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Substance Name: Erythromycin [USP:INN:BAN:JAN]
RN: 114-07-8
UNII: 63937KV33D
InChIKey: ULGZDMOVFRHVEP-RWJQBGPGSA-N

Note

  • A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.

Molecular Formula

  • C37-H67-N-O13

Molecular Weight

  • 733.9303
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Gastrointestinal Agents
  • Human Data
  • Mutation Data
  • Natural Product
  • Protein Synthesis Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Erythromycin
  • Erythromycin [USP:INN:BAN:JAN]

MeSH Heading

  • Erythromycin

Synonyms

  • (3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)oxacyclotetradecane-2,10-dione
  • A/T/S
  • Abboticin
  • Abomacetin
  • Acneryne
  • Acnesol
  • AI3-50138
  • Ak-Mycin
  • Akne Cordes Losung
  • Akne-Mycin
  • Aknederm Ery Gel
  • Aknemycin
  • Aknin
  • AustriaS
  • C-Solve-2
  • CCRIS 9078
  • Del-Mycin
  • Derimer
  • Deripil
  • Dotycin
  • Dumotrycin
  • E-Base
  • E-Base (base)
  • E-Glades
  • E-Mycin
  • E-Mycin (base)
  • E-solve 2
  • EC 204-040-1
  • EINECS 204-040-1
  • Emgel
  • Emu-V
  • Emu-Ve
  • Emuvin
  • Emycin
  • Endoeritrin
  • Erecin
  • Erimycin-T
  • Erisone
  • Eritomicina
  • Eritrocina
  • Eritromicina
  • Eritromicina [INN-Spanish]
  • Ermycin
  • Eros
  • Ery-B
  • Ery-Diolan
  • Ery-maxin
  • Ery-Tab
  • Ery-Tab (base)
  • Eryacne
  • Eryacnen
  • ERYC
  • ERYC (base)
  • Eryc 125
  • Eryc sprinkles
  • Eryc-125
  • Eryc-250
  • Erycen
  • Erycette
  • Erycin
  • Erycinum
  • EryDerm
  • Erydermer
  • Erygel
  • Eryhexal
  • Erymax
  • Erymed
  • Erysafe
  • Erytab
  • Erythra-Derm
  • Erythro-Statin
  • Erythro-Teva
  • Erythrocin
  • Erythroderm
  • Erythrogran
  • Erythroguent
  • Erythromast 36
  • Erythromid
  • Erythromycin
  • Erythromycin A
  • Erythromycin base
  • Erythromycine
  • Erythromycine [INN-French]
  • Erythromycinum
  • Erythromycinum [INN-Latin]
  • Erytop
  • Erytrociclin
  • HSDB 3074
  • Ilocaps
  • Ilosone (estolate)
  • Iloticina
  • Ilotycin
  • Ilotycin T.S.
  • Inderm
  • Inderm Gel
  • Kesso-Mycin
  • Latotryd
  • Lederpax
  • Mephamycin
  • Mercina
  • NCI-C55674
  • NSC 55929
  • Oftalmolosa Cusi Eritromicina
  • Oftamolets
  • Paediathrocin
  • Pantoderm
  • Pantodrin
  • Pantomicina
  • PCE
  • PCE Dispertab (base)
  • Pharyngocin
  • Primacine
  • Propiocine
  • Proterytrin
  • R-P Mycin
  • Retcin
  • Robimycin
  • Romycin
  • Sans-acne
  • Sansac
  • Sentry AQ mardel maracyn
  • Skid Gel E
  • Staticin
  • Stiemicyn
  • Stiemycin
  • T-Stat
  • Taimoxin-F
  • Theramycin Z
  • Tiloryth
  • Tiprocin
  • Torlamicina
  • Udima Ery Gel
  • UNII-63937KV33D
  • Wemid

Systematic Names

  • Erythromycin
  • Erythromycin A

Mixture Names

  • Benzamycin
  • Staticin

Registry Numbers

CAS Registry Number

  • 114-07-8

FDA UNII

  • 63937KV33D

Other Registry Number

  • 374700-25-1

System Generated Number

  • 0000114078

Structure Descriptors

InChI

InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

InChIKey

ULGZDMOVFRHVEP-RWJQBGPGSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 10mg/kg/1D-I (10mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Annals of Internal Medicine. Vol. 115, Pg. 69, 1991.
child TDLo oral 250mg/kg (250mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT		 Pediatrics. Vol. 90, Pg. 624, 1992.
dog LDLo unreported > 100mg/kg (100mg/kg)   Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952.
guinea pig LD50 intraperitoneal 413mg/kg (413mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952.
hamster LD50 oral 3018mg/kg (3018mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952.
mouse LD50 intramuscular 394mg/kg (394mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 44, Pg. 199, 1955.
mouse LD50 intraperitoneal 280mg/kg (280mg/kg)   Journal of Antibiotics. Vol. 43, Pg. 938, 1990.
mouse LD50 intravenous 426mg/kg (426mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 273, 1967.
mouse LD50 oral 2580mg/kg (2580mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974.
mouse LD50 subcutaneous 1800mg/kg (1800mg/kg)   Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952.
rat LD50 oral 4600mg/kg (4600mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974.
rat LDLo subcutaneous 427mg/kg (427mg/kg)   Compilation of LD50 Values of New Drugs.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 191 deg C   EXP
pKa Dissociation Constant 8.88 (none) 25 EXP
log P (octanol-water) 3.06 (none)   EXP
Water Solubility 1.440 mg/L 25 EST
Vapor Pressure 2.28E-27 mm Hg 25 EST
Henry's Law Constant 5.42E-29 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.03E-10 cm3/molecule-sec 25 EST

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