ertapenem 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
analogues of penicillanic acid antibiotics modified in the five-membered ring	1046	153832-46-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: ertapenem invanz ertapenem sodium	Ertapenem has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria. The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3. Molecular weight: 475.52 Formula: C22H25N3O7S CLOGP: -0.83 LIPINSKI: 0 HAC: 10 HDO: 5 TPSA: 156.27 ALOGS: -3.22 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

ertapenem
invanz
ertapenem sodium

Ertapenem has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria. The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3.

Molecular weight: 475.52
Formula: C22H25N3O7S
CLOGP: -0.83
LIPINSKI: 0
HAC: 10
HDO: 5
TPSA: 156.27
ALOGS: -3.22
ROTB: 7

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
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	38 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	28.72 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.12 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.45 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.10 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	3.80 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
April 18, 2002	EMA	Merck Sharp & Dohme Ltd
Nov. 21, 2001	FDA	MERCK SHARP DOHME

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
Macular degeneration	612.71	22.52	159	4317	14229	50586419
Seizure	139.70	22.52	101	4375	117773	50482875
Hallucination	121.52	22.52	66	4410	46591	50554057
Drug ineffective	118.18	22.52	236	4240	819097	49781551
Confusional state	103.26	22.52	103	4373	185825	50414823
Encephalopathy	88.59	22.52	48	4428	33663	50566985
Renal graft infection	68.80	22.52	12	4464	150	50600498
Mental status changes	59.28	22.52	38	4438	36234	50564414
Product use in unapproved indication	54.81	22.52	59	4417	115760	50484888
Clostridium difficile infection	52.66	22.52	31	4445	25408	50575240
Avian influenza	49.92	22.52	8	4468	57	50600591
Status epilepticus	49.43	22.52	24	4452	13382	50587266
Mitochondrial toxicity	47.59	22.52	10	4466	348	50600300
Skin odour abnormal	42.43	22.52	12	4464	1460	50599188
Acute generalised exanthematous pustulosis	42.24	22.52	19	4457	8919	50591729
Generalised tonic-clonic seizure	41.58	22.52	27	4449	26283	50574365
Epilepsy	41.29	22.52	25	4451	21542	50579106
Delirium	38.97	22.52	30	4446	38162	50562486
Clostridium test positive	38.38	22.52	12	4464	2060	50598588
Drug reaction with eosinophilia and systemic symptoms	37.32	22.52	26	4450	28398	50572250
Bone marrow eosinophilic leukocyte count increased	33.24	22.52	5	4471	22	50600626
Allergic hepatitis	32.24	22.52	5	4471	28	50600620
Wound secretion	31.20	22.52	12	4464	3805	50596843
Hallucination, visual	31.17	22.52	19	4457	16563	50584085
Urinary tract infection pseudomonal	29.97	22.52	8	4468	785	50599863
Klebsiella infection	29.93	22.52	14	4462	7180	50593468
Tooth discolouration	29.16	22.52	8	4468	871	50599777
Neurotoxicity	27.99	22.52	17	4459	14723	50585925
Enterococcal infection	27.40	22.52	13	4463	6885	50593763
Cross sensitivity reaction	26.69	22.52	9	4467	1960	50598688
Pathogen resistance	26.58	22.52	12	4464	5677	50594971
Hypoglycaemia	26.54	22.52	28	4448	53553	50547095
Escherichia test positive	26.09	22.52	9	4467	2098	50598550
Seizure like phenomena	23.71	22.52	7	4469	991	50599657
Choriocarcinoma	23.48	22.52	4	4472	43	50600605
Scar	23.39	22.52	14	4462	11804	50588844

