Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H36N4O2S.ClH |
Molecular Weight | 529.137 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12[C@H]3CC[C@H](C3)[C@]1([H])C(=O)N(C[C@@H]4CCCC[C@H]4CN5CCN(CC5)C6=NSC7=C6C=CC=C7)C2=O
InChI
InChIKey=NEKCRUIRPWNMLK-SCIYSFAVSA-N
InChI=1S/C28H36N4O2S.ClH/c33-27-24-18-9-10-19(15-18)25(24)28(34)32(27)17-21-6-2-1-5-20(21)16-30-11-13-31(14-12-30)26-22-7-3-4-8-23(22)35-29-26;/h3-4,7-8,18-21,24-25H,1-2,5-6,9-17H2;1H/t18-,19+,20-,21-,24+,25-;/m0./s1
Molecular Formula | C28H36N4O2S |
Molecular Weight | 492.676 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
Lurasidone is a novel antipsychotic agent approved for the treatment of schizophrenia in a number of countries including the UK and is also approved in the USA and Canada for the treatment of bipolar depression as either a monotherapy or adjunctive therapy with lithium or valproate. In addition, lurasidone is in phase III of a clinical trial for the treatment patient with major depressive disorder and for the treatment of irritability associated with autistic disorder. The mechanism of action of lurasidone, as with other drugs having efficacy in schizophrenia, is unknown but is known, that lurasidone has a high affinity for dopamine D2, serotonin 5-HT2A and serotonin 5-HT7 receptors where it has antagonist effects. In addition, lurasidone is a partial agonist at the serotonin 5-HT1A receptor and has no appreciable affinity for histamine or muscarinic receptors.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26755968 |
1.0 nM [Ki] | ||
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26755968 |
0.5 nM [Ki] | ||
Target ID: P34969 Gene ID: 3363.0 Gene Symbol: HTR7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26755968 |
0.5 nM [Ki] | ||
Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26755968 |
6.4 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LATUDA Approved UseLATUDA is an atypical antipsychotic agent indicated for the treatment of patients with schizophrenia. Launch Date2010 |
|||
Primary | LATUDA Approved Use(Latuda, Sunovion Pharmaceuticals), already indicated for schizophrenia, to treat major depressive episodes in adults with bipolar 1 disorder. Launch Date2010 |
|||
Primary | Unknown Approved UseUnknown |
|||
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26659550 |
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26631428/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
LURASIDONE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
153 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26631428/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
LURASIDONE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26631428/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
LURASIDONE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
LURASIDONE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: Page: p.382 |
unhealthy, 42 Health Status: unhealthy Condition: Schizophrenia Age Group: 42 Sex: M+F Sources: Page: p.382 |
|
400 mg 1 times / day multiple, oral MTD Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: Page: p.382 |
unhealthy, 42 Health Status: unhealthy Condition: Schizophrenia Age Group: 42 Sex: M+F Sources: Page: p.382 |
|
560 mg single, oral Overdose Dose: 560 mg Route: oral Route: single Dose: 560 mg Sources: Page: p.37 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.37 |
|
120 mg 1 times / day multiple, oral Recommended Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: Page: p.30 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.30 |
Disc. AE: Dystonia... AEs leading to discontinuation/dose reduction: Dystonia Sources: Page: p.30 |
160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Disc. AE: Cerebrovascular disorder (NOS), Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Cerebrovascular disorder (NOS) Sources: Page: p.1Neuroleptic malignant syndrome Tardive dyskinesia Hyperglycemia Diabetes mellitus Dyslipidemia Weight gain Hyperprolactinemia Leukopenia Neutropenia Agranulocytosis Orthostatic hypotension Syncope Suicidal behavior |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dystonia | Disc. AE | 120 mg 1 times / day multiple, oral Recommended Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: Page: p.30 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.30 |
Agranulocytosis | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Cerebrovascular disorder (NOS) | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Diabetes mellitus | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Dyslipidemia | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Hyperglycemia | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Hyperprolactinemia | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Leukopenia | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Neuroleptic malignant syndrome | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Neutropenia | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Orthostatic hypotension | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Suicidal behavior | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Syncope | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Tardive dyskinesia | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Weight gain | Disc. AE | 160 mg 1 times / day multiple, oral (max) Recommended Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate [IC50 16 uM] | ||||
Page: 6,15,76, (ClinPharm) 9, 38, 52, (PMDA_I106_1) 19 |
moderate [IC50 21 uM] | |||
Page: 6,15,76, (ClinPharm) 9, 38, 52, 53-54, (PMDA_I106_1) 19 |
moderate [IC50 22 uM] | yes (co-administration study) Comment: Human liver microsomes (testosterone 6b-hydroxylation), Competitive inhibitor; Coadministration of Lurasidone (120 mg on Day 6 & Days 7-12) increased Midazolam (CYP3A4 substrate, 5 mg on Days 1 &6, day 13) AUC0-24 by 17.95% (single dose), 37.92% (steady-state), AUCinf by 19.82% (SD), 43.87% (SS) and Cmax by 4.93% (SD), 21.47% (SS)., Page: 6,15,76, (ClinPharm) 9, 38, 52, 53-54, (PMDA_I106_1) 19 |
||
Page: 6,15,76, (ClinPharm) 9, 38, 52, (PMDA_I106_1) 19 |
moderate [IC50 5.9 uM] | |||
Page: 6,15,76, (ClinPharm) 9, 38, 52, (PMDA_I106_1) 19 |
moderate [IC50 6.3 uM] | |||
moderate [IC50 6.3 uM] | ||||
Page: 6,15,76, (ClinPharm) 9, 38, 52, (PMDA_I106_1) 19 |
moderate [IC50 7.4 uM] | |||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000PharmR.pdf#page=76 Page: 6, 15, 76 |
unlikely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000PharmR.pdf#page=76 Page: 6, 15, 76 |
unlikely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000PharmR.pdf#page=76 Page: 6, 15, 76 |
unlikely | |||
weak [IC50 30 uM] | ||||
weak [IC50 35 uM] | ||||
weak [IC50 37 uM] | ||||
weak [IC50 83 uM] | ||||
weak [IC50 90 uM] | ||||
weak [IC50 >100 uM] | ||||
weak [IC50 >100 uM] | ||||
yes [IC50 0.498 uM] | ||||
yes [IC50 0.767 uM] | ||||
yes [IC50 1 uM] | likely (co-administration study) Comment: MDR1-LLC-PK cells (digoxin transportation); Coadministration of Lurasidone (120 mg on Days 6-13) increased Digoxin (0.25 mg on Days 1 & 13) AUC0-24 by 13.15%, AUClast by 10.53% and Cmax by 9.42%. Page: 79, (ClinPharm) 52, 53-54 |
|||
yes [IC50 1.21 uM] | ||||
yes [IC50 1.39 uM] | ||||
yes [IC50 2.57 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6, 15, 57, 78-79, (ClinPharm) 7, 52, 55-56, (PMDA_I106_1) 14 |
major | yes (co-administration study) Comment: Human CYP-expressed microsomes, Vmax = 102 pmol/min/mg; The metabolism of lurasidone in vitro (Human liver microsomes) was markedly reduced by ketoconazole (CYP3A4 inhibitor), as compared with quinidine (CYP2D6 inhibitor) and cimetidine (CYP3A4/CYP2D6 inhibitor).; Ketoconazole (strong CYP3A4 inhibitor, 400 mg on Days 7-13) increased lurasidone (10 mg on Days 1 & 11) AUClast and Cmax by 795% and 592%, respectively when they are coadministered together. Diltiazem (moderate CYP3A4 inhibitor, 240 mg on Days 1-7) increased lurasidone (20 mg on Day 5) AUCinf and Cmax by 116% and 110%, respectively when lurasidone is coadministered with diltiazem. Rifampin (strong CYP3A4 inducer, 600 mg on Days 1-8) decreased lurasidone (40 mg on Day 8) AUCinf and Cmax by 83% and 85%, respectively. Page: 6, 15, 57, 78-79, (ClinPharm) 7, 52, 55-56, (PMDA_I106_1) 14 |
||
Page: (ClinPharm) 56, (PMDA_I106_1) 16 |
major | yes (co-administration study) Comment: Human CYP-expressed microsomes, Remaining ID-14283 = 2.9% (0.5 mcg/mL, 5 min, 50 pmol/0.5mg protein/mL); Coadministration of Dilthiazem (moderate CYP 3A4 inhibitor, 240 mg on Days 1-7) increased ID-14823 (Lurasidon, 20 mg on Day 5) AUCinf by 138% and Cmax by 114%. Coadministration of Refampicin (strong CYP3A4 inducer, 600 mg on Days 1-8) decreased ID14283 (Lurasidone, 40 mg on Day 8) AUCinf by 93% and Cmac by 90%. Page: (ClinPharm) 56, (PMDA_I106_1) 16 |
||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=16 Page: (PMDA_I106_1) 16 |
minor | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I107_1.pdf#page=12 Page: (PMDA_I107_1) 12 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I107_1.pdf#page=13 Page: (PMDA_I107_1) 13 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I107_1.pdf#page=16 Page: (PMDA_I107_1) 16 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I107_1.pdf#page=13 Page: (PMDA_I107_1) 13 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I107_1.pdf#page=16 Page: (PMDA_I107_1) 16 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000ClinPharmR.pdf#page=7 Page: (ClinPharm) 7, 9, 38, 52 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000ClinPharmR.pdf#page=7 Page: (ClinPharm) 7, 38, 52 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes | |||
Sources: https://www.pmda.go.jp/drugs/2020/P20200417001/400093000_30200AMX00445_I106_1.pdf#page=14 Page: (PMDA_I106_1) 14 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000PharmR.pdf#page=45 Page: 5, 45 |
||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000PharmR.pdf#page=54 Page: 54.0 |
||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200603Orig1s000PharmR.pdf#page=54 Page: 54.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Iloperidone, asenapine and lurasidone: a primer on their current status. | 2012 Sep |
|
Evaluation of dopamine D₂/D₃ and serotonin 5-HT₂A receptor occupancy for a novel antipsychotic, lurasidone, in conscious common marmosets using small-animal positron emission tomography. | 2013 Jan |
Patents
Sample Use Guides
The recommended starting dose of LATUDA ((LURASIDONE HCL) is 40 mg once daily. LATUDA has been shown to be effective in a dose range of 40 mg/day to 120 mg/day. In the 6-week controlled trials, there was no suggestion of added benefit with the 120 mg/day dose, but there was a dose -related increase in certain adverse reactions. Therefore, the maximum recommended dose is 80 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21838595
[35S]GTPγS binding experiments for the human dopamine D2L or 5-HT1A receptors stably expressed in the membranes of recombinant Chinese hamster ovary (CHO) cells were performed. After dopamine (or serotonin) and/or lurasidone were incubated for 20 min at room temperature with the cell membrane preparation containing [35S]GTPγS (0.05 nM for D2L or 0.2 nM for 5-HT1A), the membranes were filtered through glass filters and the radioactivity bound to each filter was measured with a liquid scintillation counter. For nonspecific binding, cold GTPγS (20 μM for D2L or 10 μM for 5-HT1A) was added with [35S]GTPγS. in vitro receptor binding experiments revealed that lurasidone demonstrates affinity for dopamine D2 and 5-HT2A receptors higher than other tested antipsychotics. In contrast to other agents, lurasidone also displayed high affinity for 5-HT7, 5-HT1A, and noradrenaline α2C receptors.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:52:33 GMT 2023
by
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Record UNII |
O0P4I5851I
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Validated (UNII)
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NCI_THESAURUS |
C66883
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NCI_THESAURUS |
C66885
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RR-74
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DBSALT000113
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DTXSID401027714
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CHEMBL1237021
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100000127954
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1040027
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O0P4I5851I
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70732
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m6943
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367514-88-3
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SUB34204
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11237860
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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