U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H15F3N2O3
Molecular Weight 376.3292
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TECOVIRIMAT

SMILES

FC(F)(F)C1=CC=C(C=C1)C(=O)NN2C(=O)[C@H]3[C@H]([C@H]4C=C[C@@H]3[C@@H]5C[C@H]45)C2=O

InChI

InChIKey=CSKDFZIMJXRJGH-VWLPUNTISA-N
InChI=1S/C19H15F3N2O3/c20-19(21,22)9-3-1-8(2-4-9)16(25)23-24-17(26)14-10-5-6-11(13-7-12(10)13)15(14)18(24)27/h1-6,10-15H,7H2,(H,23,25)/t10-,11+,12+,13-,14-,15+

HIDE SMILES / InChI
Molecular Formula C19H15F3N2O3
Molecular Weight 376.3292
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Tecovirimat (ST-246) is a low-molecular-weight compound (molecular weight = 376), that is potent (concentration that inhibited virus replication by 50% = 0.010 microM), selective (concentration of compound that inhibited cell viability by 50% = >40 microM), and active against multiple orthopoxviruses, including vaccinia, monkeypox, camelpox, cowpox, ectromelia (mousepox), and variola viruses. The antiviral activity is specific for orthopoxviruses and the compound does not inhibit the replication of other RNA- and DNA-containing viruses or inhibit cell proliferation at concentrations of compound that are antiviral. ST-246 targets vaccinia virus p37, a viral protein required for envelopment and secretion of extracellular forms of virus. The compound is orally bioavailable and protects multiple animal species from lethal orthopoxvirus challenge. rug substance and drug product processes have been developed and commercial scale batches have been produced using Good Manufacturing Processes (GMP). Human phase I clinical trials have shown that ST-246 is safe and well tolerated in healthy human volunteers. Based on the results of the clinical evaluation, once a day dosing should provide plasma drug exposure in the range predicted to be antiviral based on data from efficacy studies in animal models of orthopoxvirus disease.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Tecovirimat (ST-246) is CNS penetrant in animals. No human data available.

Originator

Approval Year

2018
425
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
TPOXX

Approved Use

TPOXX is an inhibitor of the orthopoxvirus VP37 envelope wrapping protein and is indicated for the treatment of human smallpox disease in adults and pediatric patients weighing at least 13 kg.

Launch Date

2018
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1591 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29972742/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
2209 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29972742/
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
2106 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
25876 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29972742/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
30632 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29972742/
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
28791 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29972742/
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
20 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20.5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
600 mg 2 times / day steady-state, oral
dose: 600 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TECOVIRIMAT plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Disc. AE: Abnormal EEG, Upset stomach...
Other AEs: Headache, Nausea...
AEs leading to
discontinuation/dose reduction:
Abnormal EEG (2%)
Upset stomach (2%)
Dry mouth (2%)
Dysphoria (2%)
Fever (2%)
Palpable purpura (2%)
Chills (2%)
Facial swelling (2%)
Gastrointestinal disorders (< 2%)
Malaise (< 2%)
Hematocrit decreased (< 2%)
Hemoglobin decreased (< 2%)
Heart rate increased (< 2%)
Other AEs:
Headache (12%)
Nausea (5%)
Abdominal pain (2%)
Vomiting (2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Disc. AE: Arthralgia, Osteoarthritis...
AEs leading to
discontinuation/dose reduction:
Arthralgia (< 2%)
Osteoarthritis (< 2%)
Psychiatric disorders (< 2%)
Oropharyngeal pain (< 2%)
Skin and subcutaneous tissue disorders (< 2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Disc. AE: Abnormal EEG, Abdominal discomfort...
AEs leading to
discontinuation/dose reduction:
Abnormal EEG (grade 1, < 2%)
Abdominal discomfort (grade 1, < 2%)
Dry mouth (grade 1, < 2%)
Dysphoria (grade 1, < 2%)
Disturbance in attention (grade 1, < 2%)
Fever (grade 1, < 2%)
Diarrhea (grade 2, < 2%)
Nausea (grade 1, < 2%)
Headache (grade 3, < 2%)
Palpable purpura (grade 1, < 2%)
Chills (grade 1, < 2%)
Erythema (grade 1, < 2%)
Pruritus (grade 1, < 2%)
Facial swelling (grade 1, < 2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
2000 mg single, oral
Highest studied dose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
1000 mg single, oral
Recommended
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Other AEs: Neutropenia, Constipation...
Other AEs:
Neutropenia (12.5%)
Constipation (12.5%)
Headache (12.5%)
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Other AEs: Feeling abnormal, Back pain...
Other AEs:
Feeling abnormal (12.5%)
Back pain (12.5%)
Headache (12.5%)
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
AEs

