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Erythromycin Stearate

HCID 12559
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Basic information

CAS
643-22-1
Standard SMILES
CCCCCCCCCCCCCCCCCC(=O)O.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]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey
YAVZHCFFUATPRK-YZPBMOCRSA-N
Molecular formula
C37H67NO13.C18H36O2
Average molar mass
1,018.4 g/mol
Monoisotopic mass
1,017.73277158

Overview

Erythromycin stearate appears as fluffy colorless powder or fine white powder. (NTP, 1992)

Names & identifiers

Preferred name
Erythromycin Stearate
IUPAC
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;octadecanoic acid
English name
Erythromycin stearate
Molecular formula
C55H103NO15
Molecular weight
1018.42

Names & synonyms

ERYTHROMYCIN STEARATE643-22-1AbboticineBristamycinGallimycinEryparDowmycin EWyamycin SPfizer-EEratrexEthrilErythrocin stearate
Show more names
oe7WemidEthrynEryprim
MeberytErythromycin octadecanoate (salt)Sk-erythromycinEthril 250ETHRIL 500Erythromycin stearate (salt)Erythromycin, stearate (salt)NCI-C55674

Database identifiers

CAS
643-22-1
PubChem CID
12559
ChEMBL
CHEMBL1200510
ChEBI
CHEBI:34742
UNII
LXW024X05M
EC Number
211-396-1

Properties

Computed structural properties

Topological polar surface area
231 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
16
Rotatable bonds
23
Heavy atoms
71
Formal charge
0
Complexity
1,380

Experimental & physicochemical properties

pHSOLN IS ALKALINE TO LITMUS
OdorPRACTICALLY ODORLESS
TasteSLIGHTLY BITTER
Color/Form · 2 items

CRYSTALS

WHITE OR SLIGHTLY YELLOW CRYSTALS OR POWDER

Solubility · 3 items

less than 1 mg/mL at 72 °F (NTP, 1992)

SOL IN ALC, ETHER; PRACTICALLY INSOL IN WATER

SOL IN METHANOL, CHLOROFORM

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Dermatologic Agents; Macrolides

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point212 to 219 °F (NTP, 1992)
Physical DescriptionErythromycin stearate appears as fluffy colorless powder or fine white powder. (NTP, 1992)
Collision Cross Section258.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.9% (1 of 106) of reports.

Danger

H317 (59.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P321, P333+P317, P337+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 106 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Other Safety InformationIMAP assessments - Erythromycin, octadecanoate (salt): Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: Symptoms of exposure to this compound include nausea, vomiting, diarrhea and abdominal cramps. Chronic overexposure may cause jaundice. This may be accompanied by fever, leukocytosis, eosinophilia and elevated activities of transaminases in plasma. Allergic reactions to this compound may include fever, eosinophilia, skin eruptions, urticaria and anaphylaxis. Cholestatic hepatitis occurs rarely. Epigastric distress, possibly severe may also occur. Intramuscular injections of large quantities of this compound may cause extremely severe pain that persists for hours. Intravenous infusions of 1 gram doses have reportedly been followed by thrombophlebitis. Prolonged use may result in an overgrowth of nonsusceptible bacteria or fungi. There have been isolated reports of reversible hearing loss occurring after exposure to this chemical, chiefly in persons with renal insufficiency.

Reactive GroupAlcohols and Polyols

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

...INHIBIT PROTEIN SYNTH BY BINDING TO 50 S RIBOSOMAL SUBUNITS OF SENSITIVE MICROORGANISMS. ... ASSOC BETWEEN ERYTHROMYCIN & RIBOSOME IS REVERSIBLE BUT TAKES PLACE ONLY WHEN 50 S SUBUNIT IS FREE FROM TRNA MOLECULES BEARING NASCENT PEPTIDE CHAINS. PRODN...OF HIGHLY POLYMERIZED HOMOPEPTIDES IS SUPPRESSED. /ERYTHROMYCIN/

THE NONIONIZED FORM OF THE DRUG IS CONSIDERABLY MORE PERMEABLE TO CELLS, & THIS PROBABLY EXPLAINS INCREASED ANTIMICROBIAL ACTIVITY THAT IS OBSERVED AT ALKALINE PH. /ERYTHROMYCIN/

Metabolism/Metabolites · 2 items

IT IS HYDROLYZED IN SMALL INTESTINE & IN TISSUES TO YIELD ERYTHROMYCIN.

Hepatic. Extensively metabolized - after oral administration, less than 5% of the administered dose can be recovered in the active form in the urine. Erythromycin is partially metabolized by CYP3A4 resulting in numerous drug interactions. Half Life: 0.8 - 3 hours

MeSH Pharmacological Classification · 2 items

Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.

Substances that inhibit the growth or reproduction of BACTERIA.

Absorption, Distribution and Excretion · 5 items

PEAK CONCN IN PLASMA...0.3-0.5 UG/ML 4 HR AFTER ORAL ADMIN OF 250 MG OF BASE & ARE 0.3-1.9 UG/ML AFTER...500-MG TABLET. VARIOUS ESTERS OF ERYTHROMYCIN HAVE BEEN PREPARED TO...IMPROVE STABILITY & FACILITATE ABSORPTION. ...CONCN OF ERYTHROMYCIN IN PLASMA ARE LITTLE DIFFERENT IF STEARATE IS GIVEN ORALLY.

...DIFFUSES READILY INTO INTRACELLULAR FLUIDS, & ANTIBACTERIAL ACTIVITY... ACHIEVED AT...ALL SITES EXCEPT BRAIN & CSF. ...ONE OF FEW ANTIBIOTICS THAT PENETRATES INTO PROSTATIC FLUID, CONCN ARE APPROX 40% OF...PLASMA. EXTENT OF BINDING...TO PLASMA PROTEINS VARIES...PROBABLY EXCEEDS 70% IN ALL.../FORMS OF DRUG/. /ERYTHROMYCIN/

ERYTHROMYCIN BASE IS ADEQUATELY ABSORBED FROM UPPER PART OF SMALL INTESTINE; IT IS INACTIVATED BY GASTRIC JUICE... FOOD IN STOMACH DELAYS ITS ULTIMATE ABSORPTION. /ERYTHROMYCIN/

ERYTHROMYCIN TRAVERSES PLACENTAL BARRIER; & CONCN OF DRUG IN FETAL PLASMA ARE ABOUT 5-20% OF THOSE IN MATERNAL CIRCULATION. /ERYTHROMYCIN/

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Compound notes

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Physicochemical properties

Melting point
77 · 77-79°C
storage temp.
2 · 2-8°C
solubility
50 mg/mL, · ethanol: soluble50mg/mL, clear to very slightly hazy, colorless
color
white to off-white
Stability
Stable. Combustible. Incompatible with acids, strong oxidizing agents.
InChIKey
YAVZHCFFUATPRK-JKARSCBVNA-N
Toxicology and Carcinogenesis
Toxicology and Carcinogenesis Studies of Erythromycin Stearate (CASRN 643-22-1) in F344/N Rats and B6C3F1 Mice (Feed Studies)
FDA UNII
24 X05M · LXW024X05M
EPA Substance Registry System
Erythromycin stearate (643-22-1)
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
317 · H317-H334
Precautionary statements
261 · P261-P272-P280-P284-P302+P352-P304+P340+P312
Hazard Codes
Xn,Xi
Risk Statements
42 · 42/43-36/37/38
Safety Statements
36 · 36-26
WGK Germany
2 · 2
RTECS
5785000 · KF5785000
HS Code
29415000 · 29415000
Hazardous Substances Data
643 · 643-22-1(Hazardous Substances Data)
Special Reports · 2 items

A REVIEW, WITH APPROX 20 REFERENCES, OF THE BIOAVAILABILITY FROM VARIOUS FORMULATIONS OF ERYTHROMYCIN STEARATE.[KNOTHE H, DETTE GA; PHARMACOKINETICS OF ERYTHROMYCIN; SCOTT MED J 22(5) 397 (1977)]

DHHS/NTP; Toxicology & Carcinogenesis Studies of Erythromycin sulfate in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 338 (1988) NIH Publication No. 89-2594

Reactivity ProfileA base. Readily forms salts with acids. (NTP, 1992)
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesSkin Sens. 1 (59.4%)

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxicology

InteractionsA 77-YR-OLD WOMAN IS REPORTEDLY MAINTAINED ON 7.5 MG OF WARFARIN DAILY IN WHOM THE ADMIN OF ORAL ERYTHROMYCIN STEARATE, 500 MG 4 TIMES A DAY, RESULTED IN A PROTHROMBIN TIME OF 64 SECONDS (CONTROL, 11 SECONDS).
Exposure RoutesOrally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topical application of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.
Toxicity Summary · 1 item

Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or near the “P” or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the “A” or acceptor site to the “P” or donor site is prevented, and subsequent protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by which erythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to the antibacterial activity of the drug.

Signs and SymptomsSymptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=643-22-1]

Human Toxicity Excerpts · 5 items

AMONG ALLERGIC REACTIONS ARE FEVER, EOSINOPHILIA, & SKIN ERUPTIONS, WHICH MAY OCCUR ALONE OR IN COMBINATION; EACH DISAPPEARS SHORTLY AFTER THERAPY IS STOPPED. ...OFTEN PRODUCES IRRITATIVE EFFECTS. ORAL ADMIN...FREQUENTLY ACCOMPANIED BY EPIGASTRIC DISTRESS, WHICH MAY BE QUITE SEVERE. /ERYTHROMCYIN/

IM INJECTION OF QUANTITIES LARGER THAN 100 MG PRODUCES EXTREMELY SEVERE PAIN THAT PERSISTS FOR HOURS. IV INFUSION OF 1-G DOSES...ALMOST REGULARLY IS FOLLOWED BY THROMBOPHLEBITIS. /ERYTHROMYCIN/

...MILD ELEVATIONS OF THE SGOT /SERUM GLUTAMIC-OXALOACETIC TRANSAMINASE/ WERE ALSO NOTED IN...3 OF 97 PT TREATED WITH ERYTHROMYCIN STEARATE...

SEVERE RESP DISTRESS DEVELOPED IN A 60-YR-OLD MAN AFTER INGESTION OF 2 TABLETS OF ERYTHROMYCIN STEARATE. AUTHORS SUGGEST AN ALLERGIC REACTION OF TYPE 1 & TYPE 3 PARTICIPATED IN COURSE OF CLINICAL PICTURE.

OTOTOXICITY DUE TO ORAL ERYTHROMYCIN STEARATE DEVELOPED IN 2 PT (17 & 50-YR-OLD) RECEIVING AT LEAST 4 G DAILY. UPON WITHDRAWAL OF THE DRUG, HEARING RETURNED IN BOTH PT.

Carcinogen Classification · 6 items

Erythromycin Stearate

TR-338: Toxicology and Carcinogenesis Studies of Erythromycin Stearate (CASRN 643-22-1) in F344/N Rats and B6C3F1 Mice (Feed Studies) (1988 )

07/14/87

No Evidence

No Evidence

No Evidence

Non-Human Toxicity Excerpts · 4 items

READILY PRODUCES DIARRHEA & DEATH IN RABBITS DUE TO OVERGROWTH OF GRAM-NEGATIVE BACTERIA. /ERYTHROMYCIN/

CELLULAR DAMAGE PARALLELED KNOWN HEPATOTOXIC POTENTIAL OF THESE AGENTS IN MAN, SUGGESTING POSSIBLE USEFULNESS OF THIS SYSTEM AS AN ADDNL METHOD OF EVALUATING CYTOTOXIC POTENTIAL OF CHEMICALLY RELATED DRUGS

Erythromycin stearate was found to be negative when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). Erythromycin stearate was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.300, 1.000, 3.000, 10.000, and 33.000 ug/plate. The highest ineffective dose tested in any S. typhimurium strain was 33.000 ug/plate.

