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

Stem definitionDrug idCAS RN
angiotensin-converting enzyme inhibitors 299 86541-75-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • benazepril
  • cibacen
  • benazepril hydrochloride
  • benazepril HCl
prodrug of benazeprilat inhibit angiotensin-converting enzyme (ACE) and results in decreased plasma angiotensin II, which leads to decreased vasopressor activity and to decreased aldosterone secretion
  • Molecular weight: 424.50
  • Formula: C24H28N2O5
  • CLOGP: 1.82
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 95.94
  • ALOGS: -4.61
  • ROTB: 10

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
7.50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 78 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.13 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 18 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
June 25, 1991 FDA US PHARMS HOLDINGS I

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
Cardiac failure congestive 187.39 12.21 212 22116 92545 53234193
Angioedema 166.12 12.21 139 22189 41937 53284801
Myocardial infarction 146.90 12.21 194 22134 99160 53227578
Cerebrovascular accident 129.43 12.21 188 22140 104986 53221752
Coronary artery disease 114.77 12.21 102 22226 33335 53293403
Maternal exposure during pregnancy 52.99 12.21 3 22325 155636 53171102
Completed suicide 49.07 12.21 148 22180 138053 53188685
Off label use 44.69 12.21 81 22247 472131 52854607
Rheumatoid arthritis 44.18 12.21 40 22288 314491 53012247
Drug ineffective 43.90 12.21 185 22143 817060 52509678
Contraindicated product administered 42.22 12.21 4 22324 135625 53191113
Chest pain 41.10 12.21 173 22155 190012 53136726
Swollen tongue 40.27 12.21 57 22271 31023 53295715
Blood pressure inadequately controlled 37.05 12.21 24 22304 4887 53321851
Transient ischaemic attack 35.62 12.21 58 22270 35667 53291071
Drug intolerance 35.49 12.21 21 22307 205472 53121266
Dizziness 32.91 12.21 267 22061 371992 52954746
Treatment failure 30.55 12.21 8 22320 128395 53198343
Carotid artery stenosis 28.34 12.21 21 22307 5306 53321432
Infusion related reaction 28.27 12.21 15 22313 155942 53170796
Product complaint 28.13 12.21 30 22298 12227 53314511
Systemic lupus erythematosus 27.66 12.21 9 22319 125405 53201333
Cardiac disorder 26.65 12.21 60 22268 46906 53279832
Oropharyngeal swelling 26.54 12.21 11 22317 885 53325853
Hypertension 26.38 12.21 173 22155 225258 53101480
Vasodilatation 25.90 12.21 15 22313 2502 53324236
Exposure during pregnancy 25.76 12.21 10 22318 124850 53201888
Oedema peripheral 25.70 12.21 140 22188 170647 53156091
Arteriosclerosis 25.45 12.21 26 22302 10085 53316653
Hyperdynamic left ventricle 25.28 12.21 7 22321 161 53326577
Mitral valve incompetence 24.07 12.21 35 22293 19516 53307222
Angina unstable 24.07 12.21 22 22306 7446 53319292
Wound 23.16 12.21 5 22323 91552 53235186
Kounis syndrome 22.50 12.21 11 22317 1304 53325434
Glossodynia 22.46 12.21 7 22321 100284 53226454
Pyrexia 21.69 12.21 91 22237 403102 52923636
Blood pressure increased 20.35 12.21 114 22214 140365 53186373
Renal failure 19.80 12.21 100 22228 118352 53208386
Acute myocardial infarction 19.46 12.21 43 22285 33192 53293546
Dehydration 18.93 12.21 128 22200 168282 53158456
Swelling face 18.21 12.21 59 22269 57109 53269629
Cardiovascular disorder 17.93 12.21 24 22304 12389 53314349
Palpitations 17.52 12.21 87 22241 102261 53224477
Gastrointestinal haemorrhage 17.25 12.21 73 22255 80257 53246481
Reaction to excipient 16.96 12.21 9 22319 1266 53325472
Coronary arterial stent insertion 16.88 12.21 12 22316 2842 53323896
Tricuspid valve incompetence 16.61 12.21 25 22303 14371 53312367
C-reactive protein increased 16.58 12.21 4 22324 67882 53258856
Arteriosclerosis coronary artery 16.48 12.21 19 22309 8435 53318303
Blood glucose increased 16.38 12.21 70 22258 77291 53249447
Product use in unapproved indication 16.07 12.21 14 22314 112275 53214463
Emotional distress 15.84 12.21 39 22289 32278 53294460
Hiatus hernia 15.81 12.21 29 22299 19591 53307147
Drug abuse 15.74 12.21 4 22324 65522 53261216
Renal injury 15.63 12.21 20 22308 9884 53316854
Muscle spasms 15.47 12.21 103 22225 134692 53192046
Blood urea increased 15.43 12.21 34 22294 26197 53300541
Gastrooesophageal reflux disease 15.40 12.21 72 22256 82591 53244147
Pericarditis 15.34 12.21 4 22324 64402 53262336
Fear 15.22 12.21 26 22302 16615 53310123
Keratoacanthoma 14.98 12.21 6 22322 442 53326296
Leukopenia 14.96 12.21 6 22322 73457 53253281
Injury 14.80 12.21 51 22277 50920 53275818
Vasoplegia syndrome 14.33 12.21 8 22320 1244 53325494
Drug interaction 14.06 12.21 46 22282 219283 53107455
Atrial fibrillation 13.84 12.21 87 22241 111565 53215173
Mental status changes 13.66 12.21 42 22286 39529 53287209
Neutropenia 13.53 12.21 29 22299 159156 53167582
Coronary artery occlusion 13.50 12.21 17 22311 8270 53318468
Depression 13.36 12.21 126 22202 182926 53143812
Product use issue 13.10 12.21 24 22304 139560 53187178
Rhabdomyolysis 12.80 12.21 44 22284 43879 53282859
Cardiomegaly 12.72 12.21 25 22303 17775 53308963
Therapeutic product effect decreased 12.33 12.21 21 22307 125634 53201104

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
Angioedema 241.37 12.53 183 17900 36106 32459337
Myocardial infarction 168.62 12.53 272 17811 125404 32370039
Cardiac failure congestive 149.94 12.53 209 17874 84643 32410800
Coronary artery disease 126.68 12.53 147 17936 49559 32445884
Cerebrovascular accident 99.80 12.53 175 17908 86145 32409298
Off label use 49.15 12.53 59 18024 306261 32189182
Swollen tongue 39.22 12.53 43 18040 13596 32481847
Drug abuse 33.58 12.53 3 18080 80240 32415203
Product complaint 29.42 12.53 25 18058 5778 32489665
Drug interaction 27.16 12.53 50 18033 218135 32277308
Chest pain 24.69 12.53 135 17948 124002 32371441
Injury 24.23 12.53 44 18039 22201 32473242
Blood pressure inadequately controlled 23.25 12.53 16 18067 2706 32492737
Coronary artery bypass 21.99 12.53 20 18063 5056 32490387
Nodular rash 21.52 12.53 6 18077 105 32495338
Emotional distress 21.36 12.53 35 18048 16271 32479172
Neutropenia 20.07 12.53 30 18053 142145 32353298
Dizziness 20.03 12.53 191 17892 209427 32286016
Angina unstable 19.64 12.53 29 18054 12326 32483117
Toxicity to various agents 19.42 12.53 44 18039 177997 32317446
Completed suicide 19.32 12.53 102 17981 92415 32403028
Acute myocardial infarction 19.31 12.53 71 18012 55078 32440365
Asthenia 19.20 12.53 208 17875 235736 32259707
Blood glucose increased 18.80 12.53 79 18004 65162 32430281
Lip swelling 18.64 12.53 30 18053 13735 32481708
Product use in unapproved indication 18.42 12.53 13 18070 87191 32408252
Lymphomatoid papulosis 18.16 12.53 6 18077 190 32495253
Pyrexia 16.67 12.53 107 17976 319861 32175582
Arteriosclerosis 16.26 12.53 25 18058 11009 32484434
Blood pressure increased 15.55 12.53 86 17997 79268 32416175
Blood gases abnormal 15.21 12.53 6 18077 318 32495125
Hyperlipidaemia 14.91 12.53 28 18055 14483 32480960
Interstitial lung disease 14.66 12.53 9 18074 64992 32430451
Hypertension 14.58 12.53 124 17959 131626 32363817
Pancreatitis 14.10 12.53 50 18033 38101 32457342
Shock 13.98 12.53 37 18046 24077 32471366
Foetal exposure during pregnancy 13.88 12.53 3 18080 41298 32454145
Hepatic function abnormal 13.63 12.53 4 18079 44836 32450607
Creatinine urine increased 13.48 12.53 5 18078 224 32495219
Transient ischaemic attack 13.38 12.53 38 18045 25756 32469687
Coronary arterial stent insertion 13.29 12.53 14 18069 4228 32491215
Delirium 13.26 12.53 4 18079 44042 32451401
Electrocardiogram QT prolonged 13.07 12.53 3 18080 39638 32455805
Platelet count decreased 12.74 12.53 28 18055 114563 32380880

Pharmacologic Action:

SourceCodeDescription
ATC C09AA07 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ACE INHIBITORS, PLAIN
ACE inhibitors, plain
ATC C09BA07 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ACE INHIBITORS, COMBINATIONS
ACE inhibitors and diuretics
FDA MoA N0000000181 Angiotensin-converting Enzyme Inhibitors
FDA EPC N0000175562 Angiotensin Converting Enzyme Inhibitor
CHEBI has role CHEBI:35457 ACE inhibitor
CHEBI has role CHEBI:50266 Prodrugs
MeSH PA D000806 Angiotensin-Converting Enzyme Inhibitors
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011480 Protease Inhibitors
FDA PE N0000178477 Decreased Blood Pressure

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Chronic heart failure off-label use 48447003
Atrial fibrillation off-label use 49436004 DOID:0060224
Diabetic renal disease off-label use 127013003
Acute scleroderma renal crisis off-label use 236503001
Diastolic heart failure off-label use 418304008 DOID:9775
Hypertension due to Scleroderma off-label use
Nondiabetic Proteinuric Nephropathy off-label use
Anuria contraindication 2472002 DOID:2983
Hypercholesterolemia contraindication 13644009
Hyperkalemia contraindication 14140009
Jaundice contraindication 18165001
Secondary angle-closure glaucoma contraindication 21571006
Hypovolemia contraindication 28560003
Dehydration contraindication 34095006
Hyperuricemia contraindication 35885006 DOID:1920
Angioedema contraindication 41291007 DOID:1558
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Sympathectomy contraindication 57071006
Hepatic failure contraindication 59927004
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Hypochloremic alkalosis contraindication 70134007
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Chronic idiopathic constipation contraindication 82934008
Hereditary angioneurotic edema contraindication 82966003 DOID:14735
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Disorder of connective tissue contraindication 105969002 DOID:65
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Neonatal hyperbilirubinemia contraindication 281610001
Pregnancy, function contraindication 289908002
Renal artery stenosis contraindication 302233006
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Azotemia contraindication 445009001
Intestinal Angioedema contraindication
Head and Neck Angioedema contraindication
Hemodialysis with High-Flux Membrane contraindication
Severe Aortic Valve Stenosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.9 acidic
pKa2 5.34 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
Angiotensin-converting enzyme Enzyme INHIBITOR IC50 6.51 WOMBAT-PK CHEMBL
Angiotensin-converting enzyme Enzyme IC50 8.70 CHEMBL
Angiotensin-converting enzyme Enzyme IC50 8.77 CHEMBL

External reference:

IDSource
4020817 VUID
N0000148336 NUI
D00620 KEGG_DRUG
86541-74-4 SECONDARY_CAS_RN
86541-78-8 SECONDARY_CAS_RN
1546196 RXNORM
C0053091 UMLSCUI
CHEBI:3011 CHEBI
CHEBI:88200 CHEBI
CHEMBL838 ChEMBL_ID
CHEMBL1694 ChEMBL_ID
DB00542 DRUGBANK_ID
C044946 MESH_SUPPLEMENTAL_RECORD_UI
5362124 PUBCHEM_CID
6374 IUPHAR_LIGAND_ID
C052133 MESH_SUPPLEMENTAL_RECORD_UI
6375 IUPHAR_LIGAND_ID
6129 INN_ID
6128 INN_ID
UDM7Q7QWP8 UNII
5463984 PUBCHEM_CID
DB14125 DRUGBANK_ID
JRM708L703 UNII
1267 MMSL
4251 MMSL
48720 MMSL
d00730 MMSL
003597 NDDF
003598 NDDF
108572003 SNOMEDCT_US
108573008 SNOMEDCT_US
372511001 SNOMEDCT_US
4020025 VANDF
4020817 VANDF
C0105523 UMLSCUI
CHEMBL1192519 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Lotrel HUMAN PRESCRIPTION DRUG LABEL 2 0078-0364 CAPSULE 20 mg ORAL NDA 31 sections
Lotrel HUMAN PRESCRIPTION DRUG LABEL 2 0078-0379 CAPSULE 40 mg ORAL NDA 31 sections
Lotrel HUMAN PRESCRIPTION DRUG LABEL 2 0078-0405 CAPSULE 10 mg ORAL NDA 31 sections
Lotrel HUMAN PRESCRIPTION DRUG LABEL 2 0078-0406 CAPSULE 20 mg ORAL NDA 31 sections
Benazepril Hydrochloride and Hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0185-0211 TABLET, FILM COATED 20 mg ORAL ANDA 21 sections
Benazepril Hydrochloride and Hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0185-0236 TABLET, FILM COATED 5 mg ORAL ANDA 21 sections
Benazepril Hydrochloride and Hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0185-0277 TABLET, FILM COATED 20 mg ORAL ANDA 21 sections
Benazepril Hydrochloride and Hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0185-0325 TABLET, FILM COATED 10 mg ORAL ANDA 21 sections
benazepril hydrochloride and hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0574-0227 TABLET 10 mg ORAL NDA authorized generic 23 sections
benazepril hydrochloride and hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0574-0228 TABLET 20 mg ORAL NDA authorized generic 23 sections
benazepril hydrochloride and hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0574-0229 TABLET 20 mg ORAL NDA authorized generic 23 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-554 TABLET 20 mg ORAL ANDA 13 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-561 TABLET, FILM COATED 40 mg ORAL ANDA 13 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-566 TABLET 10 mg ORAL ANDA 13 sections
BENAZEPRIL HUMAN PRESCRIPTION DRUG LABEL 1 16590-259 TABLET 20 mg ORAL ANDA 13 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16590-280 TABLET 10 mg ORAL ANDA 12 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-327 TABLET, FILM COATED 20 mg ORAL ANDA 19 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-612 TABLET, FILM COATED 5 mg ORAL ANDA 19 sections
Amlobenz HUMAN PRESCRIPTION DRUG LABEL 2 21695-866 CAPSULE 10 mg ORAL ANDA 27 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-877 TABLET, FILM COATED 40 mg ORAL ANDA 19 sections
Amlobenz HUMAN PRESCRIPTION DRUG LABEL 2 21695-916 CAPSULE 20 mg ORAL ANDA 27 sections
Lotensin HUMAN PRESCRIPTION DRUG LABEL 1 30698-448 TABLET 10 mg ORAL NDA 26 sections
Lotensin HUMAN PRESCRIPTION DRUG LABEL 1 30698-449 TABLET 20 mg ORAL NDA 26 sections
Lotensin HUMAN PRESCRIPTION DRUG LABEL 1 30698-450 TABLET 40 mg ORAL NDA 26 sections
Lotensin HCT HUMAN PRESCRIPTION DRUG LABEL 2 30698-452 TABLET 10 mg ORAL NDA 25 sections
Lotensin HCT HUMAN PRESCRIPTION DRUG LABEL 2 30698-453 TABLET 20 mg ORAL NDA 25 sections
Lotensin HCT HUMAN PRESCRIPTION DRUG LABEL 2 30698-454 TABLET 20 mg ORAL NDA 25 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-179 TABLET 10 mg ORAL ANDA 13 sections
Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-180 TABLET 20 mg ORAL ANDA 13 sections
Amlodipine Besylate and Benazepril Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 33261-823 CAPSULE 10 mg ORAL ANDA 30 sections