Compound Detail

CHEMBL90

HISTAMINE

💊 Approved Drug

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💊 Approved Drug

NCCc1c[nH]cn1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL90
Name	HISTAMINE
Phase	Approved
Structure Type	MOL
InChI Key	NTYJJOPFIAHURM-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

.beta.-aminoethylglyoxaline Ergamine Ergotidine Histamine NSC-33792

Targets

194

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

111.2

MW (Da)

-0.09

ALogP

HBA

HBD

54.7

PSA (Å²)

0.56

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1939
Availability	Discontinued
Chirality	Achiral

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product

USAN Year

1988

Extended Properties

Molecular Formula	C5H9N3
MW	111.15
Aromatic Rings	1
Heavy Atoms	8

Indications

Chronic Urticaria Inflammation Lymphoma, Non-Hodgkin Osteoarthritis, Knee Pterygium Multiple Sclerosis Rhinitis, Allergic, Seasonal Rhinitis, Allergic, Seasonal Asthma Hypersensitivity

Activity Summary

EC50 99 meas. best 8.6

Ki 74 meas. best 9.84

Kd 18 meas. best 9.11

IC50 3 meas. best 6.8

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histamine H3 receptor CHEMBL5076	Ki	9.84	8.91	0.1	2
Histamine H1 receptor CHEMBL3943	Kd	9.11	8.9086	0.8	7
Cavia porcellus CHEMBL369	Kd	9.07	9.07	0.9	1
Histamine H4 receptor CHEMBL3759	Ki	9.0	7.9768	1.0	19
Histamine H3 receptor CHEMBL264	Ki	8.6	7.5025	2.5	20
Histamine H3 receptor CHEMBL264	EC50	8.6	7.7342	2.5	19
Histamine H3 receptor CHEMBL264	Kd	8.52	8.52	3.0	1
Histamine H1 receptor CHEMBL231	Kd	8.35	8.35	4.5	1
Histamine H4 receptor CHEMBL3759	Kd	8.3	8.05	5.0	2
Histamine H4 receptor CHEMBL1255160	Ki	8.22	8.22	6.0	1
Histamine H3 receptor CHEMBL4124	Ki	8.2	8.2	6.3	1
Histamine H4 receptor CHEMBL3759	EC50	8.13	7.6659	7.4	22
Histamine H1 receptor CHEMBL4701	Kd	8.0	8.0	10.0	1
Histamine H2 receptor CHEMBL1941	Kd	7.91	7.91	12.2	1
Histamine H1 receptor CHEMBL231	EC50	7.89	6.9178	13.0	9
Histamine H4 receptor CHEMBL5657	Kd	7.38	7.38	42.0	1
Histamine H4 receptor CHEMBL5657	Ki	7.38	7.24	42.0	2
Rattus norvegicus CHEMBL376	EC50	7.21	6.28	62.0	2
Histamine H4 receptor CHEMBL4468	Ki	7.2	7.035	63.1	2
Unchecked CHEMBL612545	Ki	7.2	7.2	63.1	1
Histamine H3 receptor CHEMBL3263	Ki	7.17	7.17	68.0	1
Histamine H4 receptor CHEMBL5657	EC50	7.06	6.038	87.1	5
Histamine H2 receptor CHEMBL1941	EC50	6.94	5.9459	114.8	17
Histamine H4 receptor CHEMBL4468	Kd	6.87	6.87	134.0	1
Cavia porcellus CHEMBL369	EC50	6.85	6.3329	140.0	7
Histamine H4 receptor CHEMBL4468	EC50	6.8	5.76	158.5	4
Histamine H1 receptor CHEMBL231	IC50	6.8	6.8	158.5	1
Histamine H1 receptor CHEMBL3943	EC50	6.79	6.73	162.2	3
Histamine H2 receptor CHEMBL2882	EC50	6.6	6.0844	251.2	9
Histamine H2 receptor CHEMBL1941	Ki	6.58	5.7529	263.0	7
Plasmodium falciparum CHEMBL364	IC50	6.18	6.18	660.0	1
Histamine H1 receptor CHEMBL231	Ki	5.62	4.7956	2398.8	9
Histamine H1 receptor CHEMBL4701	EC50	5.35	5.35	4466.8	1
Histamine H1 receptor CHEMBL3943	Ki	4.9	4.9	12589.2	1
Macrophage migration inhibitory factor CHEMBL2085	Ki	4.21	4.21	62000.0	1
Histamine H2 receptor CHEMBL2882	Kd	4.16	4.16	69183.1	1
Macrophage migration inhibitory factor CHEMBL2085	IC50	4.13	4.13	73600.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
KA	2.0	uM	-
KA	125.0	uM	-
KA	41.0	uM	-
Ka	2.0	uM	-
Ka	125.0	uM	-
Ka	41.0	uM	-
KA	2.1	uM	-
KA	125.0	uM	-
KA	41.0	uM	-
KA	2.0	uM	-
KA	125.0	uM	-
KA	41.0	uM	-
KA	37.0	uM	Homo sapiens
KA	4.6	uM	Mus musculus
KA	125.0	uM	Homo sapiens
KA	2.1	uM	Homo sapiens
KA	2.1	uM	Homo sapiens
KA	125.0	uM	Homo sapiens
KA	37.5	uM	Homo sapiens
KA	0.01	uM	Homo sapiens
Ka	0.05	uM	Homo sapiens
Ka	74.0	uM	Homo sapiens
Ka	31.0	uM	Homo sapiens
Ka	2.5	uM	Homo sapiens
Ka	1.3	uM	Homo sapiens
Ka	1.9	uM	Homo sapiens
KA	0.01	uM	Homo sapiens
KA	3.52	uM	Homo sapiens
KA	2.1	uM	Homo sapiens
KA	125.0	uM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histamine H3 receptor	Ki	=	0.1445	nM	9.84	Binding affinity towards histamine H3 receptor using [3H](R)-alpha-methylhistami...	10406649
Histamine H1 receptor	Kd	=	0.7762	nM	9.11	Compound was tested for the contractile effects antagonized by mepyramine (1-100...	9873585
Histamine H1 receptor	Kd	=	0.7762	nM	9.11	Compound was evaluated for mepyramine antagonism effects in guinea pig ileum (co...	10737740
Histamine H1 receptor	Kd	=	0.8511	nM	9.07	Contractile effects antagonized by mepyramine (0.3-100 nM) against Histamine H1 ...	9873585
Histamine H1 receptor	Kd	=	0.8511	nM	9.07	Compound was evaluated for mepyramine antagonism effects in guinea pig ileum (co...	10737740
Cavia porcellus	Kd	=	0.8511	nM	9.07	Full pA2 value of compound at 0.3-100 nM concentration of mepyramine in guinea p...	14640554
Histamine H1 receptor	Kd	=	1.0	nM	9.0	Compound was evaluated for mepyramine antagonism effects in guinea pig aorta (co...	10737740
Histamine H4 receptor	Ki	=	1.0	nM	9.0	Displacement of [3H]-Histamine from human histamine 4 receptor transfected in HE...	33333448
Histamine H1 receptor	Kd	=	1.0	nM	9.0	Relative potency against Histamine H1 receptor in endothelium-Denuded rings of g...	14640554
Histamine H4 receptor	Ki	=	1.6	nM	8.8	Binding affinity to histamine H4 receptor (unknown origin)	27692832
Histamine H3 receptor	EC50	=	2.512	nM	8.6	Agonist activity at human H3R expressed on HEK293T cells assessed as inhibition ...	31675226
Histamine H3 receptor	Ki	=	2.512	nM	8.6	Displacement of [3H]-Histamine from human histamine 3 receptor transfected in HE...	33333448
Histamine H3 receptor	Kd	=	3.0	nM	8.52	Displacement of [3H]Nalpha-methylhistamine from human histamine H3 receptor stab...	34110814
Histamine H3 receptor	EC50	=	4.0	nM	8.4	Agonist activity at human H3 receptor expressed in CHO cells assessed as increas...	32105981
Histamine H3 receptor	EC50	=	4.074	nM	8.39	Inhibition of the forskolin-stimulated cAMP production in SK-N-MC cells expressi...	12825954
Histamine H1 receptor	Kd	=	4.5	nM	8.35	Displacement of [3H] mepyramine from human histamine H1 receptor stably expresse...	34110814
Histamine H4 receptor	Ki	=	4.8	nM	8.32	Binding affinity to human histamine H4 receptor	25993395
Histamine H4 receptor	Kd	=	5.0	nM	8.3	Binding affinity to human H4R	31469288
Histamine H3 receptor	EC50	=	5.012	nM	8.3	Agonist activity at human H3R expressed on SK-N-MC cells assessed as inhibition ...	31675226
Histamine H3 receptor	EC50	=	5.012	nM	8.3	Agonist activity at human histamine H3 receptor expressed in human SK-N-MC cells...	21044842

Literature References

PubMed	DOI	Target Context	# Activities
21044842	10.1016/j.bmcl.2010.10.041	Histamine H4 receptor	13
22396231	10.1124/dmd.111.042432	Equilibrative nucleoside transporter 4	13
31469288	10.1021/acs.jmedchem.9b01342	Histamine H4 receptor	12
14640554	10.1021/jm0309147	Histamine H1 receptor	11
16408006	10.1038/nchembio714	Histamine H1 receptor	10
34600035	10.1016/j.bmcl.2021.128388	Histamine H2 receptor	10
34110814	10.1021/acs.jmedchem.1c00692	Histamine H2 receptor	10
10737740	10.1021/jm991056a	Cavia porcellus	9
7731015	10.1021/jm00008a007	Histamine H1 receptor	8
9873585	10.1016/s0960-894x(98)00461-2	Histamine H1 receptor	8
31675226	10.1021/acs.jmedchem.9b01462	Histamine H3 receptor	6
20409707	10.1016/j.bmcl.2010.03.082	Histamine H2 receptor	6
2342063	10.1021/jm00168a024	Cavia porcellus	6
20129782	10.1016/j.bmcl.2010.01.054	Carbonic anhydrase	6
34758374	10.1016/j.bmcl.2021.128445	Macrophage migration inhibitory factor	5
25993395	10.1021/acs.jmedchem.5b00516	Histamine H4 receptor	5
10197963	10.1021/jm980408v	Histamine H3 receptor	5
3806596	10.1021/jm00384a036	Histamine H2 receptor	5
37974943	10.1021/acsmedchemlett.3c00413	Histamine H3 receptor	5
10737740	10.1021/jm991056a	Rattus norvegicus	4

Data from ChEMBL 36 via Core Engine