ID
`
`Pharmacology
`
`Interactions
`
`References
`
`Trials
`
`Economics
`
`Properties
`
`Spectra
`
`Taxonomy
`
`2 Comments
`
`Targets (4) Enzymes (3) Transporters (1) Biointeractions (7)
`
`Show Drugs with Similar Structures
`
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`
`Identification
`Identification
`
`Name
`
`Azithromycin
`
`Accession Number DB00207 (APRD00397)
`
`Type
`
`Groups
`
`Description
`
`Structure
`
`Small Molecule
`
`Approved
`
`Azithromycin is a semi-synthetic macrolide antibiotic of the azalide class. Like other macrolide antibiotics, azithromycin
`inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding
`inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its
`effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half life,
`which enables once daily dosing and shorter administration durations, is a property distinct from other macrolides.
`
`H3C
`
`HO
`
`H3C
`
`H3C
`
`CH 3
`
`N
`
`OH
`
`H3C
`
`O
`
`O
`
`CH 3
`
`CH 3
`
`OH
`CH 3
`
`O
`
`O
`
`O
`
`H3C
`
`OH
`
`N
`
`CH 3
`
`CH 3
`
`O
`
`H3C
`
`O
`
`CH 3
`
`CH 3
`
`OH
`
` MOL
`
`SDF
`
`PDB
`
`SMILES
`
`InChI
`
`Synonyms
`
`Azithromycine
`
`Azithromycinum
`
`Azitromicina
`
`External IDs
`
`
`
`Not Available
`
`UNII
`
`CAS
`
`InChI Key
`
`Details
`
`Product
`
`Ingredients
`
`Approved
`Prescription
`Products
`
`Ingredient
`
`Azithromycin dihydrate
`
`5FD1131I7S
`
`
`
`117772-70-0
`
`SRMPHJKQVUDLQE-KUJJYQHYSA-N
`
`Azithromycin monohydrate
`
`JTE4MNN1MD
`
`
`
`121470-24-4 HQUPLSLYZHKKQT-WVVFQGGUSA-N
`
`Details
`
`Details
`
`Show 10
`
` entries
`
`Search
`
`Name
`
`Dosage
`
`Strength
`
`Route
`
`Labeller
`
`Marketing
`Start
`
`Marketing
`End
`
`Act Azithromycin
`
`Tablet
`
`250 mg
`
`Oral
`
`Act Azithromycin
`
`Tablet
`
`600 mg
`
`Oral
`
`Actavis Pharma
`Company
`
`2005-11-02 Not
`applicable
`
`Actavis Pharma
`Company
`
`2005-11-02 Not
`applicable
`
`Ava-azithromycin
`
`Tablet
`
`250 mg
`
`Oral
`
`Oral
`
`Avanstra Inc
`
`2011-09-19
`
`2014-08-21
`
`Avanstra Inc
`
`2011-09-19
`
`2014-08-21
`
`100 mg
`
`Powder, for
`suspension
`
`Powder, for
`suspension
`
`Ava-azithromycin
`
`Ava-azithromycin
`
`Azasite
`
`Azasite
`
`200 mg
`
`Oral
`
`Avanstra Inc
`
`2011-09-19
`
`2014-08-21
`
`Solution
`
`1 %
`
`Ophthalmic
`
`Insite Vision
`Incorporated
`
`Not
`applicable
`
`Not
`applicable
`
`Solution /
`
`10 mg/mL Ophthalmic Akorn
`
`2014-05-14 Not
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 001
`
`

`

`drops
`
`applicable
`
`Azasite
`
`Solution
`
`1 %
`
`Ophthalmic
`
`Inspire
`Pharmaceuticals,
`Inc.
`
`Not
`applicable
`
`Not
`applicable
`
`Azithromycin
`
`Azithromycin
`
`Tablet, film
`coated
`
`Powder, for
`suspension
`
`500 mg/1
`
`Oral
`
`Greenstone, Llc
`
`1 g/1
`
`Oral
`
`Preferreed
`Pharmaceuticals
`Inc.
`
`2002-05-24 Not
`applicable
`
`1999-02-12 Not
`applicable
`
`Showing 1 to 10 of 112 entries
`
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`
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`
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`
`Approved Generic
`Prescription
`Products
`
`Show 10
`
` entries
`
`Search
`
`Name
`
`Dosage
`
`Strength
`
`Route
`
`Labeller
`
`Apo-azithromycin
`
`Tablet
`
`250 mg
`
`Oral
`
`Apo-azithromycin Z
`
`Tablet
`
`250 mg
`
`Oral
`
`Apotex
`Corporation
`
`Apotex
`Corporation
`
`Marketing
`Start
`
`Marketing
`End
`
`2005-11-02 Not
`applicable
`
`2014-03-06 Not
`applicable
`
`Azithromycin
`
`Azithromycin
`
`Tablet, film
`coated
`
`Powder,
`for
`suspension
`
`600 mg/1
`
`Oral
`
`Physicians Total
`Care, Inc.
`
`2012-04-26 Not
`applicable
`
`200
`mg/5mL
`
`Oral
`
`Rebel
`Distributors
`
`2008-06-24 Not
`applicable
`
`Azithromycin
`
`Azithromycin
`
`Azithromycin
`
`Azithromycin
`
`Azithromycin
`
`Azithromycin
`
`Tablet, film
`coated
`
`Tablet, film
`coated
`
`Tablet, film
`coated
`
`Tablet, film
`coated
`
`Powder,
`for
`suspension
`
`Tablet, film
`coated
`
`600 mg/1
`
`Oral
`
`A S Medication
`Solutions
`
`2005-11-16 Not
`applicable
`
`600 mg/1
`
`Oral
`
`Wockhardt
`
`250 mg/1
`
`Oral
`
`Pd Rx
`Pharmaceuticals,
`Inc.
`
`2008-02-11 Not
`applicable
`
`2005-11-14 Not
`applicable
`
`500 mg/1
`
`Oral
`
`A S Medication
`Solutions
`
`2005-11-16 Not
`applicable
`
`200
`mg/5mL
`
`Oral
`
`Teva
`
`2010-12-17 Not
`applicable
`
`250 mg/1
`
`Oral
`
`Remedy Repack
`
`2017-02-02 Not
`applicable
`
`Showing 1 to 10 of 203 entries
`
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`
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`
`Approved Over the
`Counter Products
`
`Unapproved/Other
`
`Products
`
`Not Available
`
`Not Available
`
`International
`Brands
`
`Show 10
`
` entries
`
`Name
`
`Azenil
`
`Azibiot
`
`Azifast
`
`Azigram
`
`Azimakrol
`
`Search
`
`Company
`
`Not Available
`
`Not Available
`
`Not Available
`
`Not Available
`
`Not Available
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 002
`
`

`

`Azin
`Azithrocin
`
`Azitromax
`
`Azitromin
`
`Aztrin
`
`Brand mixtures
`
`Not Available
`
`Not Available
`Not Available
`
`Not Available
`
`Not Available
`
`Not Available
`
`Showing 1 to 10 of 18 entries
`
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`Categories
`
`Anti-Bacterial Agents
`Anti-Infective Agents
`Antibacterials for Systemic Use
`Antiinfectives for Systemic Use
`Combined Inhibitors of CYP3A4 and P-glycoprotein
`Cytochrome P-450 CYP1A2 Inhibitors
`Cytochrome P-450 CYP1A2 Inhibitors (moderate)
`Cytochrome P-450 CYP2A6 Inhibitors
`Cytochrome P-450 CYP3A Inhibitors
`Cytochrome P-450 CYP3A4 Substrates
`Erythromycin
`Lactones
`Macrolide Antibiotics
`Macrolides
`Moderate Risk QTc-Prolonging Agents
`P-glycoprotein/ABCB1 Inhibitors
`Polyketides
`
`UNII
`
`J2KLZ20U1M
`
`
`
`CAS number
`
`83905-01-5
`
`Weight
`
`Average: 748.9845
`Monoisotopic: 748.508525778
`
`Chemical Formula
`
`C H N O
`38 72 2 12
`
`InChI Key
`
`MQTOSJVFKKJCRP-BICOPXKESA-N
`
`InChI
`
`IUPAC Name
`
`SMILES
`
`Pharmacology
`Pharmacology
`
`Indication
`
`Structured
`Indications
`
`
`
`InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-
`29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-
`43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
`
`(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-
`ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-
`heptamethyl-1-oxa-6-azacyclopentadecan-15-one
`
`CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H]
`(O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
`
`For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated
`microorganisms in the specific conditions: H. influenzae, M. catarrhalis, S. pneumoniae, C. pneumoniae, M. pneumoniae, S.
`pyogenes, S. aureus, S. agal
`
`COPD Exacerbation
`Cervicitis
`Chancroid
`Community Acquired Pneumonia (CAP)
`Conjunctivitis, Bacterial
`Mycobacterium avium complex infection
`Otitis Media (OM)
`Pelvic Inflammatory Disease (PID)
`Skin bacterial infection
`Urethritis
`
`Pharmacodynamics Azithromycin, a semisynthetic antibiotic belonging to the macrolide subgroup of azalides, is used to treat STDs due to
`chlamydia and gonorrhea, community-acquired pneumonia, pelvic inflammatory disease, pediatric otitis media and
`pharyngitis, and Mycobacterium avium complex (MAC) in patients with advanced HIV disease. Similar in structure to
`erythromycin. azithromycin reaches higher intracellular concentrations than erythromycin, increasing its efficacy and
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 003
`
`

`

`duration of action.
`
`Mechanism of
`action
`
`Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes, and therefore inhibits RNA-dependent protein
`synthesis in bacterial cells.
`
`details
`
`details
`
`details
`
`Target
`
`23S rRNA
`
`Kind
`
`Pharmacological
`action
`
`Actions
`
`Organism
`
`UniProt ID
`
`Nucleotide
`
`yes
`
`inhibitor
`
`Enteric bacteria and other
`eubacteria
`
`not
`applicable
`
` 
`
`inhibitor
`
`Escherichia coli O157:H7
`
`P60725
`
`inhibitor
`
`Escherichia coli O157:H7
`
`P61177
`
`50S ribosomal protein L4
`
`Protein
`
`50S ribosomal protein
`L22
`
`Protein
`
`yes
`
`yes
`
`Protein-arginine
`deiminase type-4
`
`Protein
`
`unknown
`
`Not
`Available
`
`Human
`
`Q9UM07
`
`
`
`details
`
`Related Articles
`
`Absorption
`
`Volume of
`distribution
`
`Protein binding
`
`Bioavailability is 37% following oral administration. Absorption is not affected by food. Azithromycin is extensively
`distributed in tissues with tissue concentrations reaching up to 50 times greater than plasma concentrations. Drug
`becomes concentrated within macrophages and polymorphonucleocytes giving it good activity against Chlamydia
`trachomatis.
`
`31.1 L/kg
`
`Serum protein binding is variable in the concentration range approximating human exposure, decreasing from 51% at
`0.02 µg/mL to 7% at 2 µg/mL.
`
`Metabolism
`
`Hepatic. In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed.
`
`Route of
`elimination
`
`Half life
`
`Clearance
`
`Toxicity
`
`Affected organisms
`
`Biliary excretion of azithromycin, predominantly as unchanged drug, is a major route of elimination.
`
`68 hours
`
`apparent plasma cl=630 mL/min [following single 500 mg oral and i.v. doses]
`
`Potentially serious side effects of angioedema and cholestatic jaundice were reported
`
`Enteric bacteria and other eubacteria
`Corynebacterium diphtheriae
`Treponema pallidum
`Streptococcus pyogenes
`Chlamydia pneumoniae
`Chlamydia trachomatis
`Chlamydophila psittaci
`Mycoplasma pneumoniae
`Neisseria gonorrhoeae
`Legionella pneumophila
`Bordetella pertussis
`
`Pathways
`
`Pathway
`
`Azithromycin Action Pathway
`
`Category
`
`Drug action
`
`SMPDB ID
`
`SMP00247
`
`Not Available
`
`Not Available
`
`SNP Mediated
`Effects
`
`SNP Mediated
`Adverse Drug
`Reactions
`
`Interactions
`Interactions
`
`Drug Interactions
`
`Show 10
`
` entries
`
`Search
`
`Drug
`
`Acebutolol
`
`Interaction
`
`The serum concentration of Acebutolol can be increased when it is combined
`with Azithromycin.
`
`Acenocoumarol
`
`The metabolism of Acenocoumarol can be decreased when combined with
`Azithromycin.
`
`Drug group
`
`Approved
`
`Approved
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 004
`
`

`

`Acetaminophen
`
`The serum concentration of Acetaminophen can be increased when it is
`combined with Azithromycin.
`
`Approved
`
`Acetyldigitoxin
`
`The serum concentration of Acetyldigitoxin can be increased when it is combined
`with Azithromycin.
`
`Approved
`
`Acetylsalicylic acid
`
`The serum concentration of Acetylsalicylic acid can be increased when it is
`combined with Azithromycin.
`
`Approved, Vet
`Approved
`
`Afatinib
`
`Agomelatine
`
`Albendazole
`
`Aldosterone
`
`The serum concentration of Afatinib can be increased when it is combined with
`Azithromycin.
`
`Approved
`
`The serum concentration of Agomelatine can be increased when it is combined
`with Azithromycin.
`
`Approved,
`Investigational
`
`The metabolism of Albendazole can be decreased when combined with
`Azithromycin.
`
`The serum concentration of Aldosterone can be increased when it is combined
`with Azithromycin.
`
`Approved, Vet
`Approved
`
`Experimental
`
`Approved,
`Investigational
`
`Alfuzosin
`
`Alfuzosin may increase the QTc-prolonging activities of Azithromycin.
`
`Showing 1 to 10 of 469 entries
`
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`
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`
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`
`Food Interactions
`
`Do not take Aluminum or magnesium antacids or supplements while on this medication.
`Take on empty stomach: 1 hour before or 2 hours after meals.
`
`References
`References
`
`Synthesis
`Reference
`
`William Heggie, Zita Maria De Mouro Vaz Azevedo Mendes, “Process for the preparation of azithromycin.” U.S. Patent
`US6013778, issued November, 1994.
`
`
`US6013778
`
`General References
`
`1. Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M,
`Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or
`quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand.
`
`Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. [PubMed:17051490
`]
`
`External Links
`
`Resource
`
`Link
`
` 
`
`C06838
`
`447043
`
` 
`
`46507743
`
`50197040
`
`2955
`
`
`
` 
`
`CHEMBL529
`
`KEGG Compound
`
`PubChem Compound
`
`PubChem Substance
`
`BindingDB
`
`ChEBI
`
`ChEMBL
`
`Therapeutic Targets Database
`
`DNC001539
`
`PA448519
`
`
`
` 
`
`ZIT
`
`424
`
`http://www.rxlist.com/cgi/generic/zithromax.htm
`
`
`
`
`http://www.drugs.com/cdi/azithromycin-drops.html
`
`Azithromycin
`
`
`
`PharmGKB
`
`HET
`
`Drug Product Database
`
`RxList
`
`Drugs.com
`
`Wikipedia
`
`ATC Codes
`
`J01FA10
`J01FA — Macrolides
`J01F — MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
`J01 — ANTIBACTERIALS FOR SYSTEMIC USE
`J — ANTIINFECTIVES FOR SYSTEMIC USE
`S01AA26
`S01AA — Antibiotics
`S01A — ANTIINFECTIVES
`S01 — OPHTHALMOLOGICALS
`S — SENSORY ORGANS
`J01RA07
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 005
`
`

`

`J01RA — Combinations of antibacterials
`J01R — COMBINATIONS OF ANTIBACTERIALS
`J01 — ANTIBACTERIALS FOR SYSTEMIC USE
`J — ANTIINFECTIVES FOR SYSTEMIC USE
`
`AHFS Codes
`
`08:12.12.92
`
`PDB Entries
`
`Not Available
`
`FDA label
`
`Download (76.3 KB)
`
`MSDS
`
`Download (73.9 KB)
`
`Clinical Trials
`Clinical Trials
`
`Clinical Trials
`
`
`
`Show 10
`
` entries
`
`Phase
`
`Status
`
`Purpose
`
`Conditions
`
`Count
`
`Search
`
`0
`
`0
`
`0
`
`1
`
`1
`
`1
`
`1
`
`1
`
`1
`
`1
`
`Not Yet
`Recruiting
`
`Treatment Acne Vulgaris
`
`Recruiting
`
`Treatment Osteomyelitis
`
`Recruiting
`
`Treatment Respiratory Syncytial Virus (RSV)
`
`Active Not
`Recruiting
`
`Treatment Gonorrhoea
`
`Completed Not
`Available
`
`Fasting
`
`Completed Not
`Available
`
`Completed Not
`Available
`
`Completed Basic
`Science
`
`Completed Basic
`Science
`
`Completed Basic
`Science
`
`Healthy Volunteers
`
`Prophylaxis of Malaria
`
`Pharmacokinetics
`
`Prebiotics / Probiotics / Quorum Sensing / Sepsis
`
`Inflammatory processes
`
`Showing 1 to 10 of 228 entries
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`Next
`
`1
`
`1
`
`1
`
`1
`
`1
`
`7
`
`1
`
`1
`
`1
`
`1
`
`Pharmacoeconomics
`Pharmacoeconomics
`
`Manufacturers
`
`Packagers
`
`Pfizer chemicals div pfizer inc
`Pfizer global research development
`Pliva inc
`Sandoz inc
`Teva pharmaceuticals usa
`Pfizer central research
`App pharmaceuticals llc
`Gland pharma ltd
`Hospira inc
`Pliva hrvatska doo
`Sagent strides llc
`Teva parenteral medicines inc
`Pfizer inc
`Inspire pharmaceuticals inc
`Mylan pharmaceuticals inc
`Teva pharmaceuticals usa inc
`Wockhardt ltd
`
`Advanced Pharmaceutical Services Inc.
`Aidarex Pharmacuticals LLC
`Amerisource Health Services Corp.
`Apotheca Inc.
`APP Pharmaceuticals
`AQ Pharmaceuticals Inc.
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 006
`
`

`

`A-S Medication Solutions LLC
`Baxter International Inc.
`Cardinal Health
`Catalent Pharma Solutions
`Comprehensive Consultant Services Inc.
`Dept Health Central Pharmacy
`Direct Dispensing Inc.
`Dispensing Solutions
`Diversified Healthcare Services Inc.
`Eon Labs
`Greenstone LLC
`H.J. Harkins Co. Inc.
`Hospira Inc.
`Innoviant Pharmacy Inc.
`Inspire Pharmaceuticals
`Kaiser Foundation Hospital
`Lake Erie Medical and Surgical Supply
`Liberty Pharmaceuticals
`Major Pharmaceuticals
`Medisca Inc.
`Murfreesboro Pharmaceutical Nursing Supply
`Mylan
`Nucare Pharmaceuticals Inc.
`Palmetto Pharmaceuticals Inc.
`Patheon Inc.
`PD-Rx Pharmaceuticals Inc.
`Pfizer Inc.
`Pharmaceutical Utilization Management Program VA Inc.
`Pharmpak Inc.
`Physicians Total Care Inc.
`Pliva Inc.
`Preferred Pharmaceuticals Inc.
`Prepackage Specialists
`Prepak Systems Inc.
`Public Health Department Seattle and King County
`Rebel Distributors Corp.
`Redpharm Drug
`Remedy Repack
`Sagent Pharmaceuticals
`Sandoz
`Sicor Pharmaceuticals
`Southwood Pharmaceuticals
`Stat Rx Usa
`Stat Scripts LLC
`Strides Arcolab Limited
`Teva Pharmaceutical Industries Ltd.
`Tya Pharmaceuticals
`UDL Laboratories
`US Pharmaceutical Group
`Warner Chilcott Co. Inc.
`Wockhardt Ltd.
`
`Dosage forms
`
`Show 10
`
` entries
`
`Form
`
`Tablet
`
`Solution
`
`Solution / drops
`
`Injection
`
`Injection, powder, lyophilized, for solution
`
`Injection, powder, lyophilized, for solution
`
`Injection, powder, lyophilized, for solution
`
`Search
`
`Route
`
`Oral
`
`Strength
`
`250 mg
`
`Ophthalmic
`
`1 %
`
`Ophthalmic
`
`10 mg/mL
`
`Intravenous
`
`500 mg/10mL
`
`Intravenous
`
`100 mg/mL
`
`Intravenous
`
`2 mg/mL
`
`Intravenous
`
`500 mg/1
`
`Injection, powder, lyophilized, for solution
`
`Intravenous
`
`500 mg/5mL
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 007
`
`

`

`Powder, for suspension
`
`Powder, for suspension
`
`Oral
`
`Oral
`
`1 g/1
`
`100 mg/5mL
`
`Prices
`
`Show 10
`
` entries
`
`Showing 1 to 10 of 29 entries
`
`Previous
`
`1
`
`2
`
`3
`
`Next
`
`Search
`
`Unit description
`
`Zithromax 3 1 gm Packets Box
`
`Azithromycin 2.5 gm bulk vial
`
`Zmax adult-ped 2 g/60 ml susp
`
`Zithromax Tri-Pak 3 500 mg tablet Disp Pack
`
`Zithromax Z-Pak 6 250 mg tablet Disp Pack
`
`Zmax 2 g/60 ml susp sr
`
`Zmax pediatric 2 g/60 ml susp
`
`Zithromax 200 mg/5ml Suspension 30ml Bottle
`
`Zithromax 100 mg/5ml Suspension 15ml Bottle
`
`Zithromax 200 mg/5ml Suspension 15ml Bottle
`
`Cost
`
`118.26USD
`
`75.6USD
`
`70.39USD
`
`69.67USD
`
`68.62USD
`
`67.04USD
`
`67.04USD
`
`52.0USD
`
`51.6USD
`
`50.46USD
`
`Unit
`
`box
`
`each
`
`each
`
`disp
`
`disp
`
`each
`
`each
`
`bottle
`
`bottle
`
`bottle
`
`Showing 1 to 10 of 45 entries
`
`Previous
`
`1
`
`2
`
`3
`
`4
`
`5
`
`Next
`
`
`
` DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
`
`Patents
`
`Show 10
`
` entries
`
`Patent Number
`
`Pediatric Extension
`
`Approved
`
`Expires (estimated)
`
`Search
`
`No
`
`No
`
`No
`
`No
`
`No
`
`No
`
`No
`
`No
`
`No
`
`No
`
`2000-10-17
`
`2015-04-27
`
`2010-03-30
`
`2024-05-18
`
`1993-03-09
`
`2010-03-09
`
`1997-05-30
`
`2017-05-30
`
`1997-11-04
`
`2017-11-04
`
`1999-03-31
`
`2019-03-31
`
`1998-07-31
`
`2018-07-31
`
`1999-03-31
`
`2019-03-31
`
`1998-11-25
`
`2018-11-25
`
`2004-02-14
`
`2024-02-14
`
`Showing 1 to 10 of 12 entries
`
`Previous
`
`1
`
`2
`
`Next
`
`Value
`
`114 °C
`
`slight
`
`4.02
`
`Source
`
`PhysProp
`
`Not Available
`
`MCFARLAND,JW ET AL. (1997)
`
`8.74 (at 25 °C)
`
`MCFARLAND,JW ET AL. (1997)
`
`         
`
`CA2148071
`
`CA2467611
`
`US5192535
`
`US6068859
`
`US6159458
`
`US6239113
`
`US6268489
`
`US6569443
`
`US6861411
`
`US6984403
`
`Properties
`Properties
`
`State
`
`Experimental
`Properties
`
`Predicted
`
`Solid
`
`Property
`
`melting point
`
`water solubility
`
`logP
`
`pKa
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 008
`
`

`

`Properties
`
`Property
`
`Water Solubility
`
`logP
`
`logP
`
`logS
`
`pKa (Strongest Acidic)
`
`pKa (Strongest Basic)
`
`Physiological Charge
`
`Hydrogen Acceptor Count
`
`Hydrogen Donor Count
`
`Polar Surface Area
`
`Rotatable Bond Count
`
`Refractivity
`
`Polarizability
`
`Number of Rings
`
`Bioavailability
`
`Rule of Five
`
`Ghose Filter
`
`Veber's Rule
`
`MDDR-like Rule
`Property
`
`Human Intestinal Absorption
`
`Predicted ADMET
`features
`
`Value
`
`0.514 mg/mL
`
`3.03
`
`2.44
`
`-3.2
`
`12.43
`
`9.57
`
`2
`
`13
`
`5
`
`180.08 Å
`
`2
`
`7
`
`3
`194.11 m ·mol
`
`-1
`
`83.11 Å
`
`3
`
`3
`
`0
`
`Yes
`
`Yes
`
`Yes
`
`Yes
`
`Value
`
`-
`
`Source
`
`ALOGPS
`
`ALOGPS
`
`ChemAxon
`
`ALOGPS
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`
`ChemAxon
`Probability
`
`0.5518
`
`0.9739
`
`Blood Brain Barrier
`
`Caco-2 permeable
`
`P-glycoprotein substrate
`
`P-glycoprotein inhibitor I
`
`P-glycoprotein inhibitor II
`
`Renal organic cation transporter
`
`CYP450 2C9 substrate
`
`CYP450 2D6 substrate
`
`CYP450 3A4 substrate
`
`CYP450 1A2 substrate
`
`CYP450 2C9 inhibitor
`
`CYP450 2D6 inhibitor
`
`CYP450 2C19 inhibitor
`
`CYP450 3A4 inhibitor
`
`-
`
`-
`
`Substrate
`
`Inhibitor
`
`Non-inhibitor
`
`Non-inhibitor
`
`Non-substrate
`
`Non-substrate
`
`Substrate
`
`Non-inhibitor
`
`Non-inhibitor
`
`Non-inhibitor
`
`Non-inhibitor
`
`Non-inhibitor
`
`CYP450 inhibitory promiscuity
`
`Low CYP Inhibitory Promiscuity
`
`Ames test
`
`Carcinogenicity
`
`Biodegradation
`
`Rat acute toxicity
`
`hERG inhibition (predictor I)
`
`hERG inhibition (predictor II)
`
`Non AMES toxic
`
`Non-carcinogens
`
`Not ready biodegradable
`
`2.5423 LD50, mol/kg
`
`Weak inhibitor
`
`Non-inhibitor
`
`0.7578
`
`0.8765
`
`0.8513
`
`0.8893
`
`0.8753
`
`0.8373
`
`0.9116
`
`0.6403
`
`0.9295
`
`0.9021
`
`0.8904
`
`0.9023
`
`0.9533
`
`0.9751
`
`0.9133
`
`0.9397
`
`0.9673
`
`Not applicable
`
`0.9929
`
`0.8555
`
`
`
` ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. ( 23092397
`
`
`
`)
`
`Spectra
`Spectra
`
`Mass Spec (NIST)
`
`Not Available
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 009
`
`

`

`Spectra
`
`Spectrum Type
`
`Description
`
`Predicted LC-MS/MS
`
`Predicted LC-MS/MS Spectrum - 10V, Positive
`
`Predicted LC-MS/MS
`
`Predicted LC-MS/MS Spectrum - 20V, Positive
`
`Predicted LC-MS/MS
`
`Predicted LC-MS/MS Spectrum - 40V, Positive
`
`Predicted LC-MS/MS
`
`Predicted LC-MS/MS Spectrum - 10V, Negative
`
`Predicted LC-MS/MS
`
`Predicted LC-MS/MS Spectrum - 20V, Negative
`
`Predicted LC-MS/MS
`
`Predicted LC-MS/MS Spectrum - 40V, Negative
`
`Splash Key
`
`Not Available
`
`Not Available
`
`Not Available
`
`Not Available
`
`Not Available
`
`Not Available
`
`This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion
`of a molecule composed of amino-modified sugars.
`
`Organic compounds
`
`
`
` 
`
`Organic oxygen compounds
`
`Organooxygen compounds
`
`Carbohydrates and carbohydrate conjugates
`
`
`
`Taxonomy
`Taxonomy
`
`Description
`
`Kingdom
`
`Super Class
`
`Class
`
`Sub Class
`
`Direct Parent
`
`Aminoglycosides
`
`
`
`
`
`
`
` 
`
` 
`
` 
`
`Macrolides and analogues
`
`O-glycosyl compounds
`
`Oxanes
`Monosaccharides
`Tertiary alcohols
`
`Trialkylamines
`Secondary alcohols
`1,2-aminoalcohols
`Amino acids and derivatives
`
`Carboxylic acid esters
`
`Lactones
`Polyols
`Acetals
`Oxacyclic compounds
`Azacyclic compounds
`Monocarboxylic acids and derivatives
`
`Dialkyl ethers
`
`Carbonyl compounds
`Hydrocarbon derivatives
`
`Organic oxides
`Organopnictogen compounds
`
`
`
` 
`
`
`
`
`
`Aminoglycoside core
`Macrolide
`Glycosyl compound
`O-glycosyl compound
`Monosaccharide
`Oxane
`Tertiary alcohol
`1,2-aminoalcohol
`Amino acid or derivatives
`Carboxylic acid ester
`Lactone
`Secondary alcohol
`Tertiary amine
`Tertiary aliphatic amine
`Oxacycle
`Acetal
`Monocarboxylic acid or derivatives
`Organoheterocyclic compound
`Polyol
`Azacycle
`Ether
`Dialkyl ether
`Carboxylic acid derivative
`
`Alternative Parents
`
`Substituents
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 010
`
`

`

`Organic nitrogen compound
`Alcohol
`Carbonyl group
`Organonitrogen compound
`Organopnictogen compound
`Amine
`Organic oxide
`Hydrocarbon derivative
`Aliphatic heteromonocyclic compound
`
`Aliphatic heteromonocyclic compounds
`
`macrolide antibiotic (CHEBI:2955
`
`
`
`)
`
`Molecular
`Framework
`
`External
`Descriptors
`
`Targets
`
`1. 23S rRNA
`
`Kind
`Nucleotide
`Organism
`Enteric bacteria and other eubacteria
`Pharmacological action
`yes
`Actions
`
`inhibitor
`
`References
`
`1. Ng LK, Martin I, Liu G, Bryden L: Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae. Antimicrob Agents
`
`Chemother. 2002 Sep;46(9):3020-5. [PubMed:12183262
`]
`2. Jalava J, Vaara M, Huovinen P: Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes.
`
`Ann Clin Microbiol Antimicrob. 2004 May 6;3:5. [PubMed:15128458
`]
`3. Pereyre S, Renaudin H, Charron A, Bebear C, Bebear CM: Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of
`the intrinsic resistance to erythromycin and azithromycin. J Antimicrob Chemother. 2006 Apr;57(4):753-6. Epub 2006 Feb 7.
`
`[PubMed:16464889
`]
`
`2. 50S ribosomal protein L4
`
`Kind
`Protein
`Organism
`Escherichia coli O157:H7
`Pharmacological action
`yes
`Actions
`
`inhibitor
`
`
`
` Details
`
`General Function:
`Structural constituent of ribosome
`Specific Function:
`One of the primary rRNA binding proteins, this protein initially binds near the 5'-end of the 23S rRNA. It is important during the early
`stages of 50S assembly. It makes multiple contacts with different domains of the 23S rRNA in the assembled 50S subunit and
`ribosome.Protein L4 is a both a transcriptional repressor and a translational repressor protein. It regulates transcription of the S10 op...
`Gene Name:
`rplD
`Uniprot ID:
`
`P60725
`Molecular Weight:
`22086.36 Da
`
`References
`
`1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-
`
`Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. [PubMed:17014718
`]
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 011
`
`

`

`2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural
`
`explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. [PubMed:15851032
`]
`3. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and
`
`azalides. Structure. 2003 Mar;11(3):329-38. [PubMed:12623020
`]
`4. Petropoulos AD, Kouvela EC, Starosta AL, Wilson DN, Dinos GP, Kalpaxis DL: Time-resolved binding of azithromycin to Escherichia coli
`
`ribosomes. J Mol Biol. 2009 Jan 30;385(4):1179-92. doi: 10.1016/j.jmb.2008.11.042. Epub 2008 Nov 27. [PubMed:19071138
`]
`5. Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin.
`
`Curr Microbiol. 2002 Jun;44(6):418-24. [PubMed:12000992
`]
`
`3. 50S ribosomal protein L22
`
`Kind
`Protein
`Organism
`Escherichia coli O157:H7
`Pharmacological action
`yes
`Actions
`
`inhibitor
`
`
`
` Details
`
`General Function:
`Structural constituent of ribosome
`Specific Function:
`This protein binds specifically to 23S rRNA; its binding is stimulated by other ribosomal proteins, e.g. L4, L17, and L20. It is important
`during the early stages of 50S assembly. It makes multiple contacts with different domains of the 23S rRNA in the assembled 50S
`subunit and ribosome (By similarity).The globular domain of the protein is located near the polypeptide exit tunnel on the outside...
`Gene Name:
`rplV
`Uniprot ID:
`
`P61177
`Molecular Weight:
`12226.165 Da
`
`References
`
`1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-
`
`Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. [PubMed:17014718
`]
`2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural
`
`explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. [PubMed:15851032
`]
`3. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and
`
`azalides. Structure. 2003 Mar;11(3):329-38. [PubMed:12623020
`]
`4. Petropoulos AD, Kouvela EC, Starosta AL, Wilson DN, Dinos GP, Kalpaxis DL: Time-resolved binding of azithromycin to Escherichia coli
`
`ribosomes. J Mol Biol. 2009 Jan 30;385(4):1179-92. doi: 10.1016/j.jmb.2008.11.042. Epub 2008 Nov 27. [PubMed:19071138
`]
`5. Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin.
`
`Curr Microbiol. 2002 Jun;44(6):418-24. [PubMed:12000992
`]
`
`4. Protein-arginine deiminase type-4
`
`
`
` Details
`
`Kind
`Protein
`Organism
`Human
`Pharmacological action
`unknown
`
`General Function:
`Protein-arginine deiminase activity
`Specific Function:
`Catalyzes the citrullination/deimination of arginine residues of proteins such as histones, thereby playing a key role in histone code and
`regulation of stem cell maintenance. Citrullinates histone H1 at 'Arg-54' (to form H1R54ci), histone H3 at 'Arg-2', 'Arg-8', 'Arg-17'
`and/or 'Arg-26' (to form H3R2ci, H3R8ci, H3R17ci, H3R26ci, respectively) and histone H4 at 'Arg-3' (to form H4R3ci). Acts as...
`Gene Name:
`PADI4
`Uniprot ID:
`
`Q9UM07
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 012
`
`

`

`Molecular Weight:
`74078.65 Da
`
`References
`
`1. Knuckley B, Luo Y, Thompson PR: Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med
`
`Chem. 2008 Jan 15;16(2):739-45. Epub 2007 Oct 13. [PubMed:17964793
`]
`
`Enzymes
`
`1. Cytochrome P450 2A6
`
`Kind
`Protein
`Organism
`Human
`Pharmacological action
`unknown
`Actions
`
`inhibitor
`
`
`
` Details
`
`General Function:
`Steroid hydroxylase activity
`Specific Function:
`Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and
`ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-
`exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
`Gene Name:
`CYP2A6
`Uniprot ID:
`
`P11509
`Molecular Weight:
`56501.005 Da
`
`References
`
`1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a
`comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010
`
`Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256
`]
`
`2. Cytochrome P450 1A2
`
`Kind
`Protein
`Organism
`Human
`Pharmacological action
`unknown
`Actions
`
`inhibitor
`
`
`
` Details
`
`General Function:
`Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as
`one donor, and incorporation of one atom of oxygen
`Specific Function:
`Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-
`dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and
`xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an
`initial N...
`Gene Name:
`CYP1A2
`Uniprot ID:
`
`P05177
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 013
`
`

`

`Molecular Weight:
`58293.76 Da
`
`3. Cytochrome P450 3A4
`
`Kind
`Protein
`Organism
`Human
`Pharmacological action
`unknown
`Actions
`
`substrate
`
`inhibitor
`
`
`
` Details
`
`General Function:
`Vitamin d3 25-hydroxylase activity
`Specific Function:
`Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-
`dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole
`sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids,
`fatty acids, and xenobiot...
`Gene Name:
`CYP3A4
`Uniprot ID:
`
`P08684
`Molecular Weight:
`57342.67 Da
`
`References
`
`1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a
`comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010
`
`Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256
`]
`
`Transporters
`
`1. Multidrug resistance protein 1
`
`
`
` Details
`
`Kind
`Protein
`Organism
`Human
`Pharmacological action
`unknown
`Actions
`
`inhibitor
`
`General Function:
`Xenobiotic-transporting atpase activity
`Specific Function:
`Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
`Gene Name:
`ABCB1
`Uniprot ID:
`
`P08183
`Molecular Weight:
`141477.255 Da
`
`References
`
`1. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-
`
`glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [PubMed:11743742
`]
`2. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses
`anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9.
`
`Par Pharm., Inc.
`Exhibit 1063
`Page 014
`
`

`

`
`[PubMed:14744620
`
`]
`
`Comments
`
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`
`Bmorale2 • 4 years ago
`
`I think the Spanish version of this should be translated to "Azitromicina" not as it shows as "Aritromicina".
`
`Craig Knox • 4 years ago
`
`Hi, thanks for the tip, looks like it was a spelling error. I've corrected it.
`
`Drug created on June 13, 2005 07:24 / Updated on April 14, 2017 05:13
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