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

Stem definition	Drug id	CAS RN
angiotensin-converting enzyme inhibitors	1587	76547-98-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: lisinopril linopril nanopril lisinopril hydrate lisinopril dihydrate anhydrous lisinopril	One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure. Molecular weight: 405.50 Formula: C21H31N3O5 CLOGP: -1.82 LIPINSKI: 0 HAC: 8 HDO: 4 TPSA: 132.96 ALOGS: -3.27 ROTB: 12 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

lisinopril
linopril
nanopril
lisinopril hydrate
lisinopril dihydrate
anhydrous lisinopril

One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure.

Molecular weight: 405.50
Formula: C21H31N3O5
CLOGP: -1.82
LIPINSKI: 0
HAC: 8
HDO: 4
TPSA: 132.96
ALOGS: -3.27
ROTB: 12

Status: OFP

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

Drug dosage:

Dose	Unit	Route
10	mg	O

ADMET properties:

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Property	Value	Reference
S (Water solubility)	97 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	94 %	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	42 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	25 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	1.41 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
CL (Clearance)	1.20 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	1 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.89 L/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Dec. 29, 1987	FDA	MERCK

FDA Adverse Event Reporting System (Female)

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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
Angioedema	1650.09	9.59	1441	254424	46524	63186633
Intestinal angioedema	629.50	9.59	191	255674	464	63232693
Cardiac failure congestive	570.60	9.59	1194	254671	91239	63141918
Myocardial infarction	495.96	9.59	1183	254682	98710	63134447
Swollen tongue	339.43	9.59	548	255317	34252	63198905
Drug ineffective	320.76	9.59	2688	253177	1042077	62191080
Cerebrovascular accident	308.75	9.59	1048	254817	106976	63126181
Off label use	248.77	9.59	1646	254219	672816	62560341
Acute kidney injury	236.45	9.59	1843	254022	261572	62971585
Coronary artery disease	232.85	9.59	446	255419	31931	63201226

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FDA Adverse Event Reporting System (Male)

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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
Angioedema	11128.91	10.93	5073	200499	32301	34719058
Myocardial infarction	649.90	10.93	1869	203703	119216	34632143
Cardiac failure congestive	645.68	10.93	1477	204095	81793	34669566
Hyperkalaemia	597.82	10.93	1284	204288	68105	34683254
Swollen tongue	530.01	10.93	535	205037	14070	34737289
Lip swelling	483.73	10.93	533	205039	15547	34735812
Off label use	477.51	10.93	1107	204465	418417	34332942
Completed suicide	380.72	10.93	1356	204216	96812	34654547
Coronary artery disease	365.37	10.93	849	204723	47456	34703903
Acute kidney injury	341.42	10.93	3002	202570	301986	34449373

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FDA Adverse Event Reporting System (Geriatric)

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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
Angioedema	12191.35	9.70	6243	357827	69792	79310526
Myocardial infarction	1331.23	9.70	2730	361340	181399	79198919
Cardiac failure congestive	1286.64	9.70	2321	361749	140081	79240237
Hyperkalaemia	798.76	9.70	1673	362397	112725	79267593
Swollen tongue	773.33	9.70	963	363107	41607	79338711
Intestinal angioedema	736.71	9.70	238	363832	645	79379673
Acute kidney injury	706.30	9.70	4415	359655	514989	78865329
Coronary artery disease	706.12	9.70	1155	362915	64319	79315999
Completed suicide	658.39	9.70	2538	361532	243229	79137089
Cerebrovascular accident	628.41	9.70	1843	362227	153449	79226869

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	C09AA03	CARDIOVASCULAR SYSTEM AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM ACE INHIBITORS, PLAIN ACE inhibitors, plain
ATC	C09BA03	CARDIOVASCULAR SYSTEM AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM ACE INHIBITORS, COMBINATIONS ACE inhibitors and diuretics
ATC	C09BB03	CARDIOVASCULAR SYSTEM AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM ACE INHIBITORS, COMBINATIONS ACE inhibitors and calcium channel blockers
ATC	C10BX07	CARDIOVASCULAR SYSTEM LIPID MODIFYING AGENTS LIPID MODIFYING AGENTS, COMBINATIONS Lipid modifying agents in combination with other drugs
CHEBI has role	CHEBI:35674	antihypertensive drugs
MeSH PA	D000806	Angiotensin-Converting Enzyme Inhibitors
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002316	Cardiotonic Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D004791	Enzyme Inhibitors

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

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Disease	Relation	SNOMED_ID	DOID
Myocardial infarction	indication	22298006	DOID:5844
Hypertensive disorder	indication	38341003	DOID:10763
Chronic heart failure	indication	48447003
Superficial Ocular Infection	indication
Diabetic retinopathy	off-label use	4855003	DOID:8947
Atrial fibrillation	off-label use	49436004	DOID:0060224
Blepharoconjunctivitis	off-label use	68659002	DOID:2456
Dacryocystitis	off-label use	85777005	DOID:9938
Corneal ulcer	off-label use	91514001	DOID:8463
Diabetic renal disease	off-label use	127013003

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🐶 Veterinary Drug Use

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🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.18	acidic
pKa2	3.18	acidic
pKa3	11.0	Basic
pKa4	6.95	Basic

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10039800	Nov. 6, 2035	ACUTE MYOCARDIAL INFARCTION
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10039800	Nov. 6, 2035	METHOD OF TREATING HYPERTENSION
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10039800	Nov. 6, 2035	METHOD OF TREATMENT OF HEART FAILURE
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10039800	Nov. 6, 2035	REDUCTION OF MORTALITY IN ACUTE MYOCARDIAL INFARCTION
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10039800	Nov. 6, 2035	TREATMENT OF HEART FAILURE
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10039800	Nov. 6, 2035	TREATMENT OF HYPERTENSION
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10039800	Nov. 6, 2035	TREATMENT OF MYOCARDIAL INFARCTION
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10406199	Nov. 6, 2035	ACUTE MYOCARDIAL INFARCTION
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10406199	Nov. 6, 2035	METHOD OF TREATING HYPERTENSION
1MG/ML	QBRELIS	AZURITY	N208401	July 29, 2016	RX	SOLUTION	ORAL	10406199	Nov. 6, 2035	METHOD OF TREATMENT OF HEART FAILURE

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Angiotensin-converting enzyme	Enzyme	P12821	ACE_HUMAN	INHIBITOR	IC50	8.92		WOMBAT-PK	CHEMBL
Angiotensin-converting enzyme	Enzyme		ACE_RABIT		Ki	7.29		CHEMBL

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External reference:

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ID	Source
LPR	PDB_CHEM_ID
000658	NDDF
108575001	SNOMEDCT_US
29046	RXNORM
31907	MMSL
341000220102	SNOMEDCT_US
386873009	SNOMEDCT_US
4019380	VUID
4019380	VANDF
44066	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9713	TABLET	20 mg	ORAL	ANDA	26 sections
Lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9714	TABLET	10 mg	ORAL	ANDA	26 sections
Lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9715	TABLET	5 mg	ORAL	ANDA	26 sections
lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0025	TABLET	2.50 mg	ORAL	ANDA	25 sections
lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0101	TABLET	10 mg	ORAL	ANDA	25 sections
lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0102	TABLET	20 mg	ORAL	ANDA	25 sections
lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0103	TABLET	30 mg	ORAL	ANDA	25 sections
lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0104	TABLET	40 mg	ORAL	ANDA	25 sections
lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0602	TABLET	2.50 mg	ORAL	ANDA	25 sections
lisinopril	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0605	TABLET	5 mg	ORAL	ANDA	25 sections

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