Extended Spectrum Macrolide

Aka: Extended Spectrum Macrolide, Azithromycin, Zithromax, Clarithromycin, Biaxin, Telithromycin, Ketek

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II. Pharmacokinetics: Half Life

  1. Clarithromycin: 5 hours
  2. Telithromycin: 10 hours
  3. Azithromycin: 68 hours

III. Precautions

  1. Increasing Macrolide resistance for most indications (see below)
  2. QT Prolongation with Azithromycin (see below)
  3. Calcium Channel Blocker interaction with Clarithromycin (see below)
  4. Macrolides in general (including Azithromycin) may increase heart defects with first trimester exposure of 5-7 days
    1. Previously only Clarithromycin was considered a potential Teratogen (Cleft Lip association)
    2. Fan (2020) BMJ 368: m331 +PMID:32075790 [PubMed]

IV. Dosing: Azithromycin (Zithromax)

  1. Directions
    1. Take more than 1 hour before or 2 hours after food
    2. Adult
      1. Day 1: 500 mg PO qd
      2. Day 2 to 5: 250 mg PO qd
    3. Child
      1. Day 1: 10 mg/kg PO qd (maximum: 500 mg)
      2. Day 2 to 5: 5 mg/kg PO qd (maximum: 250 mg)
    4. Infant under age 6 months
      1. 10 mg/kg/day for 5 days
  2. New preparations
    1. ZMax 2 grams orally x1 dose (Available in 2005)
      1. For uncomplicated Community Acquired Pneumonia
      2. Vomiting >1 hour after dose - no additional med
      3. Use within 12 hours of reconstituting
    2. References
      1. (2005) Prescribers Letter 12(8):44

V. Dosing: Clarithromycin (Biaxin)

  1. May take with or without food
  2. Adult: 250 to 500 mg PO bid
  3. Child: 7.5 mg/kg PO bid

VI. Dosing: Telithromycin

  1. Adult: 800 mg PO daily
  2. Course
    1. Acute Exacerbation of Chronic Bronchitis: 5 days
    2. Acute Sinusitis: 5 days
    3. Community Acquired Pneumonia: 7 days

VII. Adverse Effects

  1. Class
    1. Less Nausea and Vomiting than with Erythromycin
    2. QT Prolongation (see below)
      1. Three fold increased risk of Sudden Cardiac Death while on Azithromycin
      2. Ray (2013) N Engl J Med 366(20): 1881-90 [PubMed]
  2. Clarithromycin
    1. Dysgeusia or distorted taste (20%)
    2. Calcium Channel BlockerDrug Interaction (see below)
    3. Increased cardiovascular deaths
      1. Observation in some studies as of 2018, but needs confirmation
      2. Inghammer (2017) Am J Epidemiol +PMID:29155931 [PubMed]
      3. Svanström (2014) BMJ 349:g4930 +PMID:25139799 [PubMed]

VIII. Drug Interactions: Clarithromycin

  1. Calcium Channel Blockers
    1. Clarithromycin increases Calcium Channel Blocker levels via CYP3A4 inhibition
    2. Highest risk with Dihydropyridine Calcium Channel Blockers (Nifedipine, Felodipine)
    3. Highest risk in age over 65 years old
    4. Provokes Hypotension and Bradycardia
    5. Risk of Acute Kidney Injury (often requiring hospitalization)
      1. Number needed to harm: 1 in 465 for over age 65 years
    6. References
      1. Gandhi (2013) JAMA 310(23):2544-53 [PubMed]

IX. Indications: Major indications for broad spectrum Macrolides

  1. Single dose Chlamydia trachomatis treatment
  2. Respiratory infections
    1. Otitis Media (Azithromycin)
      1. Not recommended due to increased resistance rates
    2. Community Acquired Pneumonia
      1. Limit to suspected Mycoplasma pneumonia or Legionella pneumonia
      2. Macrolide resistant pneumococcus is common
      3. Consider Doxycycline as alternative
    3. Acute Sinusitis (Azithromycin)
      1. Not recommended due to growing resistance rates
    4. Streptococcal Pharyngitis
      1. Macrolides are only indicated in significant allergy to beta-lactams
    5. Non-tuberculous Mycobacterial infections
    6. Helicobacter infections
  3. References
    1. (2013) Presc Lett 20(8): 44

X. Contraindications

  1. Telithromycin (Ketek) may cause repiratory failure in Myasthenia Gravis (FDA Black Box Warning)

XI. Preparations: Activity Spectrum

  1. Macrolide resistance is increasing
    1. Resistance to one Macrolide is resistance to all
  2. Spectrum includes organisms covered by Erythromycin
  3. Clarithromycin
    1. Streptococcus Pneumoniae (Pneumococcus)
    2. Staphylococcus aureus
    3. Toxoplasmosis gondii
    4. Mycobacterium leprae
    5. Mycobacterium Avium Complex
    6. Borrelia Burgdorferi
  4. Azithromycin
    1. HaemophilusInfluenzae
    2. Moraxella catarrhalis
    3. Toxoplasmosis gondii
    4. Mycobacterium Avium Complex (Clarithromycin better)
    5. Borrelia Burgdorferi
  5. Telithromycin
    1. Avoid in patients with Myasthenia Gravis due to risk of Respiratory Failure (FDA Black Box Warning)
    2. Similar to other Extended Spectrum Macrolides
    3. Appears to have greater activity for pneumococcus
    4. May be used in place of other broad spectrum agents
      1. Augmentin
      2. Extended spectrum Fluoroquinolones
    5. References
      1. Fogarty (2003) J Antimicrob Chemother 51:947-55 [PubMed]

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Related Studies

Cost: Medications

azithromycin (on 12/21/2022 at Medicaid.Gov Survey of pharmacy drug pricing)
AZITHROMYCIN 1 GM PWD PACKET Generic $19.97 each
AZITHROMYCIN 100 MG/5 ML SUSP Generic $0.48 per ml
AZITHROMYCIN 200 MG/5 ML SUSP Generic $0.41 per ml
AZITHROMYCIN 250 MG TABLET Generic $0.33 each
AZITHROMYCIN 500 MG TABLET Generic $0.64 each
AZITHROMYCIN 600 MG TABLET Generic $1.29 each
zithromax (on 2/23/2022 at Medicaid.Gov Survey of pharmacy drug pricing)
ZITHROMAX 250 MG TABLET Generic $0.33 each
ZITHROMAX 250 MG Z-PAK TABLET Generic $0.33 each
clarithromycin (on 12/21/2022 at Medicaid.Gov Survey of pharmacy drug pricing)
CLARITHROMYCIN 125 MG/5 ML SUS Generic $0.86 per ml
CLARITHROMYCIN 250 MG TABLET Generic $0.47 each
CLARITHROMYCIN 250 MG/5 ML SUS Generic $1.43 per ml
CLARITHROMYCIN 500 MG TABLET Generic $0.41 each
CLARITHROMYCIN ER 500 MG TAB Generic $4.32 each
FPNotebook does not benefit financially from showing this medication data or their pharmacy links. This information is provided only to help medical providers and their patients see relative costs. Insurance plans negotiate lower medication prices with suppliers. Prices shown here are out of pocket, non-negotiated rates. See Needy Meds for financial assistance information. GoodRx is another tool for finding lower drug prices.

Ontology: Azithromycin (C0052796)

Definition (CHV) a kind of antibiotic drug
Definition (CHV) a kind of antibiotic drug
Definition (NCI) An azalide, derived from erythromycin, and a member of a subclass of macrolide antibiotics with bacteriocidal and bacteriostatic activities. Azithromycin reversibly binds to the 50S ribosomal subunit of the 70S ribosome of sensitive microorganisms, thereby inhibiting the translocation step of protein synthesis, wherein a newly synthesized peptidyl tRNA molecule moves from the acceptor site on the ribosome to the peptidyl (donor) site, and consequently inhibiting RNA-dependent protein synthesis leading to cell growth inhibition and cell death.
Definition (CSP) semi-synthetic macrolide antibiotic; related to erythromycin.
Definition (MSH) A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D017963
SnomedCT 391804001, 387531004, 96034006
LNC LP16090-0, MTHU006795
English Azythromycin, 1-Oxa-6-azacyclopentadecan-15-one, 13-((2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-, (2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*))-, N-methyl-11-aza-10-deoxy-10-dihydroerythromycin A, azithromycin, Azithromycin, AZITHROMYCIN, Azithromycin [Chemical/Ingredient], 1-Oxa-6-azacyclopentadecan-15-one, 13-((2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-, (2R-(2R*,3S*,4R*,5R*,8R, azythromycin, AZITHROMYCIN, UNSPECIFIED FORM, Azithromycin - chemical (substance), Azithromycin - chemical, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[(3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy]-1-oxa-6-azacyclopentade, antibacterial azithromycin, azithromycin (medication), Azithromycin (product), Azithromycin (substance)
Swedish Azitromycin
Czech azithromycin
Finnish Atsitromysiini
Russian AZITROMITSIN, АЗИТРОМИЦИН
Japanese アジスロマイシン
Croatian AZITROMICIN
Polish Azytromycyna
Spanish azitromicina (producto), azitromicina (sustancia), azitromicina, Azitromicina
French Azithromycine
German Azithromycin
Italian Azitromicina
Portuguese Azitromicina
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Clarithromycin (C0055856)

Definition (NCI_NCI-GLOSS) An antibiotic drug used to treat infection. It belongs to the family of drugs called macrolides.
Definition (NCI) A semisynthetic 14-membered ring macrolide antibiotic. Clarithromycin binds to the 50S ribosomal subunit and inhibits RNA-dependent protein synthesis in susceptible organisms. Clarithromycin has been shown to eradicate gastric MALT (mucosa-associated lymphoid tissue) lymphomas, presumably due to the eradication of tumorigenic Helicobacter pylori infection. This agent also acts as a biological response modulator, possibly inhibiting angiogenesis and tumor growth through alterations in growth factor expression. (NCI04)
Definition (MSH) A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.
Definition (CSP) semi-synthetic macrolide antibiotic; derivative of erythromycin.
Definition (PDQ) A semisynthetic 14-membered ring macrolide antibiotic. Clarithromycin binds to the 50S ribosomal subunit and inhibits RNA-dependent protein synthesis in susceptible organisms. Clarithromycin has been shown to eradicate gastric MALT (mucosa-associated lymphoid tissue) lymphomas, presumably due to the eradication of tumorigenic Helicobacter pylori infection. This agent also acts as a biological response modulator, possibly inhibiting angiogenesis and tumor growth through alterations in growth factor expression. Check for "http://www.cancer.gov/Search/ClinicalTrialsLink.aspx?id=42308&idtype=1" active clinical trials or "http://www.cancer.gov/Search/ClinicalTrialsLink.aspx?id=42308&idtype=1&closed=1" closed clinical trials using this agent. ("http://nciterms.nci.nih.gov:80/NCIBrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C1054" NCI Thesaurus)
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D017291
SnomedCT 387487009, 83999008
LNC LP15406-9, MTHU006897
English 6-O-Methylerythromycin, Clarithromycin, Erythromycin, 6-O-methyl-, clarithromycin, clarithromycin (medication), CLARITHROMYCIN, Clarithromycin [Chemical/Ingredient], Clarithromycin (product), Clarithromycin (substance), CLARITH
Swedish Klaritromycin
Finnish Klatritromysiini
Russian KLARITROMITSIN, КЛАРИТРОМИЦИН
Japanese クラリスロマイシン
Italian 6-O-Metileritromicina, Claritromicina
Polish Klarytromycyna
Czech klarithromycin, clarithromycin, klaritromycin
Spanish 6-O-metileritromicina, claritromicina (producto), claritromicina (sustancia), claritromicina, Claritromicina
French Clarithromycine
German Clarithromycin
Portuguese Claritromicina
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Zithromax (C0678143)

Definition (CHV) brand name of azithromycin
Definition (CHV) brand name of azithromycin
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D017963
English zithromax [brand name], zithromax, Bayer Brand of Azithromycin Dihydrate, Pfizer Brand of Azithromycin Dihydrate, Mack Brand of Azithromycin Dihydrate, Azadose, Azithromycin Pfizer Brand, Azitrocin, Pfizer Brand of Azithromycin, Ultreon, Zitromax, Zithromax
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Biaxin (C0701281)

Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D017291
English biaxin, Biaxin
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: telithromycin (C0907410)

Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH C106791
SnomedCT 395260006, 410908003
LNC LP33364-8, MTHU016681
English telithromycin (medication), telithromycin [Chemical/Ingredient], telithromycin, (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone, Telithromycin (product), Telithromycin, Telithromycin (substance), TELITHROMYCIN
Spanish telitromicina (producto), telitromicina, telitromicina (sustancia)
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Ketek (C1452484)

Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH C106791
English Aventis brand of telithromycin, Ketek
Derived from the NIH UMLS (Unified Medical Language System)

Related Topics in Pharmacology

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