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Compound Detail

CHEMBL905

RIZATRIPTAN
💊 Approved Drug
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💊 Approved Drug
CN(C)CCc1c[nH]c2ccc(Cn3cncn3)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL905
Name RIZATRIPTAN
Phase Approved
Structure Type MOL
InChI Key ULFRLSNUDGIQQP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

L-705126 Maxalt MK-462 FREE BASE Rizatriptan
10
Targets
22
Activities
3
Assay Types
10
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

269.4
MW (Da)
1.91
ALogP
4
HBA
1
HBD
49.7
PSA (Ų)
0.77
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -triptan
USAN Year 1996

Extended Properties

Molecular Formula C15H19N5
MW 269.35
Aromatic Rings 3
Heavy Atoms 20
NP-Likeness -1.44

Indications

Migraine Disorders Migraine with Aura Migraine without Aura

ATC Classification

N02CC04
rizatriptan
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

IC50 11 meas. best 7.96
Ki 8 meas. best 8.52
EC50 3 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 8.52 8.26 3.0 2
5-hydroxytryptamine receptor 1D
CHEMBL1983
 EC50 8.52 8.3 3.0 2
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 8.52 8.04 3.0 4
5-hydroxytryptamine receptor 1D
CHEMBL1983
 IC50 7.96 7.53 11.0 2
5-hydroxytryptamine receptor 1B
CHEMBL1898
 IC50 7.39 7.39 41.0 1
5-hydroxytryptamine receptor 1D
CHEMBL4105
 IC50 7.3 7.3 50.1 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 6.85 6.69 140.0 2
Oryctolagus cuniculus
CHEMBL374
 EC50 6.6 6.6 251.2 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 IC50 6.5 6.45 316.2 2
Unchecked
CHEMBL612545
 IC50 5.54 5.54 2900.0 1
Serotonin 3 (5-HT3) receptor
CHEMBL2094116
 IC50 5.4 5.4 3981.1 1
5-hydroxytryptamine receptor 2A
CHEMBL322
 IC50 5.2 5.2 6309.6 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 IC50 5.1 5.1 7943.3 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 IC50 5.1 5.1 7943.3 1

Pharmacokinetic Data

Parameter Value Units Species
CL 79.0 mL.min-1.kg-1 Rattus norvegicus
CL 19.0 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
Cmax 1006.13 nM Rattus norvegicus
F 45.0 % Homo sapiens
Fu 0.86 - Homo sapiens
MRT 1.98 hr Homo sapiens
T1/2 0.8 hr Rattus norvegicus
T1/2 2.2 hr Homo sapiens
Tmax 0.75 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1D EC50 = 3.0 nM 8.52 Ability to inhibit forskolin-stimulated adenylate cyclase in a cell line express... 9986723
5-hydroxytryptamine receptor 1D Ki = 3.0 nM 8.52 Binding affinity to 5-HT1DR (unknown origin) assessed as inhibition constant 38516587
5-hydroxytryptamine receptor 1B Ki = 3.0 nM 8.52 Binding affinity to 5-HT1B receptor (unknown origin) assessed as inhibition cons... 38516587
5-hydroxytryptamine receptor 1D Ki = 4.3 nM 8.37 In vitro receptor binding affinity for cloned human 5-hydroxytryptamine 1D recep... 9986723
5-hydroxytryptamine receptor 1D EC50 = 8.4 nM 8.08 Measurement of agonist induced [35S]GTP-gamma-S, binding in CHO cells stably tra... 9357514
5-hydroxytryptamine receptor 1B Ki = 10.1 nM 8.0 In vitro receptor binding affinity for cloned human 5-hydroxytryptamine 1B recep... 9986723
5-hydroxytryptamine receptor 1D IC50 = 11.0 nM 7.96 Binding affinity by displacement to human cloned 5-hydroxytryptamine 1D receptor... 9357514
5-hydroxytryptamine receptor 1D Ki = 13.5 nM 7.87 Binding affinity to recombinant human 5-hydroxytryptamine 1D receptor alpha 7658447
5-hydroxytryptamine receptor 1D Ki = 40.0 nM 7.4 Binding affinity for cloned human 5-hydroxytryptamine 1D receptor beta 7658447
5-hydroxytryptamine receptor 1B IC50 = 41.0 nM 7.39 Binding affinity to human cloned 5-hydroxytryptamine 1B receptor in CHO cells by... 9357514
5-hydroxytryptamine receptor 1D IC50 = 50.12 nM 7.3 Binding activity against 5-hydroxytryptamine 2C receptor from human brain cortex... 7752204
5-hydroxytryptamine receptor 1D IC50 = 79.43 nM 7.1 Binding activity against 5-hydroxytryptamine 3 receptor from rat cortex homogena... 7752204
5-hydroxytryptamine receptor 1A Ki = 140.0 nM 6.85 In vitro receptor binding affinity for cloned human 5-hydroxytryptamine 1A recep... 9986723
Oryctolagus cuniculus EC50 = 251.19 nM 6.6 Functional activity was determined by the contraction of New Zealand white rabbi... 7752204
5-hydroxytryptamine receptor 1A Ki = 293.0 nM 6.53 Binding affinity for cloned human 5-hydroxytryptamine 1A receptor 7658447
5-hydroxytryptamine receptor 1A IC50 = 316.23 nM 6.5 Binding activity against 5-hydroxytryptamine 1A receptor from pig cortex membran... 7752204
5-hydroxytryptamine receptor 1A IC50 = 398.11 nM 6.4 Binding activity against 5-hydroxytryptamine 3 receptor from rat cortex homogena... 7752204
Unchecked IC50 = 2900.0 nM 5.54 Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes 18182301
Serotonin 3 (5-HT3) receptor IC50 = 3981.07 nM 5.4 Binding activity radioligand. 7752204
5-hydroxytryptamine receptor 2A IC50 = 6309.57 nM 5.2 Binding activity against 5-hydroxytryptamine 2C receptor from pig cortex membran... 7752204

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 83
31158845 10.1038/s41586-019-1291-3 ADMET 49
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.1016/0960-894X(96)00324-1 Rattus norvegicus 5
24960305 10.1021/jm500364u Homo sapiens 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
9986723 10.1021/jm9805945 5-hydroxytryptamine receptor 1D 3
18182301 10.1016/j.bmc.2007.12.040 Unchecked 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
30048589 10.1021/acs.jmedchem.7b01768 Uracil nucleotide/cysteinyl leukotriene receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
- 10.1016/0960-894X(96)00324-1 5-hydroxytryptamine receptor 1D 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
7658447 10.1021/jm00018a020 Oryctolagus cuniculus 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
7752204 10.1021/jm00010a025 Serotonin 3 (5-HT3) receptor 2

Data from ChEMBL 36 via Core Engine