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sulbactam Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
beta-lactamase inhibitors	2492	68373-14-8

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: sulbactam penicillanic acid dioxide sulbactam sodium	A beta-lactamase inhibitor with very weak antibacterial action. The compound prevents antibiotic destruction of beta-lactam antibiotics by inhibiting beta-lactamases, thus extending their spectrum activity. Combinations of sulbactam with beta-lactam antibiotics have been used successfully for the therapy of infections caused by organisms resistant to the antibiotic alone. Molecular weight: 233.24 Formula: C8H11NO5S CLOGP: 0.31 LIPINSKI: 0 HAC: 6 HDO: 1 TPSA: 91.75 ALOGS: -0.68 ROTB: 1 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

sulbactam
penicillanic acid dioxide
sulbactam sodium

A beta-lactamase inhibitor with very weak antibacterial action. The compound prevents antibiotic destruction of beta-lactam antibiotics by inhibiting beta-lactamases, thus extending their spectrum activity. Combinations of sulbactam with beta-lactam antibiotics have been used successfully for the therapy of infections caused by organisms resistant to the antibiotic alone.

Molecular weight: 233.24
Formula: C8H11NO5S
CLOGP: 0.31
LIPINSKI: 0
HAC: 6
HDO: 1
TPSA: 91.75
ALOGS: -0.68
ROTB: 1

Status: OFP

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

Drug dosage:

Dose	Unit	Route
1	g	P

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	285.97 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.32 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	5.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.62 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	1.10 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Dec. 31, 1986	FDA	PFIZER

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
Enterocolitis haemorrhagic	89.50	20.58	23	5915	1544	53341584
Hepatic function abnormal	81.77	20.58	51	5887	36848	53306280
Pyrexia	73.18	20.58	147	5791	403046	52940082
Drug eruption	69.38	20.58	40	5898	25054	53318074
Klebsiella infection	59.54	20.58	25	5913	7901	53335227
Renal impairment	47.08	20.58	52	5886	83266	53259862
Enterococcal infection	44.14	20.58	20	5918	7578	53335550
Lemierre syndrome	41.29	20.58	8	5930	144	53342984
Disseminated intravascular coagulation	40.52	20.58	26	5912	19693	53323435
Infective aneurysm	37.80	20.58	9	5929	440	53342688
Fatigue	36.51	20.58	18	5920	730488	52612640
Linear IgA disease	35.46	20.58	11	5927	1459	53341669
Toxic epidermal necrolysis	34.04	20.58	25	5913	23525	53319603
Pneumonia aspiration	33.67	20.58	29	5909	34272	53308856
Arthralgia	32.71	20.58	5	5933	439778	52903350
Interstitial lung disease	32.08	20.58	36	5902	58586	53284542
Multiple organ dysfunction syndrome	31.86	20.58	35	5903	55642	53287486
Culture stool positive	30.07	20.58	7	5931	310	53342818
Pneumonia	29.70	20.58	106	5832	407063	52936065
Pathogen resistance	28.10	20.58	14	5924	6546	53336582
Eosinophilic pneumonia acute	27.95	20.58	7	5931	423	53342705
Premature delivery	27.52	20.58	23	5915	26081	53317047
Crystal nephropathy	27.50	20.58	8	5930	853	53342275
Acute disseminated encephalomyelitis	26.96	20.58	6	5932	217	53342911
Pseudomembranous colitis	26.80	20.58	11	5927	3280	53339848
Sepsis	24.74	20.58	52	5886	146377	53196751
Red blood cells urine positive	24.59	20.58	10	5928	2914	53340214
Candida infection	24.06	20.58	21	5917	25252	53317876
Platelet count decreased	23.88	20.58	43	5895	108056	53235072
Chorioretinopathy	22.89	20.58	7	5931	886	53342242
Proteus infection	22.75	20.58	7	5931	904	53342224
Acute generalised exanthematous pustulosis	22.22	20.58	14	5924	10267	53332861
Klebsiella test positive	21.88	20.58	7	5931	1026	53342102
Implant site hypersensitivity	21.66	20.58	4	5934	55	53343073
Neuromuscular block prolonged	21.54	20.58	6	5932	547	53342581
Shock haemorrhagic	21.09	20.58	13	5925	9170	53333958
Septic shock	20.95	20.58	30	5908	62199	53280929
Systemic candida	20.82	20.58	9	5929	3048	53340080

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
Hepatic function abnormal	120.38	18.58	94	7761	44746	32460925
Pneumonia	73.12	18.58	219	7636	355033	32150638
Enterocolitis haemorrhagic	72.81	18.58	21	7834	990	32504681
Pneumonia aspiration	54.38	18.58	58	7797	41098	32464573
Interstitial lung disease	53.55	18.58	72	7783	64929	32440742
Cardiac septal defect	51.29	18.58	12	7843	244	32505427
Hangover	49.86	18.58	16	7839	1083	32504588
Pathogen resistance	46.87	18.58	29	7826	9481	32496190
Kidney duplex	45.79	18.58	12	7843	394	32505277
Pyrexia	43.44	18.58	172	7683	319796	32185875
Drug eruption	42.53	18.58	36	7819	19130	32486541
Rash	41.82	18.58	128	7727	209205	32296466
Klebsiella infection	38.39	18.58	24	7831	7988	32497683
Incision site pain	36.76	18.58	15	7840	2022	32503649
Toxic epidermal necrolysis	36.37	18.58	34	7821	20559	32485112
Wound dehiscence	31.92	18.58	16	7839	3480	32502191
C-reactive protein increased	31.79	18.58	48	7807	48054	32457617
Clostridium test positive	31.64	18.58	14	7841	2303	32503368
Drug-induced liver injury	30.16	18.58	33	7822	24030	32481641
Stevens-Johnson syndrome	29.46	18.58	29	7826	18680	32486991
Liver disorder	29.04	18.58	37	7818	31617	32474054
Multiple-drug resistance	27.93	18.58	15	7840	3760	32501911
Pseudomembranous colitis	27.88	18.58	14	7841	3058	32502613
Death	27.80	18.58	31	7824	382486	32123185
Septic shock	27.43	18.58	55	7800	68934	32436737
Pneumonia bacterial	25.57	18.58	21	7834	10695	32494976
Megacolon	24.99	18.58	11	7844	1787	32503884
Acute generalised exanthematous pustulosis	24.81	18.58	17	7838	6596	32499075
Lymphocyte count decreased	24.81	18.58	28	7827	21091	32484580
Enterococcus test positive	24.79	18.58	9	7846	885	32504786
Fungaemia	24.31	18.58	12	7843	2527	32503144
Stenotrophomonas test positive	24.26	18.58	7	7848	330	32505341
Platelet count decreased	23.67	18.58	71	7784	114520	32391151
Respiratory failure	23.66	18.58	68	7787	107114	32398557
Rebound effect	23.58	18.58	11	7844	2045	32503626
Alanine aminotransferase increased	22.62	18.58	55	7800	78424	32427247
Multiple organ dysfunction syndrome	22.35	18.58	51	7804	69803	32435868
Renal impairment	21.91	18.58	60	7795	91912	32413759
Red blood cells urine positive	21.87	18.58	10	7845	1776	32503895
Pulmonary alveolar haemorrhage	21.40	18.58	16	7839	7113	32498558
Coagulopathy	21.38	18.58	25	7830	19552	32486119
Off label use	21.01	18.58	136	7719	306184	32199487
Kounis syndrome	20.94	18.58	10	7845	1958	32503713
Aspartate aminotransferase increased	20.70	18.58	48	7807	66381	32439290
Arteriospasm coronary	20.14	18.58	11	7844	2849	32502822
Paradoxical drug reaction	20.01	18.58	11	7844	2885	32502786
Toxicity to various agents	20.01	18.58	9	7846	178032	32327639
Disseminated intravascular coagulation	19.55	18.58	26	7829	23150	32482521
Fall	19.00	18.58	12	7843	196189	32309482
Blood creatine phosphokinase increased	18.96	18.58	37	7818	45439	32460232
White blood cell count increased	18.88	18.58	35	7820	41367	32464304
Protein urine present	18.88	18.58	13	7842	5084	32500587
Condition aggravated	18.88	18.58	81	7774	155580	32350091

Pharmacologic Action:

Source	Code	Description
ATC	J01CG01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE BETA-LACTAM ANTIBACTERIALS, PENICILLINS Beta-lactamase inhibitors
FDA MoA	N0000000202	beta Lactamase Inhibitors
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D065093	beta-Lactamase Inhibitors
MeSH PA	D004791	Enzyme Inhibitors
FDA EPC	N0000175930	beta Lactamase Inhibitor

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Infection due to Escherichia coli	indication	71057007
Rhinoscleroma	indication	72409005	DOID:11336
Cholangitis	indication	82403002	DOID:9446
Female genital tract infection	indication	125585007
Infectious disease of abdomen	indication	128070006
Infection due to Enterobacteriaceae	indication	128945009
Bacterial peritonitis	indication	197171003
Infection due to Staphylococcus aureus	indication	406602003
E. Coli Gynecological Infections	indication
Klebsiella Pneumoniae Peritonitis	indication
E. Coli Peritonitis	indication
Skin and Skin Structure Bacteroides Fragilis Infection	indication
Bacteroides Gynecological Infections	indication
Inflammatory Disease of Female Pelvic Organs	indication
Skin and Skin Structure Acinetobacter Infection	indication
Bacteroides Peritonitis	indication
Skin and Skin Structure Proteus Infection	indication
Intra-Abdominal E. Coli Abscess	indication
Streptococcal meningitis	off-label use	4510004	DOID:11574
Pyrexia of unknown origin	off-label use	7520000
Bacterial pneumonia	off-label use	53084003	DOID:874
Infection of bone	off-label use	111253001
Meningococcal meningitis	off-label use	192644005
Sepsis of the newborn	off-label use	206376005
Human bite - wound	off-label use	262555007
Diverticulitis of gastrointestinal tract	off-label use	271366000
Neonatal meningitis	off-label use	276674008
Dog bite - wound	off-label use	283734005
Cat bite - wound	off-label use	283782004
Infective otitis media	off-label use	312218008
Diabetic Foot Infection	off-label use
Kidney disease	contraindication	90708001	DOID:557
Infectious mononucleosis	contraindication	271558008	DOID:8568
Pseudomembranous enterocolitis	contraindication	397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.1	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Serine beta-lactamase-like protein LACTB, mitochondrial	Enzyme	P83111	LACTB_HUMAN		IC50	5.01	WOMBAT-PK
Beta-lactamase TEM	Enzyme		BLAT_ECOLX	INHIBITOR	Ki	6.10	CHEMBL	CHEMBL
Beta-lactamase	Enzyme		AMPC_ECOLI		IC50	4.18	CHEMBL
Beta-lactamase SHV-1	Enzyme		BLA1_ECOLX		IC50	5.41	CHEMBL
Beta-lactamase	Enzyme		AMPC_ENTCL		IC50	6	CHEMBL
Beta-lactamase OXA-1	Enzyme		BLO1_ECOLX		IC50	4.66	CHEMBL
Beta-lactamase	Enzyme		AMPC_PSEAE		IC50	4.57	CHEMBL
Beta-lactamase	Enzyme		A1E3K9_ECOLX		IC50	5.21	CHEMBL
Beta-lactamase	Enzyme		A8RR46_BACCS		IC50	7.12	CHEMBL
Carbapenem-hydrolizing beta-lactamase SFC-1	Enzyme		Q6JP75_SERFO		IC50	4.64	CHEMBL
Beta-lactamase GES-13	Enzyme		D1MIX9_PSEAI		IC50	6.43	CHEMBL
Class D beta-lactamase	Unclassified		Q50H31_BRAPL		IC50	4.92	CHEMBL
Beta-lactamase	Enzyme		Q7X575_ECOLX		IC50	5.62	CHEMBL
Beta-lactamase	Enzyme		Q0VTR6_ACIPI		IC50	5.95	CHEMBL
Beta-lactamase	Enzyme		Q0VTR8_ACIPI		IC50	5.11	CHEMBL
Beta-lactamase	Enzyme		D5HSX5_9GAMM		IC50	5.40	CHEMBL
Beta-lactamase TEM	Enzyme		BLAT_SALTI		Ki	6.10	WOMBAT-PK
ADC-18 protein	Enzyme		Q0VTS0_ACIPI		IC50	4.93	CHEMBL
Beta-lactamase 1	Enzyme		BLAC_BACCE		IC50	4.60	CHEMBL
Beta-lactamase	Enzyme		D2SSQ3_PSEAI		IC50	5.52	CHEMBL
Beta-lactamase	Enzyme		BLAC_STAAU		IC50	5.19	CHEMBL
Beta-lactamase	Enzyme		Q3SAW3_PSEAI		IC50	5.52	CHEMBL

External reference:

ID	Source
4019937	VUID
N0000148022	NUI
D02223	KEGG_DRUG
69388-84-7	SECONDARY_CAS_RN
4019381	VANDF
4019937	VANDF
C0038665	UMLSCUI
CHEBI:9321	CHEBI
0RN	PDB_CHEM_ID
CHEMBL403	ChEMBL_ID
DB09324	DRUGBANK_ID
CHEMBL1200944	ChEMBL_ID
D013407	MESH_DESCRIPTOR_UI
130313	PUBCHEM_CID
4845	INN_ID
10769	IUPHAR_LIGAND_ID
S4TF6I2330	UNII
10167	RXNORM
5520	MMSL
d04403	MMSL
002811	NDDF
002812	NDDF
398916003	SNOMEDCT_US
412516007	SNOMEDCT_US
96008003	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
UNASYN	HUMAN PRESCRIPTION DRUG LABEL	2	0049-0013	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAMUSCULAR	NDA	26 sections
UNASYN	HUMAN PRESCRIPTION DRUG LABEL	2	0049-0014	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	26 sections
UNASYN	HUMAN PRESCRIPTION DRUG LABEL	2	0049-0024	INJECTION, POWDER, FOR SOLUTION	50 mg	INTRAMUSCULAR	NDA	25 sections
UNASYN	HUMAN PRESCRIPTION DRUG LABEL	2	0049-0031	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAMUSCULAR	ANDA	26 sections
UNASYN	HUMAN PRESCRIPTION DRUG LABEL	2	0049-0032	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAMUSCULAR	ANDA	26 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0409-2689	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	25 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0409-2987	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6116	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	24 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6117	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	24 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6118	INJECTION, POWDER, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	24 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6119	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	25 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6120	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6121	INJECTION, POWDER, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	24 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6122	INJECTION, POWDER, FOR SOLUTION	125 mg	INTRAVENOUS	ANDA	25 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	0641-6123	INJECTION, POWDER, FOR SOLUTION	125 mg	INTRAVENOUS	ANDA	25 sections
ampicillin and sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	25021-142	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	25 sections
ampicillin and sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	25021-143	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
ampicillin and sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	25021-144	INJECTION, POWDER, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	25 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	36000-094	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	26 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	36000-095	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	26 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-150	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	23 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-210	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	23 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-211	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	23 sections
Ampicillin and Sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	44567-212	INJECTION, POWDER, FOR SOLUTION	5 g	INTRAVENOUS	ANDA	21 sections
Ampicillin and Sulbactam	Human Prescription Drug Label	2	55150-116	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAMUSCULAR	ANDA	23 sections
Ampicillin and Sulbactam	Human Prescription Drug Label	2	55150-117	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAMUSCULAR	ANDA	23 sections
Ampicillin and Sulbactam	Human Prescription Drug Label	2	55150-118	INJECTION, POWDER, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	23 sections
Ampicillin and Sulbactam	Human Prescription Drug Label	2	55150-178	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	22 sections
Ampicillin and Sulbactam	Human Prescription Drug Label	2	55150-179	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	22 sections
ampicillin and sulbactam	HUMAN PRESCRIPTION DRUG LABEL	2	66794-206	INJECTION, POWDER, FOR SOLUTION	0.50 g	INTRAVENOUS	ANDA	13 sections