Identification

Name
Aliskiren
Accession Number
DB09026  (DB01258)
Type
Small Molecule
Groups
Approved, Investigational
Description

Aliskiren is the first drug in the renin inhibitor drug class and is used for the treatment of hypertension.5 It was developed by Speedel and Novartis and initially approved by the FDA in early 2007.10 Aliskiren has been proven to efficacious in reducing blood pressure when used alone or in conjunction with other antihypertensive agents.5

Structure
Thumb
Synonyms
  • Aliskiren
  • Aliskireno
External IDs
CGP 60536 / CGP60536B / SPP 100 / SPP100
Product Ingredients
IngredientUNIICASInChI Key
Aliskiren hemifumarateC8A0P8G029173334-58-2KLRSDBSKUSSCGU-KRQUFFFQSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RasilezTablet, film coated300 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated150 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated150 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated300 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated150 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated150 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated300 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated150 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated150 mgOralNoden Pharma Dac2007-08-22Not applicableEu
RasilezTablet, film coated300 mgOralNoden Pharma Dac2007-08-22Not applicableEu
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
AliskirenTablet, film coated300 mg/1OralPar Pharmaceutical, Inc.2019-03-25Not applicableUs
AliskirenTablet, film coated150 mg/1OralPar Pharmaceutical, Inc.2019-03-25Not applicableUs
AliskirenTablet, film coated300 mg/1OralPrasco Laboratories2019-03-04Not applicableUs
AliskirenTablet, film coated150 mg/1OralPrasco Laboratories2019-03-04Not applicableUs
Sandoz AliskirenTabletOralSandoz Canada IncorporatedNot applicableNot applicableCanada
Sandoz AliskirenTabletOralSandoz Canada IncorporatedNot 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
AmturnideAliskiren hemifumarate (300 mg/1) + Amlodipine besylate (10 mg/1) + Hydrochlorothiazide (25 mg/1)Tablet, film coatedOralNovartis2010-12-212016-01-31Us
AmturnideAliskiren hemifumarate (300 mg/1) + Amlodipine besylate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralNovartis2010-12-212015-10-31Us
AmturnideAliskiren hemifumarate (300 mg/1) + Amlodipine besylate (5 mg/1) + Hydrochlorothiazide (25 mg/1)Tablet, film coatedOralNovartis2010-12-212016-03-31Us
AmturnideAliskiren hemifumarate (300 mg/1) + Amlodipine besylate (5 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralNovartis2010-12-212016-01-31Us
AmturnideAliskiren hemifumarate (150 mg/1) + Amlodipine besylate (5 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralNovartis2010-12-212015-09-30Us
Rasilez HctAliskiren (300 mg) + Hydrochlorothiazide (25 mg)Tablet, film coatedOralNoden Pharma Dac2009-01-16Not applicableEu
Rasilez HCTAliskiren (300 mg) + Hydrochlorothiazide (25 mg)TabletOralNoden Pharma Dac2009-11-242020-02-11Canada
Rasilez HctAliskiren (150 mg) + Hydrochlorothiazide (25 mg)Tablet, film coatedOralNoden Pharma Dac2009-01-16Not applicableEu
Rasilez HctAliskiren (150 mg) + Hydrochlorothiazide (25 mg)Tablet, film coatedOralNoden Pharma Dac2009-01-16Not applicableEu
Rasilez HctAliskiren (300 mg) + Hydrochlorothiazide (12.5 mg)Tablet, film coatedOralNoden Pharma Dac2009-01-16Not applicableEu
Categories
UNII
502FWN4Q32
CAS number
173334-57-1
Weight
Average: 551.7583
Monoisotopic: 551.393436443
Chemical Formula
C30H53N3O6
InChI Key
UXOWGYHJODZGMF-QORCZRPOSA-N
InChI
InChI=1S/C30H53N3O6/c1-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36/h10-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35)/t22-,23-,24-,25-/m0/s1
IUPAC Name
(2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-2-(propan-2-yl)nonanamide
SMILES
COCCCOC1=C(OC)C=CC(C[C@@H](C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)C(C)C)=C1

Pharmacology

Indication

Aliskiren is used for the treatment of hypertension in children above 6 years and adults.9 This drug may also be used in conjunction with antihypertensives such as calcium channel blockers and thiazides in products form to provide additional blood pressure control.12,13

