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

Stem definitionDrug idCAS RN
alpha-2 adrenoreceptor agonists 2381 54187-04-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • rilmenidine
  • oxaminozoline
  • rilmenidene
  • rilmenidine phosphate
  • rilmenidine dihydrogen phosphate
Oxazole derivative that acts as an agonist for ALPHA-2 ADRENERGIC RECEPTORS and IMIDAZOLINE RECEPTORS. It is used in the treatment of HYPERTENSION.
  • Molecular weight: 180.25
  • Formula: C10H16N2O
  • CLOGP: 1.42
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 33.62
  • ALOGS: -2.13
  • ROTB: 3

Drug dosage:

None

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 4.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 7.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.90 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 8.30 hours Lombardo F, Berellini G, Obach RS
BA (Bioavailability) 100 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.004 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.426 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 24.660 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 1.710 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 92.780 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 95.260 % High 1
herg hERG pIC50 4.404 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 0.887 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.388 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 93.880 % High 1
kinase-safety-class BRAF,CDK5,EIF2AK3,GRK2,PDK1,PDK2,PRKDC 7
kinase-selectivity-class PDK1 1
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.125 High 1
mh-clint Mouse hepatocyte intrinsic clearance 3.342 High 1
mppb Mouse plasma protein binding (% unbound) 93.260 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.553 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 91.150 % High 1
rh-clint Rat hepatocyte intrinsic clearance 21.827 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 93.460 % High 1
rppb Rat plasma protein binding (% unbound) 93.900 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 833.681 uM High 1

Approvals:

None

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 446.11 33.50 251 4587 320136 90303473
Lactic acidosis 298.21 33.50 109 4729 50354 90573255
Hyperkalaemia 207.31 33.50 90 4748 64874 90558735
Hyponatraemia 126.01 33.50 82 4756 133456 90490153
Allergic reaction to excipient 91.14 33.50 18 4820 770 90622839
Isosthenuria 85.09 33.50 13 4825 116 90623493
Rhabdomyolysis 83.93 33.50 45 4793 51211 90572398
Pyelitis 75.83 33.50 13 4825 250 90623359
Multiple organ dysfunction syndrome 71.89 33.50 45 4793 68291 90555318
Toxic skin eruption 71.03 33.50 28 4810 15746 90607863
Bradycardia 70.55 33.50 48 4790 83799 90539810
Mixed liver injury 70.26 33.50 23 4815 7600 90616009
Bladder hypertrophy 66.62 33.50 13 4825 522 90623087
Electrocardiogram PR shortened 66.47 33.50 13 4825 528 90623081
Hypotension 63.07 33.50 82 4756 325315 90298294
Cardiovascular insufficiency 62.31 33.50 15 4823 1620 90621989
Hypoglycaemia 56.41 33.50 39 4799 69809 90553800
Angioedema 51.86 33.50 36 4802 64840 90558769
Hypochloraemia 50.64 33.50 14 4824 2608 90621001
Carbohydrate antigen 15-3 increased 49.51 33.50 13 4825 1994 90621615
Carcinoembryonic antigen increased 47.47 33.50 13 4825 2337 90621272
Drug reaction with eosinophilia and systemic symptoms 47.08 33.50 29 4809 42729 90580880
Fall 45.13 33.50 87 4751 481723 90141886
Eye oedema 45.08 33.50 12 4826 1940 90621669
Primary hyperaldosteronism 44.48 33.50 7 4831 77 90623532
Overdose 42.40 33.50 47 4791 157662 90465947
Prevertebral soft tissue swelling of cervical space 41.36 33.50 6 4832 36 90623573
Peripheral artery haematoma 40.95 33.50 6 4832 39 90623570
Ischaemic stroke 40.63 33.50 21 4817 22145 90601464
Drug interaction 40.55 33.50 61 4777 276392 90347217
Myoclonus 40.52 33.50 20 4818 19148 90604461
Creatinine renal clearance increased 38.91 33.50 12 4826 3269 90620340
Psychomotor retardation 38.35 33.50 13 4825 4776 90618833
Intestinal transit time abnormal 37.80 33.50 6 4832 70 90623539
Breast cancer recurrent 36.58 33.50 13 4825 5490 90618119
Renin decreased 35.48 33.50 6 4832 106 90623503
Wrong patient received product 34.10 33.50 11 4827 3466 90620143

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 175.79 27.03 170 2907 367167 42251091
Lactic acidosis 79.22 27.03 46 3031 45215 42573043
Hyperkalaemia 70.35 27.03 53 3024 80405 42537853
Enterobacter pneumonia 67.91 27.03 14 3063 547 42617711
Cerebral haematoma 58.46 27.03 20 3057 5590 42612668
Necrotising oesophagitis 49.81 27.03 12 3065 959 42617299
Hypovolaemic shock 46.55 27.03 19 3058 8640 42609618
Pemphigoid 44.58 27.03 20 3057 11447 42606811
Acquired haemophilia 43.31 27.03 12 3065 1663 42616595
Primary hyperaldosteronism 36.74 27.03 7 3070 181 42618077
Peptic ulcer 34.90 27.03 12 3065 3400 42614858
Hypokalaemia 33.42 27.03 33 3044 71688 42546570
Hemiplegia 31.44 27.03 14 3063 7865 42610393
Wrong patient 28.21 27.03 7 3070 632 42617626
Product name confusion 28.08 27.03 5 3072 88 42618170

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
Acute kidney injury 557.94 24.46 418 7616 635012 109946253
Lactic acidosis 335.90 24.46 154 7880 92657 110488608
Hyperkalaemia 250.33 24.46 143 7891 135653 110445612
Hyponatraemia 102.56 24.46 101 7933 217552 110363713
Allergic reaction to excipient 85.34 24.46 18 8016 781 110580484
Isosthenuria 80.78 24.46 13 8021 119 110581146
Primary hyperaldosteronism 77.51 24.46 14 8020 266 110580999
Electrocardiogram PR shortened 66.71 24.46 13 8021 377 110580888
Pyelitis 65.51 24.46 13 8021 415 110580850
Pemphigoid 62.75 24.46 30 8004 19677 110561588
Cerebral haematoma 61.58 24.46 24 8010 9608 110571657
Enterobacter pneumonia 61.02 24.46 13 8021 592 110580673
Bradycardia 60.21 24.46 65 7969 155452 110425813
Rhabdomyolysis 56.86 24.46 56 7978 120345 110460920
Overdose 56.60 24.46 77 7957 233717 110347548
Hypokalaemia 55.00 24.46 67 7967 182381 110398884
Toxic skin eruption 53.31 24.46 30 8004 27485 110553780
Bladder hypertrophy 53.01 24.46 13 8021 1111 110580154
Hypotension 52.85 24.46 117 7917 523732 110057533
Hypovolaemic shock 51.98 24.46 24 8010 14559 110566706
Mixed liver injury 49.78 24.46 22 8012 12057 110569208
Drug interaction 49.64 24.46 111 7923 500072 110081193
Carbohydrate antigen 15-3 increased 48.55 24.46 13 8021 1574 110579691
Cardiovascular insufficiency 47.35 24.46 15 8019 3273 110577992
Angioedema 46.84 24.46 46 7988 98454 110482811
Multiple organ dysfunction syndrome 44.56 24.46 55 7979 151655 110429610
Ischaemic stroke 44.47 24.46 31 8003 41232 110540033
Necrotising oesophagitis 43.77 24.46 12 8022 1588 110579677
Hypochloraemia 41.93 24.46 14 8020 3604 110577661
Carcinoembryonic antigen increased 41.15 24.46 13 8021 2811 110578454
Rash maculo-papular 39.72 24.46 37 7997 74185 110507080
Prevertebral soft tissue swelling of cervical space 39.51 24.46 6 8028 36 110581229
Intracranial haematoma 38.99 24.46 10 8024 1024 110580241
Eye oedema 38.19 24.46 12 8022 2550 110578715
Renal failure 38.15 24.46 63 7971 226511 110354754
Acquired haemophilia 37.88 24.46 12 8022 2619 110578646
Breast cancer recurrent 37.21 24.46 13 8021 3833 110577432
Drug reaction with eosinophilia and systemic symptoms 36.56 24.46 37 7997 82058 110499207
Hypoglycaemia 35.55 24.46 43 7991 116061 110465204
Blood aldosterone increased 35.38 24.46 7 8027 220 110581045
Fall 35.31 24.46 110 7924 603372 109977893
Creatinine renal clearance increased 34.10 24.46 12 8022 3613 110577652
Intestinal transit time abnormal 33.79 24.46 6 8028 103 110581162
Peripheral artery haematoma 32.92 24.46 6 8028 120 110581145
Renin decreased 32.60 24.46 6 8028 127 110581138
Intestinal haemorrhage 32.29 24.46 14 8020 7327 110573938
Myoclonus 31.43 24.46 23 8011 32975 110548290
Hepatic cytolysis 30.53 24.46 28 8006 55025 110526240
Vascular purpura 29.90 24.46 11 8023 3760 110577505
Haemorrhagic stroke 29.35 24.46 16 8018 13773 110567492
Hemiplegia 29.05 24.46 19 8015 22763 110558502
Psychomotor retardation 28.32 24.46 13 8021 7779 110573486
Chronic kidney disease 27.95 24.46 31 8003 76260 110505005
Vascular resistance systemic 27.89 24.46 4 8030 15 110581250
Coma 27.24 24.46 38 7996 117831 110463434
Dysplastic naevus 26.20 24.46 7 8027 841 110580424
Oedema peripheral 26.12 24.46 67 7967 328593 110252672
Adenocarcinoma metastatic 26.01 24.46 6 8028 394 110580871
Peptic ulcer 25.48 24.46 12 8022 7607 110573658
Blood pressure inadequately controlled 25.46 24.46 12 8022 7621 110573644
Manufacturing materials contamination 25.23 24.46 4 8030 33 110581232
Subdural haematoma 25.15 24.46 21 8013 36433 110544832
Sinus bradycardia 24.63 24.46 19 8015 29464 110551801

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C02AC06 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, CENTRALLY ACTING
Imidazoline receptor agonists
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D013565 Sympatholytics
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018663 Adrenergic Agents
MeSH PA D058647 Adrenergic alpha-2 Receptor Agonists
CHEBI has role CHEBI:35674 antihypertensive agent

Related Drugs by ATC class:

C02AC Imidazoline receptor agonists 4 drugs
clonidineguanfacinemoxonidinetolonidine

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

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.22 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
Alpha-2A adrenergic receptor GPCR Ki 7.44 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 5.05 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 7.37 CHEMBL
Alpha-2C adrenergic receptor GPCR Ki 7.90 CHEMBL
Nischarin Membrane receptor Ki 7.23 CHEMBL
Nischarin Membrane receptor Ki 7.95 CHEMBL

External reference:

IDSource
D08482 KEGG_DRUG
C0140591 UMLSCUI
CHEBI:8862 CHEBI
CHEMBL289480 ChEMBL_ID
DB11738 DRUGBANK_ID
D000077769 MESH_DESCRIPTOR_UI
68712 PUBCHEM_CID
5846 INN_ID
13356 IUPHAR_LIGAND_ID
85409-38-7 SECONDARY_CAS_RN
P67IM25ID8 UNII
236379 RXNORM
005772 NDDF
005773 NDDF
765332006 SNOMEDCT_US
765333001 SNOMEDCT_US
P67IM25ID8 INXIGHT DRUGS

Pharmaceutical products:

None