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Compound Detail

CHEMBL511

PYRILAMINE
💊 Approved Drug
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💊 Approved Drug
COc1ccc(CN(CCN(C)C)c2ccccn2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL511
Name PYRILAMINE
Phase Approved
Structure Type MOL
InChI Key YECBIJXISLIIDS-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Mepiramina Mepyramine NSC-13136
17
Targets
78
Activities
4
Assay Types
0
PK Parameters
20
Publications
3
Known Names
2
Indications

Molecular Properties

285.4
MW (Da)
2.66
ALogP
4
HBA
0
HBD
28.6
PSA (Ų)
0.78
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1973
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral Topical

Flags

Natural Product

Extended Properties

Molecular Formula C17H23N3O
MW 285.39
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -1.16

Indications

Hypersensitivity Pruritus

ATC Classification

D04AA02
mepyramine
Level 1: DERMATOLOGICALS
Level 2: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
R06AC01
mepyramine
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

IC50 41 meas. best 10.85
Ki 25 meas. best 9.37
Kd 10 meas. best 9.5
EC50 2 meas. best 8.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
 IC50 10.85 8.5075 0.0 16
Histamine H1 receptor
CHEMBL3943
 Kd 9.5 9.124 0.3 10
Histamine H1 receptor
CHEMBL231
 Ki 9.37 8.7858 0.4 12
Histamine H1 receptor
CHEMBL3943
 IC50 8.82 8.145 1.5 2
Histamine H1 receptor
CHEMBL231
 EC50 8.59 8.59 2.6 1
Histamine H1 receptor
CHEMBL4701
 IC50 8.24 8.24 5.8 1
Cavia porcellus
CHEMBL369
 IC50 7.77 7.77 17.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 7.6 7.6 25.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.33 7.33 47.0 1
RBL-2H3
CHEMBL614632
 IC50 7.09 7.0 81.5 3
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.54 6.54 285.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 6.52 6.52 300.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 6.23 6.23 592.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.18 6.18 655.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 6.16 6.16 699.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 6.06 6.06 879.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 IC50 6.0 6.0 997.0 1
Rattus norvegicus
CHEMBL376
 Ki 5.99 5.495 1032.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.96 5.43 1100.0 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 IC50 5.95 5.95 1130.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 5.95 5.95 1116.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 IC50 5.81 5.81 1558.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 5.75 5.75 1774.0 1
Unchecked
CHEMBL612545
 Ki 5.65 5.485 2226.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 IC50 5.55 5.55 2788.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 5.53 5.53 2976.0 1
Unchecked
CHEMBL612545
 IC50 5.48 5.19 3339.0 3
Rattus norvegicus
CHEMBL376
 IC50 5.4 4.862 3981.1 5
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.2 5.2 6260.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 4.99 4.99 10337.8 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor IC50 = 0.014 nM 10.85 Displacement of [3H]pyrilamine from human recombinant histamine H1 receptor expr... 26988801
Histamine H1 receptor Kd = 0.3162 nM 9.5 Antagonist activity at histamine H1 receptor in Cavia porcellus (guinea pig) ile... -
Histamine H1 receptor Kd = 0.3802 nM 9.42 Histamine H1 receptor antagonistic activity in guinea pig ileum using fluorescen... 12657255
Histamine H1 receptor Ki = 0.432 nM 9.37 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Histamine H1 receptor Kd = 0.6607 nM 9.18 Antagonist activity at histamine H1 receptor in guinea pig ileum preincubated fo... 30881612
Histamine H1 receptor Ki = 0.71 nM 9.15 Displacement of [3H]pyrilamine from human recombinant histamine H1 receptor in H... 27997171
Histamine H1 receptor Kd = 0.7943 nM 9.1 H1-antihistamine activity on guinea pig ileum 6208360
Histamine H1 receptor Kd = 0.7943 nM 9.1 H1-antihistamine activity in guinea pig ileum 2431143
Histamine H1 receptor IC50 = 0.82 nM 9.09 Binding affinity to human histamine H1 receptor by radioligand displacement assa... 23582449
Histamine H1 receptor Kd = 0.8511 nM 9.07 Antagonist activity at H1R in guinea pig ileum assessed as inhibition of histami... 21944853
Histamine H1 receptor Kd = 0.8511 nM 9.07 Antagonism against H1 histamine receptor of guinea pig ileum -
Histamine H1 receptor Ki = 0.95 nM 9.02 Binding affinity to human histamine H1 receptor by radioligand displacement assa... 23466604
Histamine H1 receptor Kd = 1.0 nM 9.0 In vitro for histamine H1 receptor antagonist activity against histamine-induced... 1353796
Histamine H1 receptor Kd = 1.096 nM 8.96 Antagonist activity at histamine H1 receptor in guinea pig ileum assessed as his... 18990469
Histamine H1 receptor Ki = 1.259 nM 8.9 Displacement of [3H]mepyramine from human wild type N-terminal hemagglutinin-tag... 27643714
Histamine H1 receptor IC50 = 1.3 nM 8.89 Percent inhibition against Histamine H1 receptor at 1 uM 16250647
Histamine H1 receptor IC50 = 1.4 nM 8.85 Displacement of [3H]pyrilamine from human recombinant H1 receptor expressed in H... 27876250
Histamine H1 receptor Kd = 1.445 nM 8.84 Antagonist activity at histamine H1 receptor in guinea pig jejunum assessed as r... 25752982
Histamine H1 receptor IC50 = 1.5 nM 8.82 Inhibition of guinea pig histamine H1 receptor 20875743
Histamine H1 receptor IC50 = 1.5 nM 8.82 Binding affinity to human histamine H1 receptor by radioligand displacement assa... 23466604

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 332
16408006 10.1038/nchembio714 Histamine H1 receptor 7
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
3934386 10.1021/jm00150a029 Rattus norvegicus 4
3746815 10.1021/jm00159a017 Rattus norvegicus 4
- 10.6019/CHEMBL5058564 U2OS 4
2894467 10.1021/jm00398a028 No relevant target 3
- 10.6019/CHEMBL5058564 Fibroblast 3
28849908 10.1021/acschembio.7b00481 Histamine H1 receptor 3

Data from ChEMBL 36 via Core Engine