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

Stem definitionDrug idCAS RN
diuretics, sulfamoylbenzoic acid derivatives 2853 14293-44-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • xipamide
  • chronexan
  • diurex
  • diurexan
A sulfamoylbenzamide analog of CLOPAMIDE. It is diuretic and saluretic with antihypertensive activity. It is bound to PLASMA PROTEINS, thus has a delayed onset and prolonged action.
  • Molecular weight: 354.81
  • Formula: C15H15ClN2O4S
  • CLOGP: 2.12
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 3
  • TPSA: 109.49
  • ALOGS: -4.16
  • ROTB: 3

Drug dosage:

DoseUnitRoute
20 mg O

ADMET properties:

PropertyValueReference
BA (Bioavailability) 70 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AURKC,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK5,CDK9,CSF1R,DDR1,DYRK1B,EGFR,EIF2AK3,EPHA2,EPHB4,ERBB2,FLT3,FYN,GRK2,GSK3B,IKBKB,ITK,JAK1,JAK2,KIT,LYN,MAP2K6,MAP3K1,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK1,MAPK10,MAPK11,MAPK14,MAPK7,MAPK9,MAPKAPK2,MAPKAPK3,MARK4,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1,ULK2 66
kinase-selectivity-class AXL,BRAF,CSF1R,DDR1,EPHA2,EPHB4,ERBB2,GRK2,LYN,MAP2K6,MAPK11,MAPK7,MTOR,PDK4,SIK2,SIK3,TEK 17
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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
General physical health deterioration 231.17 37.21 179 5074 354936 90268258
Product prescribing error 183.15 37.21 68 5185 30077 90593117
Lymphatic fistula 182.09 37.21 36 5217 1425 90621769
Femoral hernia incarcerated 180.96 37.21 36 5217 1472 90621722
Pancreatic steatosis 171.97 37.21 35 5218 1607 90621587
Wound infection pseudomonas 170.41 37.21 36 5217 1987 90621207
Eructation 169.51 37.21 50 5203 10832 90612362
Arterial haemorrhage 168.01 37.21 37 5216 2486 90620708
Anaemia 158.99 37.21 144 5109 352658 90270536
Seroma 150.27 37.21 35 5218 3025 90620169
Aortic valve stenosis 148.91 37.21 37 5216 4203 90618991
Haemarthrosis 146.04 37.21 36 5217 3958 90619236
Tachyarrhythmia 144.78 37.21 38 5215 5368 90617826
Anuria 142.17 37.21 47 5206 14771 90608423
Faecaloma 132.65 37.21 41 5212 10390 90612804
Diverticulum intestinal 129.32 37.21 39 5214 9103 90614091
Hepatic cyst 128.28 37.21 36 5217 6532 90616662
Wound dehiscence 127.91 37.21 35 5218 5787 90617407
Oedema peripheral 121.35 37.21 108 5145 257807 90365387
Aortic arteriosclerosis 118.31 37.21 35 5218 7649 90615545
Groin pain 114.20 37.21 38 5215 12175 90611019
Inflammatory marker increased 112.04 37.21 35 5218 9179 90614015
Cardiovascular disorder 110.49 37.21 38 5215 13454 90609740
Gastrointestinal haemorrhage 109.45 37.21 67 5186 90181 90533013
Aplastic anaemia 107.21 37.21 37 5216 13232 90609962
Escherichia infection 104.40 37.21 38 5215 15857 90607337
Postoperative wound infection 102.93 37.21 36 5217 13390 90609804
Mitral valve incompetence 101.78 37.21 41 5212 22483 90600711
Osteopenia 100.95 37.21 41 5212 22961 90600233
Haematochezia 97.26 37.21 57 5196 70856 90552338
Left ventricular dysfunction 96.08 37.21 35 5218 14634 90608560
Tricuspid valve incompetence 95.20 37.21 36 5217 16695 90606499
Syncope 88.26 37.21 68 5185 132595 90490599
Hyponatraemia 85.68 37.21 67 5186 133471 90489723
Cardiogenic shock 85.22 37.21 37 5216 24431 90598763
Myelodysplastic syndrome 84.04 37.21 35 5218 20868 90602326
Product monitoring error 80.12 37.21 23 5230 4521 90618673
Coronary artery disease 79.94 37.21 39 5214 33584 90589610
Renal impairment 78.89 37.21 58 5195 105363 90517831
Hiatus hernia 77.53 37.21 35 5218 25326 90597868
Haematuria 75.57 37.21 38 5215 34899 90588295
Hyperkalaemia 73.06 37.21 46 5207 64918 90558276
Joint dislocation 69.56 37.21 39 5214 44543 90578651
Pulmonary hypertension 68.54 37.21 38 5215 42485 90580709
Acute kidney injury 67.94 37.21 88 5165 320299 90302895
Urinary retention 64.33 37.21 35 5218 37709 90585485
Therapeutic drug monitoring analysis not performed 58.93 37.21 14 5239 1315 90621879
Drug ineffective 56.68 37.21 7 5246 1384291 89238903
Fall 43.62 37.21 90 5163 481720 90141474
Flatulence 43.28 37.21 28 5225 41339 90581855
Dyspnoea 43.15 37.21 130 5123 880825 89742369
Cardiac failure 40.09 37.21 40 5213 109456 90513738

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
Product prescribing error 326.81 35.62 110 3395 26002 42591828
General physical health deterioration 216.18 35.62 141 3364 151105 42466725
Labelled drug-drug interaction medication error 196.04 35.62 66 3439 15516 42602314
Dyspnoea 120.11 35.62 163 3342 442458 42175372
Product monitoring error 111.77 35.62 32 3473 4391 42613439
Therapeutic drug monitoring analysis incorrectly performed 86.38 35.62 16 3489 309 42617521
Dehydration 80.63 35.62 77 3428 141690 42476140
Peripheral arterial occlusive disease 62.99 35.62 23 3482 6815 42611015
Hypotension 49.33 35.62 81 3424 257550 42360280
Cold sweat 48.55 35.62 22 3483 11308 42606522
Cardiac failure 47.73 35.62 51 3454 106805 42511025
Acute kidney injury 47.01 35.62 97 3408 367240 42250590
Oedema peripheral 40.87 35.62 53 3452 136023 42481807

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
Product prescribing error 502.99 30.93 178 8458 51153 110529510
General physical health deterioration 429.24 30.93 314 8322 424981 110155682
Product monitoring error 186.12 30.93 55 8581 8872 110571791
Lymphatic fistula 170.52 30.93 36 8600 1459 110579204
Femoral hernia incarcerated 170.18 30.93 36 8600 1473 110579190
Labelled drug-drug interaction medication error 158.41 30.93 66 8570 29236 110551427
Pancreatic steatosis 157.90 30.93 35 8601 1787 110578876
Wound infection pseudomonas 153.38 30.93 36 8600 2375 110578288
Oedema peripheral 152.19 30.93 156 8480 328504 110252159
Dyspnoea 147.45 30.93 288 8348 1106584 109474079
Eructation 142.18 30.93 50 8586 14007 110566656
Arterial haemorrhage 141.75 30.93 37 8599 3782 110576881
Anaemia 140.56 30.93 192 8444 546894 110033769
Seroma 137.21 30.93 35 8601 3266 110577397
Tachyarrhythmia 125.82 30.93 40 8596 8221 110572442
Aortic valve stenosis 123.13 30.93 37 8599 6313 110574350
Wound dehiscence 118.99 30.93 38 8598 7924 110572739
Hepatic cyst 115.71 30.93 37 8599 7746 110572917
Haemarthrosis 113.74 30.93 36 8600 7293 110573370
Faecaloma 109.86 30.93 42 8594 14866 110565797
Diverticulum intestinal 104.59 30.93 38 8598 11681 110568982
Haematochezia 103.91 30.93 80 8556 115444 110465219
Acute kidney injury 99.96 30.93 178 8458 635252 109945411
Anuria 96.25 30.93 44 8592 24297 110556366
Aortic arteriosclerosis 95.88 30.93 35 8601 10903 110569760
Groin pain 94.43 30.93 38 8598 15390 110565273
Osteopenia 90.51 30.93 41 8595 22168 110558495
Renal impairment 89.85 30.93 91 8545 188354 110392309
Inflammatory marker increased 89.81 30.93 36 8600 14433 110566230
Cardiovascular disorder 89.54 30.93 41 8595 22719 110557944
Dehydration 88.56 30.93 109 8527 279402 110301261
Drug ineffective 87.23 30.93 9 8627 1520531 109060132
Postoperative wound infection 86.85 30.93 36 8600 15717 110564946
