`
`norfloxacin | C16H18FN303 - PubChem
`
`NIH
`
`U.S. National Library of Medicine
`
`National Center for Biotechnology Information
`
`Pub@ hem CHEMISTRY
`
`OPEN
`
`DATABASE
`
`Search Compounds
`
`Q
`
`O Compound Summary for CID 4539
`
`N O rT| OXd C] N
`
`> Cite this Record
`
`$$ ¢ 2? @ & Wi
`
`STRUCTURE
`
`VENDORS
`
`DRUG INFO
`
`PHARMACOLOGY
`
`LITERATURE
`
`PATENTS
`
`BIOACTIVITIES
`
`PubChem CID:
`
`4539
`
`
`
`Chemical Names: Norfloxacin; 70458-96-7; Norfloxacine; Noroxin; Chibroxin; Baccidal—More...
`
`Molecular Formula:
`
`CigHigFN303
`
`Molecular Weight:
`
`319.336 g/mol
`
`DrugInformation:
`
`Drug Indication
`
`Therapeutic Uses
`
`Clinical Trials
`
`FDA Orange Book
`
`FDA UNII
`
`Safety Summary:
`
`Laboratory Chemical Safety Summary (LCSS)
`
`Norfloxacin is a synthetic fluoroquinolone (FLUOROQUINOLONES)with broad-spectrum antibacterial activity against most
`gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.
`
`> from MeSH
`
`Norfloxacin is a Quinolone Antimicrobial. The chemical classification of norfloxacin is Quinolones.
`
`> FDA Pharmacology Summary from FDA Pharm Classes
`
`Norfloxacin is a synthetic, broad-spectrum fluoroquinolone with antibacterial activity. Norfloxacin inhibits activity of DNA
`gyrase, thereby blocking bacterial DNAreplication. Norfloxacin concentrates in the renal tubules and bladder and is
`bactericidal against a wide range of aerobic gram-positive and gram-negative organisms.
`
`> Pharmacology from NCIt
`
`PUBCHEM > COMPOUND > NORFLOXACIN
`
`Modify Date: 2017-04-09; Create Date: 2005-03-25
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`1/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 001
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 001
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`© Contents
`
`1 2D Structure
`
`2 3D Conformer
`
`3 Namesand Identifiers
`
`4 Chemical and Physical Properties
`
`5 Related Records
`
`6 Chemical Vendors
`
`7 Drug and Medication Information
`
`8 Pharmacology and Biochemistry
`
`9 Use and Manufacturing
`
`10 Identification
`
`11 Safety and Hazards
`
`12 Toxicity
`
`13 Literature
`
`14 Patents
`
`15 Biomolecular Interactions and Pathways
`
`16 Biological Test Results
`
`17 Classification
`
`18 Information Sources
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`2/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 002
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 002
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`1 2D Structure
`
`Q Search
`
`= Download
`
`[a] Get Image
`
`Q Magnify
`
`> from PubChem
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`3/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 003
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 003
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`2 3D Conformer
`
`Q Search
`
`& Download
`
`Gal Get Image
`
`ye
`
`Q Magnify
`
`( Show Hydrogens
`
`&ShowAtoms
`
`O Animate
`
`> from PubChem
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`4/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 004
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 004
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`3 Names and Identifiers
`
`3.1 Other Identifiers
`
`3.1.1 CAS
`
`70458-96-7
`
`> from DrugBank, European Chemicals Agency - ECHA, Chem/Dplus, Human Metabolome Database
`
`> from European Chemicals Agency - ECHA
`
`> from FDA/SPL Indexing Data
`
`> from Wikipedia
`
`3.1.2 EC Number
`
`274-614-4
`
`3.1.3 UNII
`
`NOF8P22L1P
`
`3.1.4 Wikipedia
`
`Title
`
`Description
`
`3.2 Synonyms
`
`3.2.1 MeSH Synonyms
`
`1 AM 0715
`
`2. AM 715
`
`3. AM-0715
`
`4, AM-715
`
`5. AMO715
`
`6. Merck Brand of Norfloxacin
`
`7. MK 0366
`
`8 MK 366
`
`9. MK-0366
`
`10. MK-366
`
`norfloxacin
`
`chemical compound
`
`11. MK0366
`
`12. MK366
`
`13. Norfloxacin
`
`14, Norfloxacin Merck Brand
`
`15. Noroxin
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`5/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 005
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 005
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`3.2.2 Depositor-Supplied Synonyms
