Identification

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Name
Enalapril
Accession Number
DB00584  (APRD00510)
Type
Small Molecule
Groups
Approved, Vet approved
Description

Enalapril is a prodrug belonging to the angiotensin-converting enzyme (ACE) inhibitor drug class that works on the renin-angiotensin-aldosterone system, which is responsible for the regulation of blood pressure and fluid and electrolyte homeostasis. Enalapril is an orally-active and long-acting nonsulphydryl antihypertensive agent that suppresses the renin-angiotensin-aldosterone system to lower blood pressure. It was developed from a targeted research programmed using molecular modelling.2 Being a prodrug, enalapril is rapidly biotransformed into its active metabolite, enalaprilat, which is responsible for the pharmacological actions of enalapril. The active metabolite of enalapril competitively inhibits the ACE to hinder the production of angiotensin II, a key component of the renin-angiotensin-aldosterone system that promotes vasoconstriction and renal reabsorption of sodium ions in the kidneys. Ultimately, enalaprilat works to reduce blood pressure and blood fluid volume.

Commonly marketed under the trade name Vasotec, enalapril was first approved by the FDA in 1985 for the management of hypertension, heart failure, and asymptomatic left ventricular dysfunction. It is also found in a combination product containing hydrochlorothiazide that is used for the management of hypertension. The active metabolite enalaprilat is also available in oral tablets and intravenous formulations for injection.

Structure
Thumb
Synonyms
  • (S)-1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline
  • (S)-1-{(S)-2-[1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid
  • 1-(N-((S)-1-carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester
  • ánalapril
  • Enalapril
  • Enalaprila
  • Enalaprilum
External IDs
L 154739-01 D / MK 421
Product Ingredients
IngredientUNIICASInChI Key
Enalapril maleate9O25354EPJ76095-16-4OYFJQPXVCSSHAI-QFPUQLAESA-N
Enalapril sodium94A7UFL2SI149404-21-7FTTHROYWFRGKST-BDURURIASA-M
Active Moieties
NameKindUNIICASInChI Key
EnalaprilatprodrugQ508Q118JM76420-72-9LZFZMUMEGBBDTC-QEJZJMRPSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act EnalaprilTabletOralTEVA Canada Limited2007-10-17Not applicableCanada
Act EnalaprilTabletOralTEVA Canada Limited2007-10-17Not applicableCanada
Act EnalaprilTabletOralTEVA Canada Limited2007-10-17Not applicableCanada
Act EnalaprilTabletOralTEVA Canada Limited2007-10-17Not applicableCanada
EnalaprilTabletOralSivem Pharmaceuticals Ulc2015-08-10Not applicableCanada
EnalaprilTabletOralFrosst A Division Of Merck Canada IncNot applicableNot applicableCanada
EnalaprilTabletOralFrosst A Division Of Merck Canada IncNot applicableNot applicableCanada
EnalaprilTabletOralCobalt LaboratoriesNot applicableNot applicableCanada
EnalaprilTabletOralSanis Health Inc2013-02-13Not applicableCanada
EnalaprilTabletOralFrosst A Division Of Merck Canada IncNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-enalapril Tab 10mgTabletOralApotex Corporation1993-12-31Not applicableCanada
Apo-enalapril Tab 2.5mgTabletOralApotex Corporation1993-12-31Not applicableCanada
Apo-enalapril Tab 20mgTabletOralApotex Corporation1993-12-31Not applicableCanada
Apo-enalapril Tab 5mgTabletOralApotex Corporation1993-12-31Not applicableCanada
Ava-enalaprilTabletOralAvanstra Inc2011-10-112014-08-21Canada
Ava-enalaprilTabletOralAvanstra Inc2011-10-112014-08-21Canada
Ava-enalaprilTabletOralAvanstra Inc2011-10-112014-08-21Canada
Ava-enalaprilTabletOralAvanstra Inc2011-10-112014-08-21Canada
Dom-enalaprilTabletOralDominion PharmacalNot applicableNot applicableCanada
Dom-enalaprilTabletOralDominion PharmacalNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (5 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralTaro Pharmaceuticals U.S.A., Inc.2001-09-18Not applicableUs51672 4045 01 nlmimage10 f30579bb
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralOceanside Pharmaceuticals1986-10-312018-08-31Us
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralAv Kare, Inc.2013-07-222016-04-06Us00093 1052 01 nlmimage10 ae29d76e
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (5 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralMed Health Pharma2011-04-282012-06-13Us
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralbryant ranch prepack2001-09-182018-10-25Us51672 4046 01 nlmimage10 0005807c
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralbryant ranch prepack2016-03-31Not applicableUs
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralApotex Corporation2007-06-192011-01-31Us60505 0209 01 nlmimage10 5a462d51
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralNucare Pharmaceuticals,inc.2001-09-18Not applicableUs
Enalapril maleate and hydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralMed Pharma Co., Ltd.2011-04-132012-04-25Us
Enalapril Maleate and HydrochlorothiazideEnalapril maleate (10 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralRebel Distributors2001-09-18Not applicableUs
International/Other Brands
Acetec (Alphapharm) / Acetensil (Grünenthal) / Alapren (Ranbaxy) / Amotac (Mass Pharma) / Amprace (Merck Sharp & Dohme) / Dilvas (Cipla) / Diotensil (Mintlab) / Drepatil (Fada) / Enace (Abbott) / EnaHexal (Sandoz) / Enal (East West) / Enalapoten (Del Bel) / Enpril (Wockhardt) / Feliberal (Silanes) / Gadopril (Gador (Argentina)) / Glioten (Bago) / Kinfil (Nova Argentia (Argentina)) / Vasotec IV (Sandoz (Canada))
Categories
UNII
69PN84IO1A
CAS number
75847-73-3
Weight
Average: 376.4467
Monoisotopic: 376.199822016
Chemical Formula
C20H28N2O5
InChI Key
GBXSMTUPTTWBMN-XIRDDKMYSA-N
InChI
InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1
IUPAC Name
(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O

Pharmacology

Indication

Indicated for the management of essential or renovascular hypertension 10 as monotherapy or in combination with other antihypertensive agents, such as thiazide diuretics, for an additive effect.Label

Indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis.Label

Indicated for the management of asymptomatic left ventricular dysfunction in patients with an ejection fraction of ≤ to 35 percent to decrease the rate of development of overt heart failure and the incidence of hospitalization for heart failure.Label

Associated Conditions
Pharmacodynamics

Enalapril is an antihypertensive agent that exhibits natriuretic and uricosuric properties. Enalapril lowers blood pressure in all grades of essential and renovascular hypertension, and peripheral vascular resistance without causing an increase in heart rate.6 Individuals with low-renin hypertensive population were still responsive to enalapril.Label The duration of hypertensive effect in the systolic and diastolic blood pressure persists for at least 24 hours following initial administration of a single oral dose, and repeated daily administration of enalapril confers an additional reduction in blood pressure and a steady-state antihypertensive response may take several weeks.7 In patients with severe congestive heart failure and inadequate clinical response to conventional antihypertensive therapies, treatment with enalapril resulted in improvements in cardiac performance as observed by a reduction in both preload and afterload, and improved clinical status long-term.6 Furthermore, enalapril was shown to increase cardiac output and stroke volume while decreasing pulmonary capillary wedge pressure in patients with congestive heart failure refractory to conventional treatment with digitalis and diuretics. In clinical studies, enalapril reduced left ventricular mass, and did not affect cardiac function or myocardial perfusion during exercise.5 Enalapril is not highly associated with the risk of bradycardia unlike most diuretics and beta-blockers 6 and it does not produce rebound hypertension upon discontinuation of therapy.5

Enalapril is not reported to produce hypokalaemia, hyperglycaemia, hyperuricaemia or hypercholesterolaemia. In the kidneys, enalapril was shown to increase renal blood flow and decrease renal vascular resistance. It also augmented the glomerular filtration rate in patients with a glomerular filtration rate less than 80 mL/min.5 When used in combination, enalapril was shown to attenuate the extent of drug-induced hypokalemia caused by hydrochlorothiazide 6 and the antihypertensive effects of both drugs were potentiated.2

Mechanism of action

The renin-angiotensin-aldosterone system (RAAS) is a signaling pathway that works in synergism with the sympathetic system to regulate blood pressure and fluid and electrolyte homeostasis. Activation of this system upon stimulation by different factors, such as low blood pressure and nerve impulses, leads to increased release of norepinephrine (NE) from sympathetic nerve terminals and effects on the vascular growth, vasoconstriction, and salt retention in the kidneys.9 Renin is released from Renin acts on the precursor prottein angiotensinogen, which is a plasma globulin synthesized from the liver, to produce cleaved peptide hormone angiotensin I.9 Angiotensin I then can be further cleaved by ACE to produce angiotensin II, a vasoconstrictive peptide hormone.Label Present in different isoforms, angiotensin converting enzyme (ACE) is peptidyl dipeptidase enzyme expressed in various tissues, including the vascular tissues, such as the heart, brain, and kidneys.9 ACE also plays a role in inactivation of bradykinin, a potent vasodepressor peptide.9,Label Angiotensin II mediates various actions on the body by working on its G-protein coupled receptors, AT1 and AT2.9 It causes direct vasoconstriction of precapillary arterioles and postcapillary venules, inhibits the reuptake of NE thereby increasing available levels, stimulates the release of catecholamines from the adrenal medulla, reduces urinary excretion of sodium ions and water by promoting proximal tubular reabsorption, stimulates synthesis and release of aldosterone from the adrenal cortex, and stimulates hypertrophy of both vascular smooth muscle cells and cardiac myocytes.11

Enalapril is a pharmacologically inactive prodrug that requires hepatic biotransformation to form enalaprilat, its active metabolite that works on the RAAS to inhibit ACE.Label Biotransformation is critial for the therapeutic actions of the drug, as enalapril itself is only a weak inhibitor of ACE.4 ACE inhibition results in reduced production and plasma levels of angiotensin II, increased plasma renin activity due to the loss of feedback inhibition by angiotensin II, and decreased aldosterone secretion.10 However, plasma aldosterone levels usually return to normal during long-term administration of enalapril.7 Decreased levels of angiotensin II subsequently leads to the dilatation of peripheral vessles and reduced vascular resistance which in turn lower blood pressure.7 While inhibition of ACE leading to suppression of RAAS is thought to be the primary mechanism of action of enalapril, the drug was shown to still exert antihypertensive effects on individuals with low-renin hypertension. It is suggested that enalapril may mediate its pharmacological actions via other modes of action that are not fully understood.Label As ACE is structurally similar to kininase I, which is a carboxypeptidase that degrades bradykinin, whether increased levels of bradykinin play a role in the therapeutic effects of enalapril remains to be elucidated.Label

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Humans
Additional Data Available
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Absorption

Following oral administration, the peak plasma concentrations (Cmax) of enalapril is achieved within 1 hour post dosing while the Cmax of enalaprilat occurs at three to four hours post dosing.Label The steady-state is achieved by the fourth daily dose and there is no accumulation with repeated dosing.5 However, accumulation of enalaprilat may occur in patients with creatinine clearance less than 30 mL/min.4 Food intake is reported to have a minimal effect on drug absorption.1 Following oral administration, about 60% of enalapril was absorbed.Label Bioavailability of enalapril averaged about 40% when intravenous enalaprilat was used as a reference standard.2

Volume of distribution

The volume of distribution of enalapril has not been established. Enalaprilat is shown to penetrate into most tissuesm, in particular the kidneys and vascular tissuem, although penetration of the blood-brain barrier has not been demonstrated after administration at therapeutic doses.7 In dog studies, enalapril and enalaprilat cross the blood-brain barrier poorly.10 Minimal penetration occurs into breast milk but significant fetal transfer occurs.7 The drug crosses the placental barrier in rats and hamsters.10

Protein binding

It is reported that less than 50% of enalaprilat is bound to human plasma proteins, based on limited data from binding studies of enalaprilat in human plasma both by equilibrium dialysis and by ultrafiltration.2,7

Metabolism

About 60% of the absorbed dose is extensively hydrolyzed to enalaprilat via de-esterification mediated by hepatic esterases.Label In humans, metabolism beyond bioactivation to enalaprilat is not observed.5

Route of elimination

Enalapril is mainly eliminated through renal excretion, where approximately 94% of the total dose is excreted via urine or feces as either enalaprilat or unchanged parent compound.Label About 61% and 33% of the total dose can be recovered in the urine and feces, respectively.7 In the urine, about 40% of the recovered dose is in the form of enalaprilat.Label

Half life

The average terminal half life of enalaprilat is 35-38 hours. The effective half life following multiple doses is 11-14 hours. The prolonged terminal half-life is due to the binding of enalaprilat to ACE.5

Clearance

Following oral administration in healthy male volunteers, the renal clearance was approximately 158 ± 47 mL/min.8 It is reported that enalapril and enalaprilat are undetectable in the plasma by 4 hours post-dosing.3

Toxicity

LD50 and Overdose

Oral LD50 in rats is 2973 mg/kg.MSDS Lethality was observed with single oral doses of enalapril above 1000 mg/kg in mice and greater than or equal to 1775 mg/kg in rats. Serum enalaprilat levels 100- and 200-fold higher than usually seen after therapeutic doses have been reported after ingestion of 300 mg and 440 mg of enalapril, respectively.10 While there is limited data about enalapril overdose in humans, overdosage may result in marked hypotension and stupor based on the pharmacological properties of the drug. Most common adverse effects of enalapril include cough, hypotension, stupor, headache, dizziness and fatigue. If hypotension is seen, usual treatment of intravenous infusion of normal saline solution is recommended. Enalaprilat may be removed from systemic circulation with the use of hemodialysis. It has been removed from neonatal circulation by peritoneal dialysis.Label

Nonclinical toxicology

Maternal and fetal toxicity occudred in some rabbits treated with enalapril at doses of 1 mg/kg/day or more. There was no fetotoxicity, expressed as a decrease in average fetal weight, or teratogenicity in rats treated with enalapril at doses up to 200 mg/kg/day, which is about 333 times the maximum human dose.10 In mice and rats receiving enalapril at doses ranging from 90 to 180 mg/kg/day, there was no evidence of a tumorigenic effect. Neither enalapril or its active metabolite were shown to be mutagenic or genotoxic in in vitro and in vivo studies. There were no adverse effects on reproductive performance of male and female rats treated with up to 90 mg/kg/day of enalapril. Label

Use in special populations

Caution is warranted in patients who are concurrently using another ACE inhibitors with enalapril, as there have been incidences of agranulocytosis with the use of captopril, which is another ACE inhibitor. This adverse event may be particularly significant in patients with renal impairment or collagen vascular disease.Label As enalapril and enalaprilat were shown to be secreted in human milk in trace amounts, the use of enalaprilat in nursing women is not recommended.10 Significant fetal transfer occurs with enalapril and enalaprilat thus the use of the drug in pregnant women should be strongly avoided. Caution is advised when enalapril is used in patients who are elderly or with renal impairment, as dosage adjustments may be appropriate. The antihypertensive effect of angiotensin converting enzyme inhibitors is generally lower in individuals of African descent, usually a low-renin hypertensive population.Label

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Enalapril Metabolism PathwayDrug metabolism
Enalapril Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Enalapril.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Enalapril.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Enalapril.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Enalapril.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Enalapril.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Enalapril.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Enalapril.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Enalapril.
AbediterolAbediterol may decrease the antihypertensive activities of Enalapril.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Enalapril.
Additional Data Available
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  • Severity
    Severity

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Food Interactions
  • Enalapril decreases the excretion of potassium. Salt substitutes containing potassium increase the risk of hyperkalemia.
  • Herbs that may attenuate the antihypertensive effect of enalapril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
  • High salt intake may attenuate the antihypertensive effect of enalapril.
  • Take without regard to meals.

References

Synthesis Reference

K. S. Keshava Murthy, Andrew Burchat, Gamini Weeratunga, "Sodium enalapril complex and the use thereof to make sodium enalapril." U.S. Patent US5637730, issued February, 1983.

US5637730
General References
  1. Swanson BN, Vlasses PH, Ferguson RK, Bergquist PA, Till AE, Irvin JD, Harris K: Influence of food on the bioavailability of enalapril. J Pharm Sci. 1984 Nov;73(11):1655-7. [PubMed:6097665]
  2. Davies RO, Gomez HJ, Irvin JD, Walker JF: An overview of the clinical pharmacology of enalapril. Br J Clin Pharmacol. 1984;18 Suppl 2:215S-229S. [PubMed:6099737]
  3. MacFadyen RJ, Meredith PA, Elliott HL: Enalapril clinical pharmacokinetics and pharmacokinetic-pharmacodynamic relationships. An overview. Clin Pharmacokinet. 1993 Oct;25(4):274-82. doi: 10.2165/00003088-199325040-00003. [PubMed:8261712]
  4. Vlasses PH, Larijani GE, Conner DP, Ferguson RK: Enalapril, a nonsulfhydryl angiotensin-converting enzyme inhibitor. Clin Pharm. 1985 Jan-Feb;4(1):27-40. [PubMed:2982541]
  5. Gomez HJ, Cirillo VJ, Irvin JD: Enalapril: a review of human pharmacology. Drugs. 1985;30 Suppl 1:13-24. doi: 10.2165/00003495-198500301-00004. [PubMed:2994984]
  6. Todd PA, Heel RC: Enalapril. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in hypertension and congestive heart failure. Drugs. 1986 Mar;31(3):198-248. doi: 10.2165/00003495-198631030-00002. [PubMed:3011386]
  7. Todd PA, Goa KL: Enalapril. A reappraisal of its pharmacology and therapeutic use in hypertension. Drugs. 1992 Mar;43(3):346-81. doi: 10.2165/00003495-199243030-00005. [PubMed:1374319]
  8. Ulm EH, Hichens M, Gomez HJ, Till AE, Hand E, Vassil TC, Biollaz J, Brunner HR, Schelling JL: Enalapril maleate and a lysine analogue (MK-521): disposition in man. Br J Clin Pharmacol. 1982 Sep;14(3):357-62. doi: 10.1111/j.1365-2125.1982.tb01991.x. [PubMed:6289858]
  9. 22. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 270-271). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  10. Enalapril Oral Tablets - Product Monograph [Link]
  11. Angiotensin Converting Enzyme Inhibitors (ACEI) - StatPearls [Link]
External Links
Human Metabolome Database
HMDB0014722
KEGG Drug
D07892
KEGG Compound
C06977
PubChem Compound
5388962
PubChem Substance
46507920
ChemSpider
4534998
BindingDB
50017129
ChEBI
4784
ChEMBL
CHEMBL578
Therapeutic Targets Database
DAP001374
PharmGKB
PA449456
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Enalapril
ATC Codes
C09BA02 — Enalapril and diureticsC09BB06 — Enalapril and nitrendipineC09BB02 — Enalapril and lercanidipineC09AA02 — Enalapril
AHFS Codes
  • 24:32.04 — Angiotensin-converting Enzyme Inhibitors
  • 24:32.20 — Mineralocorticoid (Aldosterone) Receptor Antagonists
FDA label
Download (120 KB)
MSDS
Download (173 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceEsophagus, Barrett1
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Enalapril1
1CompletedTreatmentErectile Dysfunction1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentRenal Transplant Patients / Transplant, Kidney1
1RecruitingTreatmentHypertension, Resistant to Conventional Therapy1
1Unknown StatusNot AvailableDiabetic Macular Ischemia1
1Unknown StatusTreatmentHeart Failure1
1, 2RecruitingBasic ScienceHypertension,Essential1
1, 2Unknown StatusTreatmentRenal Insufficiency,Chronic1
2CompletedNot AvailableType 1 Insulin-Dependent Diabetes Mellitus1
2CompletedPreventionLung Cancers / Radiation Pneumonitis1
2CompletedPreventionRheumatoid Arthritis1
2CompletedTreatmentBlood Pressures / Plasma Total Homocysteine Level1
2CompletedTreatmentCardiovascular Heart Disease / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases1
2CompletedTreatmentCerebral Hemorrhage1
2CompletedTreatmentHigh Blood Pressure (Hypertension)2
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentPseudohypoaldosteronism1
2Not Yet RecruitingTreatmentC3 Glomerulonephritis / C3 Glomerulopathy / Complement Abnormality / Dense Deposit Disease / Membranoproliferative Glomerulonephritis1
2RecruitingTreatmentCardiovascular Heart Disease / Pre-Eclampsia Onset Less Than 37 Weeks (Diagnosis)1
2RecruitingTreatmentCerebral Hemorrhage1
2RecruitingTreatmentHeart Failure / Hypertension,Essential1
2TerminatedTreatmentMetastatic Malignant Melanoma / Unresectable Malignant Melanoma1
2WithdrawnBasic ScienceChronic heart failure with reduced ejection fraction (NYHA Class II) / Chronic heart failure with reduced ejection fraction (NYHA Class III) / NYHA Class I Congestive heart failure1
2, 3Active Not RecruitingPreventionHypertension Secondary to Kidney Transplant1
2, 3Not Yet RecruitingTreatmentCongenital Heart Disease (CHD) / Congestive Cardiomyopathy / Heart Failure1
2, 3Not Yet RecruitingTreatmentCongenital Heart Disease (CHD) / Heart Failure1
2, 3Not Yet RecruitingTreatmentCongestive Cardiomyopathy / Heart Failure1
2, 3RecruitingTreatmentAngioplasty, Balloon, Coronary / Contrast Media / Coronary Heart Disease (CHD) / High Blood Pressure (Hypertension) / Homocysteine / Renal Dysfunction1
2, 3RecruitingTreatmentPediatric Heart Failure1
3Active Not RecruitingTreatmentHeart Failure With Preserved Ejection Fraction (HFpEF)1
3Active Not RecruitingTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
3Active Not RecruitingTreatmentMalignancies1
3CompletedPreventionAutologous Hematopoietic Stem Cell Transplantation / Leukemia Acute Myeloid Leukemia (AML) / Lymphoid Neoplasms / Malignant Lymphomas / Multiple Myeloma (MM) / Precursor-cell Lymphoblastic Leukemia-Lymphoma1
3CompletedPreventionCardiovascular Heart Disease / Coronary Heart Disease (CHD) / Heart Diseases / Heart Failure / High Blood Pressure (Hypertension) / Myocardial Ischemia1
3CompletedPreventionHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
3CompletedSupportive CareCardiac Toxicity / Unspecified Childhood Solid Tumor, Protocol Specific1
3CompletedTreatmentCardiovascular Heart Disease / Heart Diseases / Heart Failure / Myocardial Diseases1
3CompletedTreatmentChronic Heart Failure (CHF)1
3CompletedTreatmentChronic Heart Failure With Reduced Ejection Fraction (HFrEF)1
3CompletedTreatmentCongestive Cardiomyopathy / High Blood Pressure (Hypertension)1
3CompletedTreatmentCongestive Heart Failure / Heart Defects,Congenital1
3CompletedTreatmentCongestive Heart Failure / Heart Failure With Preserved Ejection Fraction (HFpEF)1
3CompletedTreatmentHeart Failure1
3CompletedTreatmentHigh Blood Pressure (Hypertension)5
3CompletedTreatmentMuscular Dystrophy / Myocardial Fibrosis1
3CompletedTreatmentProteinuria1
3RecruitingPreventionBreast Cancer1
3RecruitingTreatmentErectile Dysfunction / Heart Failure / Heart Failure, Systolic1
3TerminatedTreatmentCongestive Heart Failure / Heart Defects,Congenital / Heart Septal Defects, Ventricular1
3TerminatedTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
4CompletedBasic ScienceCarboxylesterase 1 (CES1) Genotype / CES1 Activity1
4CompletedBasic ScienceHigh Blood Pressure (Hypertension) / Metabolic Syndromes1
4CompletedBasic ScienceType 2 Diabetes Mellitus1
4CompletedOtherHeart Failure With Reduced Ejection Fraction (HFrEF)1
4CompletedPreventionCardiotoxicity / Chemotherapeutic Toxicity / Chemotherapy-Induced Cardiotoxicity Revealed by TnI Increase1
4CompletedPreventionHypertension,Essential1
4CompletedSupportive CareAcute Heart Failure (AHF)1
4CompletedTreatmentCardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke1
4CompletedTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
4CompletedTreatmentHeart Failure / Left Ventricular Dysfunction1
4CompletedTreatmentHigh Blood Pressure (Hypertension)3
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Induction of intra-operative hypotension1
4CompletedTreatmentIgA Nephropathy1
4CompletedTreatmentMacroalbuminuric Diabetic Nephropathy1
4Enrolling by InvitationTreatmentHigh Blood Pressure (Hypertension) / Hyperhomocysteinaemia1
4Not Yet RecruitingTreatmentChagas Disease / Heart Failure1
4Not Yet RecruitingTreatmentHeart Failure1
4Not Yet RecruitingTreatmentHypertension,Essential1
4RecruitingScreeningHealthy Volunteers1
4RecruitingTreatmentBody Composition / Exercise Tolerance / Heart Failure / Strength, Muscle / Vasodilation1
4RecruitingTreatmentChronic Heart Failure With Reduced Ejection Fraction (HFrEF)1
4RecruitingTreatmentHeart Diseases / Type 2 Diabetes Mellitus1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentRecurrent IgA Nephropathy1
4TerminatedPreventionDiabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
4TerminatedTreatmentHigh Blood Pressure (Hypertension)1
4Unknown StatusPreventionAtherosclerosis / Cardiovascular Heart Disease1
4Unknown StatusPreventionContinuous ambulatory peritoneal dialysis therapy1
4Unknown StatusTreatmentCardiovascular Heart Disease / Chronic Renal Failure (CRF)1
4Unknown StatusTreatmentHeart Failure1
4Unknown StatusTreatmentPeritoneal Membrane Failure1
4WithdrawnPreventionHigh Blood Pressure (Hypertension) / Hyperhomocysteinaemia1
4WithdrawnTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
Not AvailableCompletedNot AvailableFabry's Disease / Proteinuria1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailableSalt-sensitive Hypertension1
Not AvailableCompletedSupportive CareOrthognathic Surgery1
Not AvailableCompletedTreatmentAtrial Fibrillation (AF) / Chronic Heart Failure (CHF)1
Not AvailableCompletedTreatmentBreast Cancer1
Not AvailableCompletedTreatmentDiabetic Nephropathies / Microalbuminuria1
Not AvailableCompletedTreatmentDiabetic Nephropathies / Proteinuria1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentIgA Glomerulonephritis1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingBasic ScienceAngiotensin-Converting Enzyme Inhibitors / Exercise1
Not AvailableRecruitingPreventionAtherosclerosis / Nephritis, Lupus1
Not AvailableTerminatedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableTerminatedTreatmentSickle Cell Disorders1
Not AvailableUnknown StatusPreventionMicroalbuminuria / Sickle Cell Nephropathy1
Not AvailableUnknown StatusPreventionPre-Diabetic / Pre-Hypertension1
Not AvailableWithdrawnNot AvailableCoronary Heart Disease (CHD)1

Pharmacoeconomics

Manufacturers
  • Apotex inc
  • Apothecon inc div bristol myers squibb
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Krka dd novo mesto
  • Lek pharmaceuticals d d
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Wockhardt americas inc
  • Biovail laboratories international srl
  • Bedford laboratories div ben venue laboratories inc
  • Hikma farmaceutica (portugal) sa
  • Hospira inc
  • Teva parenteral medicines inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apace Packaging
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • BTA Pharmaceuticals
  • California Clinical Pharmacy Inc.
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Emcure Pharmaceuticals Ltd.
  • Eon Labs
  • Heartland Repack Services LLC
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Ivax Pharmaceuticals
  • Krka d.d. Novo Mesto
  • Lake Erie Medical and Surgical Supply
  • Lek Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Medisca Inc.
  • Merck & Co.
  • Merrell Pharmaceuticals Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Patheon Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
Dosage forms
FormRouteStrength
TabletOral
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral20 mg/1
TabletOral5 mg/1
Tablet, solubleOral10 mg/1
Tablet, solubleOral2.5 mg/1
Tablet, solubleOral20 mg/1
Tablet, solubleOral5 mg/1
TabletOral
KitOral1 mg/1mL
SolutionOral1 mg/1mL
Tablet, extended releaseOral
TabletOral16 mg
TabletOral2 mg
TabletOral4 mg
TabletOral8 mg
Prices
Unit descriptionCostUnit
Enalapril maleate powder9.18USD g
Enalaprilat 1.25 mg/ml vial3.6USD ml
Vasotec 20 mg tablet3.36USD tablet
Vaseretic 10-25 mg tablet3.15USD tablet
Vasotec 10 mg tablet2.63USD tablet
Vasotec 5 mg tablet2.08USD tablet
Vasotec 2.5 mg tablet1.65USD tablet
Enalapril maleate 20 mg tablet1.56USD tablet
Vaseretic 5-12.5 mg tablet1.49USD tablet
Vasotec 20 mg Tablet1.34USD tablet
Vasotec 10 mg Tablet1.11USD tablet
Enalapril maleate 10 mg tablet1.09USD tablet
Enalapril maleate 5 mg tablet1.03USD tablet
Vasotec 5 mg Tablet0.92USD tablet
Enalapril maleate 2.5 mg tablet0.82USD tablet
Vasotec 2.5 mg Tablet0.78USD tablet
Apo-Enalapril 20 mg Tablet0.75USD tablet
Co Enalapril 20 mg Tablet0.75USD tablet
Mylan-Enalapril 20 mg Tablet0.75USD tablet
Novo-Enalapril 20 mg Tablet0.75USD tablet
Pms-Enalapril 20 mg Tablet0.75USD tablet
Ratio-Enalapril 20 mg Tablet0.75USD tablet
Sandoz Enalapril 20 mg Tablet0.75USD tablet
Taro-Enalapril 20 mg Tablet0.75USD tablet
Apo-Enalapril 10 mg Tablet0.62USD tablet
Co Enalapril 10 mg Tablet0.62USD tablet
Mylan-Enalapril 10 mg Tablet0.62USD tablet
Novo-Enalapril 10 mg Tablet0.62USD tablet
Pms-Enalapril 10 mg Tablet0.62USD tablet
Ratio-Enalapril 10 mg Tablet0.62USD tablet
Sandoz Enalapril 10 mg Tablet0.62USD tablet
Taro-Enalapril 10 mg Tablet0.62USD tablet
Apo-Enalapril 5 mg Tablet0.52USD tablet
Co Enalapril 5 mg Tablet0.52USD tablet
Mylan-Enalapril 5 mg Tablet0.52USD tablet
Novo-Enalapril 5 mg Tablet0.52USD tablet
Pms-Enalapril 5 mg Tablet0.52USD tablet
Ratio-Enalapril 5 mg Tablet0.52USD tablet
Sandoz Enalapril 5 mg Tablet0.52USD tablet
Taro-Enalapril 5 mg Tablet0.52USD tablet
Apo-Enalapril 2.5 mg Tablet0.44USD tablet
Co Enalapril 2.5 mg Tablet0.44USD tablet
Mylan-Enalapril 2.5 mg Tablet0.44USD tablet
Novo-Enalapril 2.5 mg Tablet0.44USD tablet
Pms-Enalapril 2.5 mg Tablet0.44USD tablet
Ratio-Enalapril 2.5 mg Tablet0.44USD tablet
Sandoz Enalapril 2.5 mg Tablet0.44USD tablet
Taro-Enalapril 2.5 mg Tablet0.44USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8778366No2014-07-152032-11-06Us
US8568747No2013-10-292032-11-06Us
US9669008No2017-06-062036-03-25Us
US9808442No2017-11-072036-03-25Us
US9855214No2018-01-022032-11-06Us
US9968553No2018-05-152032-11-06Us
US10039745No2018-08-072036-03-25Us
US10154987No2018-12-182036-03-25Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)143-144.5MSDS
water solubility1.64E+004 mg/LMCFARLAND,JW ET AL. (2001)
logP0.07HANSCH,C ET AL. (1995)
Caco2 permeability-5.64ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.213 mg/mLALOGPS
logP0.19ALOGPS
logP0.59ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity99.57 m3·mol-1ChemAxon
Polarizability40.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7428
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.7691
P-glycoprotein inhibitor INon-inhibitor0.6681
P-glycoprotein inhibitor IINon-inhibitor0.5136
Renal organic cation transporterNon-inhibitor0.8442
CYP450 2C9 substrateNon-substrate0.8632
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5696
CYP450 1A2 substrateNon-inhibitor0.9125
CYP450 2C9 inhibitorNon-inhibitor0.9154
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6825
Ames testNon AMES toxic0.9383
CarcinogenicityNon-carcinogens0.9216
BiodegradationNot ready biodegradable0.8686
Rat acute toxicity1.8269 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9719
hERG inhibition (predictor II)Non-inhibitor0.7456
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0809000000-0e192d1573028e60641c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-003r-1859000000-8b202071e8860792a59f

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Proline and derivatives / Alpha amino acid esters / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Aralkylamines / Fatty acid esters / Benzene and substituted derivatives / Dicarboxylic acids and derivatives
show 10 more
Substituents
Alpha-dipeptide / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / N-acyl-l-alpha-amino acid / Proline or derivatives / Alpha-amino acid ester / Alpha-amino acid amide / Alpha-amino acid or derivatives / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine carboxylic acid
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
dicarboxylic acid monoester, dipeptide (CHEBI:4784)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [PubMed:17618628]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  3. Liu YH, Liu LY, Wu JX, Chen SX, Sun YX: Comparison of captopril and enalapril to study the role of the sulfhydryl-group in improvement of endothelial dysfunction with ACE inhibitors in high dieted methionine mice. J Cardiovasc Pharmacol. 2006 Jan;47(1):82-8. [PubMed:16424790]
  4. Natesh R, Schwager SL, Evans HR, Sturrock ED, Acharya KR: Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme. Biochemistry. 2004 Jul 13;43(27):8718-24. [PubMed:15236580]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Trbojevic-Stankovic J, Aleksic M, Odovic J: Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data. Srp Arh Celok Lek. 2015 Jan-Feb;143(1-2):50-5. [PubMed:25845252]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. [PubMed:9706043]
  2. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994]
  3. Temple CS, Boyd CA: Proton-coupled oligopeptide transport by rat renal cortical brush border membrane vesicles: a functional analysis using ACE inhibitors to determine the isoform of the transporter. Biochim Biophys Acta. 1998 Aug 14;1373(1):277-81. [PubMed:9733984]
  4. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [PubMed:15100168]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [PubMed:12065749]
  2. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [PubMed:9650585]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Abu-Zahra TN, Wolkoff AW, Kim RB, Pang KS: Uptake of enalapril and expression of organic anion transporting polypeptide 1 in zonal, isolated rat hepatocytes. Drug Metab Dispos. 2000 Jul;28(7):801-6. [PubMed:10859154]
  2. Pang KS, Wang PJ, Chung AY, Wolkoff AW: The modified dipeptide, enalapril, an angiotensin-converting enzyme inhibitor, is transported by the rat liver organic anion transport protein. Hepatology. 1998 Nov;28(5):1341-6. [PubMed:9794920]

Drug created on June 13, 2005 07:24 / Updated on December 08, 2019 20:10