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
Confusional state	219.01	22.49	173	4567	127704	29442083
Seizure	208.35	22.49	148	4592	92975	29476812
Hallucination	130.56	22.49	84	4656	44628	29525159
Encephalopathy	104.83	22.49	64	4676	30979	29538808
Hallucination, visual	89.38	22.49	45	4695	14970	29554817
Myoclonus	85.47	22.49	42	4698	13267	29556520
Delirium	79.46	22.49	59	4681	39338	29530449
Product use in unapproved indication	69.03	22.49	77	4663	86798	29482989
Generalised tonic-clonic seizure	65.93	22.49	40	4700	19099	29550688
Status epilepticus	51.76	22.49	28	4712	10766	29559021
Serotonin syndrome	51.23	22.49	33	4707	17479	29552308
Pathogen resistance	47.32	22.49	24	4716	8092	29561695
Epilepsy	47.28	22.49	32	4708	18400	29551387
Biliary sepsis	46.43	22.49	12	4728	568	29569219
Agitation	41.57	22.49	46	4694	51258	29518529
Drug interaction	41.53	22.49	95	4645	197290	29372497
Neurotoxicity	41.42	22.49	27	4713	14586	29555201
Clostridium difficile colitis	41.38	22.49	26	4714	13186	29556601
Toxic encephalopathy	40.24	22.49	18	4722	4594	29565193
Disorientation	39.87	22.49	35	4705	29480	29540307
Myasthenia gravis crisis	38.54	22.49	10	4730	481	29569306
Pseudomonal sepsis	37.39	22.49	15	4725	2927	29566860
Neuromyopathy	36.84	22.49	11	4729	888	29568899
Drug resistance	34.13	22.49	28	4712	21512	29548275
Eosinophilia	31.38	22.49	27	4713	22134	29547653
Appendicitis perforated	29.95	22.49	11	4729	1692	29568095
Rash morbilliform	25.88	22.49	11	4729	2482	29567305
Metabolic acidosis	24.20	22.49	30	4710	37632	29532155
Vitamin B1 deficiency	23.80	22.49	6	4734	257	29569530
Vitamin A deficiency	23.32	22.49	4	4736	23	29569764
Anticonvulsant drug level decreased	23.30	22.49	8	4732	1011	29568776

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
Confusional state	300.19	19.65	256	8053	260888	64229535
Seizure	280.82	19.65	205	8104	166687	64323736
Hallucination	251.61	19.65	141	8168	72647	64417776
Encephalopathy	184.48	19.65	107	8202	58712	64431711
Delirium	118.21	19.65	86	8223	69108	64421315
Hallucination, visual	112.82	19.65	60	8249	27774	64462649
Myoclonus	107.06	19.65	56	8253	25062	64465361
Product use in unapproved indication	101.19	19.65	119	8190	176499	64313924
Generalised tonic-clonic seizure	100.29	19.65	63	8246	39794	64450629
Status epilepticus	97.21	19.65	50	8259	21613	64468810
Epilepsy	89.40	19.65	55	8254	33476	64456947
Mental status changes	71.90	19.65	61	8248	61101	64429322
Pathogen resistance	68.23	19.65	33	8276	12510	64477913
Neurotoxicity	68.12	19.65	43	8266	27361	64463062
Clostridium difficile infection	64.10	19.65	46	8263	36117	64454306
Clostridium test positive	60.52	19.65	22	8287	4093	64486330
Clostridium difficile colitis	58.53	19.65	39	8270	27184	64463239
Renal graft infection	53.08	19.65	12	8297	401	64490022
Drug reaction with eosinophilia and systemic symptoms	49.69	19.65	47	8262	54170	64436253
Disorientation	48.52	19.65	47	8262	55781	64434642
Toxic encephalopathy	47.94	19.65	24	8285	9791	64480632
Drug resistance	45.36	19.65	37	8272	35065	64455358
Avian influenza	44.58	19.65	8	8301	79	64490344
Eosinophilia	42.73	19.65	37	8272	38039	64452384
Agitation	40.01	19.65	53	8256	88314	64402109
Cross sensitivity reaction	38.60	19.65	15	8294	3352	64487071
Myasthenia gravis crisis	34.87	19.65	10	8299	874	64489549
Acute generalised exanthematous pustulosis	34.77	19.65	22	8287	14036	64476387
Neuromyopathy	34.66	19.65	11	8298	1357	64489066
Biliary sepsis	34.19	19.65	11	8298	1417	64489006
Bone marrow eosinophilic leukocyte count increased	31.36	19.65	5	8304	22	64490401
Skin odour abnormal	31.30	19.65	11	8298	1856	64488567
Eosinophilic pneumonia	30.94	19.65	14	8295	4563	64485860
Escherichia test positive	30.32	19.65	12	8297	2813	64487610
Allergic hepatitis	29.92	19.65	5	8304	31	64490392
Tooth discolouration	29.67	19.65	9	8300	956	64489467
Pseudomonal sepsis	29.31	19.65	14	8295	5158	64485265
Disorganised speech	28.73	19.65	10	8299	1640	64488783
Metabolic acidosis	28.24	19.65	40	8269	70918	64419505
Fatigue	27.24	19.65	34	8275	748696	63741727
Pyrexia	26.77	19.65	142	8167	558502	63931921
Urinary tract infection pseudomonal	26.16	19.65	9	8300	1425	64488998
Seizure like phenomena	24.92	19.65	9	8300	1643	64488780
Arthralgia	24.88	19.65	13	8296	442247	64048176
Vitamin B1 deficiency	24.86	19.65	7	8302	573	64489850
Drug interaction	24.64	19.65	102	8207	361981	64128442
Anticonvulsant drug level decreased	24.02	19.65	9	8300	1821	64488602
Mitochondrial toxicity	23.92	19.65	10	8299	2696	64487727
Metabolic encephalopathy	23.53	19.65	14	8295	8011	64482412
Appendicitis perforated	23.52	19.65	10	8299	2810	64487613
Rash morbilliform	23.43	19.65	12	8297	5129	64485294
Wound secretion	23.24	19.65	12	8297	5220	64485203
Enterococcal infection	23.10	19.65	17	8292	13849	64476574
Off label use	22.66	19.65	149	8160	632657	63857766
Pain in extremity	21.87	19.65	6	8303	303079	64187344
Klebsiella infection	21.49	19.65	16	8293	13265	64477158
Unresponsive to stimuli	20.93	19.65	29	8280	50364	64440059
Vitamin A deficiency	20.62	19.65	4	8305	62	64490361
Choriocarcinoma	20.62	19.65	4	8305	62	64490361
Endotracheal intubation	20.43	19.65	10	8299	3885	64486538
Haematidrosis	20.39	19.65	4	8305	66	64490357
HER2 positive breast cancer	19.93	19.65	5	8304	262	64490161

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J01DH03	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE OTHER BETA-LACTAM ANTIBACTERIALS Carbapenems
FDA CS	M0024174	Carbapenems
FDA EPC	N0000175496	Penem Antibacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
CHEBI has role	CHEBI:36047	antibacterial drugs

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Acute bacterial peritonitis	indication	31860008
Bacterial pneumonia	indication	53084003	DOID:874
Miscarriage with sepsis	indication	67465009
Haemophilus influenzae pneumonia	indication	70036007
Abdominal abscess	indication	75100008
Female genital tract infection	indication	125585007
Infectious disease of abdomen	indication	128070006
Pneumococcal pneumonia	indication	233607000
Escherichia coli urinary tract infection	indication	301011002
Peptostreptococcus infection	indication	135341000119101
Urinary tract infection caused by Klebsiella	indication	369001000119100
Complicated Bacterial Peritonitis	indication
Complicated Skin and Skin Structure Streptococcus Pyogenes Infection	indication
Septic Abortion due to Porphyromonas	indication
Post-Op Gynecologic Infection due to Porphyromonas	indication
Klebsiella Pyelonephritis	indication
Post-Op Gynecological Peptostreptococcus Infection	indication
Complicated E. Coli Peritonitis	indication
Postpartum Endomyometritis due to E. Coli	indication
Postpartum Endomyometritis due to Streptococcus	indication
Diabetic Foot Infection	indication
Streptococcal Septic Abortion	indication
Postpartum Endomyometritis due to Peptostreptococcus	indication
Post-Op Gynecologic Infection due to Bacteroides	indication
Postpartum Endomyometritis due to Bacteroides	indication
E. Coli Septic Abortion	indication
E. Coli Pyelonephritis	indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection	indication
Complicated Skin and Skin Structure E. Coli Infection	indication
Peptostreptococcus Septic Abortion	indication
Complicated Bacteroides Peritonitis	indication
Moraxella Catarrhalis Pneumonia	indication
Post-Op Gynecologic Infection due to Prevotella	indication
Bacteroides Septic Abortion	indication
Colorectal Surgery Infection Prevention	indication
Postpartum Endomyometritis due to Porphyromonas	indication
Post-Op Gynecological Infection due to E. Coli	indication
Postpartum Endomyometritis due to Prevotella	indication
Post-Op Gynecologic Infection, due to Streptococcus	indication
Prevotella Septic Abortion	indication
Complicated Skin and Skin Structure Infection	indication
Gas gangrene caused by clostridium perfringens	off-label use	266093005
Clostridium Perfringens Empyema	off-label use
Acute nephropathy	contraindication	58574008
Kidney disease	contraindication	90708001	DOID:557
Seizure disorder	contraindication	128613002
Lesion of brain	contraindication	301766008
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	4.1	acidic
pKa3	6.83	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	UniProt	Action	Bioact source	MoA source
D-alanyl-D-alanine carboxypeptidase DacB	Enzyme	DACB_ECOLI	INHIBITOR	DRUGBANK	CHEMBL
Penicillin-binding protein 1A	Enzyme	PBPA_ECOLI	INHIBITOR	DRUGBANK	CHEMBL
Penicillin-binding protein 1B	Enzyme	PBPB_ECOLI	INHIBITOR	DRUGBANK	CHEMBL
Penicillin-binding protein 1	Enzyme	A1KS91_NEIMF		WOMBAT-PK
Penicillin-binding protein 2	Enzyme	Q9X6V3_PSEAI		WOMBAT-PK
D-alanyl-D-alanine carboxypeptidase; D-alanyl-D-alanine carboxypeptidase penicillin-binding protein 6	Enzyme	Q7CHG0_YERPE		WOMBAT-PK
Penicillin-binding protein 4	Enzyme	Q5D1E9_STAAU		WOMBAT-PK
D-ala-D-ala-carboxypeptidase; D-alanyl-D-alanine carboxypeptidase; D-alanyl-D-alanine carboxypeptidase family protein; Penicillin-binding protein 5	Enzyme	Q9X6V7_PSEAI		WOMBAT-PK

External reference:

ID	Source
4021283	VUID
N0000148720	NUI
D04049	KEGG_DRUG
153773-82-1	SECONDARY_CAS_RN
4021283	VANDF
C1120106	UMLSCUI
CHEBI:404903	CHEBI
CHEMBL1359	ChEMBL_ID
CHEMBL1232	ChEMBL_ID
D000077727	MESH_DESCRIPTOR_UI
DB00303	DRUGBANK_ID
10906	IUPHAR_LIGAND_ID
8049	INN_ID
G32F6EID2H	UNII
150610	PUBCHEM_CID
325642	RXNORM
16218	MMSL
173352	MMSL
274067	MMSL
42474	MMSL
d04783	MMSL
009554	NDDF
009555	NDDF
385573008	SNOMEDCT_US
385574002	SNOMEDCT_US
396346003	SNOMEDCT_US
1RG	PDB_CHEM_ID
2RG	PDB_CHEM_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
INVANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0006-3843	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	28 sections
INVANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0006-3843	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	28 sections
INVANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0006-3845	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	NDA	28 sections
INVANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0006-3845	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	NDA	28 sections
ertapenem sodium	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9398	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	ANDA	28 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	0409-3510	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	ANDA	28 sections
ERTAPENEM SODIUM	HUMAN PRESCRIPTION DRUG LABEL	1	16714-889	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
ERTAPENEM	HUMAN PRESCRIPTION DRUG LABEL	1	42023-221	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	29 sections
ERTAPENEM	HUMAN PRESCRIPTION DRUG LABEL	1	42023-221	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	29 sections
ERTAPENEM	HUMAN PRESCRIPTION DRUG LABEL	1	42023-221	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	29 sections
ERTAPENEM	HUMAN PRESCRIPTION DRUG LABEL	1	42023-221	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	29 sections
ERTAPENEM SODIUM	HUMAN PRESCRIPTION DRUG LABEL	1	43598-901	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	44567-820	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAMUSCULAR	ANDA	28 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	44647-051	INJECTION	1 g	INTRAVENOUS	ANDA	29 sections
Ertapenem	Human Prescription Drug Label	1	55150-282	INJECTION	1 g	INTRAVENOUS	ANDA	25 sections
Ertapenem	Human Prescription Drug Label	1	55150-282	INJECTION	1 g	INTRAVENOUS	ANDA	25 sections
Ertapenem	Human Prescription Drug Label	1	55150-282	INJECTION	1 g	INTRAVENOUS	ANDA	25 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	60505-6196	INJECTION	1 g	INTRAVENOUS	ANDA	29 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	60505-6196	INJECTION	1 g	INTRAVENOUS	ANDA	29 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	63323-823	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	29 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	68001-408	INJECTION	1 g	INTRAVENOUS	ANDA	29 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	68001-408	INJECTION	1 g	INTRAVENOUS	ANDA	29 sections
Ertapenem	Human Prescription Drug Label	1	68083-351	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
Ertapenem	Human Prescription Drug Label	1	68083-351	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	72266-159	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
Ertapenem	HUMAN PRESCRIPTION DRUG LABEL	1	72266-159	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections