erythromycin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, produced by Streptomyces strains 1048 114-07-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • erythromycin gluceptate
  • erythromycin lactobionate
  • erythromycin stearate
  • erythromycin
  • Erythromycin A
  • erythrocin
A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. 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.
  • Molecular weight: 733.94
  • Formula: C37H67NO13
  • CLOGP: 1.61
  • LIPINSKI: 2
  • HAC: 14
  • HDO: 5
  • TPSA: 193.91
  • ALOGS: -3.20
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O
2 g O
1 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 2.10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 90.88 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 35 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.95 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.10 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 24, 1964 FDA ARBOR PHARMS LLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 4915.33 12.56 2162 15197 241663 46427040
International normalised ratio fluctuation 173.32 12.56 54 17305 2139 46666564
Bloody discharge 85.06 12.56 26 17333 965 46667738
Necrosis ischaemic 63.40 12.56 20 17339 825 46667878
Lyme disease 59.60 12.56 25 17334 2338 46666365
Exposure during pregnancy 57.14 12.56 125 17234 108087 46560616
Anaphylactic reaction 54.60 12.56 82 17277 53030 46615673
Seronegative arthritis 53.07 12.56 17 17342 737 46667966
Beta haemolytic streptococcal infection 51.07 12.56 21 17338 1868 46666835
Pneumonia streptococcal 49.79 12.56 20 17339 1675 46667028
Drug interaction 49.59 12.56 177 17182 202917 46465786
Drug intolerance 44.64 12.56 138 17221 146911 46521792
Amniotic cavity infection 42.02 12.56 16 17343 1162 46667541
Completed suicide 37.41 12.56 5 17354 145915 46522788
Rash 37.18 12.56 243 17116 356269 46312434
Caesarean section 35.46 12.56 37 17322 16566 46652137
Purpura senile 35.38 12.56 12 17347 623 46668080
Death 35.10 12.56 44 17315 335504 46333199
Ototoxicity 32.74 12.56 13 17346 1056 46667647
Pneumococcal infection 32.38 12.56 10 17349 384 46668319
Tarsal tunnel syndrome 31.16 12.56 11 17348 644 46668059
Umbilical erythema 30.84 12.56 7 17352 78 46668625
Vomiting 28.63 12.56 275 17084 452519 46216184
Death neonatal 28.26 12.56 8 17351 226 46668477
Serum sickness-like reaction 27.58 12.56 9 17350 414 46668289
Faecal volume decreased 26.84 12.56 7 17352 144 46668559
Wheezing 26.27 12.56 60 17299 53326 46615377
Infection 25.65 12.56 108 17251 133484 46535219
Oligohydramnios 25.51 12.56 19 17340 5446 46663257
Stevens-Johnson syndrome 25.41 12.56 37 17322 23260 46645443
Resorption bone increased 25.37 12.56 11 17348 1116 46667587
Infusion related reaction 24.70 12.56 4 17355 101204 46567499
Dislocation of vertebra 23.76 12.56 11 17348 1302 46667401
Vestibular disorder 23.34 12.56 11 17348 1355 46667348
Premature baby 23.08 12.56 31 17328 18081 46650622
Lip swelling 23.00 12.56 37 17322 25358 46643345
Mass excision 22.54 12.56 7 17352 274 46668429
Abortion spontaneous 22.52 12.56 50 17309 43596 46625107
Therapeutic product effect incomplete 21.54 12.56 71 17288 78082 46590621
Maternal drugs affecting foetus 21.01 12.56 17 17342 5501 46663202
Bronchial obstruction 20.62 12.56 10 17349 1312 46667391
