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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) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: HEMORRHAGE
Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 1453, 1988.
mouse LD50 intraperitoneal 850mg/kg (850mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
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: CHANGE IN RATE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
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.