Compound Detail

CHEMBL17157

TERFENADINE

💊 Approved Drug

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💊 Approved Drug

CC(C)(C)c1ccc(C(O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL17157
Name	TERFENADINE
Phase	Approved
Structure Type	MOL
InChI Key	GUGOEEXESWIERI-UHFFFAOYSA-N
Therapeutic	✓ Yes
Active Moiety	CHEMBL914

Known Names

Antihistamine Histafen Histafen 120 NSC-665802 NSC-758627 RMI 9918 RMI-9918 Seldane Terfenadina Terfenadine Terfenor Terfenor fte +5 more

39

Targets

128

Activities

4

Assay Types

28

PK Parameters

20

Publications

17

Known Names

12

Indications

1

Mechanisms

Molecular Properties

471.7

MW (Da)

6.45

ALogP

3

HBA

2

HBD

43.7

PSA (Å²)

0.40

QED

1

Ro5 Violations

8

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1985
Availability	Withdrawn
Chirality	Racemic

Flags

Withdrawn Natural Product Prodrug

USAN Year

1975

Extended Properties

Molecular Formula	C32H41NO2
MW	471.69
Aromatic Rings	3
Heavy Atoms	35
NP-Likeness	-0.46

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Histamine H1 receptor antagonist	ANTAGONIST	Histamine H1 receptor	✓	✓

Indications

Hypersensitivity Mucopolysaccharidosis I Multiple Sclerosis Multiple Sclerosis, Chronic Progressive Asthma Hepatitis B, Chronic Hepatitis D Lymphoma, Large B-Cell, Diffuse Peanut Hypersensitivity Breast Neoplasms Esophageal Neoplasms Urinary Bladder Neoplasms

ATC Classification

R06AX12

terfenadine

Level 1: RESPIRATORY SYSTEM

Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Drug Warnings

Withdrawn

General Warning

Fatal drug interactions with commonly use drugs

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

cardiotoxicity

Use of terfenadine products with certain other drugs or foods and in certain medical conditions is associated with the potential to result in rare and serious cardiac side effects primarily involving ...

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

cardiotoxicity

cardiac arrhythmias

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

cardiotoxicity

Prolonged QT interval; ventricular tachycardia

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

cardiotoxicity

Prolonged QT interval; ventricular tachycardia

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

cardiotoxicity

Risk of cardiac arrhythmia

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

General Warning

Use of terfenadine products with certain other drugs or foods and in certain medical conditions is associated with the potential to result in rare and serious cardiac side effects primarily involving ...

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

General Warning

Fatal drug interactions with commonly use drugs; Rare but serious heart problems when taken with certain drugs, including antibiotics and antifungal drugs

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Withdrawn

cardiotoxicity

serious cardiotoxic effects reported in conjunction with other drug

Country: Morocco; Singapore; France; Mauritius; Bhutan; Saudi Arabia; United States; Oman; Chile; Brazil; Argentina Year: 1997

