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

Stem definitionDrug idCAS RN
1073 74-55-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ethambutol
  • etambutol
  • diambutol
  • (S,S)-Ethambutol
  • ethambutol hydrochloride
  • ethambutol dihydrochloride
  • ethambutol HCl
An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)
  • Molecular weight: 204.31
  • Formula: C10H24N2O2
  • CLOGP: 0.12
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 4
  • TPSA: 64.52
  • ALOGS: -1.43
  • ROTB: 9

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1.20 g O
1.20 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 79 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 122.36 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 77 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.18 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 6, 1967 FDA STI PHARMA 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 reaction with eosinophilia and systemic symptoms 644.44 19.22 242 9948 29306 46646566
Paradoxical drug reaction 443.05 19.22 103 10087 2273 46673599
Drug resistance 337.67 19.22 131 10059 17237 46658635
Drug-induced liver injury 267.72 19.22 124 10066 25244 46650628
Mycobacterium avium complex infection 261.79 19.22 69 10121 2579 46673293
Immune reconstitution inflammatory syndrome 254.29 19.22 80 10110 5645 46670227
Tuberculosis 248.71 19.22 91 10099 10174 46665698
Acute hepatic failure 223.59 19.22 93 10097 14628 46661244
Pulmonary tuberculosis 189.02 19.22 61 10129 4670 46671202
Tuberculoma of central nervous system 184.63 19.22 35 10155 268 46675604
Hepatitis 149.38 19.22 91 10099 32124 46643748
Hepatotoxicity 145.93 19.22 82 10108 24927 46650945
Disseminated tuberculosis 145.63 19.22 44 10146 2708 46673164
Optic neuropathy 140.87 19.22 39 10151 1757 46674115
Immune reconstitution inflammatory syndrome associated tuberculosis 140.15 19.22 29 10161 362 46675510
Drug interaction 137.83 19.22 194 9996 202900 46472972
Eosinophilia 117.52 19.22 65 10125 19152 46656720
Pyrexia 104.98 19.22 233 9957 348569 46327303
Hepatic encephalopathy 98.86 19.22 47 10143 10110 46665762
Jaundice 97.92 19.22 67 10123 28778 46647094
Rash maculo-papular 97.61 19.22 66 10124 27808 46648064
Mycobacterial infection 90.23 19.22 27 10163 1606 46674266
Hepatocellular injury 80.46 19.22 60 10130 29462 46646410
Hepatitis fulminant 74.42 19.22 28 10162 3374 46672498
Hepatitis toxic 70.41 19.22 26 10164 2974 46672898
Atypical mycobacterial infection 67.87 19.22 19 10171 891 46674981
Optic neuritis 67.48 19.22 32 10158 6839 46669033
Transaminases increased 61.68 19.22 50 10140 27711 46648161
Lymphadenopathy 61.41 19.22 54 10136 33434 46642438
Lymph node tuberculosis 56.83 19.22 16 10174 766 46675106
Meningitis tuberculous 56.79 19.22 15 10175 564 46675308
Alanine aminotransferase increased 54.65 19.22 81 10109 88370 46587502
Peritoneal tuberculosis 52.68 19.22 14 10176 539 46675333
Hepatic failure 51.72 19.22 49 10141 33367 46642505
Uveitis 49.46 19.22 28 10162 8613 46667259
Hepatitis B 48.29 19.22 21 10169 3672 46672200
Toxic optic neuropathy 46.61 19.22 10 10180 150 46675722
Fatigue 45.27 19.22 40 10150 608657 46067215
Aspartate aminotransferase increased 44.25 19.22 69 10121 78631 46597241
Pathogen resistance 44.03 19.22 23 10167 6037 46669835
Hypertransaminasaemia 42.90 19.22 19 10171 3469 46672403
Ocular toxicity 40.28 19.22 11 10179 470 46675402
Hepatic function abnormal 39.59 19.22 43 10147 34378 46641494
Transplant rejection 39.11 19.22 25 10165 9571 46666301
Fall 38.53 19.22 12 10178 329085 46346787
Granuloma 38.25 19.22 18 10172 3780 46672092
Serpiginous choroiditis 36.27 19.22 6 10184 18 46675854
Drug level decreased 36.12 19.22 20 10170 5892 46669980
Hemianopia heteronymous 35.81 19.22 7 10183 64 46675808
Visual acuity reduced 35.30 19.22 33 10157 22080 46653792
Choroiditis 35.27 19.22 8 10182 157 46675715
Pain in extremity 34.97 19.22 7 10183 258673 46417199
Pain 34.61 19.22 32 10158 476916 46198956
Tuberculosis gastrointestinal 33.70 19.22 9 10181 353 46675519
Visual field defect 32.90 19.22 19 10171 6064 46669808
Rheumatoid arthritis 31.44 19.22 7 10183 240208 46435664
Multiple-drug resistance 28.45 19.22 13 10177 2552 46673320
Neuropathy peripheral 26.32 19.22 60 10130 90833 46585039
Liver injury 25.77 19.22 24 10166 15977 46659895
Face oedema 25.72 19.22 26 10164 19127 46656745
Liver transplant rejection 25.31 19.22 10 10180 1373 46674499
Bovine tuberculosis 24.34 19.22 5 10185 60 46675812
Ototoxicity 24.11 19.22 9 10181 1060 46674812
Product dose omission issue 23.96 19.22 4 10186 168516 46507356
Gamma-glutamyltransferase increased 23.93 19.22 32 10158 31708 46644164
Cryptococcosis 22.28 19.22 8 10182 844 46675028
Pneumothorax 21.76 19.22 21 10169 14608 46661264
Immunosuppressant drug level decreased 21.58 19.22 8 10182 924 46674948
Immune system disorder 21.21 19.22 16 10174 7979 46667893
Thrombocytopenia 20.06 19.22 67 10123 126514 46549358
Acute respiratory distress syndrome 19.51 19.22 24 10166 21898 46653974
Tinnitus 19.49 19.22 27 10163 27646 46648226

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
Paradoxical drug reaction 808.30 18.61 197 13457 2465 29936359
Immune reconstitution inflammatory syndrome 580.66 18.61 200 13454 8901 29929923
Drug reaction with eosinophilia and systemic symptoms 422.80 18.61 222 13432 28266 29910558
Drug-induced liver injury 359.49 18.61 181 13473 21093 29917731
Tuberculosis 344.76 18.61 132 13522 7945 29930879
Drug resistance 270.60 18.61 147 13507 19986 29918838
Hepatotoxicity 259.28 18.61 138 13516 18007 29920817
Tuberculoma of central nervous system 199.45 18.61 42 13612 253 29938571
Mycobacterium avium complex infection 197.93 18.61 66 13588 2645 29936179
Jaundice 194.41 18.61 142 13512 32344 29906480
Immune reconstitution inflammatory syndrome associated tuberculosis 178.80 18.61 41 13613 384 29938440
Mycobacterial infection 158.61 18.61 50 13604 1671 29937153
Pulmonary tuberculosis 157.03 18.61 65 13589 4792 29934032
Disseminated tuberculosis 137.00 18.61 47 13607 2055 29936769
Hepatitis 116.47 18.61 90 13564 22266 29916558
Optic neuropathy 115.82 18.61 39 13615 1610 29937214
Optic neuritis 106.97 18.61 44 13610 3190 29935634
Meningitis tuberculous 98.90 18.61 27 13627 538 29938286
Immune system disorder 98.27 18.61 45 13609 4232 29934592
Atypical mycobacterial infection 89.68 18.61 27 13627 771 29938053
Drug interaction 88.57 18.61 244 13410 199324 29739500
Serpiginous choroiditis 80.61 18.61 16 13638 68 29938756
Acute hepatic failure 75.90 18.61 54 13600 11773 29927051
Pyrexia 74.07 18.61 297 13357 294192 29644632
Lymphadenopathy 73.79 18.61 72 13582 24304 29914520
Granuloma 67.26 18.61 29 13625 2363 29936461
Death 65.86 18.61 41 13613 357242 29581582
Drug level decreased 58.06 18.61 35 13619 5770 29933054
Hepatic failure 55.67 18.61 73 13581 33970 29904854
Skin disorder 54.54 18.61 44 13610 11564 29927260
Eosinophilia 53.55 18.61 58 13596 22102 29916722
Tuberculosis of central nervous system 52.94 18.61 13 13641 167 29938657
Condition aggravated 49.00 18.61 156 13498 137710 29801114
Tubulointerstitial nephritis 48.89 18.61 50 13604 17841 29920983
Fall 47.90 18.61 12 13642 181860 29756964
Ocular toxicity 47.39 18.61 12 13642 176 29938648
Liver function test abnormal 46.97 18.61 64 13590 30886 29907938
Hydrocephalus 46.17 18.61 27 13627 4210 29934614
Bone tuberculosis 45.20 18.61 13 13641 315 29938509
Cytomegalovirus chorioretinitis 44.22 18.61 24 13630 3244 29935580
Multiple-drug resistance 40.91 18.61 22 13632 2919 29935905
Tuberculosis gastrointestinal 40.58 18.61 11 13643 213 29938611
Lymph node tuberculosis 40.38 18.61 13 13641 465 29938359
Fatigue 39.73 18.61 53 13601 320620 29618204
Ototoxicity 39.49 18.61 17 13637 1379 29937445
Disseminated Bacillus Calmette-Guerin infection 37.52 18.61 9 13645 104 29938720
Cholestasis 36.96 18.61 51 13603 24899 29913925
Chylothorax 36.66 18.61 13 13641 627 29938197
Cachexia 35.24 18.61 27 13627 6584 29932240
Hepatic function abnormal 34.97 18.61 66 13588 41879 29896945
Hepatitis fulminant 34.93 18.61 22 13632 3919 29934905
Rash maculo-papular 34.75 18.61 50 13604 25368 29913456
Blindness 34.71 18.61 35 13619 12274 29926550
Optic atrophy 34.21 18.61 13 13641 763 29938061
Mycobacterium abscessus infection 33.89 18.61 12 13642 576 29938248
Alanine aminotransferase increased 31.96 18.61 90 13564 74186 29864638
Colour blindness 31.26 18.61 9 13645 219 29938605
Lymphopenia 31.00 18.61 34 13620 13129 29925695
Drug eruption 30.86 18.61 39 13615 17487 29921337
Lymphadenitis 30.06 18.61 15 13639 1705 29937119
Unmasking of previously unidentified disease 29.95 18.61 11 13643 587 29938237
Tuberculosis of eye 29.60 18.61 6 13648 29 29938795
Completed suicide 29.39 18.61 5 13649 99487 29839337
Transaminases increased 28.98 18.61 44 13610 23413 29915411
Vanishing bile duct syndrome 28.77 18.61 11 13643 657 29938167
Atrial fibrillation 28.69 18.61 7 13647 108117 29830707
Acid fast bacilli infection 28.50 18.61 7 13647 90 29938734
Hyperuricaemia 28.48 18.61 25 13629 7369 29931455
Myocardial infarction 28.20 18.61 11 13643 125614 29813210
Tuberculosis of genitourinary system 27.96 18.61 6 13648 40 29938784
Hepatitis toxic 27.26 18.61 15 13639 2082 29936742
Mitochondrial neurogastrointestinal encephalopathy 27.07 18.61 5 13649 13 29938811
Mycobacterium kansasii infection 26.65 18.61 8 13646 226 29938598
Papilloma 26.41 18.61 7 13647 124 29938700
Hepatocellular injury 26.27 18.61 44 13610 25427 29913397
Macular degeneration 24.98 18.61 14 13640 2014 29936810
Splenic abscess 24.59 18.61 8 13646 296 29938528
Pulmonary cavitation 24.42 18.61 10 13644 716 29938108
Granulomatous liver disease 24.21 18.61 9 13645 497 29938327
Aspartate aminotransferase increased 23.60 18.61 73 13581 63349 29875475
Constipation 23.56 18.61 11 13643 112895 29825929
Repetitive speech 23.39 18.61 6 13648 93 29938731
Pericarditis tuberculous 22.98 18.61 6 13648 100 29938724
Thrombocytopenia 22.94 18.61 123 13531 136921 29801903
Febrile neutropenia 22.87 18.61 10 13644 106683 29832141
Diaphragmatic injury 22.61 18.61 5 13649 39 29938785
Central nervous system vasculitis 22.46 18.61 8 13646 391 29938433
Product use in unapproved indication 22.22 18.61 79 13575 73614 29865210
Purpura 22.19 18.61 25 13629 9942 29928882
Thalamic infarction 22.01 18.61 9 13645 642 29938182
Lichenoid keratosis 21.91 18.61 13 13641 2081 29936743
Type III immune complex mediated reaction 21.89 18.61 7 13647 245 29938579
Pain 21.86 18.61 28 13626 172613 29766211
Diarrhoea 21.64 18.61 79 13575 334024 29604800
Toxic optic neuropathy 21.60 18.61 9 13645 673 29938151
Bovine tuberculosis 21.54 18.61 6 13648 129 29938695
Liver transplant rejection 21.33 18.61 13 13641 2185 29936639
Trisomy 21 21.23 18.61 8 13646 459 29938365
Dilatation intrahepatic duct acquired 20.99 18.61 5 13649 56 29938768
Pulmonary sequestration 20.91 18.61 5 13649 57 29938767
Cell death 20.73 18.61 13 13641 2298 29936526
Product dose omission issue 20.59 18.61 8 13646 91623 29847201
Axonal neuropathy 20.18 18.61 9 13645 795 29938029
Oral candidiasis 20.07 18.61 25 13629 11046 29927778
Granulomatous lymphadenitis 19.77 18.61 5 13649 73 29938751
Gastrointestinal disorder 19.50 18.61 41 13613 28096 29910728
Intra-abdominal haemorrhage 19.29 18.61 12 13642 2090 29936734
Urinary tract infection 19.09 18.61 5 13649 73654 29865170
Peritoneal tuberculosis 18.65 18.61 7 13647 397 29938427

Pharmacologic Action:

SourceCodeDescription
ATC J04AK02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Other drugs for treatment of tuberculosis
ATC J04AM03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Combinations of drugs for treatment of tuberculosis
ATC J04AM06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Combinations of drugs for treatment of tuberculosis
ATC J04AM07 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Combinations of drugs for treatment of tuberculosis
FDA EPC N0000175483 Antimycobacterial
CHEBI has role CHEBI:33231 antitubercular
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:78298 environmental contaminants
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000995 Antitubercular Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute tuberculosis indication 25629007
Pulmonary tuberculosis indication 154283005 DOID:2957
Tuberculosis of meninges off-label use 58437007
Atypical mycobacterial infection off-label use 111812000
Pulmonary Mycobacterium avium complex infection off-label use 186342000
Diabetic retinopathy contraindication 4855003 DOID:8947
Optic neuritis contraindication 66760008 DOID:1210
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Bilateral cataracts contraindication 95722004

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.58 Basic
pKa2 5.58 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
Cytochrome P450 3A4 Enzyme IC50 6.25 WOMBAT-PK
Cytochrome P450 3A5 Enzyme IC50 4.72 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR IC50 5.48 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR IC50 5.16 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR IC50 5.15 WOMBAT-PK
Probable arabinosyltransferase A Enzyme INHIBITOR CHEMBL CHEMBL
Probable arabinosyltransferase B Enzyme WOMBAT-PK
Probable arabinosyltransferase C Enzyme WOMBAT-PK
Probable arabinosyltransferase A Enzyme WOMBAT-PK

External reference:

IDSource
4019747 VUID
N0000147838 NUI
D00878 KEGG_DRUG
1070-11-7 SECONDARY_CAS_RN
4017912 VANDF
4019747 VANDF
C0014964 UMLSCUI
CHEBI:4877 CHEBI
95E PDB_CHEM_ID
14052 PUBCHEM_CID
CHEMBL44884 ChEMBL_ID
CHEMBL1788373 ChEMBL_ID
CHEMBL3140361 ChEMBL_ID
CHEMBL1628240 ChEMBL_ID
DB00330 DRUGBANK_ID
D004977 MESH_DESCRIPTOR_UI
1074 INN_ID
8G167061QZ UNII
142435 RXNORM
32076 MMSL
4692 MMSL
d00068 MMSL
002850 NDDF
004868 NDDF
24450004 SNOMEDCT_US
26346008 SNOMEDCT_US
387129004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0923 TABLET, FILM COATED 400 mg ORAL ANDA 18 sections
ETHAMBUTOL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-101 TABLET, FILM COATED 100 mg ORAL ANDA 17 sections
ETHAMBUTOL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-102 TABLET, FILM COATED 400 mg ORAL ANDA 17 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-2337 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 16 sections
Myambutol HUMAN PRESCRIPTION DRUG LABEL 1 50090-2607 TABLET, FILM COATED 400 mg ORAL NDA 17 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-3948 TABLET, FILM COATED 400 mg ORAL ANDA 18 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-5140 TABLET 100 mg ORAL ANDA 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-5142 TABLET 400 mg ORAL ANDA 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0977 TABLET 400 mg ORAL NDA 10 sections
Myambutol HUMAN PRESCRIPTION DRUG LABEL 1 54868-2876 TABLET 400 mg ORAL NDA 17 sections
Ethambutol HUMAN PRESCRIPTION DRUG LABEL 1 54868-6219 TABLET, FILM COATED 400 mg ORAL ANDA 17 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54879-001 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54879-002 TABLET, FILM COATED 400 mg ORAL NDA authorized generic 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55695-023 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55695-035 TABLET, FILM COATED 400 mg ORAL NDA authorized generic 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 61748-011 TABLET, FILM COATED 100 mg ORAL ANDA 17 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 61748-014 TABLET, FILM COATED 400 mg ORAL ANDA 17 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68084-280 TABLET 400 mg ORAL ANDA 18 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68151-0149 TABLET 100 mg ORAL ANDA 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68180-280 TABLET 100 mg ORAL ANDA 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68180-281 TABLET 400 mg ORAL ANDA 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68850-004 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 16 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68850-005 TABLET, FILM COATED 400 mg ORAL NDA authorized generic 16 sections
Myambutol HUMAN PRESCRIPTION DRUG LABEL 1 68850-010 TABLET, FILM COATED 100 mg ORAL NDA 17 sections
Myambutol HUMAN PRESCRIPTION DRUG LABEL 1 68850-012 TABLET, FILM COATED 400 mg ORAL NDA 17 sections
Myambutol HUMAN PRESCRIPTION DRUG LABEL 1 70518-2691 TABLET, FILM COATED 400 mg ORAL NDA 17 sections
Ethambutol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-2966 TABLET 400 mg ORAL ANDA 16 sections