Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
diuretics, sulfamoylbenzoic acid derivatives	2853	14293-44-8

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
20	mg	O

ADMET properties:

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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value
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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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

chlortalidone clofenamide clopamide clorexolone fenquizone indapamide mefruside meticrane metolazone quinethazone

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

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

ID	Source
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

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

Description:

Drug dosage:

ADMET properties:

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Approvals:

FDA Adverse Event Reporting System (Female)

FDA Adverse Event Reporting System (Male)

FDA Adverse Event Reporting System (Geriatric)

FDA Adverse Event Reporting System (Pediatric)

Pharmacologic Action:

Related Drugs by ATC class:

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

🐶 Veterinary Drug Use

🐶 Veterinary products

Acid dissociation constants calculated using MoKa v3.0.0

Orange Book patent data (new drug applications)

Orange Book exclusivity data (new drug applications)

Bioactivity Summary:

External reference:

Pharmaceutical products: