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Erythromycin estolate

Erythromycin estolate structure

CAS No:
3521-62-8
Formula:
C40H71NO14.C12H26O4S
Chemical Name:
Erythromycin estolate
Synonyms:
Erythromycin,2′-propanoate,dodecyl sulfate (1:1);Erythromycin,2′-propionate,dodecyl sulfate (salt);Erythromycin,2′-propanoate,dodecyl sulfate (salt);Erythromycin,propionate,compd. with dodecyl sulfate;Propionic acid,2′-ester with erythromycin,dodecyl sulfate salt;Sulfuric acid,monododecyl ester,compd. with erythromycin 2′-propionate (1:1);Oxacyclotetradecane,erythromycin deriv.;Sulfuric acid,monododecyl ester,compd. with erythromycin 2′-propanoate (1:1);Erythromycin estolate;Erythromycin propionate lauryl sulfate;Ilosone;Lauryl sulfate propionyl erythromycin ester;Propionylerythromycin lauryl sulfate;Eriscel;Estomicina;Erytrarco;Eromycin;Marcoeritrex;Lauromicina;Neo-Erycinum;PELS;Roxomicina;Stellamicina;Erythromycin,monopropanoate (ester),dodecyl sulfate (salt);Erythromycin,monopropionate (ester),compd. with monododecyl sulfate (1:1);Lubomycine B;Propiocine Enfant;Eritroger;Eupragin;Togiren;NSC 263364;Eltocin DS;12167-63-4;28375-06-6;31261-46-8
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Erythromycin estolate, erythromycin derivative[1], is a macrolide antibiotic used in the treatment of a wide variety of bacterial infections. Erythromycin estolate causes several cases of liver injury which mostly include cholestatic hepatitis. Erythromycin estolate toxicity is related to its inhibitory effect on bile acid transport[2].

A macrolide antibiotic, produced by Streptomyces erythreus. It is the lauryl sulfate salt of the propionic ester of erythromycin. This erythromycin salt acts primarily as a bacteriostatic agent. 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.

Erythromycin estolate Basic Attributes

Molecular Weight：

1056.39000

Exact Mass：

1055.64000

EC Number：

222-532-4

DSSTox ID：

DTXSID1037224

HScode：

29419000

Characteristics

PSA：

271.96000

Density：

1.0053 (rough estimate)

Melting Point：

137 °C (decomp)

Boiling Point：

827.7ºC at 760 mmHg

Flash Point：

454.4ºC

Refractive Index：

1.6550 (estimate)

Water Solubility：

chloroform: soluble 4.0ML, clear, colorless (200 mg + 4.0 mL Chloroform)

Toxicity：

LD50 orally in rats: >5000 mg/kg (Goldenthal)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22; R42/43

safety instructions：

S22-S36

RTECS Number：

KF5775000

Marks：

Precautionary statement(s)：

P261-P280-P342 + P311

Hazard Statements：

H302-H317-H334

GHS Classification：

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P285, P301+P312, P302+P352, P304+P341, P321, P330, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 117 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)

MeSH Entry Terms：

Eromycin

Erythromycin estolate Use and Manufacturing

Used as an antibacterial agent. LD50 >5000 mg/kg for oral administration to rats

Computed Properties

Molecular Weight:1056.4
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:19
Rotatable Bond Count:22
Exact Mass:1055.64263642
Monoisotopic Mass:1055.64263642
Topological Polar Surface Area:272
Heavy Atom Count:72
Complexity:1550
Defined Atom Stereocenter Count:9
Undefined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Material

Erythromycin

Sodium dodecyl sulfate

Acetone

Drug Function and Efficacy

This product belongs to the macrolide antibiotics, which is the dodecyl sulfate of erythromycin propionate. It has antibacterial activity against Staphylococcus, various groups of streptococci and Gram-positive bacilli. Neisseria, Haemophilus influenzae, Bordetella pertussis, etc. may also be sensitive to this product. This product also has antibacterial activity against various anaerobic bacteria except Bacteroides fragilis and Fusobacterium; it also has inhibitory effects on Legionella, Campylobacter fetus, some spirochetes, Mycoplasma pneumoniae, Rickettsia and Chlamydia. This product is an antibacterial agent, but it also has a bactericidal effect on some bacteria at high concentrations. This product can pass through the bacterial cell membrane and reversibly bind to the 50S subunit of the bacterial ribosome near the donor site (P site), blocking the transfer RNA (t-RNA) binding to the P site, and also blocking the displacement of the polypeptide chain from the acceptor site (A site) to the P site, thereby inhibiting bacterial protein synthesis. This product is only effective against bacteria with active division.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Erythromycin Ester Tablets
Ingredients	Main ingredients: Erythromycin.
Indication	1. This product can inhibit the metabolism of anti-epileptic drugs such as carbamazepine and valproic acid, resulting in increased blood concentrations and toxic reactions. Combination with fentanyl can inhibit the metabolism of the latter and prolong its duration of action. Combination with antihistamines such as astemizole or terfenadine can increase cardiac toxicity, and combination with cyclosporine can increase the latter's blood concentration and produce nephrotoxicity. 2. This product has an antagonistic effect with chloramphenicol and lincosamides, and it is not recommended to use them at the same time. 3. This product is an antibacterial agent and can interfere with the bactericidal efficacy of penicillin. Therefore, when rapid bactericidal effects are required, such as the treatment of meningitis, the two should not be used at the same time. 4. Patients who take warfarin for a long time can prolong the prothrombin time when using this product, thereby increasing the risk of bleeding. Elderly patients should pay special attention. When the two must be used at the same time, the dose of warfarin should be appropriately adjusted and the prothrombin time should be closely observed. 5Except for dihydroxypropylphylline, the simultaneous use of this product with xanthine drugs can reduce the hepatic clearance of aminophylline, leading to increased serum aminophylline concentrations and (or) increased toxic reactions. This phenomenon is more likely to occur after 6 days of combined use, and the reduction in aminophylline clearance is proportional to the serum peak value of this product. Therefore, the dose of xanthine drugs should be adjusted during and after the combination of the two. 6This product may enhance hepatotoxicity when used in combination with other hepatotoxic drugs. 7The combination of large doses of this product with ototoxic drugs, especially in patients with renal impairment, may increase ototoxicity. 8When used in combination with lovastatin, its metabolism can be inhibited and blood concentrations can be increased, which may cause rhabdomyolysis; when used in combination with midazolam or triazolam, the clearance of both can be reduced and their effects can be enhanced.
Specifications	0.125 g (125,000 units) of erythromycin
Manufacturer	Sancai Shiqi Pharmaceutical Co., Ltd.