... Conclusions: Under the conditions of these 2 yr studies, there was no evidence of carcinogenic activity of erythromycin stearate for male or female F344/N rats administered erythromycin stearate in the diet at 5,000 or 10,000 ppm. There was no evidence of carcinogenic activity of erythromycin stearate for male or female B6C3F1 mice administered erythromycin stearate in the diet at 2,500 or 5,000 ppm. ... /Erythromycin stearate/

National Toxicology Program Studies · 1 item

Toxicology and carcinogenesis studies of erythromycin stearate (USP grade, greater than 96% pure) were conducted by admin ... in feed to groups of F344/N rats and B6C3F1 mice for ... 2 yr studies of erythromycin stearate were conducted by feeding diets containing 0, 5,000 or 10,000 ppm erythromycin stearate to groups of 50 rats of each sex for 103 wk. Diets containing 0, 2,5000 or 5000 ppm were fed to groups of 50 mice of each sex for 103 wk. Conclusions: Under the conditions of these 2 yr studies, there was no evidence of carcinogenic activity of erythromycin stearate for male or female F344/N rats administered erythromycin stearate in the diet at 5,000 or 10,000 ppm. There was no evidence of carcinogenic activity of erythromycin stearate for male or female B6C3F1 mice administered erythromycin stearate in the diet at 2,500 or 5,000 ppm. ... /Erythromycin stearate/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
2
rtecs
KF5785000
hs_code
29415000
risk_code
42/43-36/37/38
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
Xn,Xi
safety_code
36-26
Hazard statements
H317-H334
Precautionary statements
P261-P272-P280-P284-P302+P352-P304+P340+P312
Hazardous Substances Data
643-22-1(Hazardous Substances Data)

For more Absorption, Distribution and Excretion (Complete) data for ERYTHROMYCIN STEARATE (11 total), please visit the HSDB record page.

Uses & manufacturing

Uses · 1 item

For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases: respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct to antitoxin in infections due to <i>Corynebacterium diphtheriae</i>, in the treatment of infections due to <i>Corynebacterium minutissimum</i>, intestinal amebiasis caused by <i>Entamoeba histolytica</i>, acute pelvic inflammatory disease caused by <i>Neisseria gonorrhoeae</i>, skin and soft tissue infections of mild to moderate severity caused by <i>Streptococcus pyogenes</i> and <i>Staphylococcus aureus</i>, primary syphilis caused by <i>Treponema pallidum</i>, infections caused by <i>Chlamydia trachomatis</i>, nongonococcal urethritis caused by <i>Ureaplasma urealyticum</i>, and Legionnaires' disease caused by <i>Legionella pneumophila</i>.

Methods of Manufacturing · 2 items

PREPN OF ERYTHROMCYIN STEARATE (ESTER) IS DESCRIBED IN BOOTH, MURRAY, US PATENT 2,862,921 (1958 TO UPJOHN).

BY REACTING ERYTHROMYCIN WITH PROPER QUANT OF STEARIC ACID IN ACETONE SOLN & THEN DILUTING SOLN WITH WATER TO PPT SALT.

Formulations/Preparations · 2 items

ERYTHROMYCIN STEARATE TABLETS, USP (BRISTAMYCIN, ERYTHROCIN STEARATE, ETHRIL), CONTAIN 125, 250, OR 500 MG EACH.

ERYTHROMYCIN STEARATE: ...STEARIC ACID SALT OF ERYTHROMYCIN, WITH EXCESS OF STEARIC ACID. IT CONTAINS NOT LESS THAN 55% OF ERYTHROMYCIN.

Applications · 5 items

UsesSemi-synthetic macrolide antibiotic. Antibacterial

Usesoil lubricant, plasticizer, solvent

UsesMacrodiles antibacterial

General DescriptionErythromycin stearate (Ethril, Wyamycin S, Erypar) is thestearic acid salt of erythromycin. Like erythromycin base,the stearate is acid labile. It is film coated to protect it fromacid degradation in the stomach. In the alkaline pH of theduodenum, the free base is liberated from the stearateand absorbed. Erythromycin stearate is a crystalline powderthat is practically insoluble in water but soluble in alcoholand ether.

General DescriptionFluffy colorless powder or fine white powder.

Upstream & downstream products

Upstream raw materials

Stearic acidSTEAROYL CHLORIDEErythromycin1-Ethylpiperidine

Downstream products

Complex heat stabilizerPVC composite stabilizer

Additional notes

DefinitionChEBI: Erythromycin stearate is an aminoglycoside.