AEs

AESignificanceDosePopulation
Headache 12%
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Abdominal pain 2%
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Vomiting 2%
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Abnormal EEG 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Chills 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Dry mouth 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Dysphoria 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Facial swelling 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Fever 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Palpable purpura 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Upset stomach 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Nausea 5%
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Gastrointestinal disorders < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Heart rate increased < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Hematocrit decreased < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Hemoglobin decreased < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Malaise < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Arthralgia < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Oropharyngeal pain < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Osteoarthritis < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Psychiatric disorders < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Skin and subcutaneous tissue disorders < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208627s000lbl.pdf
Abdominal discomfort grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Abnormal EEG grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Chills grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Disturbance in attention grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Dry mouth grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Dysphoria grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Erythema grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Facial swelling grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Fever grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Nausea grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Palpable purpura grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Pruritus grade 1, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Diarrhea grade 2, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Headache grade 3, < 2%
Disc. AE
600 mg 2 times / day steady, oral
Recommended
Dose: 600 mg, 2 times / day
Route: oral
Route: steady
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
healthy, 18-79 years
Health Status: healthy
Age Group: 18-79 years
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208627Orig1s000SumR.pdf
Constipation 12.5%
1000 mg single, oral
Recommended
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Headache 12.5%
1000 mg single, oral
Recommended
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Neutropenia 12.5%
1000 mg single, oral
Recommended
Dose: 1000 mg
Route: oral
Route: single
Dose: 1000 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Back pain 12.5%
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Feeling abnormal 12.5%
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Headache 12.5%
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
healthy, 30-33 years
Health Status: healthy
Age Group: 30-33 years
Sex: M+F
Sources:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346641/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252
inducer
440

substrate
1193

inhibitor
2438
substrate
1388

inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C8
1057

CYP2C19
2057

CYP1A2
2153

CYP2A6
879

CYP2B6
926

CYP2E1
1060

P-gp
1741

OATP1B1
1079

OATP1B3
961

OAT1
725

OAT3
747

OCT2
779

BCRP
910
UGT1A1
479

UGT1A4
399

P-gp
2052

BCRP
697

CYP1A2
1197

CYP2B6
776

CYP2C8
810

CYP2C19
1119

OATP1B1
503

OATP1B3
435

UGT1A3
470
CYP2B6
669

CYP3A
142
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no
CYP2A6
911
 no
CYP2B6
1160
 no
CYP2D6
2546
 no
CYP2E1
1146
 no
CYP3A4
2633
 no
OAT1
730
 no
OAT3
749
 no
OATP1B1
1095
 no
OATP1B3
970
 no
OCT2
782
 no
P-gp
1932
 no
CYP2C9
2497
 no
no (co-administration study)
Comment: flurbiprofen increased tecovirimat Cmax by 7% and AUC by 4%
Page: 24, 70, 72
CYP2B6
1160
 weak
no (co-administration study)
Comment: tecovirimat induced mRNA expression of CYP2B6 at concentrations higher than 10 uM; bupropion decreased tecovirimat Cmax by 14% and AUC by 16%; tecovirimat is an inducer of CYP2B6/2C9/3A4 activities at 100 uM
Page: 24, 73
CYP2C9
2497
 weak
no (co-administration study)
Comment: tecovirimat is an inducer of CYP2B6/2C9/3A4 activities at 100 uM
Page: 73.0
CYP2C19
2141
 weak
yes (co-administration study)
Comment: tecovirimat increased omeprazole Cmax by 86% and AUC by 72%; tecovirimat is not a TDI of CYP2C19
Page: 2, 3, 10, 24, 70
CYP2C8
1117
 weak
yes (co-administration study)
Comment: tecovirimat increased repaglinide Cmax by 27% and AUC by 29%; tecovirimat is not a TDI of CYP2C8
Page: 2, 3, 10, 24, 70
CYP3A
317
 weak
yes (co-administration study)
Comment: tecovirimat decreased midazolam Cmax by 39% and AUC by 32%; tecovirimat induced mRNA expression of CYP3A4 at concentrations higher than 10 uM; tecovirimat is an inducer of CYP2B6/2C9/3A4 activities at 100 uM
Page: 2, 3, 10, 24, 73
BCRP
985
 yes [IC50 6.03 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
697
 no
CYP1A2
1197
 no
CYP2B6
776
 no
CYP2C19
1119
 no
CYP2C8
810
 no
CYP2C9
1193
 no
CYP2D6
1388
 no
CYP3A4
1946
 no
OATP1B1
503
 no
OATP1B3
435
 no
P-gp
2052
 no
UGT1A3
470
 yes
UGT1A1
479
 yes
yes (co-administration study)
Comment: tecovirimat exposures can be increased or decreased by the use of UGT1A1/4 inhibitor or inducers, respectively
Page: 10, 24, 68
UGT1A4
399
 yes
yes (co-administration study)
Comment: tecovirimat exposures can be increased or decreased by the use of UGT1A1/4 inhibitor or inducers, respectively
Page: 10, 24, 68
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
Ambinter
Amb24076326
http://www.ambinter.com/reference/24076326
AN PharmaTech
AN-27268
ApexBio Technology
B4829
http://www.apexbt.com/tecovirimat.html
BioCrick
BCC5518
http://www.biocrick.com/Tecovirimat-BCC5518.html
BOC Sciences
816458-31-8
Chem Scene
CS-3464
Chemieliva Pharmaceutical Co., Ltd
PBCM1443390
ChemShuttle
139092
http://www.chemshuttle.com/catalogsearch/result/?q=869572-92-9&cat=
eMolecules
82744279
Excenen
EX-A4340
https://www.excenen.com/searchresultlist.php?id=EX-A4340
Lab Network
LN01342004
Lan Pharmatech
LAN-B47248
Lan Pharmatech
LQT-B47339
mcule
MCULE-1536691472
MedChem Express
HY-14805
MolPort
MolPort-047-769-294
https://www.molport.com/shop/molecule-link/MolPort-047-769-294
Norris Pharm
NSZB-A271256
OChem
27601
http://www.ocheminc.com/index.php?act=psearch&pid=458T318
Race Chemical
RV022513667
Selleck Chemicals
S3380
http://www.selleckchem.com/products/tecovirimat.html
ZINC
ZINC000035323125
http://zinc15.docking.org/substances/ZINC000035323125
PubMed

PubMed

TitleDatePubMed
Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents.
2010-09
An orally bioavailable antipoxvirus compound (ST-246) inhibits extracellular virus formation and protects mice from lethal orthopoxvirus Challenge.
2005-10
Patents