Associated Conditions
Pharmacodynamics

Aliskiren reduces blood pressure by inhibiting renin. This leads to a cascade of events that decreases blood pressure, lowering the risk of fatal and nonfatal cardiovascular events including stroke and myocardial infarction.2,9

Mechanism of action

Aliskiren is a renin inhibitor.9 Renin is secreted by the kidneys when blood volume and renal perfusion decrease. It normally cleaves the protein angiotensinogen to form angiotensin I. Angiotensin I is then converted to angiotensin II, an active protein. Angiotensin II is a potent vasoconstrictor that causes the release of catecholamines into the circulation. It also promotes the secretion of aldosterone in addition to sodium reabsorption, increasing blood pressure. Additionally, angiotensin II acts on the adrenal cortex where it stimulates aldosterone release. Aldosterone increases sodium reabsorption and potassium excretion in the nephron. 11

Aliskiren prevents the above process via binding to renin at its active site, stopping the cleavage of angiotensin, in turn inhibiting the formation of angiotensin I. This ends the cascade of angiotensin II mediated mechanisms that normally increase blood pressure.5

TargetActionsOrganism
ARenin
inhibitor
Humans
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Aliskiren is absorbed in the gastrointestinal tract and is poorly absorbed with a bioavailability between 2.0 and 2.5%.6 Peak plasma concentrations of aliskiren are achieved between 1 to 3 hours after administration.6,9 Steady-state concentrations of aliskiren are achieved within 7-8 days of regular administration.1

Volume of distribution

Unchanged aliskiren accounts for about 80% of the drug found in the plasma.7,9

Protein binding

The plasma protein binding of aliskiren ranges from 47-51%.1,6

Metabolism

About 80% of the drug in plasma following oral administration is unchanged. Two major metabolites account for about 1-3% of aliskiren in the plasma. One metabolite is an O-demethylated alcohol derivative and the other is a carboxylic acid derivative. Minor oxidized and hydrolyzed metabolites may also be found in the plasma.7,9

Route of elimination

Aliskiren is mainly excreted via the hepatobiliary route and by oxidative metabolism by hepatic cytochrome enzymes.1 Approximately one-quarter of the absorbed dose appears in the urine as unchanged parent drug. 9 One pharmacokinetic study of radiolabeled aliskiren detected 0.6% radioactivity in the urine and more than 80% in the feces, suggesting that aliskiren is mainly eliminated by the fecal route.7

Half life

Plasma half-life for aliskiren can range from 30 to 40 hours 7 with an accumulation half-life of about 24 hours.7

Clearance

Aliskiren is partially cleared in the kidneys, and safety data have not been established for patients with a creatinine clearance of less than 30 mL/min.9 One pharmacokinetic study revealed an average renal clearance of 1280 +/- 500 mL/hour in healthy volunteers.8

Toxicity

The oral LD50 of aliskiren in rats is >2000 mg/kg.14 Overdose information is limited in the literature, however, an overdose with aliskiren is likely to result in hypotension. Supportive treatment should be initiated in the case of an overdose.9,15

Affected organisms
  • Humans and other mammals
Pathways
Not Available
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-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Aliskiren.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Aliskiren.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Aliskiren.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Aliskiren.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Aliskiren.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Aliskiren.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Aliskiren.
AbediterolAbediterol may decrease the antihypertensive activities of Aliskiren.
AcebutololThe risk or severity of hyperkalemia can be increased when Acebutolol is combined with Aliskiren.
AceclofenacThe risk or severity of renal failure and hypertension can be increased when Aceclofenac is combined with Aliskiren.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Do not take with or immediately after a high-fat meal. The absorption of aliskiren is substantially reduced by taking it with high-fat meals.
  • Take with or without food. Take consistently at the same time in regard to meals.

