Erythromycin

Modify Date: 2024-01-02 01:24:17

Erythromycin Structure
Erythromycin structure
 Common Name Erythromycin
CAS Number 114-07-8 Molecular Weight 733.927
Density 1.2±0.1 g/cm3 Boiling Point 818.4±65.0 °C at 760 mmHg
Molecular Formula C37H67NO13 Melting Point 138-140ºC
MSDS Chinese USA Flash Point 448.8±34.3 °C

 Use of Erythromycin


Erythromycin, an oral macrolide antibiotic produced by Streptomyces erythreus, reversibly binds to the 50S ribosome of bacteria, and inhibits protein synthesis.Target: AntibacterialErythromycin is a macrolide antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often prescribed for people who have an allergy to penicillins. For respiratory tract infections, it has better coverage of atypical organisms, including Mycoplasma and legionellosis. It was first marketed by Eli Lilly and Company, and it is today commonly known as EES (erythromycin ethylsuccinate, an ester prodrug that is commonly administered). It is also occasionally used as a prokinetic agent.Erythromycin estolate has been associated with reversible hepatotoxicity in pregnant women in the form of elevated serum glutamic-oxaloacetic transaminase and is not recommended during pregnancy. Some evidence suggests similar hepatotoxicity in other populations. Erythromycin displays bacteriostatic activity or inhibits growth of bacteria, especially at higher concentrations, but the mechanism is not fully understood. By binding to the 50s subunit of the bacterial 70s rRNA complex, protein synthesis and subsequent structure and function processes critical for life or replication are inhibited. Erythromycin interferes with aminoacyl translocation, preventing the transfer of the tRNA bound at the A site of the rRNA complex to the P site of the rRNA complex. Without this translocation, the A site remains occupied and, thus, the addition of an incoming tRNA and its attached amino acid to the nascent polypeptide chain is inhibited. This interferes with the production of functionally useful proteins, which is the basis of this antimicrobial action.

 Names

Name Erythromycin
Synonym More Synonyms

 Erythromycin Biological Activity

Description Erythromycin, an oral macrolide antibiotic produced by Streptomyces erythreus, reversibly binds to the 50S ribosome of bacteria, and inhibits protein synthesis.Target: AntibacterialErythromycin is a macrolide antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often prescribed for people who have an allergy to penicillins. For respiratory tract infections, it has better coverage of atypical organisms, including Mycoplasma and legionellosis. It was first marketed by Eli Lilly and Company, and it is today commonly known as EES (erythromycin ethylsuccinate, an ester prodrug that is commonly administered). It is also occasionally used as a prokinetic agent.Erythromycin estolate has been associated with reversible hepatotoxicity in pregnant women in the form of elevated serum glutamic-oxaloacetic transaminase and is not recommended during pregnancy. Some evidence suggests similar hepatotoxicity in other populations. Erythromycin displays bacteriostatic activity or inhibits growth of bacteria, especially at higher concentrations, but the mechanism is not fully understood. By binding to the 50s subunit of the bacterial 70s rRNA complex, protein synthesis and subsequent structure and function processes critical for life or replication are inhibited. Erythromycin interferes with aminoacyl translocation, preventing the transfer of the tRNA bound at the A site of the rRNA complex to the P site of the rRNA complex. Without this translocation, the A site remains occupied and, thus, the addition of an incoming tRNA and its attached amino acid to the nascent polypeptide chain is inhibited. This interferes with the production of functionally useful proteins, which is the basis of this antimicrobial action.
Related Catalog
References

[1]. McCormack WM, et al. Hepatotoxicity of erythromycin estolate during pregnancy. Antimicrob Agents Chemother. 1977 Nov;12(5):630-5.

[2]. Peeters T, et al. Erythromycin is a motilin receptor agonist. Am J Physiol. 1989 Sep;257(3 Pt 1):G470-4.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 818.4±65.0 °C at 760 mmHg
Melting Point 138-140ºC
Molecular Formula C37H67NO13
Molecular Weight 733.927
Flash Point 448.8±34.3 °C
Exact Mass 733.461243
PSA 193.91000
LogP 2.83
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.535

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KF4375000
CHEMICAL NAME :
Erythromycin
CAS REGISTRY NUMBER :
114-07-8
LAST UPDATED :
199504
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C37-H67-N-O13
MOLECULAR WEIGHT :
734.05
WISWESSER LINE NOTATION :
T-14-VO GVTJ C2 DQ D1 EQ F1 H1 JQ J1 L1 N1 KO- BT6OTJ CQ DN1&1 F1& MO- FT6OTJ B1 CQ DO1 D1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
10 mg/kg/1D-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
427 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2580 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
280 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
426 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
394 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
413 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
3018 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
33600 mg/kg/6W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 10-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
50 mg/kg
SEX/DURATION :
female 6-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12 gm/kg
SEX/DURATION :
female 8-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :
DNA repair
TEST SYSTEM :
Bacteria - Escherichia coli
DOSE/DURATION :
600 ug/disc
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 97,1,1982 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0. ppm (11 mg/m3) JAN 1993 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - A1050 No. of Facilities: 58 (estimated) No. of Industries: 2 No. of Occupations: 4 No. of Employees: 1133 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - A1050 No. of Facilities: 667 (estimated) No. of Industries: 4 No. of Occupations: 12 No. of Employees: 44142 (estimated) No. of Female Employees: 37992 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn:Harmful
Risk Phrases R42/43
Safety Phrases S24-S37-S45
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS KF4375000
HS Code 2941500000

 Synthetic Route

 Customs

HS Code 2941500000

 Articles494

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 Synonyms

ROBIMYCIN
UNII-63937KV33D
Theramycin Z
E-BASE
Inderm
Erythromast 36
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2,10-dion
ERYMAX
Retcin
Ak-Mycin
Ery-Diolan
Eryhexal
Ery-Tab
E.E.S
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred name)
Erythromycin
EMU
Torlamicina
(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-((2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-((3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl)oxy)oxacyclotetradecane-2,10-dione
PCE
MFCD00084654
Paediathrocin
Erycen
Erycin
Erycinum
ERYTHROPED
Erythrogran
Aknemycin
Eritrocina
E-MYCIN
erythromycine
Aknin
ILOTYCIN
Erythrocin
Erythromid
eritromicina
ERYC
Staticin
EINECS 204-040-1
Erythroguent
Ergel
Estomicina
Stiemycin
Pharyngocin
Erythromycin A
USP
Dotycin
EMGEL
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
knin
erythromycinum
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(R)-3-Amino-1,1-difluoropropan-2-ol
2227833-40-9
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
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