Teneligliptin Property

Melting point:

>100°C (dec.)

Boiling point:

663.4±55.0 °C(Predicted)

Density 

1.38

storage temp. 

Refrigerator

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

8.70±0.10(Predicted)

color 

Off-White

InChI

InChI=1S/C22H30N6OS/c1-17-13-21(28(24-17)18-5-3-2-4-6-18)26-9-7-25(8-10-26)19-14-20(23-15-19)22(29)27-11-12-30-16-27/h2-6,13,19-20,23H,7-12,14-16H2,1H3/t19-,20-/m0/s1

InChIKey

WGRQANOPCQRCME-PMACEKPBSA-N

SMILES

C([C@@H]1C[C@H](N2CCN(C3N(C4=CC=CC=C4)N=C(C)C=3)CC2)CN1)(N1CCSC1)=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Teneligliptin Chemical Properties,Usage,Production

Description

Teneligliptin was approved in September 2012 in Japan for the treatment of patients with Type 2 diabetes mellitus (T2DM). Teneligliptin is a member of the dipeptidyl peptidase 4 (DPP-4) inhibitor class of antidiabetes agents. DPP-4 is an enzyme that degrades GLP-1, a 30-amino acid peptide that is secreted in response to food intake. GLP-1 stimulates insulin secretion and inhibits glucagon secretion, which leads to lower levels of plasma glucose. Teneligliptin is one of a growing numbers of DPP-4 inhibitors to be approved worldwide. The discovery of teneligliptin was guided by structure-based design, with a key element being binding of the phenyl group in the S2 pocket, which not only increases potency for DPP-4, but also improves selectivity versus DPP-8 and DPP- 9. Teneligliptin is a potent inhibitor of DPP-4 in the enzyme inhibition assay (IC₅₀=0.37 nM).

Originator

Mitsubishi Tanabe Pharma (Japan)

Uses

Teneligliptin, is a dipeptidyl peptidase-4 (DPP-4) inhibitor that is used to treat type 2 diabetes. It is eliminated via excretion, and has a half-life of 24.2 hours in the human body.

Definition

ChEBI: Teneligliptin is an amino acid amide.

brand name

Tenelia

Pharmacokinetics

Reported evidence suggests that with teneligliptin 20 mg therapy, Tmax was 1 hour, and t1/2 was 18.9 hours. Maximum (89.7%) inhibition in plasma DPP-4 activity was noted within 2 hours and maintained >60% at 24 hours. Compared to the placebo, active plasma GLP-1 concentration was higher throughout the day and even 24 hours after administration of 20 mg of teneligliptin. Metabolism of teneligliptin was majorly mediated through CYP3A4, a cytochrome P450 isozyme, and flavin-containing monooxygenases (FMO1 and FMO3). A weak inhibitory activity of teneligliptin on CYP2D6, CYP3A4, and FMO was noted, while there was no inhibitory activity on CYP1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C8/9, CYP2C19, and CYP2E1. There was no induction of expression of CYP1A2 or CYP3A4. Reported evidence suggests that teneligliptin is metabolized and eliminated via renal and hepatic routes. Approximately 34% of teneligliptin is excreted unchanged via the renal route, while 66% is metabolized and eliminated via the hepatic and renal routes[1].

Side effects

The DPP-4 molecule in teneligliptin reduces the risk of hypoglycemia, although it is possible. These are some of teneligliptin’s major and minor side effects:
Hypoglycemia
Headache
Upper respiratory tract infection
Gastrointestinal symptoms
Constipation
Fatigue
Kidney problems
Nasopharyngitis
Skin rashes
Itching
Loss of appetite
Abdominal pain

References

[1] Surendra Kumar Sharma. “Teneligliptin in management of type 2 diabetes mellitus.” Diabetes, Metabolic Syndrome and Obesity: Targets and Therapy 9 (2016): 251–60.