References

Synthesis Reference

Hanessian S, Guesné S, Chénard E. Total synthesis of "aliskiren": the first Renin inhibitor in clinical practice for hypertension. Org Lett. 2010;12(8):1816‐1819. doi:10.1021/ol100427v

General References
  1. Vaidyanathan S, Jarugula V, Dieterich HA, Howard D, Dole WP: Clinical pharmacokinetics and pharmacodynamics of aliskiren. Clin Pharmacokinet. 2008;47(8):515-31. [PubMed:18611061]
  2. Gradman AH, Schmieder RE, Lins RL, Nussberger J, Chiang Y, Bedigian MP: Aliskiren, a novel orally effective renin inhibitor, provides dose-dependent antihypertensive efficacy and placebo-like tolerability in hypertensive patients. Circulation. 2005 Mar 1;111(8):1012-8. Epub 2005 Feb 21. [PubMed:15723979]
  3. Staessen JA, Li Y, Richart T: Oral renin inhibitors. Lancet. 2006 Oct 21;368(9545):1449-56. [PubMed:17055947]
  4. Sanoski CA: Aliskiren: an oral direct renin inhibitor for the treatment of hypertension. Pharmacotherapy. 2009 Feb;29(2):193-212. doi: 10.1592/phco.29.2.193. [PubMed:19170589]
  5. Oh BH: Aliskiren, the first in a new class of direct renin inhibitors for hypertension: present and future perspectives. Expert Opin Pharmacother. 2007 Nov;8(16):2839-49. doi: 10.1517/14656566.8.16.2839. [PubMed:17956203]
  6. Buczko W, Hermanowicz JM: Pharmacokinetics and pharmacodynamics of aliskiren, an oral direct renin inhibitor. Pharmacol Rep. 2008 Sep-Oct;60(5):623-31. [PubMed:19066408]
  7. Waldmeier F, Glaenzel U, Wirz B, Oberer L, Schmid D, Seiberling M, Valencia J, Riviere GJ, End P, Vaidyanathan S: Absorption, distribution, metabolism, and elimination of the direct renin inhibitor aliskiren in healthy volunteers. Drug Metab Dispos. 2007 Aug;35(8):1418-28. doi: 10.1124/dmd.106.013797. Epub 2007 May 17. [PubMed:17510248]
  8. Vaidyanathan S, Bigler H, Yeh C, Bizot MN, Dieterich HA, Howard D, Dole WP: Pharmacokinetics of the oral direct renin inhibitor aliskiren alone and in combination with irbesartan in renal impairment. Clin Pharmacokinet. 2007;46(8):661-75. doi: 10.2165/00003088-200746080-00003. [PubMed:17655373]
  9. FDA Approved Products: Tekturna (Aliskiren) oral tablets and pellets [Link]
  10. The Pharmaletter: Novartis and Speedel [Link]
  11. NIH StatPearls: Physiology, Renin Angiotensin System [Link]
  12. FDA Approved Products: Tekamlo (amlodipine and aliskiren) oral tablets [Link]
  13. FDA Approved Products: Tekturna HCT (aliskiren and hydrochlorothiazide) oral tablets [Link]
  14. Product monograph: Rasilez HCT (Aliskiren fumarate and hydrochlorothiazide oral tablets) [Link]
  15. NIH StatPearls: Aliskiren [Link]
External Links
Human Metabolome Database
HMDB0015387
KEGG Drug
D03208
PubChem Compound
5493444
PubChem Substance
310264980
ChemSpider
4591452
BindingDB
17950
RxNav
325646
ChEBI
601027
ChEMBL
CHEMBL1639
ZINC
ZINC000004393164
PharmGKB
PA143487910
PDBe Ligand
C41
Drugs.com
Drugs.com Drug Page
Wikipedia
Aliskiren
ATC Codes
C09XA54 — Aliskiren, amlodipine and hydrochlorothiazideC09XA53 — Aliskiren and amlodipineC09DX02 — Valsartan and aliskirenC09XA02 — AliskirenC09XA52 — Aliskiren and hydrochlorothiazide
AHFS Codes
  • 24:32.40 — Renin Inhibitors
PDB Entries
2v0z
FDA label
Download (612 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableEnd Stage Renal Disease (ESRD)1
1CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
1CompletedBasic ScienceRenal Function1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHigh Blood Pressure (Hypertension)3
1WithdrawnTreatmentHigh Blood Pressure (Hypertension) / Metabolic Syndromes1
1, 2CompletedTreatmentHigh Blood Pressure (Hypertension)1
1, 2CompletedTreatmentType 2 Diabetes Mellitus3
2CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
2CompletedOtherDiabetic Nephropathies1
2CompletedTreatmentEndothelial Dysfunction / High Blood Pressure (Hypertension) / Insulin Resistance / Metabolic Syndromes1
2CompletedTreatmentHeart Failure2
2CompletedTreatmentHigh Blood Pressure (Hypertension)3
2CompletedTreatmentMyocardial Ischemia / Post Acute Coronary Syndrome1
2Not Yet RecruitingTreatmentC3 Glomerulonephritis / C3 Glomerulopathy / Complement Abnormality / Dense Deposit Disease / Membranoproliferative Glomerulonephritis1
2TerminatedTreatmentAnkle Edema / High Blood Pressure (Hypertension)1
2TerminatedTreatmentDiabetic Macular Edema (DME)1
2TerminatedTreatmentHeart Failure / Renal Failure1
2TerminatedTreatmentHigh Blood Pressure (Hypertension) / Obesity, Abdominal1
2TerminatedTreatmentNon-diabetic Nephropathy1
2WithdrawnTreatmentDiabetes / High Blood Pressure (Hypertension)1
2, 3TerminatedTreatmentAtherosclerosis1
3CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
3CompletedDiagnosticHigh Blood Pressure (Hypertension)1
3CompletedOtherHeart Failure1
3CompletedTreatmentAcute Decompensated Heart Failure (ADHF) / Congestive Heart Failure1
3CompletedTreatmentArterial Hypertension1
3CompletedTreatmentBMI >27 kg/m2 / High Blood Pressure (Hypertension) / Left Ventricular Hypertrophy1
3CompletedTreatmentChronic Heart Failure (CHF)1
3CompletedTreatmentCoronary Artery Atherosclerosis / Coronary Artery Disease1