Pain 20.22 12.56 100 17259 476848 46191855
Cardiac arrest neonatal 19.96 12.56 5 17354 87 46668616
Premature rupture of membranes 19.81 12.56 15 17344 4408 46664295
Pharyngeal oedema 18.79 12.56 25 17334 14446 46654257
Urticaria 18.64 12.56 90 17269 117802 46550901
Corneal perforation 18.51 12.56 7 17352 499 46668204
Hypersensitivity 18.45 12.56 107 17252 150214 46518489
Acute generalised exanthematous pustulosis 18.38 12.56 20 17339 9385 46659318
Thrombophlebitis superficial 18.18 12.56 15 17344 4988 46663715
Diffuse panbronchiolitis 17.75 12.56 3 17356 5 46668698
Fall 17.64 12.56 63 17296 329034 46339669
Infantile haemangioma 16.65 12.56 4 17355 58 46668645
Vertigo positional 16.60 12.56 11 17348 2619 46666084
Starvation ketoacidosis 15.95 12.56 4 17355 70 46668633
Stenotrophomonas infection 15.94 12.56 9 17350 1611 46667092
Ergot poisoning 15.45 12.56 5 17354 224 46668479
Drug tolerance decreased 15.10 12.56 11 17348 3048 46665655
Alopecia 14.28 12.56 24 17335 162390 46506313
Off label use 14.21 12.56 83 17276 379758 46288945
Corneal neovascularisation 14.13 12.56 4 17355 113 46668590
Anal candidiasis 14.11 12.56 3 17356 24 46668679
Product packaging issue 13.95 12.56 7 17352 989 46667714
Abdominal pain upper 13.85 12.56 97 17262 145208 46523495
Neutropenia 13.70 12.56 20 17339 143184 46525519
Anaemia 13.67 12.56 49 17310 255730 46412973
Enterocolitis 13.62 12.56 14 17345 6154 46662549
Arthralgia 13.46 12.56 80 17279 364523 46304180
Blepharitis 13.33 12.56 9 17350 2212 46666491
Nodule 13.13 12.56 22 17337 15583 46653120
Drug ineffective 13.01 12.56 176 17183 677662 45991041
SJS-TEN overlap 12.97 12.56 4 17355 153 46668550
Ketonuria 12.85 12.56 5 17354 385 46668318
Campylobacter gastroenteritis 12.75 12.56 5 17354 393 46668310

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 445.98 14.77 257 7676 68262 29876283
Product packaging issue 66.34 14.77 17 7916 464 29944081
Drug interaction 51.69 14.77 142 7791 199426 29745119
Dystonia 43.83 14.77 29 7904 9698 29934847
Hyphaema 39.97 14.77 11 7922 397 29944148
Stupor 36.14 14.77 17 7916 2936 29941609
Rhabdomyolysis 35.78 14.77 62 7871 63518 29881027
Obstruction gastric 34.79 14.77 12 7921 926 29943619
Oligohydramnios 33.36 14.77 9 7924 301 29944244
Pyloric stenosis 31.89 14.77 10 7923 572 29943973
Brain oedema 31.11 14.77 26 7907 12372 29932173
Foetal death 30.36 14.77 8 7925 244 29944301
Toxic epidermal necrolysis 30.07 14.77 30 7903 17910 29926635
Learning disorder 29.54 14.77 9 7924 467 29944078
Deafness bilateral 29.42 14.77 11 7922 1071 29943474
SAPHO syndrome 28.87 14.77 6 7927 62 29944483
Caesarean section 28.32 14.77 13 7920 2124 29942421
Premature baby 28.14 14.77 28 7905 16663 29927882
Product dispensing error 27.60 14.77 18 7915 5871 29938674
Foetal arrhythmia 27.13 14.77 6 7927 85 29944460
Maternal drugs affecting foetus 24.91 14.77 15 7918 4258 29940287
Acute generalised exanthematous pustulosis 24.65 14.77 17 7916 6081 29938464
Oculogyric crisis 23.50 14.77 10 7923 1365 29943180
Myasthenia gravis crisis 23.37 14.77 7 7926 343 29944202
Ototoxicity 23.35 14.77 10 7923 1386 29943159
Tricuspid valve disease 22.77 14.77 6 7927 183 29944362
Pneumonia mycoplasmal 22.65 14.77 7 7926 381 29944164
Respiratory acidosis 22.57 14.77 14 7919 4188 29940357
Hepatic necrosis 21.08 14.77 13 7920 3850 29940695
Accidental exposure to product 20.92 14.77 19 7914 10096 29934449
Vasculitic rash 19.99 14.77 8 7925 935 29943610
Torsade de pointes 19.97 14.77 16 7917 7174 29937371
Altered state of consciousness 19.20 14.77 25 7908 19894 29924651
Ischaemic hepatitis 19.15 14.77 9 7924 1550 29942995
Impaired gastric emptying 18.03 14.77 11 7922 3195 29941350
Myoglobinuria 17.84 14.77 7 7926 777 29943768
Hepatic failure 17.58 14.77 32 7901 34011 29910534
Cardio-respiratory arrest neonatal 17.55 14.77 3 7930 9 29944536
Stevens-Johnson syndrome 16.86 14.77 22 7911 17534 29927011
Pupillary disorder 16.85 14.77 5 7928 237 29944308
Neonatal disorder 16.71 14.77 7 7926 919 29943626
Brain herniation 16.48 14.77 11 7922 3729 29940816
Febrile neutropenia 16.48 14.77 4 7929 106689 29837856
Exposure during pregnancy 16.47 14.77 16 7917 9245 29935300
Sepsis neonatal 16.46 14.77 5 7928 257 29944288
Premature rupture of membranes 16.18 14.77 3 7930 16 29944529
Multiple organ dysfunction syndrome 16.16 14.77 45 7888 63442 29881103
Conjunctival hyperaemia 15.97 14.77 9 7924 2258 29942287
Liver injury 15.92 14.77 18 7915 12382 29932163
Swelling face 15.06 14.77 23 7910 21181 29923364
Pneumonia escherichia 14.96 14.77 5 7928 350 29944195

Pharmacologic Action:

SourceCodeDescription
ATC D10AF02 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Antiinfectives for treatment of acne
ATC D10AF52 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Antiinfectives for treatment of acne
ATC J01FA01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
Macrolides
ATC S01AA17 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antibiotics
FDA CS M0028311 Macrolides
FDA PE N0000009982 Decreased Sebaceous Gland Activity
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011500 Protein Synthesis Inhibitors
FDA EPC N0000175877 Macrolide
FDA EPC N0000175935 Macrolide Antimicrobial

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Listeriosis indication 4241002 DOID:11573
Gonorrhea indication 15628003 DOID:7551
Infection of skin AND/OR subcutaneous tissue indication 19824006
Acute gonococcal cervicitis indication 20943002 DOID:10615
Pertussis indication 27836007
Acute gonococcal urethritis indication 29864006
Neonatal conjunctivitis indication 34298002 DOID:9699
Gonorrhea of rectum indication 42746002
Pneumonia due to Mycoplasma pneumoniae indication 46970008
Bacterial pneumonia indication 53084003 DOID:874
Acute gonococcal endometritis indication 65295003 DOID:7527
Acute bacterial sinusitis indication 75498004
Syphilis indication 76272004
Pneumococcal pharyngitis indication 76651006
Nongonococcal urethritis indication 84619001
Acne vulgaris indication 88616000
Urethritis due to Chlamydia trachomatis indication 179101003
Chlamydial conjunctivitis indication 231861005 DOID:13800
Pneumococcal pneumonia indication 233607000
Chlamydial pneumonia indication 233609002
Neonatal pneumonia indication 233619008
Erythrasma indication 238418005 DOID:4131
Streptococcus pyogenes infection indication 302809008
Infective otitis media indication 312218008
Diphtheria indication 397428000
Infection due to Staphylococcus aureus indication 406602003
Recurrent Persistent Urethritis indication
Superficial Ocular Infection indication
Preoperative Bowel Preparation indication
Prevention of Bacterial Endocarditis indication
Chlamydia Cervicitis indication
