10/5/21, 11:10 PM
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`Robalzotan | C18H23FN2O2 - PubChem
`
`COVID-19 Information
`Public health information (CDC) Research information (NIH) SARS-CoV-2 data (NCBI) Prevention and treatment information (HHS) Español
`
`COMPOUND SUMMARY
`
`Robalzotan
`
`PubChem CID
`
`3055171
`
`Structure
`
`Molecular Formula
`
`Synonyms
`
`Molecular Weight
`
`Dates
`
`2D
`Find Similar Structures
`
`3D
`
`C H FN O
`18 23
`2 2
`Robalzotan
`169758-66-1
`UNII-I18M56OGME
`NAD-299
`NAD 299
`More...
`
`318.4
`Modify
`2021-10-02
`
`Create
`2005-08-09
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
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`1 Structures
`1.1 2D Structure
`
`Chemical Structure
`Depiction
`
`PubChem
`
`1.2 3D Conformer
`
`Interactive Chemical
`Structure Model
`Ball and Stick
`
`Sticks
`
`Wire-Frame
`
`Space-Filling
`
`Show Hydrogens
`
`Animate
`
`PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`Robalzotan | C18H23FN2O2 - PubChem
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`2 Names and Identifiers
`2.1 Computed Descriptors
`2.1.1 IUPAC Name
`(3R)-3-[di(cyclobutyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
`Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)
`PubChem
`
`2.1.2 InChI
`InChI=1S/C18H23FN2O2/c19-16-8-7-14(18(20)22)15-9-13(10-23-17(15)16)21(11-3-1-4-11)12-5-2-6-12/h7-8,11-13H,1-6,9-10H2,(H2,20,22)/t13-/m1/s1
`Computed by InChI 1.0.6 (PubChem release 2021.05.07)
`PubChem
`
`2.1.3 InChI Key
`MQTUXRKNJYPMCG-CYBMUJFWSA-N
`Computed by InChI 1.0.6 (PubChem release 2021.05.07)
`PubChem
`
`2.1.4 Canonical SMILES
`C1CC(C1)N(C2CCC2)C3CC4=C(C=CC(=C4OC3)F)C(=O)N
`Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
`PubChem
`
`2.1.5 Isomeric SMILES
`C1CC(C1)N([C@@H]2CC3=C(C=CC(=C3OC2)F)C(=O)N)C4CCC4
`Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
`PubChem
`
`2.2 Molecular Formula
`C18H23FN2O2
`Computed by PubChem 2.1 (PubChem release 2021.05.07)
`PubChem
`
`2.3 Other Identifiers
`2.3.1 CAS
`169758-66-1
`CAS Common Chemistry; ChemIDplus; DrugBank; EPA DSSTox
`
`2.3.2 UNII
`I18M56OGME
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
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`10/5/21, 11:10 PM
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`FDA/SPL Indexing Data
`
`2.3.3 DSSTox Substance ID
`DTXSID30168743
`EPA DSSTox
`
`2.3.4 Wikipedia
`Robalzotan
`Wikipedia
`
`2.4 Synonyms
`2.4.1 MeSH Entry Terms
`
`3-N,N-dicyclobutylamino-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxamide hydrogen tartrate monohydrate
`NAD 299
`NAD-299
`robalzotan
`
`Medical Subject Headings (MeSH)
`
`2.4.2 Depositor-Supplied Synonyms
`
`Robalzotan
`169758-66-1
`UNII-I18M56OGME
`NAD-299
`NAD 299
`I18M56OGME
`AZD-7371
`(R)-3-(Dicyclobutylamino)-8-fluoro-5-chromancarboxamide
`(3R)-3-[di(cyclobutyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
`(R)-3-(Dicyclobutylamino)-8-fluorochroman-5-carboxamide
`Robalzotan [INN:BAN]
`GTPL72
`
`SCHEMBL115079
`NAD299
`CHEMBL1628569
`DTXSID30168743
`ZINC3811952
`DB06538
`VC30713
`NCGC00370859-01
`3-N,N-dicyclobutylamino-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxamide hydrogen
`A13092
`Q7340703
`(R)-3-(Dicyclobutylamino)-8-fluoro-5-chromancarboxamide.
`
`PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`Robalzotan | C18H23FN2O2 - PubChem
`
`3 Chemical and Physical Properties
`3.1 Computed Properties
`
`Property Name
`
`Molecular Weight
`XLogP3-AA
`Hydrogen Bond Donor Count
`Hydrogen Bond Acceptor Count
`Rotatable Bond Count
`Exact Mass
`Monoisotopic Mass
`Topological Polar Surface Area
`Heavy Atom Count
`Formal Charge
`Complexity
`Isotope Atom Count
`Defined Atom Stereocenter Count
`Undefined Atom Stereocenter Count
`Defined Bond Stereocenter Count
`Undefined Bond Stereocenter Count
`Covalently-Bonded Unit Count
`Compound Is Canonicalized
`
`PubChem
`
`Property Value
`
`Reference
`
`318.4
`2.8
`1
`4
`4
`318.17435614
`318.17435614
`55.6 Ų
`23
`0
`438
`0
`1
`0
`0
`0
`1
`Yes
`
`Computed by PubChem 2.1 (PubChem release 2021.05.07)
`Computed by XLogP3 3.0 (PubChem release 2021.05.07)
`Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
`Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
`Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
`Computed by PubChem 2.1 (PubChem release 2021.05.07)
`Computed by PubChem 2.1 (PubChem release 2021.05.07)
`Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
`Computed by PubChem
`Computed by PubChem
`Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
`Computed by PubChem
`Computed by PubChem
`Computed by PubChem
`Computed by PubChem
`Computed by PubChem
`Computed by PubChem
`Computed by PubChem (release 2021.05.07)
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`4 Related Records
`4.1 Related Compounds with Annotation
`Page 7 of 104 items View More Rows & Details
`
`Structure
`
`Compound CID Name
`
`Molecular Formula Molecular Weight, g/mol
`
`SORT BY
`
`Compound CID
`
`22118796
`
`3-[Cyclobutyl(cyclopentyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-
`carboxamide
`
`C H FN O
`19 25
`2 2
`
`332.4
`
`22118797
`
`3-[Tert-butyl(propyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
`
`C H FN O
`17 25
`2 2
`
`308.4
`
`22118798
`
`3-[Cyclobutyl(propyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
`
`C H FN O
`17 23
`2 2
`
`306.37
`
`22118799
`
`3-[Cyclobutyl(propan-2-yl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-
`carboxamide
`
`C H FN O
`17 23
`2 2
`
`306.37
`
`22118800
`
`3-[Cyclohexyl(propyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
`
`C H FN O
`19 27
`2 2
`
`334.4
`
`PubChem
`
`Previous
`
`1 ... 5
`
`6
`
`7
`
`8
`
`9 ... 21
`
`Next
`
`4.2 Related Compounds
`Same Connectivity
`6 Records
`Same Stereo
`4 Records
`Same Isotope
`3 Records
`Same Parent, Connectivity
`8 Records
`Same Parent, Stereo
`5 Records
`Same Parent, Isotope
`5 Records
`Same Parent, Exact
`2 Records
`Mixtures, Components, and
`Neutralized Forms
`Similar Compounds
`
`10 Records
`
`90 Records
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`Similar Conformers
`
`27 Records
`
`PubChem
`
`4.3 Substances
`4.3.1 Related Substances
`All
`96 Records
`Same
`43 Records
`Mixture
`53 Records
`
`PubChem
`
`4.3.2 Substances by Category
`7 Categories Expanded View
`
`Chemical Vendors (9)
`
`Curation Efforts (9)
`
`Governmental Organizations (6)
`
`Journal Publishers (2)
`
`NIH Initiatives (1)
`
`Research And Development (11)
`
`Subscription Services (1)
`
`Legacy Depositors (14)
`
`PubChem
`
`4.4 Entrez Crosslinks
`PubMed
`17 Records
`Taxonomy
`1 Record
`Gene
`1 Record
`
`PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`5 Chemical Vendors
`Showing 1 Substance per Vendor View All
`
`Achemtek
`PubChem SID: 381390571
`Adooq BioScience
`PubChem SID: 383545347
`Vesino Industrial Co., Ltd
`PubChem SID: 206245617
`Smolecule
`PubChem SID: 438488328
`MuseChem
`PubChem SID: 355200693
`THE BioTek
`PubChem SID: 434310108
`BLD Pharm
`PubChem SID: 383826190
`ZINC
`PubChem SID: 257070938
`Ambinter
`PubChem SID: 369755011
`
`PubChem
`
`Purchasable Chemical: 0101-002296
`
`Purchasable Chemical: A13092
`
`Purchasable Chemical: VC30713
`
`Purchasable Chemical: S541728
`
`Purchasable Chemical: M039709
`
`Purchasable Chemical: bt-281867
`
`Purchasable Chemical: BD150476
`
`Purchasable Chemical: ZINC3811952
`
`Purchasable Chemical: Amb22747834
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`Robalzotan | C18H23FN2O2 - PubChem
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`6 Drug and Medication Information
`6.1 Drug Indication
`Investigated for use/treatment in anxiety disorders and depression.
`DrugBank
`
`6.2 Clinical Trials
`6.2.1 EU Clinical Trials Register
`1 item
`
`EudraCT
`
`Title
`
`Phase
`
`Status
`
`Date
`
`2004-
`000383-27
`
`A double-blind randomized placebo controlled crossover study of AZD7371 ER 5 mg bid, 20 mg bid and placebo
`treatment for one week on visceral perception and symptoms in patients with Irritable Bowel Syndrome
`
`Phase 2
`
`Completed
`
`2004-07-28
`
`EU Clinical Trials Register
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`7 Associated Disorders and Diseases
`1 item View More Details
`
`Disease
`
`Amnesia, Anterograde
`
`Comparative Toxicogenomics Database (CTD)
`
`Evidence Type
`
`therapeutic
`
`Evidence PMID
`
`12589378
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`10/21
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`Robalzotan | C18H23FN2O2 - PubChem
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`8 Literature
`8.1 NLM Curated PubMed Citations
`
`All NLM Curated PubMed Citations
`
`PubChem
`
`8.2 Springer Nature References
`43 items View More Rows & Details
`
`Thumbnail
`
`Title
`
`Publication Name
`
`Publication Date
`
`PMID
`
`SORT BY
`
`Relevance
`
`Positron emission tomographic analysis of dose-dependent NAD-299 binding to 5-
`hydroxytryptamine-1A receptors in the human brain
`
`Psychopharmacology
`
`2003
`
`12632244
`
`Effects of NAD-299, a new, highly selective 5-HT1A receptor antagonist, on bladder
`function in rats
`
`Naunyn-Schmiedeberg's
`Archives of Pharmacology
`
`2002
`
`12444493
`
`The effect of NAD-299 and TCB-2 on learning and memory, hippocampal BDNF levels
`and amyloid plaques in Streptozotocin-induced memory deficits in male rats
`
`Psychopharmacology
`
`2018
`
`30027497
`
`In vivo labelling of the mouse brain 5-hydroxytryptamine1A receptor with the novel
`selective antagonist 3H-NAD-299
`
`Naunyn-Schmiedeberg's
`Archives of Pharmacology
`
`1998
`
`Structural insight into the serotonin (5-HT) receptor family by molecular docking,
`molecular dynamics simulation and systems pharmacology analysis
`
`Acta Pharmacologica Sinica
`
`2019
`
`30814658
`
`1
`
`2
`
`3 ... 9
`
`Next
`
`Springer Nature
`
`8.3 Depositor Provided PubMed Citations
`23 items View More Rows & Details
`
`SORT BY
`
`Publication Date
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`11/21
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`PMIDPMID
`
`
`
`Publication DatePublication Date
`
`TitleTitle
`
`22801295
`
`2012-11-01
`
`21242991
`
`2012-02-01
`
`22030713
`
`2012-02-01
`
`20413275
`
`2010-07-01
`
`20169084
`
`2010-02-16
`
`PubChem
`
`5-HT1A and 5-HT7 receptor crosstalk in the regulation of emotional memory:
`implications for effects of selective serotonin reuptake inhibitors
`Emotional memory impairments in a genetic rat model of depression: involvement of
`5-HT/MEK/Arc signaling in restoration
`α- and β-Adrenergic receptors differentially modulate the emission of spontaneous
`and amphetamine-induced 50-kHz ultrasonic vocalizations in adult rats
`The selective 5-HT(1A) receptor antagonist NAD-299 increases acetylcholine release
`but not extracellular glutamate levels in the frontal cortex and hippocampus of awake
`rat
`Selective serotonin reuptake inhibitors potentiate the rapid antidepressant-like effects
`of serotonin4 receptor agonists in the rat
`1
`
`2
`
`3 ... 5
`
`
`
`JournalJournal
`
`Neuropharmacology
`
`Molecular psychiatry
`
`Neuropsychopharmacology : official publication of
`the American College of Neuropsychopharmacology
`
`European neuropsychopharmacology : the journal of
`the European College of Neuropsychopharmacology
`
`PloS one
`
`Next
`
`8.4 Chemical Co-Occurrences in Literature
`
`PubChem
`
`8.5 Chemical-Gene Co-Occurrences in Literature
`
`PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`12/21
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`Robalzotan | C18H23FN2O2 - PubChem
`8.6 Chemical-Disease Co-Occurrences in Literature
`
`PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`13/21
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`Robalzotan | C18H23FN2O2 - PubChem
`
`9 Patents
`9.1 Depositor-Supplied Patent Identifiers
`
`PubChem
`
`Link to all deposited patent identifiers
`PubChem
`
`9.2 WIPO PATENTSCOPE
`Patents are available for this chemical structure:
`https://patentscope.wipo.int/search/en/result.jsf?inchikey=MQTUXRKNJYPMCG-CYBMUJFWSA-N
`PATENTSCOPE (WIPO)
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
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`10 Biomolecular Interactions and Pathways
`10.1 Drug-Gene Interactions
`
`Drug Gene Interaction database (DGIdb)
`
`10.2 Chemical-Gene Interactions
`10.2.1 CTD Chemical-Gene Interactions
`
`Comparative Toxicogenomics Database (CTD)
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`15/21
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`Robalzotan | C18H23FN2O2 - PubChem
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`11 Biological Test Results
`11.1 BioAssay Results
`
`PubChem
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`16/21
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`12 Classification
`12.1 Ontologies
`12.1.1 MeSH Tree
`
`Medical Subject Headings (MeSH)
`
`12.1.2 ChemIDplus
`
`ChemIDplus
`
`12.1.3 Guide to PHARMACOLOGY Target Classification
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`17/21
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`IUPHAR/BPS Guide to PHARMACOLOGY
`
`12.1.4 ChEMBL Target Tree
`
`ChEMBL
`
`12.1.5 NORMAN Suspect List Exchange Classification
`
`NORMAN Suspect List Exchange
`
`12.1.6 EPA DSSTox Classification
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`18/21
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`EPA DSSTox
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`19/21
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`Robalzotan | C18H23FN2O2 - PubChem
`
`13 Information Sources
`ALL SOURCES
`
`FILTER BY SOURCE
`
`1. CAS Common Chemistry
`LICENSE
`The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
`https://creativecommons.org/licenses/by-nc/4.0/
`
`Robalzotan
`https://commonchemistry.cas.org/detail?cas_rn=169758-66-1
`2. ChemIDplus
`LICENSE
`https://www.nlm.nih.gov/copyright.html
`
`Robalzotan [INN:BAN]
`https://chem.nlm.nih.gov/chemidplus/sid/0169758661
`ChemIDplus Chemical Information Classification
`https://chem.nlm.nih.gov/chemidplus/
`3. DrugBank
`LICENSE
`Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
`https://www.drugbank.ca/legal/terms_of_use
`
`Robalzotan
`https://www.drugbank.ca/drugs/DB06538
`4. EPA DSSTox
`LICENSE
`https://www.epa.gov/privacy/privacy-act-laws-policies-and-resources
`
`Robalzotan
`https://comptox.epa.gov/dashboard/DTXSID30168743
`CompTox Chemicals Dashboard Chemical Lists
`https://comptox.epa.gov/dashboard/chemical_lists/
`5. Comparative Toxicogenomics Database (CTD)
`LICENSE
`It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of the MDI Biological
`Laboratory and NC State University.
`http://ctdbase.org/about/legal.jsp
`
`http://ctdbase.org/detail.go?type=chem&acc=C108607
`6. Drug Gene Interaction database (DGIdb)
`LICENSE
`The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
`http://www.dgidb.org/downloads
`
`https://www.dgidb.org/drugs/ROBALZOTAN
`7. EU Clinical Trials Register
`https://www.clinicaltrialsregister.eu/
`8. FDA/SPL Indexing Data
`LICENSE
`Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and
`otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
`https://www.fda.gov/about-fda/about-website/website-policies#linking
`
`I18M56OGME
`https://www.fda.gov/ForIndustry/DataStandards/SubstanceRegistrationSystem-UniqueIngredientIdentifierUNII/
`9. Springer Nature
`https://pubchem.ncbi.nlm.nih.gov/substance/341296785
`https://pubchem.ncbi.nlm.nih.gov/substance/341473813
`10. Wikipedia
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`20/21
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`Robalzotan | C18H23FN2O2 - PubChem
`
`robalzotan
`https://en.wikipedia.org/wiki/Robalzotan
`11. PubChem
`https://pubchem.ncbi.nlm.nih.gov
`12. Medical Subject Headings (MeSH)
`LICENSE
`Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or
`reproduced without permission in the U.S.
`https://www.nlm.nih.gov/copyright.html
`
`robalzotan
`https://www.ncbi.nlm.nih.gov/mesh/67108607
`MeSH Tree
`http://www.nlm.nih.gov/mesh/meshhome.html
`13. ChEMBL
`LICENSE
`Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons
`Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
`http://www.ebi.ac.uk/Information/termsofuse.html
`
`Target Tree
`https://www.ebi.ac.uk/chembl/target/browser
`14. IUPHAR/BPS Guide to PHARMACOLOGY
`LICENSE
`The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a
`Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
`https://www.guidetopharmacology.org/about.jsp#license
`
`Target Classification
`http://www.guidetopharmacology.org/
`15. NORMAN Suspect List Exchange
`LICENSE
`Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
`https://creativecommons.org/licenses/by/4.0/
`
`NORMAN Suspect List Exchange Classification
`https://www.norman-network.com/nds/SLE/
`16. PATENTSCOPE (WIPO)
`SID 389368289
`https://pubchem.ncbi.nlm.nih.gov/substance/389368289
`
`https://pubchem.ncbi.nlm.nih.gov/compound/Robalzotan
`
`21/21
`
`Pfizer Ex. 2004, p. 21
`
`