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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H28N8O2
Molecular Weight 472.5422
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LINAGLIPTIN

SMILES

CC#CCN1C(=NC2=C1C(=O)N(CC3=NC4=CC=CC=C4C(C)=N3)C(=O)N2C)N5CCC[C@@H](N)C5

InChI

InChIKey=LTXREWYXXSTFRX-QGZVFWFLSA-N
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

HIDE SMILES / InChI
Molecular Formula C25H28N8O2
Molecular Weight 472.5422
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including

Linagliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor discovered by Boehringer Ingelheim and being developed as an oral once-daily tablet for the treatment of Type 2 diabetes. Linagliptin was first approved by FDA in 2011 under the trade name Tradjenta as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Linagliptin binds to DPP-4 (an enzyme that degrades the incretin hormones glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP)) in a reversible manner and thus increases the concentrations of incretin hormones. Linagliptin glucose dependently increases insulin secretion and lowers glucagon secretion, thus resulting in better regulation of glucose homeostasis. Linagliptin binds selectively to DPP-4, and selectively inhibits DPP-4 but not DPP-8 or DPP-9 activity in vitro at concentrations approximating therapeutic exposures.

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: Linagliptin does not cross the blood brain barrier, and therefore its effects are peripheral rather than directly in the central nervous system.

Originator

Approval Year

2011
587
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 1.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Approved
8429
TRADJENTA

Approved Use

Indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Should not be used in patients with type 1 diabetes or for the treatment of diabetic ketoacidosis. Has not been studied in combination with insulin.

Launch Date

1.30429446E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16.4 nM
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/23331248
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LINAGLIPTIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8.9 nM
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201280lbl.pdf
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LINAGLIPTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
194 nM × h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/23331248
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LINAGLIPTIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
139 nM × h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201280lbl.pdf
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LINAGLIPTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
119 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/23331248
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LINAGLIPTIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201280lbl.pdf
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LINAGLIPTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201280lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/18812608
healthy, 38.3 years (range: 23-63 years)
n = 6
Health Status: healthy
Age Group: 38.3 years (range: 23-63 years)
Sex: M
Population Size: 6
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201280lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/18812608
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201280lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/18812608
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587

inducer
781
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OATP2
4

OCT1
512

CYP2A6
707

CYP2E1
882

CYP4A11
21

CYP2C8
911

CYP1A2
1524

CYP2B6
810

CYP2C19
1478

P-gp
1461

BCRP
699

MRP2
383

OCT2
647

OAT4
146

OCTN1
29

OCTN2
66

OAT1
599

OAT3
642
P-gp
1537

BCRP
561

MRP2
205

OCT2
355

OAT4
78

OCTN1
47

OCTN2
50

OATP2
11

OCT1
327

OAT1
326

OAT3
339
CYP1A2
701

CYP2B6
547
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
965
 no [IC50 >10 uM]
no (co-administration study)
Comment: Pooled human liver microsomes (paclitaxel 6a-hydroxylation), Coadministration of linagliptin (10 mg QD days 1-12) decreased pioglitazone (CYP2C8 & CYP3A4 substrate, 45 mg QD days 6-12) AUCtau,ss by 5.6% and Cmax,ss by 14.4%.
Page: 38, (ClinPharm) 58, (PMDA in Japanese_I101-1) 78, (PMDA in Japanese_K101-1) 83-85, 201
CYP1A2
1692
 no [IC50 >100 uM]
CYP2A6
739
 no [IC50 >100 uM]
CYP2B6
1001
 no [IC50 >100 uM]
CYP2C19
1553
 no [IC50 >100 uM]
CYP2D6
1891
 no [IC50 >100 uM]
CYP2E1
970
 no [IC50 >100 uM]
CYP4A11
25
 no [IC50 >100 uM]
BCRP
773
 no
CYP1A2
1692
 no
CYP2B6
1001
 no
CYP3A4
1925
 no
MRP2
475
 no
OAT1
603
 no
OAT3
644
 no
OAT4
146
 no
OCTN2
71
 no
OCT2
648
 no
no (co-administration study)
Comment: OCT2-HEK293 cells, Coadministration of linagliptin increased metformin (OCT2 substrate) AUCtau,ss by 0.8% and decreased Cmax,ss by 11.4%.
Page: (ClinPharm) 59, (PMDA in Japanese) 37, 38
P-gp
1650
 weak [IC50 66.1 uM]
unlikely (co-administration study)
Comment: MDR1-LLC-PK cells, MDR1-MDCKII cell monolayers; IC50 = 55 mcM (Caco-2 cells), concentration dependent and saturable inhibitor, Coadministration of ligagliptin increased Digoxin (P-gp substrate) AUCtau,ss by 1.5% and decreased Cmax by 5.8%.
Page: 27, (ClinPharm) 58, (PMDA in Japanese_I101-1) 37, 38, (PMDA in Japanese_K101-1) 92-93, 211
OCTN1
29
 weak [IC50 >100 uM]
CYP2C9
1819
 weak [IC50 >100 uM]
unlikely (co-administration study)
Comment: Pooled human liver microsomes (tolbutamide hydroxylation); IC50 = 19.6 mcM (diclofenac 4'-hydroxylation); IC50 = 15.2 mcM, Ki = 8.28 mcM (flurbiprofen 4'-hydroxylation); Coadministration of linagliptin decreased R-warfarin (warfarin, CYP2C9 substrate) AUC0-inf by 1.5% and Cmax 0.3%, and increased S-warfarin AUC0-inf by 3.0% and Cmax by 0.9%. Coadministration of linagliptin decreased glyburide (CYP2C9 substrate) AUC0-inf by 14.3% and Cmax by 13.8%.
Page: 38, (ClinPharm) 57, 58, (PMDA in Japanese_I101-1) 78, (PMDA in Japanese_K101-1) 86-87, 90-91, 204, 210
