Azithromycin

Title: Azithromycin
CAS Registry Number: 83905-01-5
CAS Name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-a-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)-b-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one
Additional Names: N-methyl-11-aza-10-deoxo-10-dihydroerythromycin A; 9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A
Molecular Formula: C38H72N2O12
Molecular Weight: 748.98
Percent Composition: C 60.94%, H 9.69%, N 3.74%, O 25.63%
Literature References: Semi-synthetic macrolide antibiotic; related to erythromycin A, q.v. Prepn: BE 892357; G. Kobrehel, S. Djokic, US 4517359 (1982, 1985 both to Sour Pliva); of the crystalline dihydrate: D. J. M. Allen, K. M. Nepveux, EP 298650; eidem, US 6268489 (1989, 2001 both to Pfizer). Antibacterial spectrum: S. C. Aronoff et al., J. Antimicrob. Chemother. 19, 275 (1987); and mode of action: J. Retsema et al., Antimicrob. Agents Chemother. 31, 1939 (1987). Series of articles on pharmacology, pharmacokinetics, and clinical experience: J. Antimicrob. Chemother. 31, Suppl. E, 1-198 (1993). Clinical trial in prevention of Pneumocystis carinii pneumonia in AIDS patients: M. W. Dunne et al., Lancet 354, 891 (1999). Review of pharmacology and clinical efficacy in pediatric infections: H. D. Langtry, J. A. Balfour, Drugs 56, 273-297 (1998).
Properties: Amorphous solid, mp 113-115°. [a]D20 -37° (c = 1 in CHCl3).
Melting point: mp 113-115°
Optical Rotation: [a]D20 -37° (c = 1 in CHCl3)
Derivative Type: Dihydrate
CAS Registry Number: 117772-70-0
Manufacturers' Codes: CP-62993; XZ-450
Trademarks: Azitrocin (Pfizer); Ribotrex (Fabre); Sumamed (Pliva); Trozocina (Sigma-Tau); Zithromax (Pfizer); Zitromax (Pfizer)
Properties: White crystalline powder. mp 126°. [a]D26 -41.4° (c = 1 in CHCl3).
Melting point: mp 126°
Optical Rotation: [a]D26 -41.4° (c = 1 in CHCl3)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides.
Azlocillin Azolitmin Azomycin Azosemide Azoxybenzene

Azithromycin
Azithromycin structure.svg
Azithromycin 3d structure.png
Systematic (IUPAC) name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo- 11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadec-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
Clinical data
Trade names Azyth, Zithromax, Azithrocin, Azin, Zeto
AHFS/Drugs.com monograph
MedlinePlus a697037
Licence data US FDA:link
Pregnancy cat. B1 (AU) B (US)
Legal status -only (US)
Routes Oral (capsule or suspension), intravenous, ophthalmic
Pharmacokinetic data
Bioavailability 38% for 250 mg capsules
Metabolism Hepatic
Half-life 11–14 h (single dose)

68 h (multiple dosing)

Excretion Biliary, renal (4.5%)
Identifiers
CAS number 83905-01-5 YesY
ATC code J01FA10 S01AA26
PubChem CID 55185
DrugBank DB00207
ChemSpider 10482163 YesY
UNII J2KLZ20U1M YesY
KEGG D07486 YesY
ChEBI CHEBI:2955 YesY
ChEMBL CHEMBL529 YesY
NIAID ChemDB 007311
Synonyms 9-deoxy-9a-aza-9a-methyl-9a-homoerythromycin A
Chemical data
Formula C38H72N2O12 
Mol. mass 748.984 g·mol−1
 YesY (what is this?)  (verify)

Azithromycin (Azyth, Zithromax, Azithrocin, Zmax, Azin, Zedd, Azocam, Penalox, Azi-Once, Zeto)[1] is an azalide, a subclass of macrolide antibiotics. It is derived from erythromycin, with a methyl-substituted nitrogen atom incorporated into the lactone ring, thus making the lactone ring 15-membered.

Azithromycin prevents bacteria from growing by interfering with their protein synthesis. It binds to the 50S subunit of the bacterial ribosome, and thus inhibits translation of mRNA.

Azithromycin is used to treat or prevent certain bacterial infections, most often those causing middle ear infections, strep throat, pneumonia, typhoid, gastroenteritis, bronchitis and sinusitis. In recent years, it has been used primarily to prevent bacterial infections in infants and those with weaker immune systems. It is also effective against certain sexually transmitted infections, such as nongonococcal urethritis, chlamydia, and cervicitis. Some studies have indicated it also to be effective against late-onset asthma, but these findings are controversial and not widely accepted.[2][3]