Patents

20070287735
2
20080004452
2
20120020922
2
20130345278
2
20140316145
2

Sample Use Guides

In Vivo Use Guide
Phase 2, double-blind, randomized, placebo-controlled, multicenter trial was conducted to assess the safety, tolerability, and pharmacokinetics (PK) of tecovirimat (ST-246) when administered as a single daily oral dose (400 mg or 600 mg) for 14 days in fed adult volunteers.
Route of Administration: Oral
In Vitro Use Guide
BSC-40 cells were infected with 2 PFU/cell of vaccinia virus and incubated in the presence and absence of 5 uM tecovirimat (ST-246) . At selected times postinfection, extracellular virus in the medium and cell associated virus were quantified by plaque assay. The results show that ST-246 reduced extracellular virus titers by approximately 10 fold at 24 h postinfection, while having little effect on the level of intracellular virus titers relative to untreated controls. These results suggest that ST-246 inhibits extracellular virus formation.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:25 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:25 GMT 2025
Record UNII
F925RR824R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ST 246
Preferred Name English
TECOVIRIMAT
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
tecovirimat [INN]
Common Name English
TECOVIRIMAT [USAN]
Common Name English
BENZAMIDE, N-((3AR,4R,4AR,5AS,6S,6AS)-3,3A,4,4A,5,5A,6,6A-OCTAHYDRO-1,3-DIOXO-4,6-ETHENOCYCLOPROP(F)ISOINDOL-2(1H)-YL)-4-(TRIFLUOROMETHYL)-, REL-
Common Name English
Tecovirimat [WHO-DD]
Common Name English
TECOVIRIMAT [ORANGE BOOK]
Common Name English
TECOVIRIMAT [MI]
Common Name English
SIGA-246
Code English
ST-246
Code English
N-[(3aR,4R,4aR,5aS,6S,6aS)-1,3-dioxo-3,3a,4,4a,5,5a,6,6a-octahydro-4,6-ethenocyclopropa[f]isoindol-2(1H)-yl]-4-(trifluoromethyl)benzamide
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
FDA ORPHAN DRUG 316210
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
FDA ORPHAN DRUG 229806
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
FDA ORPHAN DRUG 233506
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
EU-Orphan Drug EU/3/10/799
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
Code System Code Type Description
FDA UNII
F925RR824R
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
MESH
C505045
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
SMS_ID
100000177253
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
USAN
TT-70
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
DRUG BANK
DB12020
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
ChEMBL
CHEMBL1242629
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID101026474
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
INN
9011
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
WIKIPEDIA
TECOVIRIMAT
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
DRUG CENTRAL
5291
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
DAILYMED
F925RR824R
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
CAS
869572-92-9
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
MERCK INDEX
m10514
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY Merck Index
PUBCHEM
16124688
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
NCI_THESAURUS
C81606
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
RXCUI
2055104
Created by admin on Mon Mar 31 17:47:25 GMT 2025 , Edited by admin on Mon Mar 31 17:47:25 GMT 2025
PRIMARY
Related Record Type Details
Structure of TECOVIRIMAT MONOHYDRATE
SOLVATE->ANHYDROUS
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Monkeypox virus
TARGET ORGANISM->INHIBITOR
Highly active against an MPXV strain MPXV/France/ IRBA2211i/2022 that was isolated from a patient in France during the 2022 monkeypox outbreak.
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
MINOR
VACCINIA VIRUS
TARGET ORGANISM->INHIBITOR
EC50
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A4
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C8
METABOLIC ENZYME -> INHIBITOR
MINOR
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A1
METABOLIC ENZYME -> SUBSTRATE
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
Structure of TECOVIRIMAT
EXCRETED UNCHANGED
MAJOR
FECAL
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
MINOR
Related Record Type Details
Structure of 4-TRIFLUOROMETHYL BENZOIC ACID
METABOLITE INACTIVE -> PARENT
MAJOR
Structure of 4,6-ETHENOCYCLOPROP(F)ISOINDOLE-1,3(2H,3AH)-DIONE, 4,4A,5,5A,6,6A-HEXAHYDRO-, (3A.ALPHA.,4.BETA.,4A.ALPHA.,5A.ALPHA.,6.BETA.,6A.ALPHA.)-
METABOLITE INACTIVE -> PARENT
Structure of 2-AMINO-4,4A,5,5A,6,6A-HEXAHYDRO-4,6-ETHENOCYCLOPROP(F)ISOINDOLE-1,3(2H,3AH)-DIONE, (3A.ALPHA.,4.BETA.,4A.ALPHA.,5A.ALPHA.,6.BETA.,6A.ALPHA.)-
METABOLITE INACTIVE -> PARENT
Related Record Type Details
Structure of TECOVIRIMAT
ACTIVE MOIETY
broad-spectrum antiviral activity against other orthopoxviruses, including VARV, CPXV, rabbitpox virus (RPXV), MPXV, ectromelia virus (ECTV), and camelpox virus (CMLV) with EC50 values in the submicromolar range. Targets the p37 protein.
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

DOSE

Biological Half-life PHARMACOKINETIC
blood-to-plasma ratio PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966