azithromycin indications/contra

Stem definitionDrug idCAS RN
antibiotics, produced by Streptomyces strains 276 83905-01-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • CP-62993
  • CP 62993
  • azithromycin
  • arzomicin
  • aziromycin
  • Azithromycin A
  • azithromycin monohydrate
  • azithromycin anhydrous
  • azithromycin dihydrate
  • azithromycin hydrate
A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.
  • Molecular weight: 749.00
  • Formula: C38H72N2O12
  • CLOGP: 2.64
  • LIPINSKI: 2
  • HAC: 14
  • HDO: 5
  • TPSA: 180.08
  • ALOGS: -3.16
  • ROTB: 7

Drug dosage:

DoseUnitRoute
0.30 g O
0.50 g P

Approvals:

DateAgencyCompanyOrphan
Nov. 1, 1991 FDA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 3764.46 27.27 999 4956 34681 3345223
Product packaging quantity issue 723.26 27.27 124 5831 392 3379512
Product quality issue 692.10 27.27 260 5695 26475 3353429
Drug dose omission 684.24 27.27 285 5670 38147 3341757
Inappropriate schedule of drug administration 514.50 27.27 176 5779 13577 3366327
Rash 455.25 27.27 262 5693 70559 3309345
Drug interaction 451.60 27.27 227 5728 46585 3333319
Vomiting 403.45 27.27 264 5691 89267 3290637
Diarrhoea 364.44 27.27 263 5692 104085 3275819
Drug-induced liver injury 342.11 27.27 102 5853 5011 3374893
Urticaria 296.05 27.27 146 5809 28581 3351323
Stevens-Johnson syndrome 281.65 27.27 94 5861 6678 3373226
Electrocardiogram QT prolonged 270.95 27.27 103 5852 10692 3369212
Dyspnoea 261.29 27.27 215 5740 102719 3277185
Drug ineffective 252.79 27.27 222 5733 115868 3264036
Pyrexia 252.08 27.27 191 5764 80924 3298980
Nausea 251.04 27.27 232 5723 129413 3250491
Anosmia 222.69 27.27 53 5902 1072 3378832
Deafness 216.26 27.27 68 5887 3986 3375918
Pruritus 212.01 27.27 139 5816 46694 3333210
Hypersensitivity 210.18 27.27 115 5840 27785 3352119
Ageusia 183.77 27.27 55 5900 2727 3377177
Drug prescribing error 181.02 27.27 60 5895 4160 3375744
International normalised ratio increased 170.52 27.27 81 5874 14534 3365370
Abdominal pain 163.68 27.27 118 5837 46107 3333797
Incorrect drug administration duration 157.39 27.27 51 5904 3290 3376614
Rhabdomyolysis 155.94 27.27 78 5877 15651 3364253
Cardiac arrest 150.69 27.27 92 5863 27227 3352677
Pneumonia 147.72 27.27 132 5823 70011 3309893
Eye irritation 145.96 27.27 51 5904 4148 3375756

Pharmacologic Action:

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SourceCodeDescription
ATC J01FA10 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
Macrolides
ATC J01RA07 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
ATC S01AA26 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antibiotics
FDA EPC N0000175935 Macrolide Antimicrobial
FDA Chemical/Ingredient N0000007529 Macrolides
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Acute gonococcal cervicitis indication 20943002 DOID:10615
Acute gonococcal urethritis indication 29864006
Streptococcal tonsillitis indication 41582007
Pneumonia due to Mycoplasma pneumoniae indication 46970008
Bacterial pneumonia indication 53084003 DOID:874
Haemophilus influenzae pneumonia indication 70036007
Acute bacterial sinusitis indication 75498004
Bacterial conjunctivitis indication 128350005 DOID:9700
Urethritis due to Chlamydia trachomatis indication 179101003
Pulmonary Mycobacterium avium complex infection indication 186342000
Chlamydial pelvic inflammatory disease indication 188463006
Acute bacterial bronchitis indication 233598009
Pneumococcal pneumonia indication 233607000
Chlamydial pneumonia indication 233609002
Chancroid indication 266143009 DOID:13778
Pelvic inflammatory disease due to Mycoplasma hominis indication 270550006
Streptococcus pyogenes infection indication 302809008
Infective otitis media indication 312218008
Infection due to Staphylococcus aureus indication 406602003
Acute exacerbation of chronic bronchitis indication 425748003
Pneumonia due to Staphylococcus aureus indication 441658007
Pneumococcal Acute Otitis Media indication
Legionella Pneumophila Pneumonia indication
Moraxella Catarrhalis Acute Otitis Media indication
Haemophilus Influenzae Acute Otitis Media indication
Chlamydia Cervicitis indication
Moraxella Catarrhalis Pneumonia indication
Pelvic Inflammatory Disease with Neisseria Gonorrhea indication
Skin and Skin Structure Streptococcus Agalactiae Infection indication
Jaundice contraindication 18165001
Torsades de pointes contraindication 31722008
Chronic heart failure contraindication 48447003
Myasthenia gravis contraindication 91637004 DOID:437
Prolonged QT interval contraindication 111975006
Hearing disorder contraindication 128540005
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185
Congenital long QT syndrome contraindication 442917000
Pyrexia of unknown origin off-label use 7520000
Traveler's diarrhea off-label use 11840006
Enteric campylobacteriosis off-label use 18081009
Pertussis off-label use 27836007
Gonorrhea of rectum off-label use 42746002
Gonorrhea of pharynx off-label use 74372003
Boutonneuse fever off-label use 186774005 DOID:14095
Toxoplasmosis associated with acquired immunodeficiency syndrome off-label use 421666009
Sexual Transmitted Disease Exposure from Sexual Assault off-label use
Inflammatory Disease of Female Pelvic Organs off-label use
Prevention of Bacterial Endocarditis off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.45 acidic
pKa2 8.87 Basic
pKa3 8.24 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1% AZASITE OAK PHARMS INC N050810 April 27, 2007 RX SOLUTION/DROPS OPHTHALMIC 6861411 Nov. 25, 2018 METHOD OF COMBATING BACTERIA IN A PATIENT
1% AZASITE OAK PHARMS INC N050810 April 27, 2007 RX SOLUTION/DROPS OPHTHALMIC 6239113 March 31, 2019 METHOD OF COMBATING BACTERIA IN A PATIENT
1% AZASITE OAK PHARMS INC N050810 April 27, 2007 RX SOLUTION/DROPS OPHTHALMIC 6569443 March 31, 2019 METHOD OF COMBATING BACTERIA IN A PATIENT
1% AZASITE OAK PHARMS INC N050810 April 27, 2007 RX SOLUTION/DROPS OPHTHALMIC 7056893 March 31, 2019 METHOD OF COMBATING BACTERIA IN A PATIENT
EQ 2GM BASE/BOT ZMAX PF PRISM CV N050797 June 10, 2005 RX FOR SUSPENSION, EXTENDED RELEASE ORAL 6984403 Feb. 14, 2024 METHOD OF TREATING BACTERIAL INFECTIONS

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 100MG BASE/5ML AZITHROMYCIN LUPIN LTD A065488 May 15, 2015 RX FOR SUSPENSION ORAL March 26, 2018 PATENT CHALLENGE
EQ 200MG BASE/5ML AZITHROMYCIN LUPIN LTD A065488 May 15, 2015 RX FOR SUSPENSION ORAL March 26, 2018 PATENT CHALLENGE

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Canalicular multispecific organic anion transporter 1 Transporter IC50 4.16 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 3.70 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 3.39 WOMBAT-PK
Motilin receptor GPCR AGONIST EC50 5.50 IUPHAR

External reference:

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IDSource
DB00207 DRUGBANK_ID
4020019 VUID
N0000148074 NUI
C0052796 UMLSCUI
6510 IUPHAR_LIGAND_ID
D02134 KEGG_DRUG
CHEMBL529 ChEMBL_ID
5FD1131I7S UNII
117772-70-0 SECONDARY_CAS_RN
4020019 VANDF
72442 MMSL
N0000006752 NDFRT
N0000148074 NDFRT
003635 NDDF
18631 RXNORM
387531004 SNOMEDCT_US
96034006 SNOMEDCT_US
4238 MMSL
d00091 MMSL
447043 PUBCHEM_CID
6197 INN_ID
D017963 MESH_DESCRIPTOR_UI
ZIT PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-0400 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS NDA 19 sections
ZITHROMAX HUMAN PRESCRIPTION DRUG LABEL 1 0069-3051 POWDER, FOR SUSPENSION 1 g ORAL NDA 19 sections
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-3060 TABLET, FILM COATED 250 mg ORAL NDA 19 sections
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-3070 TABLET, FILM COATED 500 mg ORAL NDA 19 sections
ZITHROMAX HUMAN PRESCRIPTION DRUG LABEL 1 0069-3080 TABLET, FILM COATED 600 mg ORAL NDA 19 sections
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-3110 POWDER, FOR SUSPENSION 100 mg ORAL NDA 19 sections
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-3120 POWDER, FOR SUSPENSION 200 mg ORAL NDA 19 sections
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-3130 POWDER, FOR SUSPENSION 200 mg ORAL NDA 19 sections
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-3140 POWDER, FOR SUSPENSION 200 mg ORAL NDA 19 sections
Zithromax HUMAN PRESCRIPTION DRUG LABEL 1 0069-3150 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS NDA 19 sections
ZMAX HUMAN PRESCRIPTION DRUG LABEL 1 0069-4170 POWDER, FOR SUSPENSION 2 g ORAL NDA 20 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2026 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2027 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-7146 TABLET, FILM COATED 250 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-7147 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-7148 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-7149 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-7169 TABLET, FILM COATED 500 mg ORAL ANDA 19 sections
AZITHROMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 0179-0033 TABLET, FILM COATED 600 mg ORAL ANDA 24 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0409-0144 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 18 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0781-1496 TABLET, FILM COATED 250 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0781-1497 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0781-1941 TABLET, FILM COATED 500 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0781-5776 TABLET, FILM COATED 250 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0781-5789 TABLET, FILM COATED 500 mg ORAL ANDA 19 sections
Azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 0781-5793 TABLET, FILM COATED 600 mg ORAL ANDA 18 sections
Azithromycin Dihydrate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6405 TABLET, FILM COATED 250 mg ORAL ANDA 19 sections
azithromycin HUMAN PRESCRIPTION DRUG LABEL 1 10019-648 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS NDA AUTHORIZED GENERIC 18 sections
AZITHROMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-383 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
AzaSITE HUMAN PRESCRIPTION DRUG LABEL 1 17478-307 SOLUTION/ DROPS 10 mg OPHTHALMIC NDA 16 sections