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

Stem definitionDrug idCAS RN
angiotensin-converting enzyme inhibitors 2712 87679-37-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • trandolapril
  • gopten
  • mavik
  • odrik
The effect of trandolapril in hypertension appears to result primarily from the inhibition of circulating and tissue ACE activity thereby reducing angiotensin II formation, decreasing vasoconstriction, decreasing aldosterone secretion, and increasing plasma renin. Decreased aldosterone secretion leads to diuresis, natriuresis, and a small increase of serum potassium. Trandolapril is deesterified to the diacid metabolite, trandolaprilat, which is approximately eight times more active as an inhibitor of ACE activity.
  • Molecular weight: 430.55
  • Formula: C24H34N2O5
  • CLOGP: 2.10
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 95.94
  • ALOGS: -4.32
  • ROTB: 10

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
2 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.06 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 10 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.25 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 12.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.17 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.26 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 26, 1996 FDA ABBVIE

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
Bradycardia 144.13 37.99 36 399 9945 2347705
Hypotension 106.10 37.99 37 398 32399 2325251
Angioedema 99.84 37.99 26 409 8370 2349280
Acute kidney injury 99.31 37.99 34 401 28088 2329562
Squamous cell carcinoma of the oral cavity 75.37 37.99 10 425 68 2357582
Paranoia 58.64 37.99 13 422 2094 2355556
Hallucination, auditory 58.12 37.99 13 422 2179 2355471
Hyperkalaemia 54.50 37.99 15 420 5878 2351772
Cerebellar haematoma 50.33 37.99 7 428 70 2357580
Psychotic disorder 48.33 37.99 13 422 4666 2352984
Loss of consciousness 48.17 37.99 18 417 18749 2338901
Atrioventricular block complete 46.43 37.99 10 425 1404 2356246
Cardiogenic shock 45.93 37.99 11 424 2480 2355170
Dizziness 44.75 37.99 24 411 58641 2299009
Overdose 40.04 37.99 16 419 19891 2337759

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
Hypotension 146.57 38.58 52 381 29602 1716746
Acute kidney injury 120.03 38.58 47 386 34897 1711451
Hyperkalaemia 99.79 38.58 29 404 8518 1737830
Bezoar 94.08 38.58 14 419 137 1746211
Oesophageal obstruction 91.10 38.58 13 420 92 1746256
Bradycardia 77.09 38.58 25 408 10509 1735839
Suicide attempt 72.70 38.58 22 411 7359 1738989
Pancreatitis acute 52.53 38.58 15 418 4072 1742276
Sinoatrial block 49.72 38.58 8 425 134 1746214
Angioedema 47.28 38.58 17 416 9647 1736701
Loss of consciousness 46.96 38.58 19 414 14856 1731492
Orthostatic hypotension 45.91 38.58 13 420 3418 1742930
Toxicity to various agents 43.36 38.58 22 411 29119 1717229
Malaise 43.06 38.58 22 411 29543 1716805
Atrioventricular block complete 41.08 38.58 10 423 1461 1744887
Lactic acidosis 40.75 38.58 13 420 5116 1741232
Asthenia 39.76 38.58 22 411 34648 1711700
Oesophageal haemorrhage 38.72 38.58 7 426 239 1746109

Pharmacologic Action:

SourceCodeDescription
ATC C09AA10 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ACE INHIBITORS, PLAIN
ACE inhibitors, plain
ATC C09BB10 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ACE INHIBITORS, COMBINATIONS
ACE inhibitors and calcium channel blockers
FDA EPC N0000175562 Angiotensin Converting Enzyme Inhibitor
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
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:35457 EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Chronic heart failure indication 48447003
Left ventricular cardiac dysfunction indication 429589006
Atrial fibrillation off-label use 49436004 DOID:0060224
Diabetic renal disease off-label use 127013003
Diastolic heart failure off-label use 418304008 DOID:9775
Nondiabetic Proteinuric Nephropathy off-label use
Hyperkalemia contraindication 14140009
Ventricular tachycardia contraindication 25569003
Complete atrioventricular block contraindication 27885002
Acute cerebrovascular insufficiency contraindication 29322000
Sick sinus syndrome contraindication 36083008 DOID:13884
Immunosuppression contraindication 38013005
Angioedema contraindication 41291007 DOID:1558
Low cardiac output syndrome contraindication 44088000
Low blood pressure contraindication 45007003
Bradycardia contraindication 48867003
Lown-Ganong-Levine syndrome contraindication 55475008 DOID:13087
Aortic valve stenosis contraindication 60573004 DOID:1712
Wolff-Parkinson-White pattern contraindication 74390002 DOID:384
Duchenne muscular dystrophy contraindication 76670001 DOID:11723
Transplantation contraindication 77465005
Chronic idiopathic constipation contraindication 82934008
Hereditary angioneurotic edema contraindication 82966003 DOID:14735
Left heart failure contraindication 85232009
Cardiogenic shock contraindication 89138009
Hyponatremia contraindication 89627008
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Disorder of connective tissue contraindication 105969002 DOID:65
Liver function tests abnormal contraindication 166603001
Second degree atrioventricular block contraindication 195042002
Hypertrophic cardiomyopathy contraindication 233873004 DOID:11984
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Renal artery stenosis contraindication 302233006
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Neuromuscular Transmission Deficiency contraindication
Hemodialysis with High-Flux Membrane contraindication
First Degree Atrioventricular Heart Block contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.23 acidic
pKa2 5.77 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 8.12 WOMBAT-PK CHEMBL

External reference:

IDSource
4020971 VUID
N0000148444 NUI
C0076891 UMLSCUI
D00383 KEGG_DRUG
1T0N3G9CRC UNII
5746 INN_ID
108562001 SNOMEDCT_US
4020971 VANDF
107488 MMSL
004452 NDDF
d04008 MMSL
5606 MMSL
38454 RXNORM
386871006 SNOMEDCT_US
5642 MMSL
CHEMBL1519 ChEMBL_ID
DB00519 DRUGBANK_ID
87679-71-8 SECONDARY_CAS_RN
C061095 MESH_SUPPLEMENTAL_RECORD_UI
X93 PDB_CHEM_ID
CHEBI:9649 CHEBI
CHEMBL1201387 ChEMBL_ID
5484727 PUBCHEM_CID
6453 IUPHAR_LIGAND_ID
C052035 MESH_SUPPLEMENTAL_RECORD_UI
DB14209 DRUGBANK_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tarka HUMAN PRESCRIPTION DRUG LABEL 2 0074-3287 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL NDA 13 sections
Tarka HUMAN PRESCRIPTION DRUG LABEL 2 0074-3288 TABLET, FILM COATED, EXTENDED RELEASE 1 mg ORAL NDA 13 sections
Tarka HUMAN PRESCRIPTION DRUG LABEL 2 0074-3289 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL NDA 13 sections
Tarka HUMAN PRESCRIPTION DRUG LABEL 2 0074-3290 TABLET, FILM COATED, EXTENDED RELEASE 4 mg ORAL NDA 13 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 42806-052 TABLET 1 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 42806-053 TABLET 2 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 42806-054 TABLET 4 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 50090-4120 TABLET 2 mg ORAL ANDA 13 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 50090-4128 TABLET 1 mg ORAL ANDA 16 sections
Mavik HUMAN PRESCRIPTION DRUG LABEL 1 54868-5099 TABLET 4 mg ORAL NDA 13 sections
Tarka HUMAN PRESCRIPTION DRUG LABEL 2 54868-5311 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL NDA 13 sections
Tarka HUMAN PRESCRIPTION DRUG LABEL 2 54868-5320 TABLET, FILM COATED, EXTENDED RELEASE 4 mg ORAL NDA 13 sections
Tarka HUMAN PRESCRIPTION DRUG LABEL 2 54868-5548 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL NDA 13 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 54868-6061 TABLET 4 mg ORAL ANDA 14 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 57237-089 TABLET 1 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 57237-090 TABLET 2 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 57237-091 TABLET 4 mg ORAL ANDA 12 sections
Trandolapril and Verapamil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 59762-0122 TABLET, FILM COATED, EXTENDED RELEASE 4 mg ORAL NDA 14 sections
Trandolapril and Verapamil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 59762-0132 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL NDA 14 sections
Trandolapril and Verapamil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 59762-0142 TABLET, FILM COATED, EXTENDED RELEASE 2 mg ORAL NDA 14 sections
Trandolapril and Verapamil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 59762-0152 TABLET, FILM COATED, EXTENDED RELEASE 1 mg ORAL NDA 14 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 60429-978 TABLET 1 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 60429-979 TABLET 2 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 60429-980 TABLET 4 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 63629-8003 TABLET 2 mg ORAL ANDA 15 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 65862-164 TABLET 1 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 65862-165 TABLET 2 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 65862-166 TABLET 4 mg ORAL ANDA 12 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 68151-0757 TABLET 1 mg ORAL ANDA 15 sections
Trandolapril HUMAN PRESCRIPTION DRUG LABEL 1 68180-566 TABLET 1 mg ORAL ANDA 15 sections