Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, 6-aminopenicillanic acid derivatives	2187	61477-96-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: piperacillin hydrate piperacillin piperacillin sodium pipracil piperacillin sodium salt	Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics. Molecular weight: 517.56 Formula: C23H27N5O7S CLOGP: 1.36 LIPINSKI: 2 HAC: 12 HDO: 3 TPSA: 156.43 ALOGS: -3.64 ROTB: 6 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

piperacillin hydrate
piperacillin
piperacillin sodium
pipracil
piperacillin sodium salt

Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.

Molecular weight: 517.56
Formula: C23H27N5O7S
CLOGP: 1.36
LIPINSKI: 2
HAC: 12
HDO: 3
TPSA: 156.43
ALOGS: -3.64
ROTB: 6

Status: OFP

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

Drug dosage:

Dose	Unit	Route
14	g	P
14	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	714.30 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	71 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	772.85 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	0 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.27 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	4 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.50 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.96 hours	Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	-1.886		High	1
caco2-efflux	Caco-2 efflux ratio (BA/AB)	1.050		High	1
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	0.507	10^-6 cm/s	High	1
dh-clint	Dog hepatocyte intrinsic clearance	2.051	uL/min/10^6 cells	High	1
dppb	Dog plasma protein binding (% unbound)	83.110	%	High	1
fcs-ppb	Fetal calf serum protein binding (% unbound)	63.370	%	High	1
herg	hERG pIC50	4.283	pIC50	High	1
hh-clint	Human hepatocyte intrinsic clearance	1.064	uL/min/10^6 cells	High	1
hlm-clint	Human liver microsomal intrinsic clearance	2.958	uL/min/mg protein	High	1
hppb	Human plasma protein binding (% unbound)	83.460	%	High	1
kinase-safety-class	ACVR2A,ACVR2B,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DYRK1B,EIF2AK3,ERBB2,GRK2,ITK,MAP3K7,MAPK7,MAPKAPK2,NTRK2,PDK1,PDK2,PIK3CB,PRKDC,STK33,SYK,TEK	24
kinase-selectivity-class	AXL,GRK2,MAP2K6	3
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	1.089		High	1
mh-clint	Mouse hepatocyte intrinsic clearance	1.905		High	1
mppb	Mouse plasma protein binding (% unbound)	74.990		High	1
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	1.820		High	1
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pppb	Pig plasma protein binding (% unbound)	68.130	%	High	1
rh-clint	Rat hepatocyte intrinsic clearance	1.167	uL/min/10^6 cells	High	1
rh-fuinc	Rat hepatocyte fraction unbound in incubation	89.700	%	High	1
rppb	Rat plasma protein binding (% unbound)	67.580	%	High	1
solubility-dd	Solubility at pH 7.4 in DMSO	928.966	uM	High	1

Approvals:

Date	Agency	Company	Orphan
Dec. 29, 1981	FDA

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
Sepsis	123.10	19.14	127	10456	179687	90438177
Thrombocytopenia	119.33	19.14	134	10449	208591	90409273
Toxic epidermal necrolysis	109.53	19.14	60	10523	32468	90585396
Pyrexia	106.27	19.14	236	10347	660249	89957615
Acute kidney injury	96.31	19.14	150	10433	320237	90297627
Respiratory failure	88.95	19.14	88	10495	118330	90499534
Septic shock	83.40	19.14	73	10510	84087	90533777
Rash maculo-papular	79.40	19.14	53	10530	40880	90576984
Febrile neutropenia	77.61	19.14	94	10489	158255	90459609
Renal failure	76.30	19.14	85	10498	130922	90486942
Pancytopenia	68.26	19.14	77	10506	120186	90497678
Platelet count decreased	68.23	19.14	82	10501	136887	90480977
Multiple organ dysfunction syndrome	67.14	19.14	59	10524	68277	90549587
Dermatitis exfoliative generalised	63.18	19.14	24	10559	5569	90612295
Disseminated intravascular coagulation	62.37	19.14	36	10547	21502	90596362
Blood creatinine increased	57.67	19.14	65	10518	101321	90516543
Urinary tract obstruction	54.17	19.14	17	10566	2232	90615632
Excessive eye blinking	53.26	19.14	15	10568	1357	90616507
Eosinophilia	53.06	19.14	36	10547	28497	90589367
Leukopenia	52.95	19.14	62	10521	100648	90517216
Drug reaction with eosinophilia and systemic symptoms	52.50	19.14	42	10541	42716	90575148
Tubulointerstitial nephritis	52.01	19.14	34	10549	25309	90592555
Fatigue	49.10	19.14	38	10545	1153985	89463879
Agranulocytosis	46.46	19.14	36	10547	34966	90582898
Hypokalaemia	45.87	19.14	66	10517	131050	90486814
Oliguria	45.42	19.14	23	10560	10601	90607263
Joint swelling	44.17	19.14	4	10579	503296	90114568
Anaemia	41.45	19.14	112	10471	352690	90265174
Tonic clonic movements	41.41	19.14	13	10570	1709	90616155
Alopecia	40.71	19.14	5	10578	495066	90122798
Neutropenia	40.09	19.14	84	10499	224820	90393044
Arthralgia	39.37	19.14	21	10562	778501	89839363
Haemoglobin decreased	38.05	19.14	68	10515	161888	90455976
Pseudomembranous colitis	38.00	19.14	15	10568	3853	90614011
Haemolytic anaemia	37.77	19.14	21	10562	11676	90606188
Rash morbilliform	37.41	19.14	15	10568	4014	90613850
Peripheral swelling	34.37	19.14	4	10579	413102	90204762
Pleural effusion	34.32	19.14	53	10530	111938	90505926
Heparin-induced thrombocytopenia	33.41	19.14	15	10568	5297	90612567
Stevens-Johnson syndrome	32.16	19.14	27	10556	29349	90588515
Hepatic function abnormal	32.14	19.14	33	10550	46255	90571609
Acute generalised exanthematous pustulosis	32.13	19.14	20	10563	13683	90604181
Polyglandular disorder	31.85	19.14	7	10576	227	90617637
Headache	31.13	19.14	33	10550	862713	89755151
Biloma	31.12	19.14	6	10577	100	90617764
Hypotension	30.21	19.14	95	10488	325302	90292562
Clostridium difficile colitis	30.18	19.14	25	10558	26681	90591183
Haemophagocytic lymphohistiocytosis	29.92	19.14	20	10563	15439	90602425
Systemic lupus erythematosus	28.90	19.14	4	10579	361892	90255972
Transplant rejection	28.35	19.14	18	10565	12740	90605124
Weight increased	28.29	19.14	7	10576	417920	90199944
Cytomegalovirus infection	28.20	19.14	24	10559	26578	90591286
Dizziness	28.17	19.14	17	10566	589267	90028597
Staphylococcal sepsis	28.01	19.14	16	10567	9367	90608497
Hyperacusis	27.96	19.14	11	10572	2800	90615064
Renal impairment	27.00	19.14	46	10537	105375	90512489
Autoimmune haemolytic anaemia	26.43	19.14	13	10570	5632	90612232
Endocrine disorder	26.26	19.14	8	10575	952	90616912
Streptococcal infection	25.98	19.14	14	10569	7319	90610545
Nephropathy toxic	25.97	19.14	17	10566	12671	90605193
Anaemia folate deficiency	25.96	19.14	7	10576	539	90617325
Toxic skin eruption	24.89	19.14	18	10565	15756	90602108
Unresponsive to stimuli	24.36	19.14	26	10557	38095	90579769
Musculoskeletal stiffness	24.34	19.14	3	10580	296529	90321335
Abdominal discomfort	23.90	19.14	13	10570	477315	90140549
Product dose omission issue	23.82	19.14	3	10580	291684	90326180
Linear IgA disease	22.98	19.14	9	10574	2265	90615599
Sinusitis	22.73	19.14	6	10577	343082	90274782
Wound	22.71	19.14	4	10579	302976	90314888
Ejection fraction decreased	22.49	19.14	21	10562	26232	90591632
Contraindicated product administered	22.37	19.14	5	10578	320134	90297730
Small intestinal obstruction	22.18	19.14	19	10564	21215	90596649
Respiratory distress	22.17	19.14	25	10558	38921	90578943
Cardiac arrest	22.03	19.14	42	10541	104893	90512971
Cardiac failure	21.98	19.14	43	10540	109453	90508411
Systemic candida	21.97	19.14	11	10572	4948	90612916
Hypoparathyroidism	21.77	19.14	7	10576	994	90616870
Hydronephrosis	21.52	19.14	15	10568	12387	90605477
Pain in extremity	21.51	19.14	13	10570	450516	90167348
Aspartate aminotransferase increased	21.37	19.14	41	10542	102896	90514968
Leukocytosis	21.34	19.14	22	10561	30968	90586896
Pneumonia	21.14	19.14	137	10446	637922	89979942
Mental status changes	21.00	19.14	26	10557	44653	90573211
Aspergillus infection	20.94	19.14	14	10569	10809	90607055
Chronic hepatitis	20.84	19.14	7	10576	1138	90616726
White blood cell count decreased	20.54	19.14	54	10529	167055	90450809
Bronchopulmonary aspergillosis	20.28	19.14	14	10569	11384	90606480
Product contamination microbial	20.08	19.14	5	10578	281	90617583
Infusion related reaction	19.93	19.14	12	10571	416768	90201096
Drug intolerance	19.89	19.14	14	10569	447577	90170287
International normalised ratio increased	19.81	19.14	26	10557	47290	90570574
Epidermolysis	19.78	19.14	6	10577	703	90617161
Prothrombin time prolonged	19.78	19.14	13	10570	9759	90608105
Clostridial infection	19.71	19.14	10	10573	4626	90613238
Hepatic cytolysis	19.60	19.14	21	10562	30895	90586969
Seizure	19.45	19.14	50	10533	152579	90465285

