TRELAGLIPTIN

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H20FN5O2
Molecular Weight	357.3821
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(=O)C=C(N2CCC[C@@H](N)C2)N(CC3=CC(F)=CC=C3C#N)C1=O

InChI

InChIKey=IWYJYHUNXVAVAA-OAHLLOKOSA-N

InChI=1S/C18H20FN5O2/c1-22-17(25)8-16(23-6-2-3-15(21)11-23)24(18(22)26)10-13-7-14(19)5-4-12(13)9-20/h4-5,7-8,15H,2-3,6,10-11,21H2,1H3/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H20FN5O2
Molecular Weight	357.3821
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27181699
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24622716 | https://www.ncbi.nlm.nih.gov/pubmed/21186796 | https://www.takeda.com/news/2015/20150528_6997.html

Trelagliptin (SYR-472), a novel dipeptidyl peptidase-4 inhibitor used for the treatment of type 2 diabetes mellitus. Trelagliptin (as the salt Trelagliptin succinate) was approved for use in Japan in March 2015. Takeda, the company that developed Trelagliptin, chose to not get approval for the drug in the USA and EU.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dipeptidyl peptidase 4 8 Target ID: P27487 Gene ID: 1803.0 Gene Symbol: DPP4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24622716	Inhibitor 8504		4.0 nM [IC50]
Dipeptidyl peptidase IV 37 Target ID: CHEMBL284 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21186796	Inhibitor 8504		4.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://clinicaltrials.gov/ct2/show/NCT03014479	Primary		Approved 8583	Zafatek Approved Use Unknown Launch Date 2015

C_max

Value	Dose	Analyte	Population
619.4 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
25.3 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	6.25 mg single, oral dose: 6.25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
129.8 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3334.9 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
7108.3 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
541.4 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
602.63 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1388.63 ng/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
6431.4 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
466.5 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	6.25 mg single, oral dose: 6.25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1490.9 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
25046.6 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
49416.5 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6365.2 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5292.95 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
10094.86 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
54.3 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
43.2 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	6.25 mg single, oral dose: 6.25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
50.4 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
46.1 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
39 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
60 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
35.12 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
32.51 h OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Analyte	Population
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	6.25 mg single, oral dose: 6.25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
75.15% OTHER GOV'T https://www.pmda.go.jp/files/000213963.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TRELAGLIPTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27328054/ https://pubmed.ncbi.nlm.nih.gov/24622716/ http://ndi.fda.moph.go.th/uploads/drug_detail_corporation/doc/word/805/1330e56852e1efc924102c4c3eaad4a4-a1.pdf	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27328054/ https://pubmed.ncbi.nlm.nih.gov/24622716/ http://ndi.fda.moph.go.th/uploads/drug_detail_corporation/doc/word/805/1330e56852e1efc924102c4c3eaad4a4-a1.pdf	Sources: https://pubmed.ncbi.nlm.nih.gov/27328054/ https://pubmed.ncbi.nlm.nih.gov/24622716/ http://ndi.fda.moph.go.th/uploads/drug_detail_corporation/doc/word/805/1330e56852e1efc924102c4c3eaad4a4-a1.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087 substrate 1946	substrate 1193 inhibitor 2438	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 P-gp 1741 CYP1A2 2153 CYP2C8 1057 BCRP 910 OATP1B1 1079 CYP2C19 2057 CYP2B6 926 OAT1 725 OAT3 747 OCT2 779	CYP2C19 1119 CYP2B6 776 CYP1A2 1197 P-gp 2052 CYP2C8 810	CYP2B6 669 CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 69.0	no [IC50 >100 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 69.0	no [IC50 >100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 69.0	no [IC50 >100 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 69.0	no [IC50 >100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 69.0	no [IC50 >100 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 69.0	no [IC50 >100 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 69.0	no [IC50 >100 uM]
BCRP 985	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 74.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_A100_1.pdf Page: 28.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_A100_1.pdf Page: 28.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_A100_1.pdf Page: 28.0	no
OAT1 730	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 74.0	no
OAT3 749	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 74.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 74.0	no
OATP1B3 970	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 74.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_K100_1.pdf Page: 26.0	weak
OCT2 782	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 74.0	yes [IC50 55.9 uM]

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 67.0	major
CYP2D6 1388	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 67.0	minor
CYP1A2 1197	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 67.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 67.0	no
CYP2B6 776	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 67.0	weak
CYP2C19 1119	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 67.0	weak
CYP2C8 810	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_I100_1.pdf Page: 67.0	weak
P-gp 2052	substrate 4014 Sources: https://www.pmda.go.jp/drugs/2015/P201500001/400256000_22700AMX00642_A100_1.pdf Page: 27.0	weak

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTY1MDQ0MyJ9fQ==

PubMed

Title	Date	PubMed
Trelagliptin (SYR-472, Zafatek), Novel Once-Weekly Treatment for Type 2 Diabetes, Inhibits Dipeptidyl Peptidase-4 (DPP-4) via a Non-Covalent Mechanism.	2016	27328054

Patents

Sample Use Guides

In Vivo Use Guide

Usually, for adults, 100 mg of trelagliptin is orally administered once a week

Route of Administration: Oral

In Vitro Use Guide

Trelagliptin (1 M) were incubated 0, 5, 15, 30 minute at 37 °C in phosphate buffer (50 mM, pH 7.4) containing rat or human liver microsomes (1 mg/mL protein) and NADPH (4 mM). Metabolic stability of Trelagliptin was assayed by LC/MS

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:56:48 GMT 2025` Edited by `admin` on `Mon Mar 31 20:56:48 GMT 2025`
Record UNII	Q836OWG55H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRELAGLIPTIN

Official Name

English

TRELAGLIPTIN [USAN]

Preferred Name

English

BENZONITRILE, 2-((6-((3R)-3-AMINO-1-PIPERIDINYL)-3,4-DIHYDRO-3-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL)METHYL)-4-FLUORO-

Systematic Name

English

trelagliptin [INN]

Common Name

English

2-({6-[(3R)-3-Aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl}methyl)-4-fluorobenzonitrile

Systematic Name

English

Trelagliptin [WHO-DD]

Common Name

English

TRELAGLIPTIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98086