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

Details

Stereochemistry ACHIRAL
Molecular Formula C24H25Cl2FN4O2
Molecular Weight 491.385
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TESEVATINIB

SMILES

[H][C@@]12C[C@H](COC3=CC4=NC=NC(NC5=C(F)C(Cl)=C(Cl)C=C5)=C4C=C3OC)C[C@]1([H])CN(C)C2

InChI

InChIKey=HVXKQKFEHMGHSL-QKDCVEJESA-N
InChI=1S/C24H25Cl2FN4O2/c1-31-9-14-5-13(6-15(14)10-31)11-33-21-8-19-16(7-20(21)32-2)24(29-12-28-19)30-18-4-3-17(25)22(26)23(18)27/h3-4,7-8,12-15H,5-6,9-11H2,1-2H3,(H,28,29,30)/t13-,14-,15+

HIDE SMILES / InChI

Molecular Formula C24H25Cl2FN4O2
Molecular Weight 491.385
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17575237

Tesevatinib (EXEL-7647 or XL647) was optimized as an inhibitor of a spectrum of growth-promoting and angiogenic receptor tyrosine kinases (RTKs) to simultaneously block tumor growth and vascularization. In particular, Tesevatinib potently inhibits the EGF/ErbB2, VEGF, and ephrin RTK families. The drug is being developed by Kadmon Corporation under licence from Symphony Evolution (Symphony Capital Partners). Kadmon is developing tesevatinib for the treatment of autosomal polycystic kidney disease and solid cancers.

CNS Activity

Curator's Comment: In animal models, tesevatinib penetrated the blood-brain barrier and achieved concentrations in the brain that are greater than or equivalent to levels achieved in the blood. Tesevatinib was also found to inhibit the intracranial tumour growth, suggesting its ability to target intracranial tumours

Originator

Curator's Comment: # Exelixis

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.666 ng/mL/(mg dose)
4.68 mg/kg single, oral
dose: 4.68 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.28 ng/mL/(mg dose)
4.68 mg/kg 1 times / day steady-state, oral
dose: 4.68 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.72 ng/mL/(mg dose)
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.611 ng/mL/(mg dose)
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
10 ng × h/mL/kg
4.68 mg/kg single, oral
dose: 4.68 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
24.6 ng × h/mL/kg
4.68 mg/kg 1 times / day steady-state, oral
dose: 4.68 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
34.1 ng × h/mL/kg
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
9.6 ng × h/mL/kg
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
55.5 h
4.68 mg/kg single, oral
dose: 4.68 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
64.2 h
4.68 mg/kg 1 times / day steady-state, oral
dose: 4.68 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TESEVATINIB plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 5
Health Status: unhealthy
Condition: advanced solid malignancies
Sex: M+F
Food Status: FASTED
Population Size: 5
Sources:
DLT: QTc prolongation...
Dose limiting toxicities:
QTc prolongation (grade 3, 2 patients)
Sources:
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
Disc. AE: astrointestinal bleed, pneumonia...
Other AEs: Pruritus, Dry skin...
AEs leading to
discontinuation/dose reduction:
astrointestinal bleed (grade 3, 1 pt)
pneumonia (grade 3, 1 pt)
QTc prolongation (grade 3, 1 pt)
onychomadesis (grade 2, 1 pt)
Other AEs:
Pruritus (grade 2, 5%)
Dry skin (grade 2, 2%)
Dysgeusia (grade 2, 2%)
Mucosal inflammation (grade 2, 2%)
Vomiting (grade 2, 2%)
Diarrhea (grade 3, 5%)
fatigue (grade 3, 2%)
Sources:
300 mg 1 times / day multiple, oral (total daily dose)
MTD
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 6
Health Status: unhealthy
Condition: advanced solid malignancies
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources:
DLT: pneumonitis...
Dose limiting toxicities:
pneumonitis (grade 3, 1 pt)
Sources:
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
Disc. AE: QTc prolongation, diarrhea...
Other AEs: Nausea, Fatigue...
AEs leading to
discontinuation/dose reduction:
QTc prolongation (grade 3, 1 pt)
diarrhea (grade 3, 1 pt)
rash (grade 3, 1 pt)
gastrointestinal discomfort (grade 1, 1 pt)
gastrointestinal bleed (grade 3, 1 pt)
Blood creatinine increased (grade 2, 1 pt)
Hyperkalemia (grade 2, 1 pt)
Other AEs:
Nausea (grade 2, 7%)
Fatigue (grade 2, 14%)
Anorexia (grade 2, 7%)
Sources:
7 mg/kg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 7 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 7 mg/kg, 1 times / day
Sources:
unhealthy
n = 2
Health Status: unhealthy
Condition: advanced solid malignancies
Sex: unknown
Food Status: FASTED
Population Size: 2
Sources:
DLT: diarrhea...
Dose limiting toxicities:
diarrhea (grade 4, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
QTc prolongation grade 3, 2 patients
DLT
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 5
Health Status: unhealthy
Condition: advanced solid malignancies
Sex: M+F
Food Status: FASTED
Population Size: 5
Sources:
onychomadesis grade 2, 1 pt
Disc. AE
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
Dry skin grade 2, 2%
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
Dysgeusia grade 2, 2%
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
Mucosal inflammation grade 2, 2%
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
Vomiting grade 2, 2%
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
Pruritus grade 2, 5%
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
QTc prolongation grade 3, 1 pt
Disc. AE
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
astrointestinal bleed grade 3, 1 pt
Disc. AE
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
pneumonia grade 3, 1 pt
Disc. AE
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
fatigue grade 3, 2%
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
Diarrhea grade 3, 5%
350 mg 1 times / day multiple, oral (total daily dose)
Highest studied dose
Dose: 350 mg, 1 times / day
Route: oral
Route: multiple
Dose: 350 mg, 1 times / day
Sources:
unhealthy
n = 41
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 41
Sources:
pneumonitis grade 3, 1 pt
DLT
300 mg 1 times / day multiple, oral (total daily dose)
MTD
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 6
Health Status: unhealthy
Condition: advanced solid malignancies
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources:
gastrointestinal discomfort grade 1, 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
Blood creatinine increased grade 2, 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
Hyperkalemia grade 2, 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
Fatigue grade 2, 14%
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
Anorexia grade 2, 7%
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
Nausea grade 2, 7%
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
QTc prolongation grade 3, 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
diarrhea grade 3, 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
gastrointestinal bleed grade 3, 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
rash grade 3, 1 pt
Disc. AE
300 mg 1 times / day multiple, oral
Studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
n = 14
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources:
diarrhea grade 4, 2 patients
DLT, Disc. AE
7 mg/kg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 7 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 7 mg/kg, 1 times / day
Sources:
unhealthy
n = 2
Health Status: unhealthy
Condition: advanced solid malignancies
Sex: unknown
Food Status: FASTED
Population Size: 2
Sources:
PubMed

PubMed

TitleDatePubMed
New strategies to overcome limitations of reversible EGFR tyrosine kinase inhibitor therapy in non-small cell lung cancer.
2010 Jul
EGFR-mutant lung adenocarcinomas treated first-line with the novel EGFR inhibitor, XL647, can subsequently retain moderate sensitivity to erlotinib.
2012 Feb
Phase II study of the multitargeted tyrosine kinase inhibitor XL647 in patients with non-small-cell lung cancer.
2012 May
Patents

Sample Use Guides

Two dosing schedules were evaluated; in the "intermittent 5 & 9 dosing" cohort, Tesevatinib (XL647) 350 mg for 5 days every 14 days was given; and in the "daily dosing" cohort, XL647 300 mg daily for 28 days was administered. XL647 administered on an intermittent or daily-dosing schedule demonstrated antitumor activity in patients with non-small-cell lung cancer.
Route of Administration: Oral
In A431 cells, which express WT EGFR, Tesevatinib reduced cell viability with IC50 values of 13 nmol/L, with 95% confidence intervals of 10 to 15.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:09:33 GMT 2023
Edited
by admin
on Sat Dec 16 02:09:33 GMT 2023
Record UNII
F6XM2TN5A1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TESEVATINIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
XL-647
Common Name English
XL647
Code English
EXEL-7647
Code English
KD019
Code English
4-QUINAZOLINAMINE, N-(3,4-DICHLORO-2-FLUOROPHENYL)-6-METHOXY-7-(((3A.ALPHA.,5.BETA.,6A.ALPHA.)-OCTAHYDRO-2-METHYLCYCLOPENTA(C)PYRROL-5-YL)METHOXY)-
Common Name English
KD-019
Code English
Tesevatinib [WHO-DD]
Common Name English
TESEVATINIB [USAN]
Common Name English
KD-020
Code English
N-(3,4-DICHLORO-2-FLUOROPHENYL)-6-METHOXY-7-(((3AR,6AS)-2-METHYLOCTAHYDROCYCLOPENTA(C)PYRROL-5-YL)METHOXY)QUINAZOLIN-4-AMINE
Common Name English
tesevatinib [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
FDA ORPHAN DRUG 802420
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
NCI_THESAURUS C1742
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
FDA ORPHAN DRUG 506715
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
FDA ORPHAN DRUG 584917
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
Code System Code Type Description
USAN
BC-18
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
INN
10079
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
WIKIPEDIA
Tesevatinib
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
NCI_THESAURUS
C62496
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
PUBCHEM
10458325
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID201336925
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
FDA UNII
F6XM2TN5A1
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL3544983
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
CHEBI
167674
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
SMS_ID
300000034419
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
CAS
781613-23-8
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
DRUG BANK
DB11973
Created by admin on Sat Dec 16 02:09:33 GMT 2023 , Edited by admin on Sat Dec 16 02:09:33 GMT 2023
PRIMARY
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