Erythromycin Granules
Ingredients	Main ingredients: Erythromycin.
Indication	1. This product can inhibit the metabolism of anti-epileptic drugs such as carbamazepine and valproic acid, resulting in increased blood concentrations and toxic reactions. Combination with fentanyl can inhibit the metabolism of the latter and prolong its duration of action. Combination with antihistamines such as astemizole or terfenadine can increase cardiac toxicity, and combination with cyclosporine can increase the latter's blood concentration and produce nephrotoxicity. 2. This product has an antagonistic effect with chloramphenicol and lincosamides, and it is not recommended to use them at the same time. 3. This product is an antibacterial agent and can interfere with the bactericidal efficacy of penicillin. Therefore, when rapid bactericidal effects are required, such as the treatment of meningitis, the two should not be used at the same time. 4. Patients who take warfarin for a long time can prolong the prothrombin time when using this product, thereby increasing the risk of bleeding. Elderly patients should pay special attention. When the two must be used at the same time, the dose of warfarin should be appropriately adjusted and the prothrombin time should be closely observed. 5Except for dihydroxypropylphylline, the simultaneous use of this product with xanthine drugs can reduce the hepatic clearance of aminophylline, leading to increased serum aminophylline concentrations and (or) increased toxic reactions. This phenomenon is more likely to occur after 6 days of combined use, and the reduction in aminophylline clearance is proportional to the serum peak value of this product. Therefore, the dose of xanthine drugs should be adjusted during and after the combination of the two. 6This product may enhance hepatotoxicity when used in combination with other hepatotoxic drugs. 7The combination of large doses of this product with ototoxic drugs, especially in patients with renal impairment, may increase ototoxicity. 8When used in combination with lovastatin, its metabolism can be inhibited and blood concentrations can be increased, which may cause rhabdomyolysis; when used in combination with midazolam or triazolam, the clearance of both can be reduced and their effects can be enhanced.
Specifications	75 mg (75,000 units) of erythromycin

Erythromycin Ester Tablets
Ingredients	Main ingredients: Erythromycin.
Indication	1. This product can inhibit the metabolism of anti-epileptic drugs such as carbamazepine and valproic acid, resulting in increased blood concentrations and toxic reactions. Combination with fentanyl can inhibit the metabolism of the latter and prolong its duration of action. Combination with antihistamines such as astemizole or terfenadine can increase cardiac toxicity, and combination with cyclosporine can increase the latter's blood concentration and produce nephrotoxicity. 2. This product has an antagonistic effect with chloramphenicol and lincosamides, and it is not recommended to use them at the same time. 3. This product is an antibacterial agent and can interfere with the bactericidal efficacy of penicillin. Therefore, when rapid bactericidal effects are required, such as the treatment of meningitis, the two should not be used at the same time. 4. Patients who take warfarin for a long time can prolong the prothrombin time when using this product, thereby increasing the risk of bleeding. Elderly patients should pay special attention. When the two must be used at the same time, the dose of warfarin should be appropriately adjusted and the prothrombin time should be closely observed. 5Except for dihydroxypropylphylline, the simultaneous use of this product with xanthine drugs can reduce the hepatic clearance of aminophylline, leading to increased serum aminophylline concentrations and (or) increased toxic reactions. This phenomenon is more likely to occur after 6 days of combined use, and the reduction in aminophylline clearance is proportional to the serum peak value of this product. Therefore, the dose of xanthine drugs should be adjusted during and after the combination of the two. 6This product may enhance hepatotoxicity when used in combination with other hepatotoxic drugs. 7The combination of large doses of this product with ototoxic drugs, especially in patients with renal impairment, may increase ototoxicity. 8When used in combination with lovastatin, its metabolism can be inhibited and blood concentrations can be increased, which may cause rhabdomyolysis; when used in combination with midazolam or triazolam, the clearance of both can be reduced and their effects can be enhanced.
Specifications	0.125 g (125,000 units) of erythromycin

See More Related Drugs

Registered Holders

CENTURY PHARMACEUTICALS LTD

United States
Active
CALYX CHEMICALS AND PHARMACEUTICALS LTD

United States
Active
Shanghai Yurui BIOTECHNOLOGY (Anyang) Pharmaceutical Co., Ltd.

China
Active

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