Rectal Chlamydia Trachomatis Infection indication
Prevention of Neonatal Ophthalmia indication
Pneumococcal Acute Otitis Media indication
Legionnaires' Disease indication
Rheumatic Fever Prevention indication
Haemophilus Influenzae Acute Otitis Media indication
Trachoma off-label use 2576002 DOID:11265
Inhalational anthrax off-label use 11389007
Actinomycotic infection off-label use 11817007 DOID:8478
Enteric campylobacteriosis off-label use 18081009
Lyme disease off-label use 23502006 DOID:11729
Granuloma inguinale off-label use 28867007 DOID:9113
Sinusitis off-label use 36971009
Erysipelas off-label use 44653001 DOID:11330
Blepharoconjunctivitis off-label use 68659002 DOID:2456
Cutaneous anthrax off-label use 84980006 DOID:7426
Ecthyma off-label use 85791004
Gastrointestinal anthrax off-label use 111798006 DOID:13386
Bacterial conjunctivitis off-label use 128350005 DOID:9700
Bacterial infection of skin off-label use 128936008
Lymphogranuloma venereum off-label use 186946009 DOID:13819
Gastroesophageal reflux disease off-label use 235595009 DOID:8534
Gastroparesis off-label use 235675006
Chancroid off-label use 266143009 DOID:13778
Meibomianitis off-label use 309779001
Infective blepharitis off-label use 312219000
Bacterial keratitis off-label use 314557000
Erysipeloid off-label use 400105005
Anthrax off-label use 409498004 DOID:7427
Relapsing fever off-label use 420079008 DOID:13034
Gastroscopy Adjunct off-label use
Listeria Monocytogenes Septicemia off-label use
Ureaplasma Pneumonia off-label use
Torsades de pointes contraindication 31722008
Third trimester pregnancy contraindication 41587001
Megaloblastic anemia due to folate deficiency contraindication 85649008 DOID:14026
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Cholestatic hepatitis contraindication 95556007
Anemia due to enzyme deficiency contraindication 111577008
Prolonged QT interval contraindication 111975006
Hearing disorder contraindication 128540005
Liver function tests abnormal contraindication 166603001
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Disease of liver contraindication 235856003 DOID:409
Pseudomembranous enterocolitis contraindication 397683000
Erythroderma contraindication 399992009
Porphyria contraindication 418470004
Congenital long QT syndrome contraindication 442917000
Inflammatory dermatosis contraindication 703938007

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.65 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Aldehyde oxidase Enzyme IC50 4.82 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 7.41 CHEMBL
Motilin receptor GPCR Ki 4.43 CHEMBL
Bile salt export pump Transporter IC50 5.39 CHEMBL

External reference:

IDSource
4017594 VUID
N0000145975 NUI
D00140 KEGG_DRUG
23067-13-2 SECONDARY_CAS_RN
4017591 VANDF
4017594 VANDF
4017595 VANDF
4017596 VANDF
C0699338 UMLSCUI
CHEBI:42355 CHEBI
ERY PDB_CHEM_ID
CHEMBL532 ChEMBL_ID
CHEMBL1200506 ChEMBL_ID
CHEMBL1200510 ChEMBL_ID
CHEMBL2110577 ChEMBL_ID
CHEMBL3545060 ChEMBL_ID
DB00199 DRUGBANK_ID
D004917 MESH_DESCRIPTOR_UI
C010948 MESH_SUPPLEMENTAL_RECORD_UI
C011462 MESH_SUPPLEMENTAL_RECORD_UI
12560 PUBCHEM_CID
1456 IUPHAR_LIGAND_ID
39 INN_ID
63937KV33D UNII
24346 RXNORM
33316 MMSL
3627 MMSL
4675 MMSL
4678 MMSL
4679 MMSL
4680 MMSL
4769 MMSL
4799 MMSL
72164 MMSL
d00046 MMSL
002755 NDDF
002758 NDDF
002759 NDDF
002760 NDDF
