Compound Detail

CHEMBL128

SUMATRIPTAN

💊 Approved Drug

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💊 Approved Drug

CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL128
Name	SUMATRIPTAN
Phase	Approved
Structure Type	MOL
InChI Key	KQKPFRSPSRPDEB-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Dfn-11 Dfn-11 (sumatriptan injection) Imitrex N02CC01 Sumatriptan Tosymra

Targets

108

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

295.4

MW (Da)

1.32

ALogP

HBA

HBD

65.2

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1992
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product

USAN Stem	-triptan
USAN Year	1989

Extended Properties

Molecular Formula	C14H21N3O2S
MW	295.41
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	-1.10

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Serotonin 1b (5-HT1b) receptor agonist	AGONIST	5-hydroxytryptamine receptor 1B	✓	✓
Serotonin 1d (5-HT1d) receptor agonist	AGONIST	5-hydroxytryptamine receptor 1D	✓	✓

Indications

Migraine Disorders Migraine with Aura Migraine without Aura Pain Obesity

ATC Classification

N02CC01

sumatriptan

Level 1: NERVOUS SYSTEM

Level 2: ANALGESICS

Activity Summary

Ki 46 meas. best 9.3

IC50 39 meas. best 9.3

EC50 22 meas. best 8.37

Kd 1 meas. best 6.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 1B CHEMBL1898	IC50	9.3	8.0557	0.5	7
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	9.3	7.92	0.5	14
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	9.3	8.2747	0.5	15
5-hydroxytryptamine receptor 1D CHEMBL1983	IC50	8.53	7.74	3.0	9
5-hydroxytryptamine receptor 1D CHEMBL1983	EC50	8.37	7.7833	4.3	9
5-hydroxytryptamine receptor 1B CHEMBL2304408	Ki	8.19	8.19	6.4	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	8.14	6.62	7.3	2
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	8.09	7.865	8.2	2
5-hydroxytryptamine receptor 3A CHEMBL1899	IC50	8.03	8.03	9.3	1
5-hydroxytryptamine receptor 1B CHEMBL3459	IC50	7.75	7.355	18.0	2
5-hydroxytryptamine receptor 1D CHEMBL4105	IC50	7.7	7.7	19.9	4
5-hydroxytryptamine receptor 1F CHEMBL1805	Ki	7.59	7.59	25.7	1
5-hydroxytryptamine receptor 1F CHEMBL1805	EC50	7.46	7.46	35.0	1
5-hydroxytryptamine receptor 1B CHEMBL1898	EC50	7.42	7.265	38.3	2
Canis familiaris CHEMBL373	IC50	7.31	7.31	48.6	1
5-hydroxytryptamine 1D receptor CHEMBL3638336	IC50	7.23	7.23	59.0	1
5-hydroxytryptamine receptor 1D CHEMBL5450	IC50	7.21	7.21	61.0	1
5-hydroxytryptamine receptor 1D CHEMBL5450	EC50	7.01	7.01	97.0	1
ADMET CHEMBL612558	EC50	6.92	6.92	120.0	1
Oryctolagus cuniculus CHEMBL374	EC50	6.76	6.196	173.5	5
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	6.64	6.4456	230.0	9
Unchecked CHEMBL612545	Ki	6.63	6.63	234.0	1
Molecular identity unknown CHEMBL612546	EC50	6.55	6.55	280.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.42	6.42	376.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	6.4	6.3667	398.1	3
5-hydroxytryptamine receptor 1A CHEMBL214	Kd	6.4	6.4	398.1	1
Canis familiaris CHEMBL373	EC50	6.4	6.4	400.0	1
5-hydroxytryptamine receptor 1A CHEMBL3737	IC50	6.35	6.35	450.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	6.34	6.34	459.0	1
5-hydroxytryptamine receptor 5A CHEMBL3426	IC50	6.3	6.3	501.2	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.19	6.14	640.0	2
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	6.0	6.0	1000.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	EC50	5.89	5.89	1300.0	1
5-hydroxytryptamine receptor 1E CHEMBL2182	IC50	5.26	5.26	5500.0	1
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	5.17	5.17	6700.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.1	5.1	7943.3	1
Unchecked CHEMBL612545	IC50	4.96	4.96	11000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	69.0	mL.min-1.kg-1	Rattus norvegicus
CL	19.0	mL.min-1.kg-1	Homo sapiens
CL	15.3	mL.min-1.kg-1	Homo sapiens
CL	19.0	mL.min-1.kg-1	Homo sapiens
CL	19.0	mL.min-1.kg-1	Homo sapiens
CL	3.0	mL.min-1.g-1	Homo sapiens
CL	8.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
Cmax	250.5	nM	Rattus norvegicus
F	14.0	%	Homo sapiens
F	20.0	%	Homo sapiens
Fu	0.82	-	-
Fu	0.661	-	-
Fu	0.82	-	Homo sapiens
Fu	0.724	-	Rattus norvegicus
Fu	0.83	-	Homo sapiens
Fu	0.83	-	Homo sapiens
Fu	0.68	-	Homo sapiens
MRT	1.5	hr	Homo sapiens
T1/2	1.1	hr	Rattus norvegicus
T1/2	1.7	hr	Homo sapiens
Tmax	4.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 1B	IC50	=	0.5012	nM	9.3	Binding affinity in CHO-K1 cells transfected with human recombinant 5-hydroxytry...	11262079
5-hydroxytryptamine receptor 1B	Ki	=	0.5	nM	9.3	Binding affinity to 5-HT1B receptor (unknown origin) assessed as inhibition cons...	38516587
5-hydroxytryptamine receptor 1D	Ki	=	0.5	nM	9.3	Binding affinity to 5-HT1DR (unknown origin) assessed as inhibition constant	38516587
5-hydroxytryptamine receptor 1D	Ki	=	1.2	nM	8.92	Displacement of [3H]5-hydroxytryptamine from human cloned 5HT1D receptor express...	18507369
5-hydroxytryptamine receptor 1D	Ki	=	2.0	nM	8.7	The compound was tested for CNS binding affinity towards 5-hydroxytryptamine 1D ...	9632349
5-hydroxytryptamine receptor 1D	IC50	=	2.951	nM	8.53	Binding affinity in CHO-K1 cells transfected with human 5-hydroxytryptamine 1D r...	11262079
5-hydroxytryptamine receptor 1D	Ki	=	3.4	nM	8.47	Binding affinity towards cloned human 5-hydroxytryptamine 1D receptor	14505640
5-hydroxytryptamine receptor 1D	Ki	=	3.4	nM	8.47	Binding affinity was evaluated at the cloned human 5-hydroxytryptamine 1D recept...	14741277
5-hydroxytryptamine receptor 1D	EC50	=	4.3	nM	8.37	Ability to inhibit forskolin-stimulated adenylate cyclase in a cell line express...	9986723
5-hydroxytryptamine receptor 1D	Ki	=	4.4	nM	8.36	In vitro receptor binding affinity for cloned human 5-hydroxytryptamine 1D recep...	9986723
5-hydroxytryptamine receptor 1D	IC50	=	5.0	nM	8.3	Binding affinity by displacement to human cloned 5-hydroxytryptamine 1D receptor...	9357514
5-hydroxytryptamine receptor 1D	IC50	=	5.0	nM	8.3	Displacement of [3H]5-HT from human 5-hydroxytryptamine 1D receptor expressed in...	9357515
5-hydroxytryptamine receptor 1D	EC50	=	5.3	nM	8.28	Ability to inhibit forskolin-stimulated adenylate cyclase activity in Chinese ha...	14643336
5-hydroxytryptamine receptor 1D	Ki	=	5.5	nM	8.26	Binding affinity for human 5-hydroxytryptamine 1D receptor	10937729
5-hydroxytryptamine receptor 1B	Ki	=	5.5	nM	8.26	Binding affinity was measured on 5-hydroxytryptamine 1D receptor beta in CHO cel...	8071931
5-hydroxytryptamine receptor 1D	Ki	=	5.7	nM	8.24	Compound was tested for binding affinity against cloned human 5-hydroxytryptamin...	8941384
5-hydroxytryptamine receptor 1B	Ki	=	6.4	nM	8.19	The compound was tested for CNS binding affinity towards 5-hydroxytryptamine 1B ...	9632349
5-hydroxytryptamine receptor 1D	IC50	=	6.7	nM	8.17	Displacement of [3H]5-HT binding from the cloned human 5-hydroxytryptamine 1D re...	10052975
5-hydroxytryptamine receptor 1D	IC50	=	6.7	nM	8.17	Displacement of [3H]5-HT binding from human 5-hydroxytryptamine 1D receptor expr...	10052976
5-hydroxytryptamine receptor 1D	IC50	=	6.8	nM	8.17	Compound was tested for the displacement of [3H]5-HT binding to cloned 5-hydroxy...	10585208

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	439
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	61
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
21051535	10.1124/dmd.110.034629	ADMET	9
20070106	10.1021/jm901371v	Homo sapiens	8
18572411	10.1016/j.bmc.2008.06.005	Aquaporin-4	7
8941384	10.1021/jm9604890	Cavia porcellus	5
12061889	10.1021/jm0200409	ADMET	5
-	10.1016/0960-894X(96)00324-1	Rattus norvegicus	5
11602674	-	ATP-dependent translocase ABCB1	5
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	4
18426954	10.1124/dmd.108.020479	ADMET	4
9357515	10.1021/jm9704560	5-hydroxytryptamine receptor 1D	4
9871581	10.1016/s0960-894x(98)00090-0	5-hydroxytryptamine receptor 1B	3
10052976	10.1021/jm980569z	5-hydroxytryptamine receptor 1D	3
10585208	10.1021/jm9910021	5-hydroxytryptamine receptor 1D	3
18182301	10.1016/j.bmc.2007.12.040	Unchecked	3
19256501	10.1021/jm801441s	No relevant target	3

Data from ChEMBL 36 via Core Engine