azilsartan medoxomil 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
angiotensin II receptor antagonists, antihypertensive (non-peptidic) 4322 863031-21-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • TAK 491
  • edarbi
  • azilsartan medoxomil
  • azilsartan kamedoxomil
an angiotensin type 1 receptor blocker; receptor blocker
  • Molecular weight: 568.54
  • Formula: C30H24N4O8
  • CLOGP: 5
  • LIPINSKI: 2
  • HAC: 12
  • HDO: 1
  • TPSA: 139.57
  • ALOGS: -4.91
  • ROTB: 10

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
40 mg O

ADMET properties:

PropertyValueReference
BA (Bioavailability) 60 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,ERBB2,GRK2,GSK3B,ITK,JAK2,MAP3K21,MAP3K7,MAPK7,MAPK9,MAPKAPK2,MARK4,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PRKDC,STK33,TEK,TTK 35
kinase-selectivity-class AXL,GRK2,MAP2K6,TEK 4
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
Feb. 25, 2011 FDA ARBOR PHARMS IRELAND
Dec. 7, 2011 EMA Takeda Pharma A/S
Jan. 18, 2001 PMDA TAKEDA PHARMACEUTICAL COMPANY LIMITED

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
Renal impairment 105.51 24.20 59 3301 105362 90519725
Platelet count decreased 88.76 24.20 58 3302 136911 90488176
Hepatic function abnormal 78.52 24.20 37 3323 46251 90578836
Cerebral infarction 73.57 24.20 30 3330 26566 90598521
Hyperkalaemia 50.74 24.20 31 3329 64933 90560154
Decreased appetite 46.26 24.20 63 3297 376477 90248610
Interstitial lung disease 46.13 24.20 31 3329 76374 90548713
Cardiac failure 38.25 24.20 32 3328 109464 90515623
Proteinuria 37.58 24.20 18 3342 23273 90601814
Altered state of consciousness 35.19 24.20 19 3341 31513 90593574
Glomerular filtration rate decreased 27.05 24.20 13 3347 16919 90608168
Blood creatinine increased 26.20 24.20 25 3335 101361 90523726
Palmar-plantar erythrodysaesthesia syndrome 26.12 24.20 15 3345 28008 90597079
Malignant neoplasm progression 25.08 24.20 25 3335 106845 90518242
Blood pressure decreased 24.32 24.20 21 3339 74874 90550213

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
Cerebral infarction 123.54 20.57 61 4230 31108 42585936
Renal impairment 103.92 20.57 87 4204 110141 42506903
Hepatic function abnormal 85.08 20.57 57 4234 51510 42565534
Interstitial lung disease 69.87 20.57 60 4231 78402 42538642
Fibrillary glomerulonephritis 48.64 20.57 8 4283 59 42616985
Proteinuria 46.72 20.57 29 4262 22954 42594090
Decreased appetite 44.70 20.57 74 4217 193063 42423981
Pemphigoid 38.24 20.57 20 4271 11447 42605597
Palmar-plantar erythrodysaesthesia syndrome 36.92 20.57 24 4267 20558 42596486
Altered state of consciousness 35.83 20.57 27 4264 29232 42587812
Cardiac failure 31.74 20.57 46 4245 106810 42510234
Nephrotic syndrome 31.35 20.57 16 4275 8702 42608342
Thalamus haemorrhage 30.55 20.57 9 4282 1110 42615934
Thrombotic cerebral infarction 28.05 20.57 7 4284 462 42616582
Hyperkalaemia 27.40 20.57 37 4254 80421 42536623
Hepatocellular carcinoma 26.49 20.57 14 4277 8180 42608864
Liver disorder 24.91 20.57 25 4266 39619 42577425
Cerebral haemorrhage 23.44 20.57 24 4267 38942 42578102
Intestinal ischaemia 22.04 20.57 13 4278 9375 42607669
Hyperuricaemia 21.99 20.57 13 4278 9411 42607633
Blood pressure decreased 21.66 20.57 28 4263 58304 42558740
Gastric ulcer haemorrhage 21.32 20.57 11 4280 6116 42610928
Gastrointestinal hypomotility 21.03 20.57 7 4284 1286 42615758
Fulminant type 1 diabetes mellitus 20.61 20.57 7 4284 1367 42615677

FDA Adverse Event Reporting System (Geriatric)

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
Renal impairment 193.87 18.06 136 7706 188309 110393148
Cerebral infarction 189.23 18.06 86 7756 51752 110529705
Hepatic function abnormal 155.66 18.06 90 7752 89205 110492252
Interstitial lung disease 114.71 18.06 88 7754 139246 110442211
Decreased appetite 79.68 18.06 130 7712 475716 110105741
Proteinuria 79.56 18.06 44 7798 39974 110541483
Platelet count decreased 76.83 18.06 88 7754 230355 110351102
Altered state of consciousness 69.56 18.06 46 7796 57580 110523877
Hyperkalaemia 68.95 18.06 65 7777 135731 110445726
Cardiac failure 64.80 18.06 73 7769 187553 110393904
Palmar-plantar erythrodysaesthesia syndrome 55.04 18.06 35 7807 40990 110540467
Thalamus haemorrhage 50.70 18.06 14 7828 1950 110579507
Fibrillary glomerulonephritis 50.22 18.06 8 7834 70 110581387
Pemphigoid 48.54 18.06 25 7817 19682 110561775
Malignant neoplasm progression 47.23 18.06 60 7782 174507 110406950
Blood pressure decreased 45.31 18.06 48 7794 115043 110466414
Thrombotic cerebral infarction 41.86 18.06 10 7832 784 110580673
Cerebral haemorrhage 38.62 18.06 34 7808 64934 110516523
Nephrotic syndrome 38.32 18.06 19 7823 13812 110567645
Aortic dissection 38.01 18.06 14 7828 4919 110576538
Hyperuricaemia 37.43 18.06 19 7823 14512 110566945
Glomerular filtration rate decreased 34.65 18.06 23 7819 28933 110552524
Hypothyroidism 33.39 18.06 33 7809 72866 110508591
Dehydration 33.35 18.06 66 7776 279445 110302012
Liver disorder 32.46 18.06 45 7797 142198 110439259
Fulminant type 1 diabetes mellitus 31.06 18.06 10 7832 2353 110579104
Pyelonephritis 30.08 18.06 20 7822 25230 110556227
Sinus node dysfunction 29.81 18.06 14 7828 9033 110572424
Hepatocellular carcinoma 28.64 18.06 14 7828 9866 110571591
Blood creatinine increased 27.86 18.06 48 7794 182841 110398616
Renal disorder 27.63 18.06 25 7817 49454 110532003
Enterocolitis 27.50 18.06 17 7825 18932 110562525
Cholangitis 27.18 18.06 16 7826 16319 110565138
Pain 24.72 18.06 19 7823 954936 109626521
Immune-mediated enterocolitis 22.45 18.06 12 7830 10173 110571284
Anaemia 22.21 18.06 87 7755 546999 110034458
Secondary adrenocortical insufficiency 21.51 18.06 9 7833 4425 110577032
Confusional state 20.82 18.06 4 7838 468676 110112781
Urinary retention 20.50 18.06 25 7817 69658 110511799
Diarrhoea 20.26 18.06 144 7698 1139361 109442096
Rhabdomyolysis 20.19 18.06 33 7809 120368 110461089
Gastric ulcer haemorrhage 19.78 18.06 11 7831 10083 110571374
Intestinal ischaemia 19.72 18.06 13 7829 16166 110565291
Joint swelling 19.21 18.06 4 7838 442841 110138616
Pneumonia aspiration 18.97 18.06 26 7816 81207 110500250
Erythema multiforme 18.81 18.06 14 7828 21083 110560374
Dyslalia 18.72 18.06 6 7836 1391 110580066
Shunt stenosis 18.64 18.06 6 7836 1410 110580047
Haemorrhagic cerebral infarction 18.32 18.06 6 7836 1489 110579968
Spinal compression fracture 18.21 18.06 13 7829 18379 110563078

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C09CA09 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), PLAIN
Angiotensin II receptor blockers (ARBs), plain
ATC C09DA09 CARDIOVASCULAR SYSTEM
AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
Angiotensin II receptor blockers (ARBs) and diuretics
FDA EPC N0000175561 Angiotensin 2 Receptor Blocker
MeSH PA D047228 Angiotensin II Type 1 Receptor Blockers
MeSH PA D057911 Angiotensin Receptor Antagonists
FDA PE N0000178477 Decreased Blood Pressure
FDA MoA N0000180999 Angiotensin 2 Type 1 Receptor Antagonists
CHEBI has role CHEBI:35554 cardiovascular drug
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:61016 angiotensin receptor antagonist
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:35526 hypoglycemic agent

Related Drugs by ATC class:

C09CA Angiotensin II receptor blockers (ARBs), plain 9 drugs
C09DA Angiotensin II receptor blockers (ARBs) and diuretics 8 drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Hypovolemia contraindication 28560003
Low blood pressure contraindication 45007003
Hyponatremia contraindication 89627008
Impaired renal function disorder contraindication 197663003
Pregnancy, function contraindication 289908002
Renal artery stenosis contraindication 302233006




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.11 acidic
pKa2 3.02 Basic
pKa3 2.4 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 40MG MEDOXOMIL;12.5MG EDARBYCLOR AZURITY N202331 Dec. 20, 2011 RX TABLET ORAL 9387249 July 1, 2031 TREATMENT OF HYPERTENSION
EQ 40MG MEDOXOMIL;25MG EDARBYCLOR AZURITY N202331 Dec. 20, 2011 RX TABLET ORAL 9387249 July 1, 2031 TREATMENT OF HYPERTENSION

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 40MG MEDOXOMIL AZILSARTAN MEDOXOMIL LUPIN A214489 July 20, 2022 RX TABLET ORAL Dec. 12, 2026 PATENT CHALLENGE
EQ 80MG MEDOXOMIL AZILSARTAN MEDOXOMIL LUPIN A214489 July 20, 2022 RX TABLET ORAL Dec. 12, 2026 PATENT CHALLENGE

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Type-1 angiotensin II receptor GPCR ANTAGONIST IC50 8.13 IUPHAR CHEMBL
Type-2 angiotensin II receptor GPCR IC50 8.59 CHEMBL
Type-1 angiotensin II receptor GPCR IC50 6.38 CHEMBL

External reference:

IDSource
D08067 KEGG_DRUG
4030593 VANDF
4030594 VANDF
C2698291 UMLSCUI
CHEBI:68845 CHEBI
CHEMBL2028661 ChEMBL_ID
CHEMBL2103795 ChEMBL_ID
DB08822 DRUGBANK_ID
C557413 MESH_SUPPLEMENTAL_RECORD_UI
6900 IUPHAR_LIGAND_ID
8874 INN_ID
LL0G25K7I2 UNII
135409642 PUBCHEM_CID
1091642 RXNORM
180314 MMSL
27787 MMSL
403028 MMSL
d07754 MMSL
013661 NDDF
013662 NDDF
448917007 SNOMEDCT_US
449042005 SNOMEDCT_US
449561004 SNOMEDCT_US
C1958569 UMLSCUI
A1IPH PDB_CHEM_ID
CHEMBL57242 ChEMBL_ID
147403-03-0 SECONDARY_CAS_RN
135415867 PUBCHEM_CID
6901 IUPHAR_LIGAND_ID
8724 INN_ID
C521273 MESH_SUPPLEMENTAL_RECORD_UI
F9NUX55P23 UNII
CHEBI:68850 CHEBI
F9NUX55P23 INXIGHT DRUGS
LL0G25K7I2 INXIGHT DRUGS

Pharmaceutical products:

None