Compound Detail

CHEMBL516

CYPROHEPTADINE

💊 Approved Drug

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💊 Approved Drug

CN1CCC(=C2c3ccccc3C=Cc3ccccc32)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL516
Name	CYPROHEPTADINE
Phase	Approved
Structure Type	MOL
InChI Key	JJCFRYNCJDLXIK-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Ciproheptadina Ciprovit Cyproheptadine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

287.4

MW (Da)

4.70

ALogP

HBA

HBD

3.2

PSA (Å²)

0.58

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1961
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula	C21H21N
MW	287.41
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	0.26

Indications

Hypersensitivity Severe Acute Respiratory Syndrome Abdominal Pain Alcoholism Mitral Valve Insufficiency Stroke

ATC Classification

R06AX02

cyproheptadine

Level 1: RESPIRATORY SYSTEM

Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Activity Summary

Ki 50 meas. best 9.56

IC50 39 meas. best 9.01

Kd 3 meas. best 9.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	9.56	9.055	0.3	4
Histamine H1 receptor CHEMBL231	Ki	9.37	9.37	0.4	1
Histamine H1 receptor CHEMBL3943	Ki	9.27	9.27	0.5	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	9.01	9.01	1.0	1
Histamine H1 receptor CHEMBL3943	Kd	9.0	9.0	1.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	8.89	8.425	1.3	2
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	8.82	8.52	1.5	2
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	8.8	8.6333	1.6	3
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	8.66	8.66	2.2	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	8.61	8.61	2.4	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	8.56	8.56	2.8	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	8.51	8.51	3.1	1
Histamine H1 receptor CHEMBL231	IC50	8.43	8.43	3.7	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	8.42	8.42	3.8	1
Muscarinic acetylcholine receptor CHEMBL1907609	Ki	8.4	8.4	4.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	8.4	8.4	3.9	1
Serotonin (5-HT) receptor CHEMBL2094123	Kd	8.1	8.1	7.9	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	8.03	8.03	9.4	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	8.02	8.02	9.7	1
5-hydroxytryptamine receptor 2C CHEMBL3006	Ki	7.96	7.96	11.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	7.92	7.92	12.0	1
D(3) dopamine receptor CHEMBL234	Ki	7.8	7.8	16.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	7.8	7.8	16.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	7.8	7.8	16.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.77	7.77	17.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	7.46	7.46	35.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	7.42	7.42	38.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	7.36	7.36	44.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	7.34	7.34	46.0	1
D(3) dopamine receptor CHEMBL234	IC50	7.32	7.32	48.0	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.3	7.1	50.1	2
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	7.3	7.3	50.1	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	7.28	7.28	53.0	1
D(2) dopamine receptor CHEMBL217	Ki	7.26	7.105	55.0	2
Dopamine receptor CHEMBL2093868	Ki	7.2	7.2	63.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.16	7.16	70.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	7.1	7.1	79.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	7.1	7.1	80.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	7.01	7.01	98.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.97	6.97	106.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	6.97	6.97	107.0	1
D(2) dopamine receptor CHEMBL3427	Ki	6.95	6.95	112.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.91	6.91	122.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.89	6.89	130.0	1
D(2) dopamine receptor CHEMBL339	IC50	6.85	6.85	140.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	6.8	6.8	158.0	1
D(2) dopamine receptor CHEMBL217	IC50	6.79	6.79	164.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.73	6.73	185.0	1
Histamine H2 receptor CHEMBL1941	Ki	6.71	6.71	195.0	1
Histamine H2 receptor CHEMBL1941	IC50	6.7	6.7	198.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	10.3	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	Ki	=	0.278	nM	9.56	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Histamine H1 receptor	Ki	=	0.43	nM	9.37	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
5-hydroxytryptamine receptor 2A	Ki	=	0.46	nM	9.34	Antagonist activity at 5HT2A receptor	22694093
Histamine H1 receptor	Ki	=	0.537	nM	9.27	Inhibition of [3H]mepyramine binding with histamine H1 receptor in guinea pig ce...	7650688
5-hydroxytryptamine receptor 2A	IC50	=	0.973	nM	9.01	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Histamine H1 receptor	Kd	=	1.0	nM	9.0	Potency against histamine H1 receptor on guinea pig ileum	7650688
5-hydroxytryptamine receptor 2C	Ki	=	1.278	nM	8.89	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2B	Ki	=	1.5	nM	8.82	Displacement of [3H]-5HT from human 5-HT2B receptor expressed in CHO-K1 cells as...	37584406
5-hydroxytryptamine receptor 2A	Ki	=	1.6	nM	8.8	Displacement of [3H]ketanserin from 5-hydroxytryptamine 2A receptor expressed NI...	11266163
5-hydroxytryptamine receptor 2A	Ki	=	1.6	nM	8.8	Binding affinity against 5-hydroxytryptamine 2A receptor from rat forebrain usin...	11229772
5-hydroxytryptamine receptor 2A	Ki	=	1.6	nM	8.8	Displacement of [3H]ketanserin from Sprague-Dawley rat cerebral cortex 5-HT2A re...	27448773
Muscarinic acetylcholine receptor M4	Ki	=	2.186	nM	8.66	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
5-hydroxytryptamine receptor 2C	IC50	=	2.44	nM	8.61	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M5	Ki	=	2.755	nM	8.56	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
5-hydroxytryptamine receptor 2A	Ki	=	3.0	nM	8.52	Binding affinity towards 5-hydroxytryptamine 2A receptor using [3H]ketanserin	15081025
Serotonin 2 (5-HT2) receptor	IC50	=	3.1	nM	8.51	Binding affinity at serotonin 5-hydroxytryptamine 2 receptor by [3H]ketanserin d...	8151622
Histamine H1 receptor	IC50	=	3.7	nM	8.43	DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine)	-
Muscarinic acetylcholine receptor M5	IC50	=	3.835	nM	8.42	DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Muscarinic acetylcholine receptor	Ki	=	4.0	nM	8.4	Displacement of [3H]- QNB binding at the muscarinic-cholinergic binding site of ...	6134835
Muscarinic acetylcholine receptor M1	Ki	=	3.943	nM	8.4	DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine)	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	339
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
7069703	10.1021/jm00345a008	Felis catus	12
27088648	10.1021/acs.jmedchem.5b01732	Histone-lysine N-methyltransferase SETD7	12
6167716	10.1021/jm00135a006	ADMET	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
18033297	10.1038/nature05991	Caenorhabditis elegans	10
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
660595	10.1021/jm00203a016	Stomach	5
3934386	10.1021/jm00150a029	Rattus norvegicus	4
660595	10.1021/jm00203a016	Rattus norvegicus	3
27088648	10.1021/acs.jmedchem.5b01732	Histone-lysine N-methyltransferase EHMT2	3
27088648	10.1021/acs.jmedchem.5b01732	MCF7	3
-	10.1016/S0960-894X(97)00291-6	Rattus norvegicus	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
660595	10.1021/jm00203a016	Ileum	3
3934386	10.1021/jm00150a029	Cavia porcellus	3
7650688	10.1021/jm00017a019	Histamine H1 receptor	2
2579237	10.1021/jm00381a019	Sodium channel alpha subunits; brain (Types I, II, III)	2
15781124	10.1016/j.pharmthera.2004.10.013	UDP-glucuronosyltransferase 1A4	2

Data from ChEMBL 36 via Core Engine