Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H25ClFN5O3.2ClH |
Molecular Weight | 558.86 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.FC1=C(Cl)C=C(NC2=NC=NC3=CC(OCCCN4CCOCC4)=C(NC(=O)C=C)C=C23)C=C1
InChI
InChIKey=JZZFDCXSFTVOJY-UHFFFAOYSA-N
InChI=1S/C24H25ClFN5O3.2ClH/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16;;/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29);2*1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C24H25ClFN5O3 |
Molecular Weight | 485.938 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Canertinib or CI-1033 (N-[4-[N-(3-Chloro-4-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazolin-6-yl]acrylamide) is a pan-erbB tyrosine kinase inhibitor. It selectively inhibits erbB1 (epidermal growth factor receptor), erbB2, erbB3, and erbB4 without inhibiting tyrosine kinase activity of receptors such as platelet-derived growth factor receptor, fibroblast growth factor receptor, and insulin receptor, even at high concentrations. Canertinib was under development by Pfizer Inc as a potential treatment for cancer.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753475 |
1.5 nM [IC50] | ||
Target ID: CHEMBL1824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753475 |
9.0 nM [IC50] | ||
Target ID: CHEMBL3009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11706399 |
7.0 nM [IC50] | ||
Target ID: CHEMBL5838 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11706399 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
337.5 mg 3 times / week multiple, intravenous (total daily dose) Highest studied dose Dose: 337.5 mg, 3 times / week Route: intravenous Route: multiple Dose: 337.5 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
DLT: hypersensitivity reaction, diarrhea... Dose limiting toxicities: hypersensitivity reaction (grade 3, 2 patients) Sources: diarrhea (grade 3, 2 patients) |
500 mg 3 times / week multiple, intravenous (total daily dose) Highest studied dose Dose: 500 mg, 3 times / week Route: intravenous Route: multiple Dose: 500 mg, 3 times / week Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
DLT: Myalgia, syncope... Dose limiting toxicities: Myalgia (grade 3, 2 patients) Sources: syncope (2 patients) |
750 mg 1 times / day multiple, oral (total daily dose) Highest studied dose Dose: 750 mg, 1 times / day Route: oral Route: multiple Dose: 750 mg, 1 times / day Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
DLT: emesis, rash... Other AEs: Diarrhea... Dose limiting toxicities: emesis (grade 2, 1 pt) Other AEs:rash (grade 2, 1 pt) mouth ulcer (grade 2, 1 pt) emesis (grade 3, 1 pt) Diarrhea (grade 1-2, 2 patients) Sources: |
225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Other AEs: Dyspnea, Infection... Other AEs: Dyspnea (1 pt) Sources: Infection (3 patients) Thrombocytopenia (1 pt) Cutaneous toxicities (7 patients) Pain (2 patients) Asthenia (2 patients) Vasodilation (2 patients) Stomatitis (2 patients) Myalgia (2 patients) Vomiting (2 patients) Nausea (2 patients) |
650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
DLT: thrombocytopenia... Other AEs: Emesis, rash... Dose limiting toxicities: thrombocytopenia (grade 4, 1 pt) Other AEs:Emesis (grade 3, 1 pt) Sources: rash (grade 1-2, 7 patients) Hypersensitivity (grade 1-2, 3 patients) Mucositis (grade 1-2, 6 patients) Nausea (grade 1-2, 5 patients) iarrhea (grade 1-2, 3 patients) |
200 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy n = 52 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 52 Sources: |
Disc. AE: Diarrhea... Other AEs: Abdominal pain, Asthenia... AEs leading to discontinuation/dose reduction: Diarrhea (13%) Other AEs:Abdominal pain (13%) Sources: Asthenia (13%) |
50 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 53 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 53 Sources: |
Disc. AE: diarrhea, Abdominal pain... AEs leading to discontinuation/dose reduction: diarrhea (10%) Sources: Abdominal pain (10%) Asthenia (10%) |
50 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
DLT: Thrombocytopenia... Dose limiting toxicities: Thrombocytopenia (grade 3, 1 pt) Sources: |
560 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 560 mg, 1 times / day Route: oral Route: multiple Dose: 560 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
DLT: Hypersensitivity... Dose limiting toxicities: Hypersensitivity (grade 3, 1 pt) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
diarrhea | grade 3, 2 patients DLT |
337.5 mg 3 times / week multiple, intravenous (total daily dose) Highest studied dose Dose: 337.5 mg, 3 times / week Route: intravenous Route: multiple Dose: 337.5 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
hypersensitivity reaction | grade 3, 2 patients DLT |
337.5 mg 3 times / week multiple, intravenous (total daily dose) Highest studied dose Dose: 337.5 mg, 3 times / week Route: intravenous Route: multiple Dose: 337.5 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
syncope | 2 patients DLT |
500 mg 3 times / week multiple, intravenous (total daily dose) Highest studied dose Dose: 500 mg, 3 times / week Route: intravenous Route: multiple Dose: 500 mg, 3 times / week Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
Myalgia | grade 3, 2 patients DLT |
500 mg 3 times / week multiple, intravenous (total daily dose) Highest studied dose Dose: 500 mg, 3 times / week Route: intravenous Route: multiple Dose: 500 mg, 3 times / week Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
Diarrhea | grade 1-2, 2 patients | 750 mg 1 times / day multiple, oral (total daily dose) Highest studied dose Dose: 750 mg, 1 times / day Route: oral Route: multiple Dose: 750 mg, 1 times / day Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
emesis | grade 2, 1 pt DLT |
750 mg 1 times / day multiple, oral (total daily dose) Highest studied dose Dose: 750 mg, 1 times / day Route: oral Route: multiple Dose: 750 mg, 1 times / day Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
mouth ulcer | grade 2, 1 pt DLT |
750 mg 1 times / day multiple, oral (total daily dose) Highest studied dose Dose: 750 mg, 1 times / day Route: oral Route: multiple Dose: 750 mg, 1 times / day Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
rash | grade 2, 1 pt DLT |
750 mg 1 times / day multiple, oral (total daily dose) Highest studied dose Dose: 750 mg, 1 times / day Route: oral Route: multiple Dose: 750 mg, 1 times / day Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
emesis | grade 3, 1 pt DLT |
750 mg 1 times / day multiple, oral (total daily dose) Highest studied dose Dose: 750 mg, 1 times / day Route: oral Route: multiple Dose: 750 mg, 1 times / day Sources: |
unhealthy n = 3 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 3 Sources: |
Dyspnea | 1 pt | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Thrombocytopenia | 1 pt | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Asthenia | 2 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Myalgia | 2 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Nausea | 2 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Pain | 2 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Stomatitis | 2 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Vasodilation | 2 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Vomiting | 2 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Infection | 3 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Cutaneous toxicities | 7 patients | 225 mg 3 times / week multiple, intravenous (total daily dose) MTD Dose: 225 mg, 3 times / week Route: intravenous Route: multiple Dose: 225 mg, 3 times / week Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: advanced nonhematologic malignancies Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Hypersensitivity | grade 1-2, 3 patients | 650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
iarrhea | grade 1-2, 3 patients | 650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
Nausea | grade 1-2, 5 patients | 650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
Mucositis | grade 1-2, 6 patients | 650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
rash | grade 1-2, 7 patients | 650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
Emesis | grade 3, 1 pt | 650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
thrombocytopenia | grade 4, 1 pt DLT |
650 mg 1 times / day multiple, oral (total daily dose) MTD Dose: 650 mg, 1 times / day Route: oral Route: multiple Dose: 650 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
Abdominal pain | 13% | 200 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy n = 52 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 52 Sources: |
Asthenia | 13% | 200 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy n = 52 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 52 Sources: |
Diarrhea | 13% Disc. AE |
200 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy n = 52 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 52 Sources: |
Abdominal pain | 10% Disc. AE |
50 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 53 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 53 Sources: |
Asthenia | 10% Disc. AE |
50 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 53 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 53 Sources: |
diarrhea | 10% Disc. AE |
50 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 53 Health Status: unhealthy Condition: ovarian cancer Sex: F Food Status: UNKNOWN Population Size: 53 Sources: |
Thrombocytopenia | grade 3, 1 pt DLT |
50 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 7 Health Status: unhealthy Condition: Refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 7 Sources: |
Hypersensitivity | grade 3, 1 pt DLT |
560 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 560 mg, 1 times / day Route: oral Route: multiple Dose: 560 mg, 1 times / day Sources: |
unhealthy n = 8 Health Status: unhealthy Condition: refractory cancer Sex: M+F Food Status: UNKNOWN Population Size: 8 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer. | 2007 Mar |
|
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry. | 2010 Nov 24 |
|
Comprehensive analysis of kinase inhibitor selectivity. | 2011 Oct 30 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16899614
According to the phase I pharmacokinetic study canertinib (CI-1033) was safely given i.v. up to 225 mg/dose on a thrice-weekly schedule, with evidence of antitumor activity. At equivalent doses, the bioavailability of i.v. CI-1033 is thrice that of the oral formulation.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17342332
The effect of canertinib (CI-1033) on esophageal cancer cell proliferation was investigated in the TT, TE2, TE6 and TE10 cell lines. After one day of treatment with CI-1033 (0.1-5.0 nM) significant inhibition of cell growth was observed in all cell lines at all concentrations of CI-1033 examined. The dose of CI-1033 required to inhibit the cell growth was as low as 0.1 nM. The inhibitory effect of CI-1033 on cancer cell growth was dose- and time-dependent.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:07:02 GMT 2023
by
admin
on
Fri Dec 15 16:07:02 GMT 2023
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Record UNII |
ICJ93X8X90
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C129825
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NCI_THESAURUS |
C2167
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admin on Fri Dec 15 16:07:02 GMT 2023 , Edited by admin on Fri Dec 15 16:07:02 GMT 2023
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C1880
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289499-45-2
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61399
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156413
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CHEMBL31965
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ICJ93X8X90
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DTXSID80183143
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SUB25455
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DBSALT002500
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100000089476
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C420268
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NN-49
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m3017
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |