TENELIGLIPTIN HYDROBROMIDE ANHYDROUS

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C22H30N6OS.5BrH
Molecular Weight	1257.716
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TENELIGLIPTIN HYDROBROMIDE ANHYDROUS

SMILES

Br.Br.Br.Br.Br.CC1=NN(C(=C1)N2CCN(CC2)[C@@H]3CN[C@@H](C3)C(=O)N4CCSC4)C5=CC=CC=C5.CC6=NN(C(=C6)N7CCN(CC7)[C@@H]8CN[C@@H](C8)C(=O)N9CCSC9)C%10=CC=CC=C%10

InChI

InChIKey=LUXIOMHUGCXFIU-MAYGPZJUSA-N

InChI=1S/2C22H30N6OS.5BrH/c2*1-17-13-21(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*2-6,13,19-20,23H,7-12,14-16H2,1H3;5*1H/t2*19-,20-;;;;;/m00...../s1

HIDE SMILES / InChI

Molecular Formula	C22H30N6OS
Molecular Weight	426.578
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count	MOL RATIO 5 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Teneligliptin is a DPP IV inhibitor which was developed by Mitsubishi Tanabe Pharma and now is used for the treatment of type 2 diabetes mellitus in Asia under the name Tenelia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dipeptidyl peptidase IV 37	Inhibitor 8,504		0.889 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262	Primary		Approved 8,583	TENELIA

C_max

Value	Dose	Analyte	Population
236.2 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
187.5 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
13.9 ng/mL	2.5 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
77.22 ng/mL	10 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
187.2 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
382.4 ng/mL	40 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
955.77 ng/mL	80 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2107.83 ng/mL	160 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
420.67 ng/mL	40 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
160.6 ng/mL	20 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
220.14 ng/mL	20 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
926.73 ng/mL	80 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
1180.9 ng/mL	80 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
176.5 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
208 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
203.6 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
191.6 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
195.8 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
219 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
164.5 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
185.9 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
229.3 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
247.6 ng/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1861.1 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
1814.6 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
298 ng × h/mL	2.5 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
876.9 ng × h/mL	10 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2028.9 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
3705.1 ng × h/mL	40 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
7649.7 ng × h/mL	80 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
18180.6 ng × h/mL	160 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
3613.5 ng × h/mL	40 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
1057.2 ng × h/mL	20 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
1514.6 ng × h/mL	20 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
5257.7 ng × h/mL	80 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
7292.2 ng × h/mL	80 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
1772.7 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2234.2 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
3090.3 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2833.3 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
1843.1 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2472.9 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2162.5 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
1548.8 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2207.9 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
2418.9 ng × h/mL	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
27.8 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
28.3 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
31.4 h	2.5 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
25.7 h	10 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
24.2 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
20.8 h	40 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
24.8 h	80 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
23.5 h	160 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
27.5 h	40 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
25.8 h	20 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
30.2 h	20 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
17.6 h	80 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
23.7 h	80 mg 1 times / day multiple, oral	TENELIGLIPTIN plasma	Homo sapiens
26.1 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
27.7 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
36 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
29.8 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
18.3 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
23.6 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
22.7 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
24.8 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
27.9 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens
30.9 h	20 mg single, oral	TENELIGLIPTIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
17.8%			TENELIGLIPTIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
40 mg 1 times / day multiple, oral Recommended	healthy, ADULT	Disc. AE: Vomiting...

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AEs

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AE	Significance	Dose	Population
Vomiting	grade 3, 5% Disc. AE	40 mg 1 times / day multiple, oral Recommended	healthy, ADULT

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PubMed

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Title	Date	PubMed
Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine): a highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes.	2012 Oct 1	22959556
Teneligliptin: a DPP-4 inhibitor for the treatment of type 2 diabetes.	2013	23671395
Efficacy and safety of teneligliptin in combination with pioglitazone in Japanese patients with type 2 diabetes mellitus.	2013 Nov 27	24843712
Efficacy, safety and dose-response relationship of teneligliptin, a dipeptidyl peptidase-4 inhibitor, in Japanese patients with type 2 diabetes mellitus.	2013 Sep	23464664
Teneligliptin improves glycemic control with the reduction of postprandial insulin requirement in Japanese diabetic patients.	2015	25252844

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Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage is 20 mg of teneligliptin administered orally once daily. If efficacy is insufficient, the dose may be increased up to 40 mg once daily while closely monitoring the clinical course.

Route of Administration: Oral

In Vitro Use Guide

Human umbilical vein endothelial cells were cultured under normal (5 mmol/L) or high glucose level (25 mmol/L) during 21 days, or at high glucose during 14 days followed by 7 days at normal glucose, to reproduce the high-metabolic memory state. At this time, different concentrations of teneligliptin (0.1, 1.0 and 3.0 umol/L) were added to cells. Teneligliptin was shown to protect human umbilical vein endothelial cells from oxidative stress.

Substance Class	Chemical
Record UNII	556RZT8JPF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TENELIGLIPTIN HYDROBROMIDE ANHYDROUS

Common Name

English

METHANONE, ((2S,4S)-4-(4-(3-METHYL-1-PHENYL-1H-PYRAZOL-5-YL)-1-PIPERAZINYL)-2-PYRROLIDINYL)-3-THIAZOLIDINYL-, HYDROBROMIDE (2:5)

Preferred Name

English

Teneligliptin hydrobromide [WHO-DD]

Common Name

English

TENELIGLIPTIN HYDROBROMIDE HYDRATE [JAN]

Common Name

English

TENELIGLIPTIN HYDROBROMIDE [JAN]

Common Name

English

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Code System

Code

Type

Description

CAS

906093-29-6

PRIMARY

FDA UNII

556RZT8JPF

PRIMARY

PUBCHEM

11996485

PRIMARY

EPA CompTox

DTXSID90238219

PRIMARY

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					15S4OCS6SS

Teneligliptin hydrobromide hydrate

SOLVATE->ANHYDROUS

Amount:


					28ZHI4CF9C

Teneligliptin

PARENT -> SALT/SOLVATE

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					28ZHI4CF9C

Teneligliptin

ACTIVE MOIETY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound