Drug Details

General Information of the Drug (ID: DR7688)
Name
Erythromycin
Synonyms
erythromycin; 114-07-8; Erythromycin A; E-Mycin; Erythrocin; Abomacetin; Erythromycinum; Erymax; Emgel; Eritromicina; Erythromycine; Erythro-Statin; Ilotycin; Erythromycin base; E-Glades; Ery-Tab; E-Base; Eryacne; Torlamicina; Erycette; Robimycin; Bristamycin; Erypar; erythro; Erythroguent; Eritrocina; Erythrogran; Stiemycin; Ermycin; Erycen; Erygel; Aknin; ERYC; Pfizer-E; Theramycin Z; Ak-Mycin; Erythromast 36; Erythromycin Lactate; T-Stat; Benzamycin; MFCD00084654; Emycin; Erytab; Inderm; Retcin; UNII-63937KV33D; CHEMBL532; erythromycin-A; Dumotrycin; Mephamycin; CHEBI:42355; Sansac; Wemid; (-)-ERYTHROMYCIN; Eryc Sprinkles; Erythra-Derm; A/T/S; Akne-Mycin; 63937KV33D; (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; R-P Mycin; Endoeritrin; Eritomicina; Erythroderm; Erytrociclin; Paediathrocin; Pharyngocin; Proterytrin; Acneryne; Acnesol; Aknemycin; Derimer; Deripil; Erisone; Eryacnen; Erydermer; Eryhexal; Erysafe; Iloticina; Latotryd; Lederpax; Mercina; Oftamolets; Pantoderm; Pantodrin; Primacine; Romycin; Stiemicyn; Tiloryth; Tiprocin; E-Solve 2; Emuvin; Erecin; Erymed; Erytop; NCI-C55674; AustriaS; Eros; Ery-maxin; Erythro-Teva; Sans-acne; DSSTox_CID_2991; Erimycin-T; Ery-Diolan; Inderm Gel; Del-Mycin; Aknederm Ery Gel; Udima Ery Gel; (-)-Erythromycin, 98%; Eryc 125; UNII-8HPH7ND0LN; DSSTox_RID_76820; DSSTox_GSID_22991; Emu-Ve; 8HPH7ND0LN; Skid Gel E; (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; Akne Cordes Losung; ERY; Ilosone (estolate); Ilotycin T.S.; E-Mycin (base); Ery-Tab (base); (-)-Erythromycin, Eur.Ph.; Emu-V; Ery-B; E-Base (base); ERYC (base); C-Solve-2; N-Methylerythromycin A; PCE Dispertab (base); Eryc-125; Eryc-250; Eritromicina [INN-Spanish]; Erythromycine [INN-French]; Erythromycinum [INN-Latin]; Oftalmolosa Cusi Eritromicina; Staticin (TN); Akne-mycin (TN); Erygel (TN); Eryc (TN); T-stat (TN); Pce (TN); SR-05000001618; Sentry AQ mardel maracyn; 7704-67-8; 9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione; erthromycin; Erythromycines; NSC55929; CCRIS 9078; NSC-55929; HSDB 3074; NCGC00094670-01; Erythromycin [USP:INN:BAN:JAN]; (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,; (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; CAS-114-07-8; Prestwick_205; EINECS 204-040-1; Erythromycin C-13; NSC 55929; Spectrum_000115; Spectrum_000659; AI3-50138; EM-A; Prestwick3_000151; Spectrum2_000759; Spectrum2_001263; Spectrum4_000538; Spectrum5_001596; E0751; Erythromycin A, B + C; EC 204-040-1; SCHEMBL2601; BSPBio_000282; BSPBio_002480; Erythromycin standard solution; KBioGR_001175; KBioSS_000555; KBioSS_001139; MLS001066618; BIDD:GT0017; DivK1c_000294; DivK1c_000397; DivK1c_000702; SPECTRUM1500280; SPBio_000778; SPBio_001226; BPBio1_000312; GTPL1456; DTXSID4022991; Erythromycin (JP17/USP/INN); HMS500O16; KBio1_000294; KBio1_000397; KBio1_000702; KBio2_000555; KBio2_001139; KBio2_003123; KBio2_003707; KBio2_005691; KBio2_006275; J01FA01; Erythromycin (mixture of A,B,C); NINDS_000294; NINDS_000397; NINDS_000702; HMS1920M04; HMS2091D05; HMS2095O04; HMS3712O04; Pharmakon1600-01500280; [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; ACT03320; HY-B0220; RKL10096; Tox21_111311; Tox21_111869; Tox21_300515; BDBM50344942; CCG-38992; LMPK04000006; NSC756759; ZINC85534336; Erythromycin, labeled with carbon-13; AKOS015895249; DB00199; MCULE-4566208867; NSC-756759; IDI1_000294; IDI1_000397; IDI1_000702; SMP1_000119; NCGC00179619-01; NCGC00179619-02; NCGC00179619-03; NCGC00254234-01; 82343-12-2; AC-12744; AC-12901; SMR000544946; Erythromycin, potency: >=850 mug per mg; Erythromycin, tested according to Ph.Eur.; SBI-0051368.P003; Erythromycin, N-demethyl-N-(methyl-11C)-; Erythromycin, meets USP testing specifications; C01912; D00140; E-3250; Erythromycin, plant cell culture tested, ~98%; 44496-EP2272846A1; 44496-EP2275422A1; 44496-EP2292608A1; 44496-EP2305644A1; 44496-EP2308866A1; 44496-EP2311814A1; 44496-EP2311828A1; 44496-EP2380568A1; AB00051981_09; AB00051981_10; Erythromycin standard solution, 1 mg/mL in H2O; Erythromycin, Biotechnology Performance Certified; 114E078; Erythromycin estolate impurity, free erythromycin-; Q213511; SR-01000799155; Erythromycin, Antibiotic for Culture Media Use Only; Erythromycin, BioReagent, suitable for cell culture; SR-01000799155-2; SR-05000001618-1; SR-05000001618-2; BRD-K63550407-001-13-5; BRD-K63550407-028-03-9; Erythromycin (mixture of A,B,C) 100 microg/mL in Acetonitrile; Erythromycin A, British Pharmacopoeia (BP) Reference Standard; Erythromycin A, European Pharmacopoeia (EP) Reference Standard; Erythromycin, United States Pharmacopeia (USP) Reference Standard; Erythromycin, for microbiological assay, European Pharmacopoeia (EP) Reference Standard; Erythromycin, Pharmaceutical Secondary Standard; Certified Reference Material; (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-3,5,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-; (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-6-[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione; (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione; (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-1-oxacyclotetradecane-2,10-dione; (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); 215031-94-0
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 7.3 +/- 3.9 mgh/L
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 1.8 mcg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.2 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The clearance of drug is 0.53 +/- 0.13 L/h/kg
Elimination
Under 5% of the orally administered dose of erythromycin is found excreted in the urine
Half-life
The concentration or amount of drug in body reduced by one-half in 3.5 hours
Metabolism
The drug is metabolized via the hepatic
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 90.87869 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.1%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.95 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 2.1 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C37H67NO13
PubChem CID
12560
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
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
CAS Number
CAS 114-07-8
ChEBI ID
CHEBI:42355
TTD Drug ID
D02YIZ
DrugBank ID
DB00199
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Pannarin      Pannaria tavaresii     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 The natural compound pannarin might be a good candidate for the individualization of novel templates for the development of new antimicrobial agents or combinations of drugs for chemotherapy.
          Spectinomycin      Legionella pneumophila     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Chlamydia trachomatis strains Microorganism model Chlamydia trachomatis
                    Experimental
                    Result(s)		 A combination of spectinomycin with erythromycin was found to be more effective against Chlamydia trachomatis.
          Caffeic acid + Chitosan     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Propionibacterium acnes KCTC 3314 Microorganism model Propionibacterium acnes
Staphylococcus aureus KCTC 1927 Microorganism model Staphylococcus aureus
Staphylococcus epidermidis KCTC 1370 Microorganism model Staphylococcus epidermidis
Pseudomonas aeruginosa KCTC 1637 Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 Among chitosan-conjugated derivatives, Chitosan-caffeic acid showed the highest antibacterial activity and also exhibited the synergistic antibacterial effect in combination with tetracycline, erythromycin, and lincomycin against acne-related bacteria.
Target and Pathway
Target(s) Bacterial 50S ribosomal RNA (Bact 50S rRNA)  Molecule Info  [5]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1456).
Reference 2 In vitro antimicrobial activity of pannarin alone and in combination with antibiotics against methicillin-resistant Staphylococcus aureus clinical isolates. Phytomedicine. 2012 May 15;19(7):596-602.
Reference 3 In vitro effects of spectinomycin and ceftriaxone alone or in combination with other antibiotics against Chlamydia trachomatis. Antimicrob Agents Chemother. 2005 Apr;49(4):1584-6.
Reference 4 Synergistic Antibacterial Effects of Chitosan-Caffeic Acid Conjugate against Antibiotic-Resistant Acne-Related Bacteria. Mar Drugs. 2017 Jun 8;15(6):167.
Reference 5 A synthetic alanyl-initiator tRNA with initiator tRNA properties as determined by fluorescence measurements: comparison to a synthetic alanyl-elongator tRNA. Nucleic Acids Res. 1991 Oct 25;19(20):5749-54.
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