedchem.1c00302 Influenza A virus 4
10447956 10.1021/jm991004l Rattus norvegicus 4
30523084 10.1126/science.aat9446 Plasmodium berghei 4
3928819 10.1021/np50039a003 NON-PROTEIN TARGET 3
6298424 10.1021/jm00356a011 Phosphodiesterase 1 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
16483771 10.1016/j.bmcl.2006.01.067 Acetylcholinesterase 3
16784847 10.1016/j.bmcl.2006.05.082 Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine