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Compound Detail

CHEMBL46

ONDANSETRON
💊 Approved Drug
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💊 Approved Drug
Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O

Basic Information

ChEMBL ID CHEMBL46
Name ONDANSETRON
Phase Approved
Structure Type MOL
InChI Key FELGMEQIXOGIFQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

A04AA01 Desmethylondansetron EUR-1025 GR-38032 NSC-757870 Ondansetron Zofran odt Zuplenz
30
Targets
91
Activities
3
Assay Types
17
PK Parameters
20
Publications
8
Known Names
20
Indications
1
Mechanisms

Molecular Properties

293.4
MW (Da)
3.13
ALogP
4
HBA
0
HBD
39.8
PSA (Ų)
0.73
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -setron
USAN Year 1989

Extended Properties

Molecular Formula C18H19N3O
MW 293.37
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -0.54

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin 3a (5-HT3a) receptor antagonist ANTAGONIST 5-hydroxytryptamine receptor 3A

Indications

Nausea Nausea Nausea Neoplasms Postoperative Nausea and Vomiting Postoperative Nausea and Vomiting Postoperative Nausea and Vomiting Alcoholism Alcoholism Gastroenteritis Genital Neoplasms, Female HIV Infections Hypotension Irritable Bowel Syndrome Pain Schizophrenia Syncope Uterine Cervical Neoplasms Vomiting Amphetamine-Related Disorders

ATC Classification

A04AA01
ondansetron
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIEMETICS AND ANTINAUSEANTS