Therapeutic drug monitoring analysis incorrectly performed 86.11 30.93 18 8618 694 110579969
Aplastic anaemia 83.90 30.93 40 8596 24268 110556395
Therapeutic drug monitoring analysis not performed 82.84 30.93 21 8615 1910 110578753
Escherichia infection 78.59 30.93 38 8598 23778 110556885
Mitral valve incompetence 77.50 30.93 42 8594 33287 110547376
Left ventricular dysfunction 76.06 30.93 37 8599 23456 110557207
Tricuspid valve incompetence 75.49 30.93 37 8599 23836 110556827
Gastrointestinal haemorrhage 75.38 30.93 78 8558 165440 110415223
Peripheral arterial occlusive disease 75.09 30.93 28 8608 9252 110571411
Joint dislocation 68.33 30.93 39 8597 34151 110546512
Hiatus hernia 67.58 30.93 36 8600 27570 110553093
Syncope 67.37 30.93 81 8555 202455 110378208
Cardiac failure 67.31 30.93 78 8558 187548 110393115
Off label use 57.23 30.93 23 8613 1500162 109080501
Myelodysplastic syndrome 54.83 30.93 35 8601 37449 110543214
Hypotension 53.71 30.93 123 8513 523726 110056937
Hyponatraemia 53.53 30.93 75 8561 217578 110363085
Coronary artery disease 52.40 30.93 44 8592 71646 110509017
Pulmonary hypertension 51.27 30.93 39 8597 55181 110525482
Cardiogenic shock 47.81 30.93 38 8598 57300 110523363
Arrhythmia 43.37 30.93 39 8597 69536 110511127
Electrolyte imbalance 43.12 30.93 30 8606 36998 110543665
Haematuria 41.18 30.93 41 8595 82964 110497699
Urinary retention 39.42 30.93 37 8599 69646 110511017
Cold sweat 38.38 30.93 23 8613 22008 110558655
Product administration error 36.12 30.93 27 8609 37190 110543473
Flatulence 34.02 30.93 30 8606 52119 110528544
Urinary hesitation 33.86 30.93 13 8623 4645 110576018
Hyperkalaemia 33.66 30.93 47 8589 135749 110444914
Hypokalaemia 32.29 30.93 54 8582 182394 110398269

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C03BA10 CARDIOVASCULAR SYSTEM
DIURETICS
LOW-CEILING DIURETICS, EXCL. THIAZIDES
Sulfonamides, plain
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004232 Diuretics
MeSH PA D045283 Natriuretic Agents
CHEBI has role CHEBI:35554 cardiovascular drug

Related Drugs by ATC class:

C03BA Sulfonamides, plain 10 drugs
chlortalidoneclofenamideclopamideclorexolonefenquizoneindapamidemefrusidemeticranemetolazonequinethazone

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

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Edema indication 267038008




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.65 acidic
pKa2 9.76 acidic
pKa3 10.4 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

IDSource
N0000166859 NUI
D06341 KEGG_DRUG
C0043355 UMLSCUI
CHEBI:135499 CHEBI
CHEMBL517199 ChEMBL_ID
DB13803 DRUGBANK_ID
D014988 MESH_DESCRIPTOR_UI
26618 PUBCHEM_CID
7900 IUPHAR_LIGAND_ID
2689 INN_ID
4S9EY0NUEC UNII
11371 RXNORM
173968 MMSL
004068 NDDF
317968004 SNOMEDCT_US
395923001 SNOMEDCT_US

Pharmaceutical products:

None