Activity Summary

IC50 96 meas. best 9.0

Ki 23 meas. best 8.59

Kd 5 meas. best 7.65

EC50 4 meas. best 5.37

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histamine H1 receptor CHEMBL231	IC50	9.0	7.6367	1.0	3
Translocator protein CHEMBL2149	IC50	9.0	9.0	1.0	1
Histamine H1 receptor CHEMBL231	Ki	8.59	7.7433	2.6	3
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	8.05	6.9574	8.9	27
Cavia porcellus CHEMBL369	Kd	7.65	7.65	22.4	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.52	7.52	30.0	1
Unchecked CHEMBL612545	IC50	7.52	6.0127	30.0	11
ADMET CHEMBL612558	Kd	7.5	7.5	31.6	1
No relevant target CHEMBL2362975	Kd	7.48	7.48	33.0	1
Histamine H1 receptor CHEMBL3943	Kd	7.45	6.985	35.5	2
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	7.32	7.32	48.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	7.25	6.9533	56.0	3
Unchecked CHEMBL612545	Ki	7.15	6.5925	71.0	4
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.14	7.14	73.0	1
Histamine H1 receptor CHEMBL3943	IC50	7.03	6.78	94.0	2
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	6.85	6.85	142.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	6.69	6.69	203.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2366456	IC50	6.6	6.4867	250.0	3
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	6.59	6.59	255.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	6.59	6.59	255.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	6.5	6.5	320.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.29	6.29	511.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.26	6.26	545.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.22	6.22	606.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.19	6.19	645.0	1
C-C chemokine receptor type 5 CHEMBL274	Ki	6.07	6.07	852.0	1
Substance-K receptor CHEMBL2327	Ki	6.05	6.05	892.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	6.03	6.03	930.0	1
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	6.01	6.01	971.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	5.96	5.7633	1100.0	6
C-C chemokine receptor type 5 CHEMBL274	IC50	5.96	5.96	1103.0	1
Cytochrome P450 2J2 CHEMBL3491	IC50	5.95	5.5933	1130.0	3
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	5.91	5.91	1231.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL1940	IC50	5.88	5.88	1320.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	5.88	5.88	1306.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	5.87	5.87	1337.0	1
D(3) dopamine receptor CHEMBL234	IC50	5.82	5.82	1503.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	5.73	5.73	1846.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.72	5.72	1912.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.71	5.71	1928.0	1
Plasmodium falciparum CHEMBL364	IC50	5.7	5.3714	1995.3	7
ATP-dependent translocase ABCB1 CHEMBL3467	IC50	5.7	5.7	2000.0	2
D(2) dopamine receptor CHEMBL217	Ki	5.69	5.69	2056.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	IC50	5.63	5.63	2340.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	5.57	5.57	2673.0	1
Substance-K receptor CHEMBL2327	IC50	5.57	5.57	2677.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	5.54	5.54	2900.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	5.48	5.48	3335.0	1
Epidermal growth factor receptor CHEMBL203	IC50	5.45	5.45	3566.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	5.43	5.43	3748.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	232.0	mL.min-1.g-1	Homo sapiens
CL	34.67	uL.min-1.(10^6cells)-1	Homo sapiens
CL	87.1	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	95.5	mL.min-1.g-1	Homo sapiens
CL	774.0	mL.min-1.g-1	Homo sapiens
CL	108.0	mL.min-1.kg-1	Homo sapiens
CL	578.3	mL.min-1.g-1	Homo sapiens
CL	115.5	mL.min-1.kg-1	Homo sapiens
CL	167.5	mL.min-1.g-1	Homo sapiens
CL	75.8	mL.min-1.g-1	Rattus norvegicus
CL	410.1	mL.min-1.g-1	Homo sapiens
Inhibitory activity	88.2	%	Homo sapiens
T1/2	23.0	hr	Homo sapiens
T1/2	0.4978	hr	Homo sapiens
T1/2	0.3523	hr	Homo sapiens
T1/2	0.3523	hr	Homo sapiens
T1/2	0.2583	hr	Homo sapiens
T1/2	0.1167	hr	Mus musculus
T1/2	0.15	hr	Homo sapiens
T1/2	0.1492	hr	Homo sapiens
T1/2	0.3833	hr	Homo sapiens
T1/2	0.1492	hr	Homo sapiens
T1/2	60.0	hr	Homo sapiens
T1/2	0.25	hr	Homo sapiens
T1/2	0.23	hr	Homo sapiens
T1/2	0.51	hr	Rattus norvegicus
T1/2	0.2817	hr	Homo sapiens
Vd	2.9	L.kg-1	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histamine H1 receptor	IC50	=	1.0	nM	9.0	Inhibition of histamine H1 receptor (unknown origin)	25494650
Translocator protein	IC50	=	1.0	nM	9.0	Inhibition of mouse TSPO	38295689
Histamine H1 receptor	Ki	=	2.587	nM	8.59	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	8.9	nM	8.05	Inhibition of hERG K channel	21300721
Histamine H1 receptor	IC50	=	22.0	nM	7.66	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	22.0	nM	7.66	Inhibition of human ERG expressed in HEK293 cells by patch clamp method	28481112
Cavia porcellus	Kd	=	22.39	nM	7.65	Inhibition of histamine-inducedcontraction of the isolated guinea-pig ileum	-
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	30.0	nM	7.52	Inhibition of wild-type human ERG expressed in HEK293 cells by whole cell patch ...	19260734
Unchecked	IC50	=	30.0	nM	7.52	Inhibition of human ERG td[wt:Y652A] mutant expressed in HEK293 cells by whole c...	19260734
Unchecked	IC50	=	30.0	nM	7.52	Inhibition of human ERG td[wt:F656A] mutant expressed in HEK293 cells by whole c...	19260734
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	30.0	nM	7.52	Inhibition of human ERG S624A mutant expressed in HEK293 cells by whole cell pat...	19260734
5-hydroxytryptamine receptor 2B	Ki	=	30.0	nM	7.52	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
ADMET	Kd	=	31.62	nM	7.5	pA2 value is determined compared to standard H1-antagonists	7562938
No relevant target	Kd	=	33.0	nM	7.48	Dissociation constant (KD) of the compound	7562938
Histamine H1 receptor	Kd	=	35.48	nM	7.45	Dissociation constant was determined against H1 receptor of guinea pig lung memb...	7608912
Histamine H1 receptor	Ki	=	40.0	nM	7.4	Displacement of [3H]pyrilamine from human recombinant histamine H1 receptor expr...	19660947
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	41.0	nM	7.39	Inhibition of hERG potassium channel stably expressed in HEK293 cells by whole-c...	36649216
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	45.0	nM	7.35	Inhibition of hERG expressed in HEK293 cells at -80 mV holding potential by patc...	38564512
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	45.0	nM	7.35	Inhibition of hERG potassium channel current	38159286
5-hydroxytryptamine receptor 2B	IC50	=	48.0	nM	7.32	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	214
-	10.6019/CHEMBL4295262	Unchecked	44
16472241	10.2174/1570163043334794	Hepatotoxicity	18
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
12699389	10.1021/jm021012t	ATP-dependent translocase ABCB1	10
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
25238555	10.1021/jm5010682	Staphylococcus aureus	8
28364659	10.1016/j.ejmech.2017.03.063	Trypanosoma cruzi	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
11602674	-	ATP-dependent translocase ABCB1	5
22761000	10.1002/jat.2784	Voltage-dependent L-type calcium channel subunit alpha-1C	4
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	4
19260734	10.1021/jm801236n	Voltage-gated inwardly rectifying potassium channel KCNH2	4
30523084	10.1126/science.aat9446	Plasmodium berghei	4
32302123	10.1021/acs.jmedchem.9b01573	ADMET	4
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	4
-	10.6019/CHEMBL3301361	ADMET	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	4

Data from ChEMBL 36 via Core Engine