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Substance Name: Azithromycin [USAN:INN:BAN]
RN: 83905-01-5
UNII: J2KLZ20U1M
InChIKey: MQTOSJVFKKJCRP-BICOPXKESA-N

Note

  • 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 Formula

  • C38-H72-N2-O12

Molecular Weight

  • 748.9888
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Azithromycin
  • Azithromycin [USAN:INN:BAN]

MeSH Heading

  • Azithromycin

Synonyms

  • (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-azacyclopentadecan-15-one
  • 9-Deoxo-9a-aza-9a-methyl-9a-homoerythromycin A
  • Aritromicina
  • Aritromicina [Spanish]
  • Azasite
  • Azenil
  • Azithromycin
  • Azithromycin (anhydrous)
  • Azithromycine
  • Azithromycine [French]
  • Azithromycinum
  • Azithromycinum [Latin]
  • Azitrocin
  • Azitromax
  • Azitromicine
  • Aziwok
  • Aztrin
  • BRN 5387583
  • CCRIS 1961
  • DRG-0104
  • EC 617-500-5
  • Hemomycin
  • HSDB 7205
  • Misultina
  • Mixoterin
  • Setron
  • Sumamed
  • Tobil
  • Tromix
  • Trulimax
  • UNII-J2KLZ20U1M
  • Z-Pak
  • Z-Pak (Azithromycin)
  • Zeto
  • Zifin
  • Zithrax
  • Zithromax
  • Zithromax IV
  • Zitrim
  • Zitromax
  • Zitrotek
  • Zmas
  • Zmax

Systematic Names

  • (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-((2S,3R,4S,6R)-
  • 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,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
  • 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*))-
  • Azithromycin

Registry Numbers

CAS Registry Number

  • 83905-01-5

FDA UNII

  • J2KLZ20U1M

Other Registry Numbers

  • 104491-80-7
  • 142556-82-9

Related Registry Numbers

  • 117772-70-0 (dihydrate)
  • 121470-24-4 (monohydrate)

System Generated Number

  • 0083905015

Structure Descriptors

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

InChIKey

MQTOSJVFKKJCRP-BICOPXKESA-N

Smiles

CC[C@@H]1[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 21mg/kg/3D-I (21mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"

LIVER: "JAUNDICE, CHOLESTATIC"
American Journal of Medicine. Vol. 102, Pg. 217, 1997.
man TDLo oral 32mg/kg/9D-I (32mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Annals of Internal Medicine. Vol. 119, Pg. 636, 1993.
mouse LD50 oral 3gm/kg (3000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.
mouse LDLo intraperitoneal 400mg/kg (400mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.
rat LD50 oral > 2gm/kg (2000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.
rat LDLo intraperitoneal 900mg/kg (900mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 114 deg C   EXP
pKa Dissociation Constant 8.74 (none) 25 EXP
log P (octanol-water) 4.02 (none)   EXP
Water Solubility 7.090 mg/L 25 EST
Vapor Pressure 3.91E-27 mm Hg 25 EST
Henry's Law Constant 5.30E-29 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.23E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.