Linagliptin

Linagliptin
Clinical data
Pronunciation	/ˌlɪnəˈɡlɪptɪn/ LIN-ə-GLIP-tin
Trade names	Tradjenta, Trajenta, others
Other names	BI-1356
AHFS/Drugs.com	Monograph
MedlinePlus	a611036
License data	EU EMA: by INN; US FDA: Linagliptin;
Pregnancy; category	US: B (No risk in non-human studies) ;
Routes of; administration	By mouth (tablets)
ATC code	A10BH05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ; UK: POM (Prescription only) ; US: ℞-only ; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	~30% (Tmax = 1.5 hours)
Protein binding	75–99% (concentration-dependent)
Metabolism	Minimal (~10% metabolized)
Metabolites	Pharmacologically inactive
Elimination half-life	~24 hours
Excretion	Feces (80%), urine (5%)[1]
Identifiers
	IUPAC name 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;
CAS Number	668270-12-0 ;
PubChem CID	10096344;
IUPHAR/BPS	6318;
ChemSpider	8271879 ;
UNII	3X29ZEJ4R2;
KEGG	D09566 ;
ChEBI	CHEBI:68610 ;
ChEMBL	ChEMBL237500 ;
Chemical and physical data
Formula	C25H28N8O2
Molar mass	472.54 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC#CCN1C2=C(N=C1N3CCC[C@H](C3)N)N(C(=O)N(C2=O)CC4=NC5=CC=CC=C5C(=N4)C)C;
	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 ; Key:LTXREWYXXSTFRX-QGZVFWFLSA-N ;
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Linagliptin, sold under the brand name Tradjenta among others, is a medication used to treat diabetes mellitus type 2.[2] It is generally less preferred than metformin and sulfonylureas.[2][3] It is used together with exercise and diet.[2] It is not recommended in type 1 diabetes.[2] It is taken by mouth.[2]

Common side effects include inflammation of the nose and throat.[2] Serious side effects may include angioedema, pancreatitis, joint pain.[3][2] Use in pregnancy and breastfeeding is not recommended.[3] Linagliptin is a dipeptidyl peptidase-4 inhibitor.[2] It works by increasing the production of insulin and decreasing the production of glucagon by the pancreas.[2]

Linagliptin was approved for medical use in the United States in 2011.[2] A month supply in the United Kingdom costs the NHS about £33.26 as of 2019.[3] In the United States the wholesale cost of this amount is about 391 USD.[4] In 2016 it was the 196th most prescribed medication in the United States with more than 3 million prescriptions.[5]

Medical uses

Results in 2010 from a Phase III clinical trial of linagliptin showed that the drug can effectively reduce blood sugar.[6]

Side effects

Linagliptin may cause severe joint pain.[1][7]

The U.S. Food and Drug Administration (FDA) is warning that the type 2 diabetes medicines like sitagliptin, saxagliptin, linagliptin, and alogliptin may cause joint pain that can be severe and disabling. FDA has added a new Warning and Precaution about this risk to the labels of all medicines in this drug class, called dipeptidyl peptidase-4 (DPP-4) inhibitors.

Trajenta's Prescribing Information[8] states the drug is contraindicated for people with bronchial hyperreactivity. Asthma is a form of bronchial hyperreactivity[9].

Mechanism of action

Linagliptin belongs to a class of drugs called DPP-4 inhibitors.

Terminology

Linagliptin is the INN.[10]

References

"Tradjenta (linagliptin) Tablets. Full Prescribing Information" (PDF). Boehringer Ingelheim Pharmaceuticals, Inc. Ridgefield, CT 06877 USA. Retrieved 10 November 2016.
"Linagliptin Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 6 April 2019.
British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 680. ISBN 9780857113382.
"NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Retrieved 3 March 2019.
"The Top 300 of 2019". clincalc.com. Retrieved 22 December 2018.
"Four Phase III Trials Confirm Benefits of BI's Oral, Once-Daily Type 2 Diabetes Therapy". Genetic Engineering & Biotechnology News. 28 June 2010.
"DPP-4 Inhibitors for Type 2 Diabetes: Drug Safety Communication - May Cause Severe Joint Pain". FDA. 2015-08-28. Retrieved 1 September 2015.
https://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Tradjenta/Tradjenta.pdf?DMW_FORMAT=pdf)
Bronchial hyperresponsiveness
"International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 61" (PDF). World Health Organization. p. 66. Retrieved 10 November 2016.

External links

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[PI-1] "Tradjenta (linagliptin) Tablets. Full Prescribing Information" (PDF). Boehringer Ingelheim Pharmaceuticals, Inc. Ridgefield, CT 06877 USA. Retrieved 10 November 2016.

[AHFS2019-2] "Linagliptin Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 6 April 2019.

[BNF76-3] British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 680. ISBN 9780857113382.

[NADAC2019-4] "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Retrieved 3 March 2019.

[5] "The Top 300 of 2019". clincalc.com. Retrieved 22 December 2018.

[6] "Four Phase III Trials Confirm Benefits of BI's Oral, Once-Daily Type 2 Diabetes Therapy". Genetic Engineering & Biotechnology News. 28 June 2010.

[7] "DPP-4 Inhibitors for Type 2 Diabetes: Drug Safety Communication - May Cause Severe Joint Pain". FDA. 2015-08-28. Retrieved 1 September 2015.

[8] ttps://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Tradjenta/Tradjenta.pdf?DMW_FORMAT=pdf)

[9] Bronchial hyperresponsiveness

[INN-10] "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 61" (PDF). World Health Organization. p. 66. Retrieved 10 November 2016.