30427009 SNOMEDCT_US
372694001 SNOMEDCT_US
39152007 SNOMEDCT_US
698006 SNOMEDCT_US
83981000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-5571 TABLET, FILM COATED 250 mg ORAL ANDA 23 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 0093-5572 TABLET, FILM COATED 500 mg ORAL ANDA 23 sections
ERYGEL HUMAN PRESCRIPTION DRUG LABEL 1 0378-8075 GEL 20 mg TOPICAL NDA 18 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8212 GEL 20 mg TOPICAL NDA authorized generic 18 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 0404-7191 OINTMENT 5 mg OPHTHALMIC ANDA 18 sections
Erythrocin Lactobionate HUMAN PRESCRIPTION DRUG LABEL 1 0409-6476 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 13 sections
Erythrocin Lactobionate HUMAN PRESCRIPTION DRUG LABEL 1 0409-6482 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS NDA 13 sections
erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 0574-4024 OINTMENT 5 mg OPHTHALMIC ANDA 18 sections
Erythrocin Stearate HUMAN PRESCRIPTION DRUG LABEL 1 10544-594 TABLET, FILM COATED 250 mg ORAL ANDA 23 sections
Erythrocin Stearate HUMAN PRESCRIPTION DRUG LABEL 1 10544-595 TABLET, FILM COATED 500 mg ORAL ANDA 23 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 13668-606 TABLET, COATED 250 mg ORAL ANDA 14 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 13668-607 TABLET, COATED 500 mg ORAL ANDA 14 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 13985-605 OINTMENT 5 mg OPHTHALMIC ANDA 18 sections
ERYTHROMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-088 CAPSULE, DELAYED RELEASE 250 mg ORAL ANDA 22 sections
ERY-TAB HUMAN PRESCRIPTION DRUG LABEL 1 16590-089 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 27 sections
ERYTHROMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-090 OINTMENT 5 mg OPHTHALMIC ANDA 9 sections
ERYTHROMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-091 TABLET, FILM COATED 250 mg ORAL ANDA 17 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 17478-070 OINTMENT 5 mg OPHTHALMIC ANDA 19 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 17478-824 OINTMENT 5 mg OPHTHALMIC ANDA 18 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 21695-173 OINTMENT 5 mg OPHTHALMIC ANDA 15 sections
ERYTHROMYCIN Base Filmtab HUMAN PRESCRIPTION DRUG LABEL 1 21695-387 TABLET, FILM COATED 250 mg ORAL ANDA 24 sections
ERYTHROMYCIN Base Filmtab HUMAN PRESCRIPTION DRUG LABEL 1 21695-389 TABLET, FILM COATED 500 mg ORAL ANDA 24 sections
ERY-TAB HUMAN PRESCRIPTION DRUG LABEL 1 21695-457 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 23 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 24208-910 OINTMENT 5 mg OPHTHALMIC ANDA 17 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 24338-102 TABLET, FILM COATED 250 mg ORAL ANDA 27 sections
Erythromycin HUMAN PRESCRIPTION DRUG LABEL 1 24338-104 TABLET, FILM COATED 500 mg ORAL ANDA 27 sections
Erythrocin Stearate HUMAN PRESCRIPTION DRUG LABEL 1 24338-106 TABLET, FILM COATED 250 mg ORAL ANDA 27 sections
ERYTHROMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 24338-120 CAPSULE, DELAYED RELEASE 250 mg ORAL ANDA 27 sections
ERY-TAB HUMAN PRESCRIPTION DRUG LABEL 1 24338-122 TABLET, DELAYED RELEASE 250 mg ORAL ANDA 27 sections
ERY-TAB HUMAN PRESCRIPTION DRUG LABEL 1 24338-124 TABLET, DELAYED RELEASE 333 mg ORAL ANDA 27 sections