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Compound Detail

CHEMBL1257073

TECOVIRIMAT
💊 Approved Drug
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💊 Approved Drug
O=C(NN1C(=O)[C@@H]2[C@@H]3C=C[C@@H]([C@H]4C[C@@H]34)[C@@H]2C1=O)c1ccc(C(F)(F)F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1257073
Name TECOVIRIMAT
Phase Approved
Structure Type MOL
InChI Key CSKDFZIMJXRJGH-VWLPUNTISA-N
Therapeutic ✓ Yes

Known Names

SIGA-246 ST 246 ST-246 Tecovirimat Tpoxx
6
Targets
25
Activities
2
Assay Types
30
PK Parameters
20
Publications
5
Known Names
2
Indications
1
Mechanisms

Molecular Properties

376.3
MW (Da)
2.40
ALogP
3
HBA
1
HBD
66.5
PSA (Ų)
0.64
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2018
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

First in Class
USAN Stem -vir-
USAN Year 2008

Extended Properties

Molecular Formula C19H15F3N2O3
MW 376.33
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness -0.70

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Envelope phospholipase OPG057 inhibitor INHIBITOR Envelope phospholipase OPG057 ✓ ✓

Indications

Smallpox Virus Diseases

ATC Classification

J05AX24
tecovirimat
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 22 meas. best 8.0
IC50 3 meas. best 8.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Envelope phospholipase OPG057
CHEMBL4296170
 IC50 8.57 8.57 2.7 1
Unchecked
CHEMBL612545
 IC50 8.27 8.18 5.3 2
Vaccinia virus
CHEMBL613493
 EC50 8.0 7.2933 10.0 6
Variola virus
CHEMBL613494
 EC50 7.72 7.5 19.0 7
Monkeypox virus
CHEMBL613120
 EC50 7.64 7.502 23.0 5
Cowpox virus
CHEMBL612672
 EC50 6.32 6.0175 480.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 9879.0 ng.hr.mL-1 Homo sapiens
AUC 21088.0 ng.hr.mL-1 Homo sapiens
AUC 24548.0 ng.hr.mL-1 Homo sapiens
AUC 34056.0 ng.hr.mL-1 Homo sapiens
AUC 9808.0 ng.hr.mL-1 Homo sapiens
AUC 24937.0 ng.hr.mL-1 Homo sapiens
AUC 25746.0 ng.hr.mL-1 Homo sapiens
AUC 35886.0 ng.hr.mL-1 Homo sapiens
AUC 9101.0 ng.hr.mL-1 Homo sapiens
AUC 13146.0 ng.hr.mL-1 Homo sapiens
AUC 20959.0 ng.hr.mL-1 Homo sapiens
AUC 11892.0 ng.hr.mL-1 Homo sapiens
AUC 15432.0 ng.hr.mL-1 Homo sapiens
AUC 23352.0 ng.hr.mL-1 Homo sapiens
AUC 10083.0 ng.hr.mL-1 Homo sapiens
AUC 1457.0 ng.hr.mL-1 Homo sapiens
AUC 22684.0 ng.hr.mL-1 Homo sapiens
AUC 13736.0 ng.hr.mL-1 Macaca fascicularis
AUC 12640.0 ng.hr.mL-1 Macaca fascicularis
AUC 13504.0 ng.hr.mL-1 Macaca fascicularis
AUC 18358.0 ng.hr.mL-1 Macaca fascicularis
AUC 18064.0 ng.hr.mL-1 Macaca fascicularis
AUC 20736.0 ng.hr.mL-1 Macaca fascicularis
AUC 15803.0 ng.hr.mL-1 Macaca fascicularis
AUC 9101.0 ng.hr.mL-1 Homo sapiens
AUC 11892.0 ng.hr.mL-1 Homo sapiens
AUC 10083.0 ng.hr.mL-1 Homo sapiens
AUC 13146.0 ng.hr.mL-1 Homo sapiens
AUC 15432.0 ng.hr.mL-1 Homo sapiens
AUC 16182.0 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Envelope phospholipase OPG057 IC50 = 2.66 nM 8.57 Inhibition of p37 in Vaccinia virus Copenhagen infected in African green monkey ... 33965861
Unchecked IC50 = 5.32 nM 8.27 Inhibition of p37 in Cowpox virus Grishak infected in African green monkey Vero ... 33965861
Unchecked IC50 = 8.06 nM 8.09 Inhibition of p37 in Ectromelia virus K1 infected in African green monkey Vero c... 33965861
Vaccinia virus EC50 = 10.0 nM 8.0 Antiviral activity against Vaccinia virus assessed as reduction in virus-induced... 36155354
Variola virus EC50 = 19.0 nM 7.72 Antiviral activity against Variola virus SUD47-juba infected in african green mo... 19075062
Variola virus EC50 = 21.0 nM 7.68 Antiviral activity against Variola virus NEP73-175 infected in african green mon... 19075062
Monkeypox virus EC50 = 23.0 nM 7.64 Antiviral activity against Monkeypox virus V78-I-3945 infected in african green ... 19075062
Variola virus EC50 = 28.0 nM 7.55 Antiviral activity against Variola virus SOM77-ali infected in african green mon... 19075062
Variola virus EC50 = 28.0 nM 7.55 Antiviral activity against Variola virus BSH74-sol infected in african green mon... 19075062
Monkeypox virus EC50 = 30.0 nM 7.52 Antiviral activity against Monkeypox virus V77-I-823 infected in african green m... 19075062
Monkeypox virus EC50 = 32.0 nM 7.5 Antiviral activity against Monkeypox virus V81-I-179 infected in african green m... 19075062
Monkeypox virus EC50 = 36.0 nM 7.44 Antiviral activity against Monkeypox virus 2003-USA-039 infected in african gree... 19075062
Variola virus EC50 = 37.0 nM 7.43 Antiviral activity against Variola virus SLN68-258 infected in african green mon... 19075062
Monkeypox virus EC50 = 39.0 nM 7.41 Antiviral activity against Monkeypox virus V1979-I-005 infected in african green... 19075062
Variola virus EC50 = 40.0 nM 7.4 Antiviral activity against Variola virus assessed as reduction in virus-induced ... 36155354
Vaccinia virus EC50 = 50.0 nM 7.3 Antiviral activity against Vaccinia virus Copenhagen infected HFF cells 17116683
Vaccinia virus EC50 = 50.0 nM 7.3 Antiviral activity against Vaccinia virus Copenhagen in HFF cells assessed as re... 17724153
Variola virus EC50 = 67.0 nM 7.17 Antiviral activity against Variola virus BRZ66-39 infected in african green monk... 19075062
Vaccinia virus EC50 = 70.0 nM 7.16 Antiviral activity against Vaccinia virus WR infected in HFF assessed as reducti... 19029322
Vaccinia virus EC50 = 100.0 nM 7.0 Antiviral activity against Vaccinia virus WR infected HFF cells 17116683

Literature References

PubMed DOI Target Context # Activities
19752270 10.1128/aac.00678-09 Vaccinia virus WR 86
19075062 10.1128/aac.01044-08 Variola virus 61
19349521 10.1128/aac.00021-09 Variola virus 56
20385870 10.1128/aac.01689-09 Homo sapiens 51
19075062 10.1128/aac.01044-08 Monkeypox virus 51
18316519 10.1128/aac.01303-07 Homo sapiens 41
17116683 10.1128/aac.00879-06 Mus musculus 38
17724153 10.1128/aac.00762-07 Cowpox virus 20
19223621 10.1128/aac.01596-08 Homo sapiens 18
17116683 10.1128/aac.00879-06 Ectromelia virus 16
19223621 10.1128/aac.01596-08 Cynomolgus monkey 14
17116683 10.1128/aac.00879-06 NON-PROTEIN TARGET 7
19349521 10.1128/aac.00021-09 Monkeypox virus 6
17116683 10.1128/aac.00879-06 Vaccinia virus 6
17116683 10.1128/aac.00879-06 Cowpox virus 5
19029322 10.1128/aac.01257-08 Vaccinia virus 5
17724153 10.1128/aac.00762-07 Vaccinia virus 3
17724153 10.1128/aac.00762-07 Unchecked 3
19029322 10.1128/aac.01257-08 Cowpox virus 3
17116683 10.1128/aac.00879-06 Unchecked 3

Data from ChEMBL 36 via Core Engine