3CompletedTreatmentDiabetes / High Blood Pressure (Hypertension)1
3CompletedTreatmentHigh Blood Pressure (Hypertension)33
3CompletedTreatmentHypertension, Diabetes Mellitus1
3CompletedTreatmentHypertension,Essential4
3CompletedTreatmentIgA Nephropathy1
3CompletedTreatmentMarfan Syndrome1
3CompletedTreatmentModerate to Severe Hypertension1
3CompletedTreatmentMyocardial Infarction1
3RecruitingTreatmentAtrial Fibrillation (AF)1
3TerminatedTreatmentCardiovascular Events1
3TerminatedTreatmentCardiovascular Heart Disease / Type 2 Diabetes Mellitus1
3TerminatedTreatmentEndothelial Dysfunction1
4CompletedNot AvailableType 2 Diabetes Mellitus1
4CompletedDiagnosticHigh Blood Pressure (Hypertension)1
4CompletedOtherCoronary Artery Disease / Type 2 Diabetes Mellitus1
4CompletedScreeningChronic Kidney Disease (CKD) / High Blood Pressure (Hypertension) / Proteinuria1
4CompletedTreatmentBlood Pressures / Chronic Kidney Disease (CKD) / Proteinuria1
4CompletedTreatmentChronic Kidney Disease (CKD) / High Blood Pressure (Hypertension)1
4CompletedTreatmentChronic Kidney Disease (CKD) / Proteinuria1
4CompletedTreatmentDiabetes Mellitus / High Blood Pressure (Hypertension)1
4CompletedTreatmentEssential Hypertension ( Mild to Moderate)1
4CompletedTreatmentHeart Failure1
4CompletedTreatmentHigh Blood Pressure (Hypertension)13
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Left Ventricle Hypertrophy1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Metabolic Syndromes / Obesity, Abdominal1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentHypertension,Essential2
4CompletedTreatmentIgA Nephropathy1
4CompletedTreatmentKidney Diseases1
4CompletedTreatmentStage 2 Hypertension1
4CompletedTreatmentStage II Hypertension1
4TerminatedHealth Services ResearchDiabetes / High Blood Pressure (Hypertension) / Pre-Hypertension1
4TerminatedTreatmentAlbuminuria / Diabetes / Macroalbuminuric Diabetic Nephropathy / Microalbuminuria / Proteinuria1
4TerminatedTreatmentCardiac Transplantation / High Blood Pressure (Hypertension)1
4TerminatedTreatmentChronic Renal Failure (CRF) / Kidney Diseases1
4TerminatedTreatmentDeficiency, Vitamin D / High Blood Pressure (Hypertension)1
4TerminatedTreatmentDiabetes / High Blood Pressure (Hypertension) / Stage 2 Hypertension1
4TerminatedTreatmentDiabetic Nephropathies / Glomerulonephritis, Membranous / Glomerulopathy (Obesity-associated) / Glomerulosclerosis, Focal Segmental / Hypertensive Nephrosclerosis / IgA Nephropathy / Proteinuric Kidney Disease1
4TerminatedTreatmentHigh Blood Pressure (Hypertension)1
4TerminatedTreatmentHypertension With Metabolic Syndrome1
4Unknown StatusTreatmentChronic Kidney Disease (CKD) / High Blood Pressure (Hypertension) / Muscle Sympathetic Nerve Activity1
4Unknown StatusTreatmentCongestive Heart Failure1
4Unknown StatusTreatmentDiabetes Mellitus1
4Unknown StatusTreatmentDialysis therapy / High Blood Pressure (Hypertension)1
4Unknown StatusTreatmentEnd Stage Renal Disease (ESRD) / High Blood Pressure (Hypertension)1
4Unknown StatusTreatmentHeart Failure1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension)2
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / IgA Glomerulonephritis1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4Unknown StatusTreatmentHypertensive Left Ventricular Hypertrophy1
4Unknown StatusTreatmentPeritoneal Membrane Failure1
4Unknown StatusTreatmentType 2 Diabetes With Nephropathy1
4WithdrawnTreatmentDiabetes Mellitus / High Blood Pressure (Hypertension)1
4WithdrawnTreatmentHigh Blood Pressure (Hypertension)1
4WithdrawnTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableArterial Hypertension1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableCompletedBasic ScienceType 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentAlbuminuria1
Not AvailableCompletedTreatmentDiabetes1
Not AvailableTerminatedTreatmentAbdominal Aortic Aneurysms (AAA) / High Blood Pressure (Hypertension)1
Not AvailableTerminatedTreatmentAortic Compliance / Diastolic Function / Insulin Sensitivity1
Not AvailableTerminatedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableUnknown StatusNot AvailableAtherosclerosis / Diabetes Mellitus1
Not AvailableUnknown StatusPreventionDiabetes Mellitus / Endocrine System Diseases / Glucose Metabolism Disorders / Metabolic Diseases1
Not AvailableUnknown StatusTreatmentHeart Failure1
Not AvailableWithdrawnTreatmentDiastolic Heart Failure1
Not AvailableWithdrawnTreatmentIdiopathic Membranous Nephropathy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, film coatedOral150 mg
Tablet, film coatedOral300 mg
TabletOral
Tablet, film coatedOral
TabletOral
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral300 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2147056No2005-10-252015-04-13Canada
US5559111Yes1996-09-242019-01-21Us
US8617595Yes2013-12-312026-08-19Us
US8618172No2013-12-312028-07-13Us
US8168616No2012-05-012026-07-03Us
US8613949No2013-12-242029-12-21Us
US8618174No2013-12-312021-11-15Us
US8183295No2012-05-222023-05-16Us
US9023893No2015-05-052022-03-03Us
Additional Data Available
  • Filed On
    Filed On

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

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>95https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022545Orig1s000EA.pdf
boiling point (°C)748.4±60.0https://m.chemicalbook.com/ChemicalProductProperty_EN_CB9966226.htm
water solubilityHighly soluble in water (as hemifumarate salt)Not Available
logP2.45https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3103912/
pKa9.49https://m.chemicalbook.com/ChemicalProductProperty_EN_CB9966226.htm
Predicted Properties
PropertyValueSource
Water Solubility0.0021 mg/mLALOGPS
logP3.87ALOGPS
logP3.12ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.56ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.13 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity154.32 m3·mol-1ChemAxon
Polarizability63.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

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/MSsplash10-0uxr-0700090000-7a3148e765b056fbdbb2
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-3901100000-cb596bd3c4d4c9e1c01f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00kr-7911000000-f660df43e70edac0517a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0079-5910000000-d3e40bdba155982e7e43
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dr-3900000000-8bce7f74c2390532741c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-3900000000-12d8e1ded46f53c83764
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0019-0000950000-e45c32fa4cac95668993
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0v4i-4920100000-82dc644fa438b541d394
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fk9-9810000000-c1c9bdda4686e3e603b1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-3900000000-f5052afca313a2f0c68b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f9f-7900000000-12cc981f01c6cad986b8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-9300000000-a3026b636a234fc9ae1f

Taxonomy

Description
This compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Delta amino acids and derivatives
Alternative Parents
Beta amino acids and derivatives / Phenylbutylamines / Anisoles / Methoxybenzenes / Phenoxy compounds / Alkyl aryl ethers / Aralkylamines / N-acyl amines / Secondary carboxylic acid amides / 1,2-aminoalcohols
show 8 more
Substituents
Delta amino acid or derivatives / Phenylbutylamine / Beta amino acid or derivatives / Phenol ether / Phenoxy compound / Methoxybenzene / Anisole / Aralkylamine / Alkyl aryl ether / Fatty acyl
show 24 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide, monomethoxybenzene (CHEBI:601027)

Targets

Details
1. Renin
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Receptor binding
Specific Function
Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of b...
Gene Name
REN
Uniprot ID
P00797
Uniprot Name
Renin
Molecular Weight
45057.125 Da
References
  1. Nussberger J, Wuerzner G, Jensen C, Brunner HR: Angiotensin II suppression in humans by the orally active renin inhibitor Aliskiren (SPP100): comparison with enalapril. Hypertension. 2002 Jan;39(1):E1-8. [PubMed:11799102]
  2. Wood JM, Maibaum J, Rahuel J, Grutter MG, Cohen NC, Rasetti V, Ruger H, Goschke R, Stutz S, Fuhrer W, Schilling W, Rigollier P, Yamaguchi Y, Cumin F, Baum HP, Schnell CR, Herold P, Mah R, Jensen C, O'Brien E, Stanton A, Bedigian MP: Structure-based design of aliskiren, a novel orally effective renin inhibitor. Biochem Biophys Res Commun. 2003 Sep 5;308(4):698-705. [PubMed:12927775]
  3. Menard J, Guyene TT, Peyrard S, Azizi M: Conformational changes in prorenin during renin inhibition in vitro and in vivo. J Hypertens. 2006 Mar;24(3):529-34. [PubMed:16467656]
  4. Azizi M, Webb R, Nussberger J, Hollenberg NK: Renin inhibition with aliskiren: where are we now, and where are we going? J Hypertens. 2006 Feb;24(2):243-56. [PubMed:16508564]
  5. Gradman AH, Vivas Y: New drugs for hypertension: what do they offer? Curr Hypertens Rep. 2006 Oct;8(5):425-32. [PubMed:16965731]
  6. Wal P, Wal A, Rai AK, Dixit A: Aliskiren: An orally active renin inhibitor. J Pharm Bioallied Sci. 2011 Apr;3(2):189-93. doi: 10.4103/0975-7406.80764. [PubMed:21687346]
  7. FDA Approved Products: Tekturna (Aliskiren) oral tablets and pellets [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Vaidyanathan S, Jarugula V, Dieterich HA, Howard D, Dole WP: Clinical pharmacokinetics and pharmacodynamics of aliskiren. Clin Pharmacokinet. 2008;47(8):515-31. [PubMed:18611061]
  2. Buczko W, Hermanowicz JM: Pharmacokinetics and pharmacodynamics of aliskiren, an oral direct renin inhibitor. Pharmacol Rep. 2008 Sep-Oct;60(5):623-31. [PubMed:19066408]
  3. FDA Approved Products: Tekturna (Aliskiren) oral tablets and pellets [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
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. Tsukimoto M, Ohashi R, Torimoto N, Togo Y, Suzuki T, Maeda T, Kagawa Y: Effects of the inhibition of intestinal P-glycoprotein on aliskiren pharmacokinetics in cynomolgus monkeys. Biopharm Drug Dispos. 2015 Jan;36(1):15-33. doi: 10.1002/bdd.1920. Epub 2014 Oct 31. [PubMed:25264342]
  2. FDA Approved Products: Tekturna (Aliskiren) oral tablets and pellets [Link]

Drug created on October 13, 2014 16:29 / Updated on July 08, 2020 06:59

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