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Compound Detail

CHEMBL505

CHLORPHENIRAMINE
💊 Approved Drug
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💊 Approved Drug
CN(C)CCC(c1ccc(Cl)cc1)c1ccccn1

Basic Information

ChEMBL ID CHEMBL505
Name CHLORPHENIRAMINE
Phase Approved
Structure Type MOL
InChI Key SOYKEARSMXGVTM-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Chlorphenamine Chlorpheniramine Clorfenamina Isoclor
15
Targets
28
Activities
3
Assay Types
18
PK Parameters
20
Publications
4
Known Names
5
Indications

Molecular Properties

274.8
MW (Da)
3.82
ALogP
2
HBA
0
HBD
16.1
PSA (Ų)
0.82
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1950
Availability OTC
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Year 1987

Extended Properties

Molecular Formula C16H19ClN2
MW 274.80
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -1.38

Indications

Hypersensitivity Influenza, Human Hepatitis B, Chronic Rhinitis, Allergic, Seasonal Sunburn

ATC Classification

R06AB04
chlorphenamine
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE
R06AB54
chlorphenamine, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

IC50 20 meas. best 8.06
Ki 6 meas. best 9.04
Kd 2 meas. best 8.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 9.04 8.5133 0.9 3
Histamine H1 receptor
CHEMBL4701
Ki 8.7 8.4067 2.0 3
No relevant target
CHEMBL2362975
Kd 8.43 8.43 3.7 1
ADMET
CHEMBL612558
Kd 8.4 8.4 4.0 1
Histamine H1 receptor
CHEMBL3943
IC50 8.06 8.06 8.8 1
RBL-2H3
CHEMBL614632
IC50 7.5 7.23 31.8 3
Histamine H1 receptor
CHEMBL231
IC50 7.18 7.18 66.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.96 4.936 1100.0 5
Plasmodium falciparum
CHEMBL364
IC50 5.41 4.81 3900.0 2
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 5.0 5.0 10000.0 1
Solute carrier family 22 member 1
CHEMBL2073670
IC50 4.85 4.85 14000.0 1
Solute carrier family 22 member 2
CHEMBL1770032
IC50 4.58 4.58 26000.0 1
ADMET
CHEMBL612558
IC50 4.48 4.48 33400.0 1
MBT domain-containing protein 1
CHEMBL1287625
IC50 4.47 4.47 34000.0 1
Lethal(3)malignant brain tumor-like protein 1
CHEMBL1287622
IC50 4.39 4.39 41000.0 1
Lethal(3)malignant brain tumor-like protein 3
CHEMBL1287623
IC50 4.38 4.38 42000.0 1
Chloroquine resistance transporter
CHEMBL1795182
IC50 4.27 4.27 54000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 2.1 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 23.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 79.0 % Homo sapiens
F 35.0 % Homo sapiens
Fu 0.3 - -
Fu 0.037 - -
Fu 0.3 - Homo sapiens
Fu 0.7 - Homo sapiens
Fu 0.7 - Homo sapiens
Fu 0.056 - Homo sapiens
MRT 22.0 hr Homo sapiens
T1/2 22.0 hr Homo sapiens
T1/2 22.0 hr Homo sapiens
Vd 5.9 L.kg-1 -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 0.92 nM 9.04 Displacement of [3H]Pyrilamine from histamine H1 receptor (unknown origin) 24365159
Histamine H1 receptor Ki = 2.0 nM 8.7 Ability to displace [3H]pyrilamine from histamine H1 receptor in male Sprague-Da... 12781173
No relevant target Kd = 3.7 nM 8.43 Dissociation constant (KD) of the compound 7562938
ADMET Kd = 3.981 nM 8.4 pA2 value is determined compared to standard H1-antagonists 7562938
Histamine H1 receptor Ki = 4.467 nM 8.35 Displacement of [3H]Pyrilamine from histamine H1 receptor (unknown origin) 24365159
Histamine H1 receptor Ki = 5.5 nM 8.26 Binding affinity against Histamine H1 receptor using receptor binding assay in r... 9934454
Histamine H1 receptor Ki = 5.5 nM 8.26 Binding affinity to histamine H1 receptor in rat brain membranes was evaluated u... 1671420
Histamine H1 receptor Ki = 7.0 nM 8.15 Binding affinity to histamine H1 receptor 21381763
Histamine H1 receptor IC50 = 8.8 nM 8.06 Inhibition of [3H]mepyramine binding to the Histamine H1 receptor in guinea pig ... 1673158
RBL-2H3 IC50 = 31.8 nM 7.5 Antiallergic activity in rat RBL2H3 cells assessed as inhibition of C48/80-induc... 31703894
RBL-2H3 IC50 = 53.6 nM 7.27 Antiallergic activity in rat RBL2H3 cells assessed as inhibition of C48/80-induc... 31703894
Histamine H1 receptor IC50 = 66.0 nM 7.18 Displacement of [3H]pyrilamine from human histamine receptor subtype 1 expressed... 17846138
RBL-2H3 IC50 = 121.0 nM 6.92 Antiallergic activity in IgE/Ag-stimulated rat RBL2H3 cells assessed as inhibiti... 31703894
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 1100.0 nM 5.96 Inhibitory concentration against IKr potassium channel 15324906
Plasmodium falciparum IC50 = 3900.0 nM 5.41 Antimalarial activity after 72 hrs against chloroquine-resistant Plasmodium falc... 17846138
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 10000.0 nM 5.0 Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol... 2579237
Solute carrier family 22 member 1 IC50 = 14000.0 nM 4.85 TP_TRANSPORTER: inhibition of TEA uptake (TEA: 50 uM) in OCT1-expressing MDCK ce... 11758759
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20892.96 nM 4.68 Inhibition of human ERG expressed in CHO cells by whole cell patch clamp techniq... 18448342
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20892.96 nM 4.68 Inhibition of human Potassium channel HERG expressed in mammalian cells 12873512
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20892.96 nM 4.68 Inhibition of human ERG 21185626

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1382
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
6167716 10.1021/jm00135a006 ADMET 6
24900883 10.1021/ml5000228 Chloroquine resistance transporter 6
24900883 10.1021/ml5000228 Plasmodium falciparum 6
12061889 10.1021/jm0200409 ADMET 5
6167716 10.1021/jm00135a006 No relevant target 5
11602674 - ATP-dependent translocase ABCB1 5
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
18426954 10.1124/dmd.108.020479 ADMET 4
17846138 10.1128/aac.00669-07 Plasmodium falciparum 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
31703894 10.1016/j.bmc.2019.115127 RBL-2H3 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
20014752 10.1021/tx900326k Hepatotoxicity 3
25799158 10.1021/acs.jmedchem.5b00201 No relevant target 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3

Data from ChEMBL 36 via Core Engine