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
Acute kidney injury	112.83	16.19	313	13304	367024	42240694
Thrombocytopenia	108.21	16.19	207	13410	190072	42417646
Pyrexia	97.43	16.19	311	13306	393731	42213987
Tubulointerstitial nephritis	85.76	16.19	75	13542	31473	42576245
Multiple organ dysfunction syndrome	79.22	16.19	124	13493	96911	42510807
Sepsis	71.21	16.19	180	13437	199154	42408564
Drug reaction with eosinophilia and systemic symptoms	70.99	16.19	77	13540	41998	42565720
Eosinophilia	64.05	16.19	65	13552	32834	42574884
Renal failure	60.08	16.19	138	13479	143588	42464130
Cholestasis	56.90	16.19	61	13556	32818	42574900
Agranulocytosis	53.34	16.19	57	13560	30555	42577163
Disseminated intravascular coagulation	48.27	16.19	49	13568	24745	42582973
Rash maculo-papular	47.12	16.19	59	13558	37444	42570274
Clostridial infection	45.47	16.19	23	13594	3851	42603867
Device related sepsis	45.39	16.19	23	13594	3864	42603854
Toxic epidermal necrolysis	40.02	16.19	46	13571	26704	42581014
Septic shock	39.34	16.19	89	13528	91583	42516135
Neutropenia	39.03	16.19	146	13471	199285	42408433
Renal tubular necrosis	38.92	16.19	38	13579	18316	42589402
Choroiditis	38.41	16.19	15	13602	1360	42606358
Dizziness	38.11	16.19	16	13601	249238	42358480
Clostridium difficile colitis	36.01	16.19	39	13578	21213	42586505
Rash	35.20	16.19	178	13439	276776	42330942
Stevens-Johnson syndrome	34.64	16.19	39	13578	22139	42585579
Heparin-induced thrombocytopenia	34.09	16.19	23	13594	6574	42601144
Death	33.83	16.19	62	13555	471123	42136595
Respiratory failure	32.20	16.19	102	13515	128030	42479688
Congenital pneumonia	30.42	16.19	7	13610	98	42607620
Blood alkaline phosphatase increased	30.27	16.19	45	13572	33552	42574166
Gamma-glutamyltransferase increased	29.96	16.19	44	13573	32453	42575265
Fatigue	29.78	16.19	59	13558	435582	42172136
Nephritis	29.14	16.19	17	13600	3772	42603946
Blood creatinine increased	28.95	16.19	89	13528	109914	42497804
Arthralgia	28.54	16.19	15	13602	205223	42402495
Pancytopenia	26.23	16.19	90	13527	117653	42490065
Rash erythematous	26.12	16.19	41	13576	32050	42575668
Nephropathy toxic	25.26	16.19	29	13588	16809	42590909
Blood bilirubin increased	25.17	16.19	47	13570	42205	42565513
Alanine aminotransferase increased	24.64	16.19	73	13544	88333	42519385
Subclavian artery occlusion	24.07	16.19	6	13611	120	42607598
Interstitial lung disease	24.00	16.19	67	13550	78395	42529323
Headache	23.62	16.19	25	13592	239344	42368374
Hepatic failure	23.47	16.19	43	13574	38057	42569661
Haemodialysis	23.18	16.19	22	13595	10238	42597480
Autoimmune haemolytic anaemia	22.88	16.19	17	13600	5654	42602064
Hepatic cytolysis	22.82	16.19	35	13582	26809	42580909
Off label use	22.78	16.19	116	13501	638219	41969499
Pneumonia staphylococcal	22.60	16.19	14	13603	3462	42604256
Enterobacter pneumonia	22.57	16.19	8	13609	553	42607165
Abdominal abscess	22.21	16.19	16	13601	5077	42602641
Weight increased	21.92	16.19	4	13613	107979	42499739
Aspartate aminotransferase increased	21.77	16.19	64	13553	77099	42530619
Chondritis	21.38	16.19	6	13611	192	42607526
Staphylococcal infection	21.34	16.19	41	13576	37602	42570116
Weight decreased	21.33	16.19	21	13596	207927	42399791
Acute respiratory distress syndrome	21.16	16.19	36	13581	30072	42577646
Rubber sensitivity	21.02	16.19	7	13610	401	42607317
Device related infection	20.96	16.19	29	13588	20250	42587468
Large intestine infection	20.34	16.19	11	13606	2110	42605608
Dialysis	20.31	16.19	22	13595	11964	42595754
Transplant rejection	19.70	16.19	23	13594	13565	42594153
Platelet count decreased	19.65	16.19	92	13525	138489	42469229
Pneumonia	18.97	16.19	212	13405	421937	42185781
Intraocular pressure increased	18.90	16.19	16	13601	6417	42601301
Tachycardia	18.89	16.19	73	13544	101014	42506704
Bacterial sepsis	18.79	16.19	16	13601	6466	42601252
Febrile neutropenia	18.60	16.19	112	13505	185591	42422127
Drug ineffective	18.46	16.19	122	13495	630075	41977643
Leukopenia	18.29	16.19	59	13558	74687	42533031
Hyperleukocytosis	18.22	16.19	11	13606	2597	42605121
Drug eruption	18.11	16.19	29	13588	23046	42584672
Toxic skin eruption	17.87	16.19	22	13595	13708	42594010
Muscle spasms	17.87	16.19	3	13614	86041	42521677
Dermatitis exfoliative	17.83	16.19	16	13601	6931	42600787
Febrile bone marrow aplasia	17.80	16.19	19	13598	10162	42597556
Bone marrow failure	17.49	16.19	35	13582	33058	42574660
Petechiae	17.41	16.19	19	13598	10416	42597302
Nasopharyngitis	17.28	16.19	3	13614	83993	42523725
Hypotension	16.79	16.19	140	13477	257491	42350227
Hepatic function abnormal	16.72	16.19	45	13572	51522	42556196
Tachypnoea	16.69	16.19	27	13590	21635	42586083
Colitis	16.49	16.19	42	13575	46530	42561188
Anaphylactic shock	16.36	16.19	28	13589	23489	42584229
Antibiotic level below therapeutic	16.34	16.19	4	13613	74	42607644
Organ failure	16.30	16.19	10	13607	2430	42605288
Hepatocellular injury	16.22	16.19	28	13589	23650	42584068
Renal impairment	16.22	16.19	74	13543	110154	42497564

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
Acute kidney injury	204.73	16.11	399	20305	635031	109933564
Pyrexia	183.45	16.11	470	20234	897795	109670800
Thrombocytopenia	180.94	16.11	271	20433	348614	110219981
Sepsis	153.83	16.11	243	20461	327103	110241492
Tubulointerstitial nephritis	134.44	16.11	98	20606	54186	110514409
Toxic epidermal necrolysis	130.58	16.11	98	20606	56629	110511966
Multiple organ dysfunction syndrome	130.06	16.11	151	20553	151559	110417036
Renal failure	128.90	16.11	184	20520	226390	110342205
Drug reaction with eosinophilia and systemic symptoms	122.08	16.11	110	20594	81985	110486610
Septic shock	118.96	16.11	147	20557	157381	110411214
Rash maculo-papular	111.44	16.11	100	20604	74122	110494473
Eosinophilia	107.22	16.11	88	20616	57848	110510747
Agranulocytosis	88.36	16.11	81	20623	61679	110506916
Fatigue	79.33	16.11	67	20637	1215891	109352704
Pancytopenia	73.75	16.11	137	20567	209476	110359119
Respiratory failure	72.36	16.11	138	20566	215194	110353401
Febrile neutropenia	69.69	16.11	171	20533	316596	110251999
Arthralgia	68.82	16.11	30	20674	779602	109788993
Disseminated intravascular coagulation	68.71	16.11	59	20645	41227	110527368
Joint swelling	66.93	16.11	4	20700	442841	110125754
Dizziness	66.31	16.11	24	20680	698169	109870426
Neutropenia	65.87	16.11	186	20518	374434	110194161
Platelet count decreased	65.82	16.11	138	20566	230305	110338290
Clostridium difficile colitis	63.75	16.11	58	20646	43720	110524875
Heparin-induced thrombocytopenia	62.21	16.11	34	20670	11390	110557205
Clostridial infection	61.87	16.11	28	20676	6274	110562321
Peripheral swelling	60.01	16.11	4	20700	404030	110164565
Blood creatinine increased	59.95	16.11	116	20588	182773	110385822
Weight increased	57.26	16.11	6	20698	419638	110148957
Stevens-Johnson syndrome	56.59	16.11	56	20648	46845	110521750
Cholestasis	56.54	16.11	65	20639	64453	110504142
Headache	55.76	16.11	50	20654	882327	109686268
Nasopharyngitis	55.48	16.11	5	20699	394356	110174239
Autoimmune haemolytic anaemia	53.57	16.11	30	20674	10537	110558058
Transplant rejection	53.33	16.11	41	20663	24526	110544069
Alopecia	53.04	16.11	4	20700	364749	110203846
Nephropathy toxic	49.28	16.11	41	20663	27437	110541158
Product dose omission issue	48.32	16.11	3	20701	321779	110246816
Leukopenia	48.29	16.11	94	20610	148697	110419898
Device related sepsis	47.95	16.11	25	20679	7622	110560973
Urinary tract obstruction	47.67	16.11	22	20682	5155	110563440
Renal tubular necrosis	47.58	16.11	42	20662	30433	110538162
Staphylococcal sepsis	46.60	16.11	33	20671	17421	110551174
Rheumatoid arthritis	44.38	16.11	3	20701	299610	110268985
Toxic skin eruption	43.12	16.11	38	20666	27477	110541118
Oliguria	42.39	16.11	32	20672	18625	110549970
Acute generalised exanthematous pustulosis	42.37	16.11	34	20670	21630	110546965
Hypotension	41.57	16.11	201	20503	523648	110044947
Pseudomembranous colitis	40.37	16.11	21	20683	6370	110562225
Choroiditis	40	16.11	14	20690	1601	110566994
Dermatitis exfoliative generalised	39.54	16.11	25	20679	10947	110557648
Dialysis	38.81	16.11	31	20673	19588	110549007
Renal impairment	38.53	16.11	99	20605	188346	110380249
Nephritis	38.33	16.11	20	20684	6106	110562489
Excessive eye blinking	38.00	16.11	14	20690	1856	110566739
Hepatic cytolysis	37.74	16.11	49	20655	55004	110513591
Pneumonia	36.20	16.11	284	20420	876430	109692165
Fall	35.95	16.11	36	20668	603446	109965149
Rash erythematous	35.92	16.11	59	20645	81773	110486822
Musculoskeletal stiffness	35.70	16.11	5	20699	279817	110288778
Staphylococcal infection	35.64	16.11	54	20650	69890	110498705
Escherichia infection	35.55	16.11	32	20672	23784	110544811
Swelling	35.13	16.11	11	20693	351030	110217565
Acute respiratory distress syndrome	34.38	16.11	46	20658	53152	110515443
Bone marrow failure	34.33	16.11	48	20656	57800	110510795
Rash	33.91	16.11	266	20438	820698	109747897
Respiratory distress	33.44	16.11	52	20652	68822	110499773
Abdominal discomfort	33.37	16.11	16	20688	393842	110174753
Pain in extremity	32.67	16.11	26	20678	487092	110081503
Interstitial lung disease	32.50	16.11	77	20627	139257	110429338
Haemoglobin decreased	32.09	16.11	111	20593	248616	110319979
Pulmonary oedema	31.93	16.11	63	20641	100596	110467999
Tachypnoea	31.70	16.11	38	20666	39357	110529238
Muscle spasms	31.08	16.11	7	20697	278150	110290445
Therapeutic product effect incomplete	31.03	16.11	3	20701	223802	110344793
Haemolytic anaemia	31.01	16.11	28	20676	20892	110547703
Pleural effusion	30.94	16.11	88	20616	177621	110390974
Hepatic function abnormal	30.91	16.11	58	20646	89237	110479358
Haemodialysis	30.86	16.11	26	20678	17693	110550902
Anaemia	30.64	16.11	191	20513	546895	110021700
Petechiae	30.30	16.11	29	20675	23288	110545307
Weight decreased	30.13	16.11	26	20678	468031	110100564
Insomnia	30.01	16.11	15	20689	360575	110208020
Aspergillus infection	29.82	16.11	30	20674	25586	110543009
Blood alkaline phosphatase increased	29.60	16.11	50	20654	70885	110497710
Hypokalaemia	29.51	16.11	88	20616	182360	110386235
Discomfort	29.44	16.11	3	20701	214704	110353891
Hepatic failure	29.41	16.11	49	20655	68690	110499905
Prothrombin time prolonged	29.39	16.11	25	20679	17236	110551359
Systemic candida	29.30	16.11	20	20684	9954	110558641
Aspartate aminotransferase increased	28.62	16.11	80	20624	159856	110408739
Contraindicated product administered	28.24	16.11	6	20698	248261	110320334
Polyglandular disorder	28.21	16.11	7	20697	239	110568356
Clostridium difficile infection	27.63	16.11	41	20663	52088	110516507
Blood bilirubin increased	27.11	16.11	50	20654	75922	110492673
Dry mouth	26.89	16.11	3	20701	199945	110368650
Drug intolerance	26.87	16.11	22	20682	406490	110162105
Sinusitis	26.78	16.11	11	20693	296677	110271918
Depression	26.71	16.11	13	20691	317322	110251273
Mobility decreased	26.47	16.11	6	20698	237416	110331179
Impaired healing	26.33	16.11	3	20701	196714	110371881
Enterococcal infection	25.84	16.11	25	20679	20341	110548254
Contusion	25.81	16.11	6	20698	233355	110335240
Intravascular haemolysis	25.81	16.11	9	20695	1018	110567577
Hyperacusis	25.49	16.11	12	20692	2940	110565655
Tonic clonic movements	25.49	16.11	12	20692	2940	110565655
Subclavian artery occlusion	25.36	16.11	6	20698	167	110568428
Inappropriate schedule of product administration	25.13	16.11	4	20700	203633	110364962
Tachycardia	24.88	16.11	96	20608	226549	110342046
Dermatitis exfoliative	24.76	16.11	19	20685	11328	110557267
Alanine aminotransferase increased	24.56	16.11	83	20621	183690	110384905
Bronchopulmonary aspergillosis	24.34	16.11	29	20675	29834	110538761
Abdominal abscess	24.30	16.11	17	20687	8802	110559793
Sleep disorder	24.30	16.11	4	20700	198640	110369955
Wound	24.07	16.11	7	20697	234430	110334165
Renal injury	23.79	16.11	23	20681	18690	110549905
Linear IgA disease	23.72	16.11	13	20691	4376	110564219
Mixed liver injury	23.71	16.11	19	20685	12060	110556535
Cytomegalovirus infection	23.55	16.11	39	20665	54405	110514190
Rash morbilliform	23.49	16.11	16	20688	7935	110560660
Antibiotic level below therapeutic	23.16	16.11	5	20699	91	110568504
Biloma	23.12	16.11	6	20698	246	110568349
Aplasia pure red cell	23.04	16.11	17	20687	9561	110559034
Encephalopathy	22.48	16.11	48	20656	81007	110487588
Treatment failure	22.37	16.11	12	20692	277222	110291373
Therapeutic product effect decreased	22.14	16.11	9	20695	244307	110324288
Pain	22.02	16.11	98	20606	954857	109613738
White blood cell count increased	22.01	16.11	53	20651	96789	110471806
Enterobacter pneumonia	21.98	16.11	7	20697	598	110567997
Antibiotic level above therapeutic	21.98	16.11	8	20696	1025	110567570
Chills	21.97	16.11	82	20622	190498	110378097
White blood cell count decreased	21.87	16.11	93	20611	229297	110339298
Bacterial sepsis	21.75	16.11	17	20687	10409	110558186
Febrile bone marrow aplasia	21.33	16.11	21	20683	17444	110551151
Endocrine disorder	21.32	16.11	8	20696	1116	110567479
Leukocytosis	21.22	16.11	37	20667	53791	110514804
Gastrooesophageal reflux disease	21.19	16.11	4	20700	179972	110388623
Pathogen resistance	21.13	16.11	21	20683	17651	110550944
Anaemia folate deficiency	20.97	16.11	7	20697	694	110567901
Dyspepsia	20.94	16.11	5	20699	190960	110377635
Injection site pain	20.85	16.11	4	20700	177918	110390677
Drug abuse	20.77	16.11	4	20700	177407	110391188
Hypoaesthesia	20.77	16.11	17	20687	314206	110254389
Type 2 diabetes mellitus	20.74	16.11	4	20700	177228	110391367
Wheezing	20.66	16.11	11	20693	255219	110313376
Maternal exposure during pregnancy	20.61	16.11	11	20693	254872	110313723
Gamma-glutamyltransferase increased	20.20	16.11	39	20665	61270	110507325
Neutrophilic dermatosis	20.13	16.11	7	20697	785	110567810
Skin exfoliation	19.95	16.11	48	20656	87603	110480992
Haemophagocytic lymphohistiocytosis	19.95	16.11	27	20677	31532	110537063
Gait disturbance	19.73	16.11	14	20690	278194	110290401
Osteoarthritis	19.60	16.11	5	20699	182618	110385977
Blood culture positive	19.52	16.11	15	20689	8961	110559634
Mucormycosis	19.35	16.11	16	20688	10612	110557983
Arthritis	19.15	16.11	4	20700	167582	110401013
Hepatocellular injury	18.92	16.11	34	20670	50608	110517987
Extravasation blood	18.91	16.11	6	20698	507	110568088
Mental status changes	18.76	16.11	43	20661	76079	110492516
Coagulopathy	18.63	16.11	30	20674	40881	110527714
Chondritis	18.23	16.11	5	20699	254	110568341
Acanthosis	18.16	16.11	6	20698	576	110568019
International normalised ratio increased	18.15	16.11	46	20658	86726	110481869
Hyperbilirubinaemia	17.53	16.11	25	20679	30646	110537949
Drug eruption	17.51	16.11	34	20670	53625	110514970
Tumour lysis syndrome	17.45	16.11	25	20679	30776	110537819
Pneumonia staphylococcal	17.39	16.11	12	20692	6079	110562516
Gastrointestinal disorder	17.38	16.11	12	20692	241940	110326655
Neutrophil count decreased	17.38	16.11	56	20648	120885	110447710
Pneumonia pseudomonal	17.27	16.11	13	20691	7533	110561062
Purpura	17.17	16.11	22	20682	24366	110544229
Colitis	17.15	16.11	50	20654	102273	110466322
Chronic hepatitis C	17.07	16.11	6	20698	695	110567900
Intraocular pressure increased	17.00	16.11	15	20689	10861	110557734
Hepatic infection fungal	16.90	16.11	5	20699	334	110568261
Intentional product use issue	16.90	16.11	13	20691	247893	110320702
Skin oedema	16.87	16.11	8	20696	1991	110566604
Neuralgic amyotrophy	16.51	16.11	5	20699	362	110568233
Complications of transplant surgery	16.45	16.11	6	20698	773	110567822
Gait inability	16.12	16.11	3	20701	136373	110432222

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J01CA12	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE BETA-LACTAM ANTIBACTERIALS, PENICILLINS Penicillins with extended spectrum
ATC	J01CR05	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE BETA-LACTAM ANTIBACTERIALS, PENICILLINS Combinations of penicillins, incl. beta-lactamase inhibitors
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000900	Anti-Bacterial Agents
CHEBI has role	CHEBI:22587	antiviral agent
CHEBI has role	CHEBI:33281	antimicrobial agent
CHEBI has role	CHEBI:33282	antibacterial agent
CHEBI has role	CHEBI:35441	antiinfective agent
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:36047	antibacterial drug
CHEBI has role	CHEBI:67079	anti-inflammatory agent

Related Drugs by ATC class:

J01CA Penicillins with extended spectrum 18 drugs

amoxicillin ampicillin aspoxicillin azlocillin bacampicillin carbenicillin carindacillin epicillin hetacillin mecillinam metampicillin mezlocillin show all 18 →

J01CR Combinations of penicillins, incl. beta-lactamase inhibitors 4 drugs

amoxicillin ampicillin sultamicillin ticarcillin

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

Disease	Relation	SNOMED_ID	DOID
Septicemia due to Escherichia coli	indication	9323009
Bacterial septicemia	indication	10001005	DOID:0040085
Infection due to Pseudomonas aeruginosa	indication	11218009
Gonorrhea	indication	15628003	DOID:7551
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Acute gonococcal cervicitis	indication	20943002	DOID:10615
Streptococcal septicemia	indication	29577008
Acute gonococcal urethritis	indication	29864006
Postoperative infection	indication	33910007
Pneumonia due to Pseudomonas	indication	41381004
Peritonitis	indication	48661000
Lower respiratory tract infection	indication	50417007
Pneumonia due to Escherichia coli	indication	51530003
Bacterial pneumonia	indication	53084003	DOID:874
Klebsiella cystitis	indication	60867007
Acute gonococcal endometritis	indication	65295003	DOID:7527
Urinary tract infectious disease	indication	68566005
Haemophilus influenzae pneumonia	indication	70036007
Infection due to Escherichia coli	indication	71057007
Bacterial infection due to Serratia	indication	71120004
Rhinoscleroma	indication	72409005	DOID:11336
Appendicitis	indication	74400008	DOID:8337
Abdominal abscess	indication	75100008
Septicemia due to Bacteroides	indication	79587009
Septicemia due to Serratia	indication	82091000
Infection of bone	indication	111253001
Female genital tract infection	indication	125585007
Infectious disease of abdomen	indication	128070006
Infection due to Enterobacteriaceae	indication	128945009
Bacterial infection due to Klebsiella pneumoniae	indication	186435004
Proteus septicemia	indication	300986008
Escherichia coli urinary tract infection	indication	301011002
Proteus urinary tract infection	indication	301012009
Septicemia due to enterococcus	indication	310669007
Infectious disorder of joint	indication	363162000
Infection due to Staphylococcus aureus	indication	406602003
Nosocomial pneumonia	indication	425464007
Sepsis due to Pseudomonas	indication	448813005
Sepsis due to Gram negative bacteria	indication	449082003
Urinary tract infection caused by Klebsiella	indication	369001000119100
Skin and Skin Structure Bacteroides Fragilis Infection	indication
E. Coli Appendicitis	indication
Bacteroides Pneumonia	indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection	indication
Bacteroides Peritonitis	indication
Skin and Skin Structure Enterococcus Infection	indication
Prevention of Perioperative Infection	indication
Pseudomonas Aeruginosa Urinary Tract Infection	indication
Bacteroides Pelvic Inflammatory Disease	indication
Bacteroides Pelvic Cellulitis	indication
Bacteroides Endometritis	indication
E. Coli Peritonitis	indication
Pseudomonas Aeruginosa Joint Infection	indication
Bacteroides Complicated Appendicitis	indication
Enterococcus Urinary Tract Infection	indication
E. Coli Pelvic Inflammatory Disease	indication
Skin and Skin Structure Serratia Infection	indication
Bacteroides Appendicitis	indication
Neisseria Gonorrhea Pelvic Cellulitis	indication
Enterococcus Peritonitis	indication
Cesarean Section Infection Prevention	indication
Vaginal Hysterectomy Infection Prevention	indication
Enterococcus Pelvic Inflammatory Disease	indication
Bacteroides Osteomyelitis	indication
Infection Prevention for GI Surgery	indication
Enterococcus Joint Infection	indication
Clostridium Peritonitis	indication
Complicated Skin and Skin Structure Infection	indication
Inflammatory Disease of Female Pelvic Organs	indication
Pseudomonas Aeruginosa Osteomyelitis	indication
Peptostreptococcus Pelvic Inflammatory Disease	indication
Complicated Proteus UTI	indication
Staphylococcus Nosocomial Pneumonia	indication
Skin and Skin Structure Acinetobacter Infection	indication
Bacteroides Joint Infection	indication
Enterococcus Complicated UTI	indication
Skin and Skin Structure Proteus Infection	indication
Enterobacter Pneumonia	indication
E. Coli Complicated Appendicitis	indication
E. Coli Endometritis	indication
Diabetic Foot Infection	indication
Enterococcus Osteomyelitis	indication
Enterococcus Endometritis	indication
Complicated UTI with Pseudomonas Aeruginosa	indication
Skin and Skin Structure Pseudomonas Aeruginosa Infection	indication
Enterococcus Pelvic Cellulitis	indication
Ecthyma gangrenosum	off-label use	17732003
Sepsis of the newborn	off-label use	206376005
Diverticulitis of gastrointestinal tract	off-label use	271366000
Pseudomonas Respiratory Tract Infection in Cystic Fibrosis	off-label use
Blood coagulation disorder	contraindication	64779008	DOID:1247
Kidney disease	contraindication	90708001	DOID:557
Infectious mononucleosis	contraindication	271558008	DOID:8568
Neutropenic disorder	contraindication	303011007	DOID:1227
Pseudomembranous enterocolitis	contraindication	397683000

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.79	acidic
pKa2	12.64	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Bacterial penicillin-binding protein	Enzyme	PBPA_ECOLI PBPB_ECOLI DACC_ECOLI PBP2_ECOLI FTSI_ECOLI DACA_ECOLI DACB_ECOLI	INHIBITOR			CHEMBL	CHEMBL
Penicillin-binding protein 1A	Enzyme	PBPA_CLOPE				WOMBAT-PK
Beta-lactamase	Enzyme	A2RP81_CITFR		Ki	6.70	CHEMBL
Streptokinase A	Enzyme	STRP_STRP1		EC50	6.55	WOMBAT-PK

External reference:

ID	Source
4019896	VUID
N0000147981	NUI
D00466	KEGG_DRUG
66258-76-2	SECONDARY_CAS_RN
59703-84-3	SECONDARY_CAS_RN
4018917	VANDF
4019896	VANDF
C0031955	UMLSCUI
CHEBI:8232	CHEBI
WPP	PDB_CHEM_ID
CHEMBL702	ChEMBL_ID
CHEMBL1200820	ChEMBL_ID
D010878	MESH_DESCRIPTOR_UI
DB00319	DRUGBANK_ID
10921	IUPHAR_LIGAND_ID
X00B0D5O0E	UNII
43672	PUBCHEM_CID
203134	RXNORM
1514	MMSL
5304	MMSL
60235	MMSL
d00057	MMSL
002688	NDDF
004832	NDDF
11644000	SNOMEDCT_US
372836004	SNOMEDCT_US
74575000	SNOMEDCT_US
X00B0D5O0E	INXIGHT DRUGS

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Zosynin Galaxy Containers	HUMAN PRESCRIPTION DRUG LABEL	2	0206-8860	INJECTION, SOLUTION	2 g	INTRAVENOUS	NDA	29 sections
Zosynin Galaxy Containers	HUMAN PRESCRIPTION DRUG LABEL	2	0206-8861	INJECTION, SOLUTION	3 g	INTRAVENOUS	NDA	29 sections
Zosynin Galaxy Containers	HUMAN PRESCRIPTION DRUG LABEL	2	0206-8862	INJECTION, SOLUTION	4 g	INTRAVENOUS	NDA	29 sections
Piperacillin and Tazobactam and Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	2	0264-3446	INJECTION, SOLUTION	2 g	INTRAVENOUS	NDA	28 sections
Piperacillin and Tazobactam and Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	2	0264-3448	INJECTION, SOLUTION	3 g	INTRAVENOUS	NDA	28 sections
Piperacillin and Tazobactam and Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	2	0264-3450	INJECTION, SOLUTION	4 g	INTRAVENOUS	NDA	28 sections
Zosyn	HUMAN PRESCRIPTION DRUG LABEL	2	0338-9632	INJECTION, SOLUTION	2 g	INTRAVENOUS	NDA	29 sections
Zosyn	HUMAN PRESCRIPTION DRUG LABEL	2	0338-9636	INJECTION, SOLUTION	3 g	INTRAVENOUS	NDA	29 sections
Zosyn	HUMAN PRESCRIPTION DRUG LABEL	2	0338-9638	INJECTION, SOLUTION	4 g	INTRAVENOUS	NDA	29 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0409-2999	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	12 g	INTRAVENOUS	ANDA	25 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0409-3383	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0409-3385	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	3 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0409-3390	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	4 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-3110	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	25 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-3113	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	3 g	INTRAVENOUS	ANDA	25 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-3114	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	4 g	INTRAVENOUS	ANDA	25 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-3117	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	12 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-3180	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	36 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-9210	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-9213	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	3 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	0781-9214	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	4 g	INTRAVENOUS	ANDA	26 sections
Piperacillin, Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	25021-181	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	36 g	INTRAVENOUS	ANDA	32 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	35369-0501	INJECTION, POWDER, FOR SOLUTION	4 g	INTRAVENOUS	ANDA	27 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	35369-0502	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	27 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	35369-0503	INJECTION, POWDER, FOR SOLUTION	3 g	INTRAVENOUS	ANDA	27 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	35369-0504	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	36 g	INTRAVENOUS	ANDA	27 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-801	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-802	INJECTION, POWDER, FOR SOLUTION	3 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-803	INJECTION, POWDER, FOR SOLUTION	4 g	INTRAVENOUS	ANDA	26 sections
Piperacillin and Tazobactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-804	INJECTION, POWDER, FOR SOLUTION	36 g	INTRAVENOUS	ANDA	26 sections

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piperacillin 🐶 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: