Linagliptin

Linagliptin
Names
Pronunciation/ˌlɪnəˈɡlɪptɪn/ LIN-ə-GLIP-tin
Trade namesTradjenta, Trajenta, others
Other namesBI-1356
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
Clinical data
Drug classDPP-4 inhibitors[1]
Main usesDiabetes mellitus type 2[1]
Side effectsInflammation of the nose and throat[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    use    		By mouth (tablets)
    Defined daily dose5 mg[2]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa611036
    Legal
    License data
    Legal status
    • AU: S4 (Prescription only)
    • UK: POM (Prescription only)
    • US: ℞-only
    • In general: ℞ (Prescription only)
    Pharmacokinetics
    Bioavailability~30% (Tmax = 1.5 hours)
    Protein binding75–99% (concentration-dependent)
    MetabolismMinimal (~10% metabolized)
    MetabolitesPharmacologically inactive
    Elimination half-life~24 hours
    ExcretionFeces (80%), urine (5%)[3]
    Chemical and physical data
    FormulaC25H28N8O2
    Molar mass472.553 g·mol−1
    3D model (JSmol)
    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 ☒N
    • Key:LTXREWYXXSTFRX-QGZVFWFLSA-N ☒N

    Linagliptin, sold under the brand name Tradjenta among others, is a medication used to treat diabetes mellitus type 2.[1] It is generally less preferred than metformin and sulfonylureas as an initial treatment.[1][4] It is used together with exercise and diet.[1] It is not recommended in type 1 diabetes.[1] It is taken by mouth.[1]

    Common side effects include inflammation of the nose and throat.[1] Serious side effects may include angioedema, pancreatitis, joint pain.[4][1] Use in pregnancy and breastfeeding is not recommended.[4] Linagliptin is a dipeptidyl peptidase-4 inhibitor (DPP-4 inhibitors).[1] It works by increasing the production of insulin and decreasing the production of glucagon by the pancreas.[1]

    Linagliptin was approved for medical use in the United States in 2011.[1] A month supply in the United Kingdom costs the NHS about £33 as of 2019.[4] In the United States the wholesale cost of this amount is about 391 USD.[5] In 2017, it was the 200th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

    Medical uses

    Results in 2010 from a Phase III clinical trial of linagliptin showed that the drug can effectively reduce blood sugar.[8]

    Dosage

    The defined daily dose is 5 mg by mouth.[2]

    Side effects

    Linagliptin may cause severe joint pain.[3][9]

    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[10] states the drug is contraindicated for people with bronchial hyperreactivity. Asthma is a form of bronchial hyperreactivity[11].

    Mechanism of action

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

    Terminology

    Linagliptin is the INN.[12]

    Society and culture

    Cost

    A month supply in the United Kingdom costs the NHS about £33 as of 2019.[4] In the United States the wholesale cost of this amount is about 391 USD.[5] In 2017, it was the 200th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

    • Linagliptin costs (US)
      Linagliptin costs (US)
    • Linagliptin prescriptions (US)
      Linagliptin prescriptions (US)

    See also

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 12 13 "Linagliptin Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 6 April 2019. Retrieved 6 April 2019.
    2. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 1 November 2020. Retrieved 8 September 2020.
    3. 1 2 "Tradjenta (linagliptin) Tablets. Full Prescribing Information" (PDF). Boehringer Ingelheim Pharmaceuticals, Inc. Ridgefield, CT 06877 USA. Archived (PDF) from the original on 6 November 2016. Retrieved 10 November 2016.
    4. 1 2 3 4 5 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 680. ISBN 9780857113382.
    5. 1 2 "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Archived from the original on 2019-03-06. Retrieved 3 March 2019.
    6. 1 2 "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
    7. 1 2 "Linagliptin - Drug Usage Statistics". ClinCalc. Archived from the original on 10 July 2020. Retrieved 11 April 2020.
    8. ↑ "Four Phase III Trials Confirm Benefits of BI's Oral, Once-Daily Type 2 Diabetes Therapy". Genetic Engineering & Biotechnology News. 28 June 2010. Archived from the original on 31 October 2018. Retrieved 12 September 2010.
    9. ↑ "DPP-4 Inhibitors for Type 2 Diabetes: Drug Safety Communication - May Cause Severe Joint Pain". FDA. 2015-08-28. Archived from the original on 2017-04-06. Retrieved 1 September 2015.
    10. ↑ https://docs.boehringer-ingelheim.com/Prescribing%20Information/PIs/Tradjenta/Tradjenta.pdf?DMW_FORMAT=pdf Archived 2020-06-01 at the Wayback Machine)
    11. ↑ Bronchial hyperresponsiveness
    12. ↑ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 61" (PDF). World Health Organization. p. 66. Archived (PDF) from the original on 3 October 2020. Retrieved 10 November 2016.
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