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

Stem definitionDrug idCAS RN
angiotensin II receptor antagonists, antihypertensive (non-peptidic) 2583 144701-48-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • telmisartan
  • tolura
  • micardis
  • pritor
A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.
  • Molecular weight: 514.63
  • Formula: C33H30N4O2
  • CLOGP: 7.29
  • LIPINSKI: 2
  • HAC: 6
  • HDO: 1
  • TPSA: 72.94
  • ALOGS: -5.17
  • ROTB: 7

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
40 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 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) 2.22 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 5.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.00 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 10, 1998 FDA BOEHRINGER INGELHEIM

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
Acute kidney injury 252.89 32.62 97 1596 28025 2328367
Hyponatraemia 226.91 32.62 74 1619 13251 2343141
Blood pressure increased 168.08 32.62 63 1630 16923 2339469
Hyperkalaemia 164.94 32.62 48 1645 5845 2350547
Hypotension 147.17 32.62 69 1624 32367 2324025
Fall 145.16 32.62 77 1616 47022 2309370
Hypoglycaemia 140.01 32.62 46 1647 8361 2348031
Loss of consciousness 134.04 32.62 55 1638 18712 2337680
Hypertensive crisis 119.11 32.62 31 1662 2482 2353910
Malaise 114.78 32.62 70 1623 55515 2300877
Suicide attempt 111.96 32.62 42 1651 11240 2345152
Toxicity to various agents 107.62 32.62 56 1637 32698 2323694
Dizziness 106.27 32.62 68 1625 58597 2297795
Rhabdomyolysis 100.83 32.62 34 1659 6670 2349722
Confusional state 95.62 32.62 47 1646 24297 2332095
Syncope 92.35 32.62 41 1652 16834 2339558
Bradycardia 91.19 32.62 35 1658 9946 2346446
Angioedema 89.63 32.62 33 1660 8363 2348029
Asthenia 86.33 32.62 55 1638 46871 2309521
Oliguria 85.35 32.62 21 1672 1336 2355056
Vomiting 84.89 32.62 64 1629 71538 2284854
Oedema peripheral 84.79 32.62 43 1650 23720 2332672
Nausea 84.51 32.62 77 1616 112112 2244280
Left ventricular hypertrophy 81.96 32.62 18 1675 693 2355699
Myalgia 79.69 32.62 41 1652 23292 2333100
Renal failure 78.68 32.62 37 1656 17312 2339080
Blood pressure inadequately controlled 77.74 32.62 18 1675 882 2355510
Hyperhidrosis 76.49 32.62 35 1658 15387 2341005
Diarrhoea 76.15 32.62 64 1629 83500 2272892
Renal impairment 73.31 32.62 30 1663 10062 2346330
Hypertension 70.82 32.62 40 1653 27321 2329071
Postprandial hypoglycaemia 65.97 32.62 9 1684 13 2356379
Orthostatic hypotension 65.42 32.62 20 1673 2859 2353533
Overdose 65.11 32.62 34 1659 19873 2336519
Bradypnoea 61.35 32.62 13 1680 421 2355971
Cough 61.23 32.62 39 1654 33078 2323314
Vasoplegia syndrome 60.56 32.62 11 1682 156 2356236
Chest pain 59.24 32.62 36 1657 28101 2328291
Pulse abnormal 58.88 32.62 12 1681 320 2356072
Hepatic function abnormal 57.87 32.62 22 1671 6070 2350322
Blood pressure abnormal 57.07 32.62 16 1677 1689 2354703
Blood pressure decreased 55.50 32.62 24 1669 9212 2347180
Blood thyroid stimulating hormone normal 55.21 32.62 8 1685 22 2356370
Labile hypertension 54.47 32.62 9 1684 70 2356322
Tinnitus 54.07 32.62 20 1673 5115 2351277
Hypokalaemia 52.21 32.62 24 1669 10630 2345762
Atrial fibrillation 52.20 32.62 26 1667 13742 2342650
Intentional overdose 50.81 32.62 24 1669 11297 2345095
Depressed level of consciousness 49.77 32.62 21 1672 7583 2348809
Drug ineffective 49.10 32.62 55 1638 101569 2254823
Seizure 48.15 32.62 30 1663 24436 2331956
Inappropriate antidiuretic hormone secretion 48.05 32.62 15 1678 2294 2354098
Carotid arteriosclerosis 47.63 32.62 9 1684 160 2356232
Shock 47.37 32.62 17 1676 3987 2352405
Rash 46.75 32.62 42 1651 59516 2296876
Dyspnoea 45.70 32.62 47 1646 78686 2277706
Weight decreased 44.08 32.62 30 1663 28341 2328051
Left atrial dilatation 43.56 32.62 9 1684 257 2356135
Dehydration 43.00 32.62 27 1666 22268 2334124
Liver disorder 42.93 32.62 18 1675 6396 2349996
Product packaging confusion 42.64 32.62 7 1686 52 2356340
Vertigo 42.43 32.62 20 1673 9364 2347028
Headache 41.43 32.62 45 1648 80134 2276258
Feeling abnormal 39.17 32.62 26 1667 23555 2332837
Muscle spasms 38.80 32.62 25 1668 21541 2334851
Drug interaction 38.69 32.62 28 1665 29135 2327257
Pancytopenia 38.64 32.62 20 1673 11432 2344960
Circulatory collapse 37.36 32.62 14 1679 3706 2352686
Medication error 37.03 32.62 16 1677 6115 2350277
Pruritus 36.82 32.62 32 1661 43308 2313084
Vision blurred 36.67 32.62 21 1672 14647 2341745
Hepatitis 36.52 32.62 16 1677 6321 2350071
Interstitial lung disease 36.39 32.62 17 1676 7795 2348597
Chronic kidney disease 35.97 32.62 14 1679 4104 2352288
Enteritis 35.46 32.62 10 1683 1076 2355316
Gamma-glutamyltransferase increased 35.18 32.62 15 1678 5547 2350845
Hyperaldosteronism 34.69 32.62 6 1687 63 2356329
Metabolic acidosis 34.10 32.62 15 1678 5983 2350409
Cold sweat 33.12 32.62 11 1682 2046 2354346
Pyrexia 32.79 32.62 33 1660 53675 2302717

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
Acute kidney injury 181.16 30.24 92 1428 34852 1710409
Hyperkalaemia 178.31 30.24 61 1459 8486 1736775
Interstitial lung disease 140.97 30.24 53 1467 9643 1735618
Hypotension 108.09 30.24 62 1458 29592 1715669
Blood pressure increased 104.55 30.24 44 1476 10709 1734552
Loss of consciousness 93.90 30.24 45 1475 14830 1730431
Blood pressure decreased 86.86 30.24 35 1485 7611 1737650
Renal impairment 86.13 30.24 40 1480 12274 1732987
Hypertension 85.29 30.24 46 1474 19402 1725859
Renal failure 75.81 30.24 43 1477 19974 1725287
Blood creatine phosphokinase increased 75.33 30.24 33 1487 8823 1736438
Dizziness 75.05 30.24 52 1468 34309 1710952
Hyponatraemia 74.81 30.24 33 1487 8967 1736294
Incontinence 73.16 30.24 19 1501 1007 1744254
Syncope 71.96 30.24 37 1483 14132 1731129
Atrioventricular block complete 70.89 30.24 20 1500 1451 1743810
Staring 69.19 30.24 15 1505 361 1744900
Angioedema 63.20 30.24 30 1490 9634 1735627
Petit mal epilepsy 63.03 30.24 15 1505 553 1744708
Nausea 62.69 30.24 55 1465 51141 1694120
Dehydration 61.64 30.24 36 1484 17622 1727639
Liver disorder 61.21 30.24 25 1495 5611 1739650
Hepatic function abnormal 58.95 30.24 26 1494 7048 1738213
Asthenia 58.65 30.24 45 1475 34625 1710636
Hyperkaliuria 58.15 30.24 8 1512 6 1745255
Hyperhidrosis 55.92 30.24 30 1490 12458 1732803
Blood pressure inadequately controlled 51.78 30.24 13 1507 600 1744661
Hepatitis acute 51.21 30.24 15 1505 1242 1744019
Dissociation 50.48 30.24 11 1509 271 1744990
Bradycardia 49.10 30.24 26 1494 10508 1734753
Haemorrhagic transformation stroke 49.06 30.24 11 1509 310 1744951
Hypokalaemia 48.53 30.24 22 1498 6352 1738909
Daydreaming 47.54 30.24 9 1511 106 1745155
Chronic kidney disease 46.34 30.24 19 1501 4298 1740963
Kinematic imbalances due to suboccipital strain 46.04 30.24 6 1514 1 1745260
Headache 44.09 30.24 38 1482 34338 1710923
Pallor 43.50 30.24 17 1503 3394 1741867
Orthostatic hypotension 39.90 30.24 16 1504 3415 1741846
Fall 38.81 30.24 32 1488 27182 1718079
Diabetic nephropathy 38.31 30.24 9 1511 313 1744948
Hypertensive crisis 36.02 30.24 12 1508 1515 1743746
Rhabdomyolysis 34.43 30.24 21 1499 11069 1734192
IgA nephropathy 33.78 30.24 8 1512 288 1744973
Hypoglycaemic coma 33.69 30.24 9 1511 531 1744730
Urinary tract infection 33.52 30.24 20 1500 10133 1735128
Haematuria 33.34 30.24 18 1502 7542 1737719
Oedema peripheral 32.54 30.24 23 1497 15527 1729734
Postrenal failure 32.49 30.24 7 1513 163 1745098
Blood creatinine increased 32.40 30.24 22 1498 13924 1731337
Diarrhoea 31.44 30.24 39 1481 53813 1691448
Renal artery restenosis 31.31 30.24 4 1516 0 1745261
Dyspnoea 30.87 30.24 38 1482 52021 1693240

Pharmacologic Action:

SourceCodeDescription
ATC C09CA07 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), PLAIN
Angiotensin II receptor blockers (ARBs), plain
ATC C09DA07 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
Angiotensin II receptor blockers (ARBs) and diuretics
ATC C09DB04 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
Angiotensin II receptor blockers (ARBs) and calcium channel blockers
FDA MoA N0000000070 Angiotensin 2 Receptor Antagonists
FDA EPC N0000175561 Angiotensin 2 Receptor Blocker
MeSH PA D047228 Angiotensin II Type 1 Receptor Blockers
MeSH PA D057911 Angiotensin Receptor Antagonists
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:35457 EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
CHEBI has role CHEBI:61016 angiotensin receptor antagonist

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Cerebrovascular accident indication 230690007
Myocardial Infarction Prevention indication
Chronic heart failure off-label use 48447003
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
Anuria contraindication 2472002 DOID:2983
Hypercholesterolemia contraindication 13644009
Hyperkalemia contraindication 14140009
Secondary angle-closure glaucoma contraindication 21571006
Hypovolemia contraindication 28560003
Obstruction of bile duct contraindication 30144000
Dehydration contraindication 34095006
Hyperuricemia contraindication 35885006 DOID:1920
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
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
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
Azotemia contraindication 445009001
Severe Aortic Valve Stenosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.65 acidic
pKa2 5.79 Basic
pKa3 5.13 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
80MG MICARDIS BOEHRINGER INGELHEIM N020850 Nov. 10, 1998 RX TABLET ORAL 7998953 June 6, 2020 REDUCTION OF CARDIAC TISSUE DAMAGE ASSOCIATED WITH MYOCARDIAL INFARCTION
80MG MICARDIS BOEHRINGER INGELHEIM N020850 Nov. 10, 1998 RX TABLET ORAL 8003679 Oct. 6, 2022 TREATMENT OR PREVENTION OF STROKE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Type-1 angiotensin II receptor GPCR ANTAGONIST IC50 9.31 CHEMBL CHEMBL
Peroxisome proliferator-activated receptor gamma Nuclear hormone receptor EC50 5.82 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 4.75 CHEMBL
Type-2 angiotensin II receptor GPCR IC50 9.48 CHEMBL
Angiotensin-converting enzyme Enzyme Ki 5.22 CHEMBL
Glycine receptor subunit alpha-1 Ion channel EC50 5.49 CHEMBL
Type-1B angiotensin II receptor GPCR IC50 8.52 CHEMBL
Type-1A angiotensin II receptor GPCR Ki 9.64 CHEMBL

External reference:

IDSource
D000077333 MESH_DESCRIPTOR_UI
4021146 VUID
N0000148599 NUI
C0248719 UMLSCUI
D00627 KEGG_DRUG
129487008 SNOMEDCT_US
4021146 VANDF
007683 NDDF
53287 MMSL
d04364 MMSL
7789 MMSL
73494 RXNORM
387069000 SNOMEDCT_US
CHEMBL1017 ChEMBL_ID
DB00966 DRUGBANK_ID
U5SYW473RQ UNII
7144 INN_ID
TLS PDB_CHEM_ID
CHEBI:9434 CHEBI
65999 PUBCHEM_CID
592 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0054-0542 TABLET 20 mg ORAL NDA authorized generic 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0054-0543 TABLET 40 mg ORAL NDA authorized generic 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0054-0544 TABLET 80 mg ORAL NDA authorized generic 18 sections
telmisartan and hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0054-0545 TABLET 40 mg ORAL NDA authorized generic 18 sections
telmisartan and hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0054-0546 TABLET 80 mg ORAL NDA authorized generic 18 sections
telmisartan and hydrochlorothiazide HUMAN PRESCRIPTION DRUG LABEL 2 0054-0547 TABLET 80 mg ORAL NDA authorized generic 18 sections
Telmisartan and Amlodipine HUMAN PRESCRIPTION DRUG LABEL 2 0378-1075 TABLET 40 mg ORAL ANDA 18 sections
Telmisartan and Amlodipine HUMAN PRESCRIPTION DRUG LABEL 2 0378-1076 TABLET 40 mg ORAL ANDA 18 sections
Telmisartan and Amlodipine HUMAN PRESCRIPTION DRUG LABEL 2 0378-1077 TABLET 80 mg ORAL ANDA 18 sections
Telmisartan and Amlodipine HUMAN PRESCRIPTION DRUG LABEL 2 0378-1078 TABLET 80 mg ORAL ANDA 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0378-2920 TABLET 20 mg ORAL ANDA 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0378-2921 TABLET 40 mg ORAL ANDA 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0378-2922 TABLET 80 mg ORAL ANDA 18 sections
Micardis HUMAN PRESCRIPTION DRUG LABEL 1 0597-0039 TABLET 20 mg ORAL NDA 18 sections
Micardis HUMAN PRESCRIPTION DRUG LABEL 1 0597-0040 TABLET 40 mg ORAL NDA 18 sections
Micardis HUMAN PRESCRIPTION DRUG LABEL 1 0597-0041 TABLET 80 mg ORAL NDA 18 sections
Micardis HCT HUMAN PRESCRIPTION DRUG LABEL 2 0597-0042 TABLET 80 mg ORAL NDA 19 sections
Micardis HCT HUMAN PRESCRIPTION DRUG LABEL 2 0597-0043 TABLET 40 mg ORAL NDA 19 sections
Micardis HCT HUMAN PRESCRIPTION DRUG LABEL 2 0597-0044 TABLET 80 mg ORAL NDA 19 sections
Twynsta HUMAN PRESCRIPTION DRUG LABEL 2 0597-0124 TABLET, MULTILAYER 40 mg ORAL NDA 18 sections
Twynsta HUMAN PRESCRIPTION DRUG LABEL 2 0597-0125 TABLET, MULTILAYER 40 mg ORAL NDA 18 sections
Twynsta HUMAN PRESCRIPTION DRUG LABEL 2 0597-0126 TABLET, MULTILAYER 80 mg ORAL NDA 18 sections
Twynsta HUMAN PRESCRIPTION DRUG LABEL 2 0597-0127 TABLET, MULTILAYER 80 mg ORAL NDA 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0781-5372 TABLET 20 mg ORAL ANDA 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0781-5374 TABLET 40 mg ORAL ANDA 18 sections
Telmisartan HUMAN PRESCRIPTION DRUG LABEL 1 0781-5378 TABLET 80 mg ORAL ANDA 18 sections
TELMISARTAN HUMAN PRESCRIPTION DRUG LABEL 1 13668-156 TABLET 20 mg ORAL ANDA 17 sections
TELMISARTAN HUMAN PRESCRIPTION DRUG LABEL 1 13668-157 TABLET 40 mg ORAL ANDA 17 sections
TELMISARTAN HUMAN PRESCRIPTION DRUG LABEL 1 13668-158 TABLET 80 mg ORAL ANDA 17 sections
telmisartan and hydrochlorthiazide HUMAN PRESCRIPTION DRUG LABEL 2 13668-159 TABLET 40 mg ORAL ANDA 18 sections