CYP3A4
1925
 weak [Ki 36.3 uM]
weak (co-administration study)
Comment: Pooled human liver microsomes (testosterone 6b-hydroxylation, IC50 = 36.3 mcM, Ki = 115 mcM; erythromycin N-demethylation, IC50 = 41.6 mcM), irreversible inhibitior (poor to moderate); Due to the high potency DPP4 inhibition of linagliptin, resulting in clinical Cmax of 20 nM, the potential for in vivo CYP3A4, MAO-B, or CYP2C9 inhibition are minimal at therapeutic exposures. Coadministration of linagliptin increased simvastatin (CYP3A4 substarate) AUCtau,ss by 34.17% and Cmax,ss by 10.01%, and simvastatin acid AUCtau,ss by 33.26% and Cmax,ss by 20.74%.
Page: 38, (ClinPharm) 57, (PMDA in Japanese_I101-1) 78, (PMDA in Japanese_K101-1) 88-89, 206-207
CYP2C9
1819
 yes [IC50 15 uM]
CD 1790
1
CYP3A4
1925
 yes [IC50 43.2 uM]
CD 1790
1
OCT1
543
 yes [IC50 45.2 uM]
OATP2
4
 yes [IC50 69.7 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 moderate [Km 187 uM]
yes (co-administration study)
Comment: MDR1-LLC-PK cells, MDR1-MDCKII cell monolayers, Coadministration of ritonavir (potent P-gp and CYP3A4 inhibitor) increased linagliptin AUC0-24 by 101.4% and Cmax by 195.7%., Coadministration of rifampicin (potent P-gp and CYP3A4 inducer) decreased linagliptin AUCtau,ss by 39.5% and Cmax,ss by 43.8%.
Page: 27, (ClinPharm) 58, 59, (PMDA in Japanese_I101-1) 37, 38, (PMDA in Japanese_K101-1) 73-76, 77-80, 198, 199
BCRP
561
 no
MRP2
205
 no
OAT1
326
 no
OAT3
339
 no
OATP2
11
 no
OCT1
327
 no
OAT4
78
 yes
OCT2
355
 yes
OCTN1
47
 yes
OCTN2
50
 yes
CYP3A4
1737
 yes
yes (co-administration study)
Comment: Coadministration of ritonavir (potent P-gp and CYP3A4 inhibitor) increased linagliptin AUC0-24 by 101.4% and Cmax by 195.7%., Coadministration of rifampicin (potent P-gp and CYP3A4 inducer) decreased linagliptin AUCtau,ss by 39.5% and Cmax,ss by 43.8%.
Page: 38, (ClinPharm) 58, 59, (PMDA in Japanese_K101-1) 73-76, 77-80, 198, 199
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:68610
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68610
ChemicalBook
CB71518518
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB71518518
MolPort
MolPort-021-783-260
https://www.molport.com/shop/molecule-link/MolPort-021-783-260
Selleck Chemicals
linagliptin-bi-1356
http://www.selleckchem.com/products/linagliptin-bi-1356.html
ZINC
ZINC000003820029
http://zinc15.docking.org/substances/ZINC000003820029
PubMed

PubMed

TitleDatePubMed
8-(3-(R)-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydropurine-2,6-dione (BI 1356), a highly potent, selective, long-acting, and orally bioavailable DPP-4 inhibitor for the treatment of type 2 diabetes.
2007 Dec 27
(R)-8-(3-amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione (BI 1356), a novel xanthine-based dipeptidyl peptidase 4 inhibitor, has a superior potency and longer duration of action compared with other dipeptidyl peptidase-4 inhibitors.
2008 Apr
3,5-Dihydro-imidazo[4,5-d]pyridazin-4-ones: a class of potent DPP-4 inhibitors.
2008 Jun 1
Safety, tolerability, pharmacokinetics, and pharmacodynamics of single oral doses of BI 1356, an inhibitor of dipeptidyl peptidase 4, in healthy male volunteers.
2008 Oct
Evaluation of the potential for steady-state pharmacokinetic and pharmacodynamic interactions between the DPP-4 inhibitor linagliptin and metformin in healthy subjects.
2009 Aug
Pharmacokinetics, pharmacodynamics and tolerability of multiple oral doses of linagliptin, a dipeptidyl peptidase-4 inhibitor in male type 2 diabetes patients.
2009 Aug
Chronic treatment with the dipeptidyl peptidase-4 inhibitor BI 1356 [(R)-8-(3-amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione] increases basal glucagon-like peptide-1 and improves glycemic control in diabetic rodent models.
2009 Feb
The centrosome protein NEDD1 as a potential pharmacological target to induce cell cycle arrest.
2009 Feb 25
Concentration-dependent plasma protein binding of the novel dipeptidyl peptidase 4 inhibitor BI 1356 due to saturable binding to its target in plasma of mice, rats and humans.
2009 Jan
Tissue distribution of the novel DPP-4 inhibitor BI 1356 is dominated by saturable binding to its target in rats.
2009 Jul
Inhibition of dipeptidyl peptidase 4 by BI-1356, a new drug for the treatment of beta-cell failure in type 2 diabetes.
2009 Jun
Binding to dipeptidyl peptidase-4 determines the disposition of linagliptin (BI 1356)--investigations in DPP-4 deficient and wildtype rats.
2009 Nov
Linagliptin, a dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes.
2009 Oct
Design, statistical analysis and sample size calculation of a phase IIb/III study of linagliptin versus voglibose and placebo.
2009 Sep 5
Incorrect description of mode of excretion of linagliptin.
2010
Dipeptidyl peptidase-4 inhibitors in the management of type 2 diabetes: safety, tolerability, and efficacy.
2010
The metabolism and disposition of the oral dipeptidyl peptidase-4 inhibitor, linagliptin, in humans.
2010 Apr
Pharmacokinetics of dipeptidylpeptidase-4 inhibitors.
2010 Aug
Impact of target-mediated drug disposition on Linagliptin pharmacokinetics and DPP-4 inhibition in type 2 diabetic patients.
2010 Aug
Linagliptin (BI 1356), a potent and selective DPP-4 inhibitor, is safe and efficacious in combination with metformin in patients with inadequately controlled Type 2 diabetes.
2010 Dec
Pharmacokinetics and pharmacodynamics of single rising intravenous doses (0.5 mg-10 mg) and determination of absolute bioavailability of the dipeptidyl peptidase-4 inhibitor linagliptin (BI 1356) in healthy male subjects.
2010 Dec
Incretin concepts.
2010 Feb
Linagliptin, a xanthine-based dipeptidyl peptidase-4 inhibitor with an unusual profile for the treatment of type 2 diabetes.
2010 Jan
The evolving place of incretin-based therapies in type 2 diabetes.
2010 Jul
Linagliptin, a dipeptidyl peptidase-4 inhibitor in development for the treatment of type 2 diabetes mellitus: a Phase I, randomized, double-blind, placebo-controlled trial of single and multiple escalating doses in healthy adult male Japanese subjects.
2010 Jun
Effect of linagliptin (BI 1356) on the steady-state pharmacokinetics of simvastatin.
2010 Jun
Type 2 diabetes: postprandial hyperglycemia and increased cardiovascular risk.
2010 Mar 24
Chronic administration of DSP-7238, a novel, potent, specific and substrate-selective DPP IV inhibitor, improves glycaemic control and beta-cell damage in diabetic mice.
2010 May
New treatments in the management of type 2 diabetes: a critical appraisal of saxagliptin.
2010 May 10
DPP-4 inhibitors: what may be the clinical differentiators?
2010 Nov
Evaluation of the pharmacokinetic interaction between the dipeptidyl peptidase-4 inhibitor linagliptin and pioglitazone in healthy volunteers.
2010 Oct
Dipeptidylpeptidase-4 inhibitors (gliptins): focus on drug-drug interactions.
2010 Sep
The dipeptidyl peptidase-4 inhibitor linagliptin exhibits time- and dose-dependent localization in kidney, liver, and intestine after intravenous dosing: results from high resolution autoradiography in rats.
2010 Sep
Exenatide once weekly: clinical outcomes and patient satisfaction.
2010 Sep 7
Effects of DPP-4 inhibitors on the heart in a rat model of uremic cardiomyopathy.
2011
Linagliptin, a dipeptidyl peptidase-4 inhibitor with a unique pharmacological profile, and efficacy in a broad range of patients with type 2 diabetes.
2012 Jan
Patents

Patents

20040097510
1
20060142310
1
JP2011529945A
21
JP2012500190A
22

Sample Use Guides

In Vivo Use Guide
The recommended dose of Tradjenta is 5 mg once daily, tablets can be taken with or without food.
Route of Administration: Oral
In Vitro Use Guide
To study dissociation of BI 1356 (linagliptin) from the DPP-4 enzyme Caco-2 cell extract was preincubated with BI 1356 at concentration of 30 nM for, high above the respective Ki value of 1 nM. The enzymatic reaction was started by adding the substrate after a 3000-fold dilution of the preincubation mixture. Enzyme rates in the presence of BI 1356 were measured at different times after dilution (v in relative fluorescence units/seconds × 1000) and corrected for the rate of an uninhibited reaction. koff rate was obtained from a one-phase exponential decay equation fitted to the data points. The calculated koff rate for BI 1356 was 3.0 × 10(–5)/s.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:04:55 UTC 2023
Edited
by admin
on Fri Dec 15 16:04:55 UTC 2023
Record UNII
3X29ZEJ4R2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LINAGLIPTIN
DASH   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
TRIJARDY XR COMPONENT LINAGLIPTIN
Brand Name English
linagliptin [INN]
Common Name English
GLYXAMBI COMPONENT LINAGLIPTIN
Brand Name English
BI-1356
Code English
8-[(3R)-3-Aminopiperidin-1-yl]-7-(but-2-yn-1-yl)-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]-3,7-dihydro-1H-purine-2,6-dione
Systematic Name English
LINAGLIPTIN [VANDF]
Common Name English
(R)-8-(3-AMINO-PIPERIDIN-1-YL)-7-BUT-2-YNYL-3-METHYL-1-(4-METHYL-QUINAZOLIN-2-YLMETHYL)-3,7-DIHYDRO-PURINE-2,6-DIONE
Systematic Name English
LINAGLIPTIN COMPONENT OF JENTADUETO
Common Name English
BS-1356-BS
Code English
BI1356
Code English
1H-PURINE-2,6-DIONE, 8-((3R)-3-AMINO-1-PIPERIDINYL)-7-(2-BUTYNYL)-3,7-DIHYDRO-3-METHYL-1-((4-METHYL-2- QUINAZOLINYL)METHYL)-
Systematic Name English
Linagliptin [WHO-DD]
Common Name English
TRAZENTA
Brand Name English
LINAGLIPTIN [MI]
Common Name English
LINAGLIPTIN COMPONENT OF TRIJARDY XR
Brand Name English
LINAGLIPTIN [USAN]
Common Name English
BI-1356-BS
Code English
LINAGLIPTIN [JAN]
Common Name English
LINAGLIPTIN [ORANGE BOOK]
Common Name English
BI-1356BS
Code English
BI 1356
Code English
TRAJENTA
Brand Name English
BI 1356 BS
Code English
LINAGLIPTIN [MART.]
Common Name English
LINAGLIPTIN COMPONENT OF GLYXAMBI
Brand Name English
JENTADUETO COMPONENT OF LINAGLIPTIN
Common Name English
BS 1356 BS
Code English
Classification Tree Code System Code
NCI_THESAURUS C98086
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
WHO-ATC A10BD11
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
WHO-VATC QA10BH05
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
WHO-ATC A10BD19
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
LIVERTOX NBK548554
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
WHO-VATC QA10BD11
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
WHO-ATC A10BH05
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
NDF-RT N0000175913
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
Code System Code Type Description
DAILYMED
3X29ZEJ4R2
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
HSDB
8204
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
MERCK INDEX
m6819
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY Merck Index
IUPHAR
6318
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
DRUG BANK
DB08882
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
EVMPD
SUB31340
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
PUBCHEM
10096344
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
USAN
WW-122
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
MESH
C568794
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
DRUG CENTRAL
4175
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
INN
9039
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
RXCUI
1100699
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL237500
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID201021653
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
LACTMED
Linagliptin
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
CHEBI
68610
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
WIKIPEDIA
LINAGLIPTIN
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
CAS
668270-12-0
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
SMS_ID
100000115340
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
FDA UNII
3X29ZEJ4R2
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
NCI_THESAURUS
C83887
Created by admin on Fri Dec 15 16:04:55 UTC 2023 , Edited by admin on Fri Dec 15 16:04:55 UTC 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
WEAK
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Linagliptin co-administration with P-gp and CYP 3A4 inducers may reduce its efficacy because of lower linagliptin exposures; therefore, it is strongly recommended to use the alternative treatments when it is to be co- administered with P-gp or CYP 3A4 inducers.
Structure of LINAGLIPTIN
EXCRETED UNCHANGED
URINE
Structure of LINAGLIPTIN
EXCRETED UNCHANGED
FECAL
DIPEPTIDYL PEPTIDASE 4 MEMBRANE FORM
TARGET -> INHIBITOR
INHIBITOR
IC50
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of N-((3R)-1-(2,3,6,7-TETRAHYDRO-7-(4-HYDROXY-2-BUTYN-1-YL)-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL-2-14C)METHYL)-2,6-DIOXO-1H-PURIN-8-YL)-3-PIPERIDINYL)ACETAMIDE
METABOLITE -> PARENT
MINOR
Structure of 5-((7-(2-BUTYN-1-YL)-2,3,6,7-TETRAHYDRO-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL)METHYL)-2,6-DIOXO-1H-PURIN-8-YL)AMINO)-2-HYDROXYPENTANOIC ACID
METABOLITE -> PARENT
MINOR
Structure of 4-((7-(2-BUTYN-1-YL)-2,3,6,7-TETRAHYDRO-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL)METHYL)-2,6-DIOXO-1H-PURIN-8-YL)AMINO)BUTANOIC ACID
METABOLITE -> PARENT
Structure of 8-((3R)-3-AMINO-1-PIPERIDINYL)-3,7-DIHYDRO-7-(4-HYDROXY-2-BUTYN-1-YL)-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL)METHYL)-1H-PURINE-2,6-DIONE
METABOLITE -> PARENT
MINOR
Structure of (2S,3S,4S,5R)-6-((1-(7-BUT-2-YNYL-3-METHYL-1-((4-METHYLQUINAZOLIN-2-YL)METHYL)-2,6-DIOXO-PURIN-8-YL)-3-PIPERIDYL)OXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
Structure of 5-((7-(2-BUTYN-1-YL)-2,3,6,7-TETRAHYDRO-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL)METHYL)-2,6-DIOXO-1H-PURIN-8-YL)AMINO)-2-OXO-PENTANOIC ACID
METABOLITE -> PARENT
MINOR
Structure of 8-((3S)-3-AMINO-4-OXO-1-PIPERIDYL)-7-BUT-2-YNYL-3-METHYL-1-((4-METHYLQUINAZOLIN-2-YL)METHYL)PURINE-2,6-DIONE
METABOLITE -> PARENT
MINOR
Structure of N-((3R)-1-(7-BUT-2-YNYL-3-METHYL-1-((4-METHYLQUINAZOLIN-2-YL)METHYL)-2,6-DIOXO-PURIN-8-YL)-2-HYDROXY-3-PIPERIDYL)ACETAMIDE
METABOLITE -> PARENT
MINOR
Structure of N-((3R)-1-(7-(2-BUTYN-1-YL)-2,3,6,7-TETRAHYDRO-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL)METHYL)-2,6-DIOXO-1H-PURIN-8-YL)-3-PIPERIDINYL)ACETAMIDE
METABOLITE -> PARENT
MINOR
Structure of 2-((8-((3R)-3-AMINO-1-PIPERIDINYL)-7-(2-BUTYN-1-YL)-2,3,6,7-TETRAHYDRO-3-METHYL-2,6-DIOXO-1H-PURIN-1-YL)METHYL)-4-QUINAZOLINECARBOXYLIC ACID
METABOLITE -> PARENT
MINOR
Structure of 3,7-DIHYDRO-7-(4-HYDROXY-2-BUTYN-1-YL)-8-((3S)-3-HYDROXY-1-PIPERIDINYL)-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL)METHYL)-1H-PURINE-2,6-DIONE
METABOLITE -> PARENT
MINOR
Structure of 7-(2-BUTYN-1-YL)-3,7-DIHYDRO-3-METHYL-1-((4-METHYL-2-QUINAZOLINYL)METHYL)-8-(3-OXO-1-PIPERIDINYL)-1H-PURINE-2,6-DIONE
METABOLITE -> PARENT
MINOR
Related Record Type Details
Structure of LINAGLIPTIN N-BOC IMPURITY
IMPURITY -> PARENT
Structure of LINAGLIPTIN S ISOMER
IMPURITY -> PARENT
Related Record Type Details
Structure of LINAGLIPTIN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
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