Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates
Name
Linagliptin
Accession Number
DB08882
Type
Small Molecule
Groups
Approved
Description

Linagliptin is a DPP-4 inhibitor developed by Boehringer Ingelheim for the treatment of type II diabetes 5. Linagliptin differs from other DPP-4 inhibitors in that it has a non-linear pharmacokinetic profile, is not primarily eliminated by the renal system, and obeys concentration dependant protein binding3. Linagliptin was approved by the FDA on May 2, 20115.

Structure
Thumb
Synonyms
  • (R)-8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methylquinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione
  • Linagliptin
  • Linagliptina
External IDs
BI 1356 / BI 1356 BS / BI-1356 / BI-1356-BS / BI-1356BS / BS 1356 BS / BS-1356-BS
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TradjentaTablet, film coated5 mg/1OralBoehringer Ingelheim Pharmaceuticals, Inc.2011-05-09Not applicableUs0597 014020180907 15195 v9gh0y
TradjentaTablet, film coated5 mg/1OralA-S Medication Solutions2011-05-09Not applicableUs
TradjentaTablet, film coated5 mg/1OralCardinal Health2011-05-09Not applicableUs00597 0140 30 nlmimage10 ed3d76cb
TrajentaTablet, film coated5 mgOralBoehringer Ingelheim2011-08-24Not applicableEu
TrajentaTablet, film coated5 mgOralBoehringer Ingelheim2011-08-24Not applicableEu
TrajentaTablet, film coated5 mgOralBoehringer Ingelheim2011-08-24Not applicableEu
TrajentaTablet, film coated5 mgOralBoehringer Ingelheim2011-08-24Not applicableEu
TrajentaTablet, film coated5 mgOralBoehringer Ingelheim2011-08-24Not applicableEu
TrajentaTabletOralBoehringer Ingelheim (Canada) Ltd Ltee2011-09-13Not applicableCanada
TrajentaTablet, film coated5 mgOralBoehringer Ingelheim2011-08-24Not 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.

    Learn more
  • Product Code
    Product Code

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

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
GlyxambiLinagliptin (5 mg) + Empagliflozin (25 mg)TabletOralBoehringer Ingelheim (Canada) Ltd Ltee2016-12-21Not applicableCanada
GlyxambiLinagliptin (5 mg/1) + Empagliflozin (10 mg/1)Tablet, film coatedOralREMEDYREPACK INC.2019-04-29Not applicableUs
GlyxambiLinagliptin (5 mg) + Empagliflozin (10 mg)TabletOralBoehringer Ingelheim (Canada) Ltd Ltee2016-12-21Not applicableCanada
GlyxambiLinagliptin (5 mg/1) + Empagliflozin (25 mg/1)Tablet, film coatedOralBoehringer Ingelheim Pharmaceuticals, Inc.2015-01-30Not applicableUs
GlyxambiLinagliptin (5 mg/1) + Empagliflozin (10 mg/1)Tablet, film coatedOralBoehringer Ingelheim Pharmaceuticals, Inc.2015-01-30Not applicableUs0597 018220180913 8702 q7fevz
JentaduetoLinagliptin (2.5 mg) + Metformin hydrochloride (1000 mg)Tablet, film coatedOralBoehringer Ingelheim2012-07-20Not applicableEu
JentaduetoLinagliptin (2.5 mg) + Metformin hydrochloride (850 mg)Tablet, film coatedOralBoehringer Ingelheim2012-07-20Not applicableEu
JentaduetoLinagliptin (2.5 mg) + Metformin hydrochloride (1000 mg)Tablet, film coatedOralBoehringer Ingelheim2012-07-20Not applicableEu
JentaduetoLinagliptin (2.5 mg) + Metformin hydrochloride (500 mg)TabletOralBoehringer Ingelheim (Canada) Ltd Ltee2013-04-17Not applicableCanada
JentaduetoLinagliptin (2.5 mg) + Metformin hydrochloride (850 mg)Tablet, film coatedOralBoehringer Ingelheim2012-07-20Not applicableEu
Categories
UNII
3X29ZEJ4R2
CAS number
668270-12-0
Weight
Average: 472.5422
Monoisotopic: 472.23352218
Chemical Formula
C25H28N8O2
InChI Key
LTXREWYXXSTFRX-QGZVFWFLSA-N
InChI
InChI=1S/C25H28N8O2/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20/h6-7,10-11,17H,8-9,12-15,26H2,1-3H3/t17-/m1/s1
IUPAC Name
8-[(3R)-3-aminopiperidin-1-yl]-7-(but-2-yn-1-yl)-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CC#CCN1C(=NC2=C1C(=O)N(CC1=NC3=C(C=CC=C3)C(C)=N1)C(=O)N2C)N1CCC[C@@H](N)C1

Pharmacology

Indication

Linagliptin is indicated for the treatment of type II diabetes in addition to diet and exercise5. It should not be used to treat type I diabetes or in diabetic ketoacidosis5.

Associated Conditions
Pharmacodynamics

A 5mg oral dose of linagliptin results in >80% inhibition of dipeptidyl peptidase 4 (DPP-4) for ≥24 hours3. Inhibition of DPP-4 increases the concentration of glucagon-like peptide 1 (GLP-1), leading to decreased glycosylated hemoglobin and fasting plasma glucose3.

Mechanism of action

Linagliptin is a competitive, reversible DPP-4 inhibitor. Inhibition of this enzyme slows the breakdown of GLP-1 and glucose-dependant insulinotropic polypeptide (GIP)3,5. GLP-1 and GIP stimulate the release of insulin from beta cells in the pancreas while inhibiting release of glucagon from pancreatic beta cells5. These effects together reduce the breakdown of glycogen in the liver and increase insulin release in response to glucose53.

TargetActionsOrganism
ADipeptidyl peptidase 4
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
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.

Learn more
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.

Learn more
Absorption

Oral bioavailability of linagliptin is 30%3.

Volume of distribution

A single intravenous dose of 5mg results in a volume of distribution of 1110L3. However an intravenous infusion of 0.5-10mg results in a volume of distribution of 380-1540L3.

Protein binding

Linagliptin is 99% protein bound at a concentration of 1nmol/L and 75-89% protein bound at a concentration of >30nmol/L3.

Metabolism

An oral dose of linagliptin is excreted primarily in the feces2. 90% of an oral dose is excreted unchanged in the urine and feces2,3. The predominant metabolite in the plasma is CD1790 and the predominant metabolite recovered after excretion was M489(1)2. Other metabolites are produced through oxidation, oxidative degradation, N-acetylation, glucuronidation, and cysteine adduct formation2. Other metabolites have been identified through mass spectrometry though no structures were determined2. Metabolism of linagliptin is mediated by cytochrome P450 3A4, aldo-keto reductases, and carbonyl reductases2.

Route of elimination

84.7% of linagliptin is eliminated in the feces and 5.4% is eliminated in the urine2,3.

Half life

The terminal half life of linagliptin is 155 hours2.

Clearance

Total clearance of linagliptin is 374mL/min2.

Toxicity

No dosage adjustment is necessary based on race, age, weight, sex, renal impairment, or hepatic impairment3.

Studies of efficacy and safety in pediatric populations were not included in the original drug approval5 but recent clinical trials show linagliptin to be well tolerated in patients 10 to 18 years old4.

Animal studies showed an increased risk of lymphoma in female rats at over 200 times the clinical dose5. Aside from this effect, linagliptin was not shown to be mutagenic, clastogenic, or have an effect on fertility5.

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
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Linagliptin.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Linagliptin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Linagliptin is combined with 2,4-thiazolidinedione.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Linagliptin.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe therapeutic efficacy of Linagliptin can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
6-Deoxyerythronolide BThe metabolism of Linagliptin can be decreased when combined with 6-Deoxyerythronolide B.
7-ethyl-10-hydroxycamptothecinThe metabolism of Linagliptin can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypoglycemic activities of Linagliptin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Linagliptin.
AbataceptThe metabolism of Linagliptin can be increased when combined with Abatacept.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

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

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Although a high fat meal reduces Cmax and increases AUC, this interaction with food is not clinically significant

References

Synthesis Reference

Pietro ALLEGRINI, Emanuele ATTOLINO, Marco ARTICO, "PROCESS FOR THE PREPARATION OF LINAGLIPTIN." U.S. Patent US20120165525, issued June 28, 2012.

US20120165525
General References
  1. Forst T, Pfutzner A: Linagliptin, a dipeptidyl peptidase-4 inhibitor with a unique pharmacological profile, and efficacy in a broad range of patients with type 2 diabetes. Expert Opin Pharmacother. 2012 Jan;13(1):101-10. doi: 10.1517/14656566.2012.642863. [PubMed:22149370]
  2. Blech S, Ludwig-Schwellinger E, Grafe-Mody EU, Withopf B, Wagner K: The metabolism and disposition of the oral dipeptidyl peptidase-4 inhibitor, linagliptin, in humans. Drug Metab Dispos. 2010 Apr;38(4):667-78. doi: 10.1124/dmd.109.031476. Epub 2010 Jan 19. [PubMed:20086031]
  3. Graefe-Mody U, Retlich S, Friedrich C: Clinical pharmacokinetics and pharmacodynamics of linagliptin. Clin Pharmacokinet. 2012 Jul 1;51(7):411-27. doi: 10.2165/11630900-000000000-00000. [PubMed:22568694]
  4. Tamborlane WV, Laffel LM, Weill J, Gordat M, Neubacher D, Retlich S, Hettema W, Hoesl CE, Kaspers S, Marquard J: Randomized, double-blind, placebo-controlled dose-finding study of the dipeptidyl peptidase-4 inhibitor linagliptin in pediatric patients with type 2 diabetes. Pediatr Diabetes. 2018 Jun;19(4):640-648. doi: 10.1111/pedi.12616. Epub 2017 Nov 24. [PubMed:29171139]
  5. FDA Approved Drug Products: Linagliptin Oral Tablets [Link]
External Links
KEGG Drug
D09566
PubChem Compound
10096344
PubChem Substance
175427132
ChemSpider
8271879
BindingDB
50228403
ChEBI
68610
ChEMBL
CHEMBL237500
HET
356
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Linagliptin
ATC Codes
A10BH05 — LinagliptinA10BD19 — Linagliptin and empagliflozinA10BD11 — Metformin and linagliptin
AHFS Codes
  • 68:20.05 — Dipeptidyl Peptidase-4 (DPP-4) Inhibitors
PDB Entries
2rgu
FDA label
Download (353 KB)
MSDS
Download (104 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingOtherDiabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
1Active Not RecruitingTreatmentHealthy Volunteers1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceType 2 Diabetes Mellitus1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedOtherHigh Blood Pressure (Hypertension)1
1CompletedTreatmentHealthy Volunteers41
1CompletedTreatmentHepatic Insufficiency1
1CompletedTreatmentImpaired Renal Function1
1CompletedTreatmentType 2 Diabetes Mellitus4
1TerminatedTreatmentSchizophrenic Disorders1
1, 2RecruitingTreatmentGastric Adenocarcinoma or Gastroesophageal Junction Adenocarcinoma1
1, 2RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1, 2RecruitingTreatmentTransitional Cell Carcinoma1
2CompletedTreatmentAlbuminuria / Impaired Renal Function / Type2 Diabetes Mellitus1
2CompletedTreatmentType 2 Diabetes Mellitus6
2Not Yet RecruitingTreatmentType 2 Diabetes Mellitus1
3CompletedNot AvailableAlbuminuria / Arterial Hypertension1
3CompletedTreatmentLeft Ventricular Systolic Dysfunction / Type 2 Diabetes Mellitus1
3CompletedTreatmentType 2 Diabetes Mellitus33
3Not Yet RecruitingTreatmentDM21
3Not Yet RecruitingTreatmentType2 Diabetes Mellitus1
3RecruitingPreventionInsulin Resistance / Prediabetic State2
3RecruitingTreatmentType 2 Diabetes Mellitus1
3TerminatedTreatmentLeft Ventricular Diastolic Dysfunction / Type 2 Diabetes Mellitus1
3TerminatedTreatmentPlaque Morphology / Type 2 Diabetes Mellitus / Vascular Inflammation1
4Active Not RecruitingTreatmentImpaired Renal Function / Type 2 Diabetes Mellitus1
4Active Not RecruitingTreatmentType 2 Diabetes Mellitus1
4CompletedBasic ScienceType 2 Diabetes Mellitus2
4CompletedPreventionChronic Renal Failure (CRF) / Type 2 Diabetes Mellitus1
4CompletedPreventionImpaired Glucose Tolerance / Insulin Resistance / Prediabetic State1
4CompletedPreventionInsulin Resistance / Prediabetic State1
4CompletedTreatmentCoronary Artery Disease / Type 2 Diabetes Mellitus1
4CompletedTreatmentDiabetes Mellitus (DM)2
4CompletedTreatmentType 2 Diabetes Mellitus8
4CompletedTreatmentType2 Diabetes1
4CompletedTreatmentType2 Diabetes Mellitus1
4Not Yet RecruitingTreatmentDiabetes Mellitus (DM) / Osteoporosis1
4Not Yet RecruitingTreatmentType 2 Diabetes Mellitus1
4RecruitingBasic ScienceSchizophrenic Disorders1
4RecruitingTreatmentKidney Transplant; Complications / New Onset Diabetes After Transplant1
4RecruitingTreatmentPeritoneal dialysis therapy / Type 2 Diabetes Mellitus1
4RecruitingTreatmentType II Diabetes in Subjects BMI 27 to 32 / Type II Diabetes in the Not so Obese1
4RecruitingTreatmentType2 Diabetes2
4TerminatedTreatmentType 2 Diabetes Mellitus1
4Unknown StatusBasic ScienceType 2 Diabetes Mellitus1
4Unknown StatusTreatmentInsulin Sensitivity/Resistance / Type 2 Diabetes Mellitus1
4Unknown StatusTreatmentType 2 Diabetes Mellitus1
4WithdrawnTreatmentAdvanced Glycation End Products / Diabetes Mellitus (DM) / SGLT-2 Inhibitors1
4WithdrawnTreatmentDiabetic Nephropathy Type 21
Not AvailableActive Not RecruitingNot AvailableType 2 Diabetes Mellitus1
Not AvailableActive Not RecruitingBasic ScienceType 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableDiabetes Mellitus (DM) / Kidney Function Affection Upon Exposure to Radiocontrast / Microalbuminuria1
Not AvailableCompletedNot AvailableTransplanted Kidney Complication1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus4
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD) / Type 2 Diabetes Mellitus1
Not AvailableRecruitingPreventionIncretinomimetics / Pancreas / Type 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableTerminatedNot AvailableType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Tablet, film coatedOral
Tablet, film coated, extended releaseOral
Tablet, film coatedOral5 mg/1
TabletOral
Tablet, film coatedOral5 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2435730No2011-03-292022-02-21Canada
CA2496249No2012-01-242023-08-18Canada
US7407955No2008-08-052023-08-12Us
US6340475No2002-01-222016-09-19Us
US6635280No2003-10-212016-09-19Us
US6488962No2002-12-032020-06-20Us
US6303661No2001-10-162017-04-24Us
US6890898No2005-05-102019-02-02Us
US7078381No2006-07-182019-02-02Us
US7459428No2008-12-022019-02-02Us
US8119648No2012-02-212023-08-12Us
US8178541No2012-05-152023-08-12Us
US8846695No2014-09-302030-06-04Us
US9173859No2015-11-032027-05-04Us
US8853156No2014-10-072031-03-05Us
US8673927No2014-03-182027-05-04Us
US8883805No2014-11-112025-11-26Us
US9155705No2015-10-132030-05-21Us
US8551957No2013-10-082029-10-19Us
US7713938No2010-05-112027-04-15Us
US7579449No2009-08-252025-11-05Us
US9486526No2016-11-082029-08-05Us
US9415016No2016-08-162029-04-02Us
US9555001No2017-01-312033-03-06Us
US9949998No2018-04-242034-06-11Us
US10034877No2018-07-312029-08-05Us
US10022379No2018-07-172029-04-02Us
US10258637No2014-04-032034-04-03Us
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)190-196http://www.chemspider.com/Chemical-Structure.8271879.html?rid=e059df1a-34ab-48c0-9c24-9d6c4d699c47&page_num=0
water solubility<1 mg/mL MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0502 mg/mLALOGPS
logP2.62ALOGPS
logP2.8ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)9.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area113.48 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity133.43 m3·mol-1ChemAxon
Polarizability51.24 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9513
Caco-2 permeable-0.5842
P-glycoprotein substrateSubstrate0.774
P-glycoprotein inhibitor IInhibitor0.5185
P-glycoprotein inhibitor IINon-inhibitor0.7716
Renal organic cation transporterNon-inhibitor0.6658
CYP450 2C9 substrateNon-substrate0.803
CYP450 2D6 substrateNon-substrate0.7335
CYP450 3A4 substrateSubstrate0.7013
CYP450 1A2 substrateNon-inhibitor0.9273
CYP450 2C9 inhibitorNon-inhibitor0.8474
CYP450 2D6 inhibitorNon-inhibitor0.9176
CYP450 2C19 inhibitorNon-inhibitor0.8163
CYP450 3A4 inhibitorNon-inhibitor0.5548
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8562
Ames testNon AMES toxic0.5444
CarcinogenicityNon-carcinogens0.8587
BiodegradationNot ready biodegradable0.9966
Rat acute toxicity2.7553 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6109
hERG inhibition (predictor II)Inhibitor0.8116
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 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-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0113900000-1cf1f79967a4761f3983
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ufr-0391100000-8df1ebbcbdc456f86470
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0114900000-928cf1c76b7fa52190f2

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
Quinazolines / 6-oxopurines / Alkaloids and derivatives / Dialkylarylamines / Pyrimidones / Aminopiperidines / Aminoimidazoles / N-substituted imidazoles / Benzenoids / Vinylogous amides
show 9 more
Substituents
Xanthine / Diazanaphthalene / 6-oxopurine / Purinone / Quinazoline / Alkaloid or derivatives / Dialkylarylamine / 3-aminopiperidine / Pyrimidone / Piperidine
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aminopiperidine, quinazolines (CHEBI:68610)

Targets

Details
1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 Da
References
  1. Forst T, Pfutzner A: Linagliptin, a dipeptidyl peptidase-4 inhibitor with a unique pharmacological profile, and efficacy in a broad range of patients with type 2 diabetes. Expert Opin Pharmacother. 2012 Jan;13(1):101-10. doi: 10.1517/14656566.2012.642863. [PubMed:22149370]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Blech S, Ludwig-Schwellinger E, Grafe-Mody EU, Withopf B, Wagner K: The metabolism and disposition of the oral dipeptidyl peptidase-4 inhibitor, linagliptin, in humans. Drug Metab Dispos. 2010 Apr;38(4):667-78. doi: 10.1124/dmd.109.031476. Epub 2010 Jan 19. [PubMed:20086031]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Graefe-Mody U, Retlich S, Friedrich C: Clinical pharmacokinetics and pharmacodynamics of linagliptin. Clin Pharmacokinet. 2012 Jul 1;51(7):411-27. doi: 10.2165/11630900-000000000-00000. [PubMed:22568694]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Graefe-Mody U, Retlich S, Friedrich C: Clinical pharmacokinetics and pharmacodynamics of linagliptin. Clin Pharmacokinet. 2012 Jul 1;51(7):411-27. doi: 10.2165/11630900-000000000-00000. [PubMed:22568694]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Graefe-Mody U, Retlich S, Friedrich C: Clinical pharmacokinetics and pharmacodynamics of linagliptin. Clin Pharmacokinet. 2012 Jul 1;51(7):411-27. doi: 10.2165/11630900-000000000-00000. [PubMed:22568694]
  2. Ishiguro N, Shimizu H, Kishimoto W, Ebner T, Schaefer O: Evaluation and prediction of potential drug-drug interactions of linagliptin using in vitro cell culture methods. Drug Metab Dispos. 2013 Jan;41(1):149-58. doi: 10.1124/dmd.112.048470. Epub 2012 Oct 16. [PubMed:23073734]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Graefe-Mody U, Retlich S, Friedrich C: Clinical pharmacokinetics and pharmacodynamics of linagliptin. Clin Pharmacokinet. 2012 Jul 1;51(7):411-27. doi: 10.2165/11630900-000000000-00000. [PubMed:22568694]

Drug created on May 21, 2013 16:46 / Updated on November 16, 2019 10:42