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Substance Name: Clarithromycin [USAN:USP:INN:BAN:JAN]
RN: 81103-11-9
UNII: H1250JIK0A
InChIKey: AGOYDEPGAOXOCK-KCBOHYOISA-N

Note

  • 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.

Molecular Formula

  • C38-H69-N-O13

Molecular Weight

  • 747.9571
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Cytochrome P-450 CYP3A Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Metabolic Side Effects of Drugs and Substances
  • Protein Synthesis Inhibitors

Names and Synonyms

Name of Substance

  • Clarithromycin
  • Clarithromycin [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Clarithromycin

Synonyms

  • 6-O-Methylerythromycin
  • 6-O-Methylerythromycin A
  • A-56268
  • Abbotic
  • Abbott-56268
  • Adel
  • Astromen
  • Biaxin
  • Biaxin filmtab
  • Biaxin HP
  • Biaxin XL
  • Biaxin xl filmtab
  • Bicrolid
  • CCRIS 8833
  • Clacine
  • Clambiotic
  • Claribid
  • Claricide
  • Clarith
  • Clarithromycin
  • Clarithromycin extended release
  • Clarithromycine
  • Clarithromycine [INN-French]
  • Clarithromycinum
  • Clarithromycinum [INN-Latin]
  • Claritromicina
  • Claritromicina [INN-Spanish]
  • Clathromycin
  • Cyllid
  • DRG-0099
  • Helas
  • Heliclar
  • HSDB 8055
  • Klacid
  • Klaciped
  • Klaricid
  • Klaricid H.P.
  • Klaricid Pediatric
  • Klarid
  • Klarin
  • Klax
  • Kofron
  • Mabicrol
  • Macladin
  • Maclar
  • Mavid
  • Naxy
  • TE-031
  • UNII-H1250JIK0A
  • Veclam
  • Zeclar

Systematic Name

  • Erythromycin, 6-O-methyl-

Superlist Name

  • Clarithromycin

Registry Numbers

CAS Registry Number

  • 81103-11-9

FDA UNII

  • H1250JIK0A

System Generated Number

  • 0081103119

Structure Descriptors

InChI

1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

InChIKey

AGOYDEPGAOXOCK-KCBOHYOISA-N

Smiles

CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[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)OC)C)C)O)(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 5gm/kg (5000mg/kg) BLOOD: HEMORRHAGE

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 1453, 1988.
mouse LD50 intraperitoneal 850mg/kg (850mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 36(Suppl,
mouse LD50 intravenous 173mg/kg (173mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 769, 1991.
mouse LD50 oral 1230mg/kg (1230mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 1433, 1988.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg) SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE Chemotherapy Vol. 36(Suppl,
rat LD50 intraperitoneal 669mg/kg (669mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Chemotherapy Vol. 36(Suppl,
rat LD50 oral 1270mg/kg (1270mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 1433, 1988.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg) SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE Chemotherapy Vol. 36(Suppl,
women TDLo oral 30mg/kg/3D-I (30mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: CHANGE IN RATE
Annals of Emergency Medicine. Vol. 30, Pg. 542, 1997.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 220 dec deg C   EXP
pKa Dissociation Constant 8.99 (none) 25 EXP
log P (octanol-water) 3.16 (none)   EXP
Water Solubility 0.342 mg/L 25 EST
Vapor Pressure 8.60E-27 mm Hg 25 EST
Henry's Law Constant 1.73E-29 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.78E-10 cm3/molecule-sec 25 EST

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