Erythrocin

Base Information

• Chemical Name: Erythrocin
• CAS No.: 114-07-8
• Molecular Formula: C37H67NO13
• Molecular Weight: 733.938
• Hs Code.: 3004.20
• NSC Number: 55929
• DSSTox Substance ID: DTXSID90859206
• Wikidata: Q105275120
• ChEMBL ID: CHEMBL1671887
• Mol file: 114-07-8.mol

Synonyms:Erythrogran;Erythrocin;Erythromid;Propiocine;Abboticin;Dotycin;Erycinum;Ilocaps;Erycin;Kesso-Mycin;Taimoxin-F;ERYTHROMYCIN A DIHYDRATE;Erythromycin-13C,d3;erythro;Eritrocina;Erythroguent;IndermRetcin;Retcin;Erythromycin A dihydrate;Erythromycin sodium lauryl sulfate;MFCD00084654;6-{[4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy]-3,5,7,9,11,13-hexamethyloxacyclotetr;959119-26-7;adecane-2,10-dione (non-preferred name);Erythromycin octadecanoate (1:1);C37H67NO13.2H2O;Erythromycin, octadecanoate (salt);Octadecanoato de Eritromicina, (1:1);C37H67NO13.C18H36O2;Erythromycin, sodium salt;C37-H67-N-O13.2H2-O;C37-H67-N-O13.C18-H36-O2;CHEMBL1671887;component of Drixin (Salt/Mix);SCHEMBL15263177;BDBM86313;component of T-stat (Salt/Mix);DTXSID90859206;ULGZDMOVFRHVEP-UHFFFAOYSA-N;(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;BBL028236;NSC_12560;STK249736;AKOS005423023;CAS_114-07-8;SY070227;FT-0603313;FT-0625700;component of Benzedrex nasal spray (Salt/Mix);(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;(3S,4R,6S,7S,9S,12R,13R)-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;[3R-(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;6-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6 dimethyl-oxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-1 oxacyclotetradecane-2,10-dione;6-{[4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy]-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione (non-preferred name);Oxacyclotetradecane-2, 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]-, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-;Oxacyclotetradecane-2,10-dione, 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]-, [3R-(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)]-;Pentadecanoic acid, 3-[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-6,11,12,13-tetrahydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-5-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, .mu.-lactone, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-;Pentadecanoic acid,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-6,11,12,13-tetrahydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-5-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, .mu.-lactone, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-;WLN: 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

Chemical Property of Erythrocin

Chemical Property:

• Appearance/Colour: white to off white crystalline powder
• Vapor Pressure: 4.94E-31mmHg at 25°C
• Melting Point: 138-140 °C
• Refractive Index: -74 ° (C=2, EtOH)
• Boiling Point: 818.401 °C at 760 mmHg
• PKA: 8.8(at 25℃)
• Flash Point: 448.753 °C
• PSA: 193.91000
• Density: 1.209 g/cm³
• LogP: 1.78560
• Storage Temp.: 0-6°C
• Solubility.: ethanol: soluble
• Water Solubility.: Soluble in water at 2mg/ml
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 733.46124119
• Heavy Atom Count: 51
• Complexity: 1180

Purity/Quality:

Above 99% ^*data from raw suppliers

Erythromycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 42/43-36/37/38
• Safety Statements: 45-37-24-36-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
• Description: Erythromycin ethyl succinate is a mixed double ester pro-drug in which one carboxyl of succinic acid esterifies the C-2′ hydroxyl of erythromycin and the other ethanol. This pro-drug frequently is used in an oral suspension for pediatric use largely to mask the bitter taste of the drug. Film-coated tablets also are used to deal with this. Some cholestatic jaundice is associated with the use of EES. Erythromycin is a macrolide antibiotic that inhibits bacterial protein synthesis by targeting the 50S ribosomal subunit, blocking the progression of nascent polypeptide chains. It is active against a host of bacterial genera, including Streptococcus, Staphylococcus, and Haemophilus (MIC90s = 0.015-2.0 mg/l). Erythromycin (10-40 mg/kg) dose-dependently inhibits the growth of S. aureus in a mouse model of thigh infection. It also inhibits the cytochrome P450 (CYP450) isoform CYP3A4 in vitro with IC50 values of 33 and 27.3 μM for α-hydroxytriazolam and 4-hydroxytriazolam formation, respectively, following administration of triazolam, which is known to be metabolized primarily by CYP3A4. Formulations containing erythromycin have been used in the treatment of bacterial respiratory and skin infections, pertussis, and a variety of other bacterial infections.
• Uses: Macrolide antibacterial Erythromycin A is a 14-membered macrocyclic lactone with broad spectrum antibiotic activity, isolated from Saccharopolyspora erythraea (formerly Streptomyces erythreus) in 1952. Erythromycin is one of only a handful of microbial metabolites to have profoundly shaped the treatment of bacterial disease in the last 50 years. Erythromycin has given rise to new generations of semi-synthetic derivatives with improved stability and potency. Our product has been HPLC-purified to remove contaminants and degradation products. 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 Labeled Erythromycin, intended for use as an internal standard for the quantification of Erythromycin by GC- or LC-mass spectrometry.
• Indications: Erythromycin is an antibiotic in the macrolide family that also has promotility effects because it is a motilin agonist.
• Therapeutic Function: Antibacterial
• Clinical Use: Erythromycin is used (offlabel indication) to accelerate gastric emptying in diabetic gastroparesis and postoperative gastroparesis. Tachyphylaxis will occur, so it cannot be used uninterruptedly for long periods.
• Drug interactions: Potentially hazardous interactions with other drugsAminophylline and theophylline: inhibits aminophylline and theophylline metabolism; if erythromycin given orally decreased erythromycin concentration.Anti-arrhythmics: increased risk of ventricular arrhythmias with IV erythromycin and amiodarone - avoid; increased toxicity with disopyramide; increased risk of ventricular arrhythmias with dronedarone - avoid.Antibacterials: increased risk of ventricular arrhythmias with moxifloxacin and IV erythromycin - avoid; possibly increased rifabutin concentration - reduce rifabutin dose; concentration of bedaquiline possibly increased - avoid if for more than 14 days; possibly increased risk of ventricular arrhythmias with delamanid; avoid with fidaxomicin.Anticoagulants: enhanced effect of coumarins; concentration of edoxaban increased - reduce edoxaban dose.Antidepressants: avoid concomitant use with reboxetine; avoid IV erythromycin with citalopram and escitalopram, risk of ventricular arrhythmias; risk of ventricular arrhythmias with venlafaxine - avoid.Antiepileptics: increased carbamazepine concentration and possibly valproate.Antifungals: avoid with fluconazole.Antihistamines: possibly increases loratadine concentration; inhibits mizolastine metabolism - avoid concomitant use; concentration of rupatadine increased.Antimalarials: avoid with artemether/lumefantrine; increased risk of ventricular arrhythmias with piperaquine with artenimol - avoid.Antimuscarinics: avoid concomitant use with tolterodine.Antipsychotics: increased risk of ventricular arrhythmias with sulpiride and zuclopenthixol and IV erythromycin avoid; possibly increases clozapine concentration leading to increased risk of convulsions; possibly increased lurasidone concentration; possibly increased risk of ventricular arrhythmias with amisulpride, droperidol and pimozide - avoid; possibly increased quetiapine concentration Antivirals: concentration of both drugs increased with telaprevir and simeprevir, avoid with simeprevir; concentration increased by ritonavir; avoid with rilpivirine, concentration increased; increased risk of ventricular arrhythmias with saquinavir - avoid. Anxiolytics and hypnotics: inhibits midazolam and zopiclone metabolism; increases buspirone concentration.Atomoxetine: increased risk of ventricular arrhythmias with parenteral erythromycin.Avanafil: concentration of avanafil increased, max dose 100 mg every 48 hours.Calcium-channel blockers: possibly inhibit metabolism of calcium channel blockers; avoid with lercanidipine.Ciclosporin: markedly elevated ciclosporin blood levels - decreased levels on withdrawing drug. Monitor blood levels of ciclosporin carefully and adjust dose promptly as necessary.Cilostazol: concentration of cilostazol increased, reduce cilostazol to 50 mg twice daily.Clopidogrel: possibly reduced antiplatelet effectColchicine: increased risk of colchicine toxicity - suspend or reduce dose of colchicine, avoid in hepatic or renal impairment.Cytotoxics: possibly increased afatinib concentration, separate administration by 6-12 hours; concentration of axitinib increased - reduce axitinib dose; concentration of bosutinib possibly increased - avoid or reduce dose of bosutinib; concentration of cabozantinib, dasatinib and ibrutinib and possibly olaparib increased - avoid with dasatinib, reduce dose of ibrutinib, avoid or reduce dose of olaparib; concentration of everolimus possibly increased; increased risk of ventricular arrhythmias with IV erythromycin and vandetanib - avoid; possible interaction with docetaxel; increased risk of ventricular arrhythmias with arsenic trioxide; increases vinblastine toxicity - avoid.Diuretics: increased eplerenone concentration - reduce eplerenone dose.Domperidone: possible increased risk of ventricular arrhythmias - avoid.Ergot alkaloids: increase risk of ergotism - avoid concomitant use.5HT1 agonists: increased eletriptan concentration - avoid concomitant use.Ivabradine: increased risk of ventricular arrhythmias - avoid concomitant use.Ivacaftor: concentration of ivacaftor possibly increasedLipid-lowering drugs: possibly increased myopathy with atorvastatin; concentration of pravastatin increased; concentration of rosuvastatin reduced; avoid concomitant use with simvastatin.1 ; concentration of lomitapide possibly increased - avoid.Pentamidine: increased risk of ventricular arrhythmias with IV erythromycin.Sildenafil: concentration of sildenafil increased - reduce initial dose for ED or reduce frequency to twice daily for PAH.Sirolimus: concentration of both drugs increased.Tacrolimus: markedly elevated tacrolimus blood levels - decreased levels on withdrawing drug. Monitor blood levels of tacrolimus carefully and adjust dose promptly as necessaryTicagrelor: concentration of ticagrelor possibly increased.

Technology Process of Erythrocin

There total 49 articles about Erythrocin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.33%

erythromycin thiocyanate A (7704-67-8) → erythromycin (114-07-8)

Guidance literature:

With sodium hydroxide; In methanol; at 40 ℃; pH=9-9.8;

Reference yield: 84.0%

erythromycin A N-oxide (992-65-4) → erythromycin (114-07-8)

Guidance literature:

With hydrogen; Raney-Ni (W₄); In ethanol; at 25 ℃; for 1h;

DOI:10.1016/0040-4039(91)80777-4

Reference yield: 66.7%

(2',4''-O-bistrimethylsilyl)-6-O-methylerythromycinA-9[O-(1-ethoxy-1-methylethyl)]oxime (119665-62-2) → erythromycin (114-07-8)

Guidance literature:

With formic acid; water; sodium hydrogensulfite; In ethanol; for 8h; Heating;

upstream raw materials:

9-deoxo-9-iminoerythromycin A

9-N,11-O-benzylidene-9-deoxo-9-iminoerythromycin A

C₄₅H₇₄N₂O₁₂

C₄₄H₇₁ClN₂O₁₂

Downstream raw materials:

anhydroerythromycin A

(2S,3S,4R,6S)-6-Ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran-3-ol

O''-(3-Cyclopentyl-propionyl)-erythromycin

erythromycin propionate

Refernces

• 1、 -. "A NOVEL PROCESS OF LIBERATION OF ERYTHROMYCIN AND PREPARATION OF ITS SALTS". Page/Page column 12. . Retrieved 2014/09/29.
• 2、 -. "CRYSTALLIZING METHOD OF ERYTHROMYCIN". Page/Page column 3. . Retrieved 2011/07/30.