`
`. norfloxacin
`
`. 70458-96-7
`
`. Norfloxacine
`
`. Noroxin
`
`OoANDMFPWN. Norfloxacino
`
`. Chibroxin
`
`. Baccidal
`
`. Sebercim
`
`. Norfloxacinum
`
`bhoO. Barazan
`
`11. Fulgram
`12. MK-366
`
`13. AM-715
`
`14, Lexinor
`
`15. NFLX
`
`16. 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
`
`17. Norfloxacine [INN-French]
`
`18. Norfloxacinum [INN-Latin]
`
`19. Norfloxacino [INN-Spanish]
`20. UNII-NOF8P22L1P
`
`> from MeSH
`
`21. AM 715
`
`22. CHEMBL
`
`23. CCRIS 6:
`
`24, Zoroxin
`
`25. Norflo
`
`26. MK 036€
`27. C16H18F
`
`28. CHEBI:1C
`
`29. 1-ethyl-¢
`30. EINECS 2
`
`»
`
`> from PubChem
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`6/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 006
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 006
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`4 Chemical and Physical Properties
`
`4.1 Computed Properties
`
`Property Value
`
`319.336 g/mol
`
`CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCNCC3)F)C(=O)O
`
`1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-
`carboxylic acid
`
`2 7 3 5
`
`19
`
`InChI=1S/C16H18FN303/c1-2-19-9-
`11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-
`6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
`
`AAADceB7MQAAAAAAAAAAAAAAAAAAAAAAAAAB8QIAA
`AAAAAACBAAAAHWAQCAAADAzBmAwyylIPAAgCIAGTWS
`ACCAAAIAGAAIIEIZMgIZD7ILNGUYYhksADI2ceY2a0eCAA
`AAAQCAAAQAAAACAQAAAAAAAAA
`
`72.9 AX2
`
`319.133 g/mol
`
`319.133 g/mol
`
`OGJPXUAPXNRGGI-UHFFFAOYSA-N
`
`-1
`
`true
`
`C16H18FN303
`
`Property Name
`
`Molecular Weight
`
`Canonical SMILES
`
`IUPAC Name
`
`Hydrogen Bond Donor Count
`
`Hydrogen Bond Acceptor Count
`
`Rotatable Bond Count
`
`Complexity
`
`InChI
`
`CACTVSSubstructure Key Fingerprint
`
`Topological Polar Surface Area
`
`Monoisotopic Mass
`
`Exact Mass
`
`InChI Key
`
`XLogP3
`
`Compound Is Canonicalized
`
`Molecular Formula
`
`Formal Charge
`
`Heavy Atom Count
`
`Defined Atom Stereocenter Count
`
`Undefined Atom Stereocenter Count
`
`Defined Bond Stereocenter Count
`
`Undefined Bond Stereocenter Count
`
`Isotope Atom Count
`
`Covalently-Bonded Unit Count
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`> from PubChem
`
`7/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 007
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 007
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`4.2 Experimental Properties
`
`4.2.1 Physical Description
`
`Solid
`
`4.2.2 Color
`
`White to light-yellow crystalline powder
`
`> from Human Metabolome Database
`
`O'Neil, MJ. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.,
`2006., p. 1158
`
`> from HSDB
`
`4.2.3 Melting Point
`
`220-221 deg C
`O'Neil, MJ. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.,
`2006., p. 1158
`
`227-228 °C
`
`PhysProp
`
`227 - 228°C
`
`4.2.4 Solubility
`
`> from HSDB
`
`> from DrugBank
`
`> from Human Metabolome Database
`
`In water, 0.28 mg/mL at 25 deg C. Solubility in water is pH dependent, increasing sharply at pH<5 or pH >10
`O'Neil, MJ. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.,
`2006., p. 1158
`
`> from HSDB
`
`Solubility at 25 deg C (mg/mL): methanol 0.98; ethanol 1.9; acetone 5.1; chloroform 5.5; diethyl ether 0.01; benzene 0.15;
`ethyl acetate 0.94; octyl alcohol 5.1; glacial acetic acid 340
`O'Neil, MJ. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.,
`2006., p. 1158
`
`WaterSolubility
`
`178000 mg/L
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`> from HSDB
`
`> from DrugBank
`
`8/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 008
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 008
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`1.01e+00 g/L
`
`4.2.5 LogP
`
`> from Human Metabolome Database
`
`log Kow = 0.46
`O'Neil, MJ. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.,
`2006., p. 1158
`
`-1.03
`
`HANSCH,C ETAL. (1995)
`
`21
`
`4.2.6 Decomposition
`
`> from HSDB
`
`> from DrugBank
`
`> from Human Metabolome Database
`
`When heated to decompostion it emits toxic fumes of /hydrogen fluoride and nitrogen oxides/.
`
`Lewis, RJ. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ.
`2004,, p. 333
`
`> from HSDB
`
`4.2.7 Dissociation Constants
`
`pKal = 6.34; pKa2 = 8.75
`
`O'Neil, MJ. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.,
`2006., p. 1158
`
`> from HSDB
`
`4.3 Crystal Structures
`
`Crystal Structures: 1 of 3
`
`CCDC Number
`
`617104
`
`Crystal Structure Data
`
`DOI:10.5517/ccng4l2
`
`Associated Article
`
`DOI:10.1021/cg060327x
`
`Crystal Structures: 2 of 3
`
`CCDC Number
`
`686995
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`> from The Cambridge Structural Database
`
`9/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 009
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 009
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`Crystal Structure Data
`
`DOI:10.5517/ccrlw4s
`
`Associated Article
`
`DOI:10.1007/s10973-006-7956-9
`
`Crystal Structures: 3 of 3
`
`CCDC Number
`
`825556
`
`Crystal Structure Data
`
`DOI:10.5517/ccwqlvg
`
`Associated Article
`
`DOI:10.1039/c1ce05966a
`
`> from The Cambridge Structural Database
`
`> from The Cambridge Structural Database
`
`4.4 Spectral Properties
`
`uv max (0.1N NaOH): approximately 274, 325, 336 nm (A(1%)(cm) approximately 1109, 437, 425)
`
`O'Neil, MJ. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.,
`2006., p. 1158
`
`> from HSDB
`
`Norfloxacin
`El mass spectrum, top peaks cisplayed
`
`
`
`240
`
`250
`
`260
`
`2/0
`
`280
`
`m/z
`
`44.1 GC-MS
`
`NIST Number
`
`148019
`
`Main library
`
`
`
`100
`
`80
`
`60
`
`40
`
`20
`
`0.0
`230
`
`19
`
`233
`
`275
`
`277
`
`oC
`
`c
`oc
`oC
`5a
`oc
`
`Library
`
`Total Peaks
`
`m/z Top Peak
`
`m/z 2nd Highest
`
`m/z 3rd Highest
`
`.
`Thumbnail
`
`© 2014 by the U.S. Secretary of Commerce.
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`10/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 010
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 010
`
`
`
`4/14/2017
`
`norfloxacin | C16H18FN303 - PubChem
`
`> from NIST
`
`> from Human Metabolome Database
`
`Norfloxacin
`MS/MS fragments, top peaks displayed
`
`3
`c
`
`oa S2
`
`o
`
`4.4.2 MS-MS
`
`1. MS-MS Spectrum
`
`2. MS-MS Spectrum
`
`3. MS-MS Spectrum
`
`4. MS-MS Spectrum
`
`5. MS-MS Spectrum
`
`6. MS-MS Spectrum
`
`1 of 3
`
`NIST Number
`
`Instrument Type
`
`Spectrum Type
`
`Precursor Type
`
`Precursor m/z
`
`Total Peaks
`
`m/z Top Peak
`
`m/z 2nd Highest
`
`m/z 3rd Highest
`
`Thumbnail
`
`1000343
`
`IT/ion trap
`
`MS2
`
`[M+H]+
`
`320.1405
`
`8 2
`
`76
`
`256
`
`320
`
`100
`
`80
`
`
`
`
`
`4
`60
`
`A0
`
`20
`
`0.0
`
`255
`
`270
`
`285
`
`330
`
`© 2014 by the U.S. Secretary of Commerce.
`
`m/z
`
`https://pubchem.ncbi.nim.nih.gov/compound/norfloxacin#section=Top
`
`> from NIST
`
`11/62
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 011
`
`Par Pharm., Inc.
`Exhibit 1055
`Page 011
`
`