Activity Summary

Ki 41 meas. best 9.11
IC50 33 meas. best 10.05
Kd 17 meas. best 10.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serotonin 3 (5-HT3) receptor
CHEMBL2094132
Kd 10.1 8.8517 0.1 6
5-hydroxytryptamine receptor 3A
CHEMBL1899
IC50 10.05 10.05 0.1 1
Cavia porcellus
CHEMBL369
Kd 9.9 7.9 0.1 3
5-hydroxytryptamine receptor 3A
CHEMBL2411
IC50 9.8 9.8 0.2 1
5-hydroxytryptamine receptor 3A
CHEMBL2411
Ki 9.11 9.11 0.8 1
Serotonin 3 (5-HT3) receptor
CHEMBL2094116
Ki 9.11 8.3147 0.8 19
Rattus norvegicus
CHEMBL376
Kd 8.99 7.895 1.0 2
Serotonin 3 (5-HT3) receptor
CHEMBL2094116
IC50 8.85 8.3914 1.4 7
Serotonin 3 (5-HT3) receptor
CHEMBL2094116
Kd 8.7 8.7 2.0 1
Unchecked
CHEMBL612545
Ki 8.68 8.64 2.1 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.6 7.47 2.5 2
5-hydroxytryptamine receptor 3A
CHEMBL1899
Ki 8.55 8.1525 2.8 4
Serotonin 3 (5-HT3) receptor
CHEMBL2094132
Ki 8.12 8.02 7.6 2
Unchecked
CHEMBL612545
IC50 8.03 6.79 9.3 2
Serotonin 3 receptor (5HT3)
CHEMBL2111333
Ki 7.92 7.92 12.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 7.52 7.0467 30.0 3
5-hydroxytryptamine receptor 3A
CHEMBL3666
Kd 7.11 6.97 77.6 3
Unchecked
CHEMBL612545
Kd 6.9 6.9 125.9 1
Multidrug and toxin extrusion protein 2
CHEMBL1743127
IC50 6.8 6.16 160.0 3
Cavia porcellus
CHEMBL369
IC50 6.62 6.62 240.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.4 6.152 400.0 5
Sigma non-opioid intracellular receptor 1
CHEMBL3602
Ki 6.17 6.17 680.0 1
Gastrin/cholecystokinin type B receptor
CHEMBL3508
Ki 6.17 6.17 680.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.14 6.14 717.0 1
Solute carrier family 22 member 2
CHEMBL1743122
IC50 6.05 5.91 890.0 2
5-hydroxytryptamine receptor 4
CHEMBL4317
Ki 5.92 5.92 1200.0 1
Mu-type opioid receptor
CHEMBL270
Ki 5.54 5.54 2900.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 5.43 5.43 3700.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
Ki 5.3 5.3 5000.0 1
GABA-A receptor; anion channel
CHEMBL1907607
IC50 5.0 5.0 10000.0 1
Muscarinic acetylcholine receptor M1
CHEMBL276
Ki 5.0 5.0 10000.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
Ki 5.0 5.0 10000.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 4.96 4.96 11000.0 1
Solute carrier family 22 member 3
CHEMBL2073673
IC50 4.76 4.76 17400.0 1
5-hydroxytryptamine receptor 1D
CHEMBL5450
Ki 4.7 4.7 20000.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 4.69 4.69 20400.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
IC50 4.6 4.6 25000.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
IC50 4.57 4.57 27000.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
Ki 4.34 4.34 46000.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
IC50 4.18 4.18 66000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 5.9 mL.min-1.kg-1 Homo sapiens
CL 5.5 mL.min-1.kg-1 Homo sapiens
CL 5.8 mL.min-1.kg-1 Homo sapiens
CL 5.8 mL.min-1.g-1 Homo sapiens
CL 5.8 mL.min-1.kg-1 Homo sapiens
CL 6.46 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
Cmax 130.0 nM Homo sapiens
F 79.0 % Homo sapiens
F 21.0 % Rattus norvegicus
F 56.0 % Homo sapiens
Fu 0.27 - Homo sapiens
Fu 0.27 - Homo sapiens
Fu 0.94 - Homo sapiens
MRT 5.2 hr Homo sapiens
T1/2 3.4 hr Homo sapiens
T1/2 3.1 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serotonin 3 (5-HT3) receptor Kd = 0.07943 nM 10.1 Evaluated for the antagonistic activity against Serotonin 5-hydroxytryptamine 3 ... -
Serotonin 3 (5-HT3) receptor Kd = 0.07943 nM 10.1 Potency at neuronal 5-hydroxytryptamine 3 receptor in the rabbit heart 2342053
5-hydroxytryptamine receptor 3A IC50 = 0.09 nM 10.05 Antagonist activity at human 5HT3A receptor expressed in xenopus oocytes assesse... 21486038
Cavia porcellus Kd = 0.1259 nM 9.9 Single-point analysis using 5(10e-9) M concentration of the antagonist (pA2= -lo... 10585211
5-hydroxytryptamine receptor 3A IC50 = 0.16 nM 9.8 Antagonist activity at rat 5HT3A receptor expressed in xenopus oocytes assessed ... 21486038
Serotonin 3 (5-HT3) receptor Kd = 0.3981 nM 9.4 Binding affinity to 5-hydroxytryptamine 3 receptor of neuronal in the afferent r... 2342053
Serotonin 3 (5-HT3) receptor Kd = 0.631 nM 9.2 Antagonistic activity against Serotonin 5-hydroxytryptamine 3 receptor in isolat... -
Serotonin 3 (5-HT3) receptor Ki = 0.77 nM 9.11 Compound was evaluated for its in vitro affinity at serotonergic 5-hydroxytrypta... 10585211
5-hydroxytryptamine receptor 3A Ki = 0.77 nM 9.11 Displacement of [3H]LY 278584 from 5-HT3 receptor in Sprague-Dawley rat cerebral... 24050112
Serotonin 3 (5-HT3) receptor Ki = 1.0 nM 9.0 In vitro affinity for 5-hydroxytryptamine 3 (5-HT3) receptor by displacement of ... 9341912
Rattus norvegicus Kd = 1.023 nM 8.99 The pA2 is the negative logarithm of the molar concentration of an antagonist wh... 8246239
Serotonin 3 (5-HT3) receptor Ki = 1.2 nM 8.92 Binding affinity for 5-hydroxytryptamine 3 receptor from rat cortex using [3H]BR... 7629808
Serotonin 3 (5-HT3) receptor IC50 = 1.4 nM 8.85 Binding affinity against 5-hydroxytryptamine 3 receptor in rat cortical membrane... 9871571
Serotonin 3 (5-HT3) receptor IC50 = 1.54 nM 8.81 Concentration required to inhibit the binding of radioligand [3H]GR-65630 to ser... 12593651
Serotonin 3 (5-HT3) receptor Ki = 1.6 nM 8.8 Displacement of [3H]GR-65630 binding to 5-hydroxytryptamine 3 receptor in rat br... 8246239
Serotonin 3 (5-HT3) receptor Ki = 1.6 nM 8.8 The binding affinity was measured on 5-hydroxytryptamine 3 receptor using [3H]GR... 8246239
Serotonin 3 (5-HT3) receptor IC50 = 1.95 nM 8.71 Compound was evaluated for the displacement of [3H]Q-ICS-205-930 from 5-HT3 reco... 1552497
Serotonin 3 (5-HT3) receptor IC50 = 1.95 nM 8.71 Compound was evaluated for the displacement of [3H]-Q-ICS 205-930 binding to 5-h... 1992112
Serotonin 3 (5-HT3) receptor Kd = 1.995 nM 8.7 In vitro antagonism of the 5-HT-3 receptor determined by inhibition of 5-HT-indu... 1578478
Unchecked Ki = 2.088 nM 8.68 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT3 radioligand binding (ligand: [... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 301
- 10.6019/CHEMBL4295262 Unchecked 28
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
1527780 10.1021/jm00096a001 Canis familiaris 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
8410977 10.1021/jm00070a008 Canis familiaris 10
1732548 10.1021/jm00080a016 Serotonin 3 (5-HT3) receptor 10
1527780 10.1021/jm00096a001 Unchecked 9
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
8230119 10.1021/jm00074a009 Rattus norvegicus 6
20851599 10.1016/j.bmcl.2010.08.128 Mus musculus 6
8496941 10.1021/jm00057a011 Canis familiaris 6
21256009 10.1016/j.bmcl.2010.12.064 Mus musculus 6
21599003 10.1021/jm2001629 ADMET 5
2342053 10.1021/jm00168a011 Serotonin 3 (5-HT3) receptor 5
8246239 10.1021/jm00075a026 Rattus norvegicus 4
1312602 10.1021/jm00083a014 Mustela putorius furo 4
8246239 10.1021/jm00075a026 Unchecked 4

Data from ChEMBL 36 via Core Engine