Scroll

sitagliptin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
dipeptidyl aminopeptidase-IV inhibitors	2448	486460-32-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: sitagliptin sitagliptin phosphate januvia ristaben sitagliptin phosphate hydrate sitagliptin phosphate monohydrate MK-0431 MK 0431 sitagliptin monophosphate monohydrate sitagliptin phosphate anhydrous sitagliptin hydrochloride monohydrate	A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES. Molecular weight: 407.32 Formula: C16H15F6N5O CLOGP: 0.69 LIPINSKI: 0 HAC: 6 HDO: 1 TPSA: 77.04 ALOGS: -4.08 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

sitagliptin
sitagliptin phosphate
januvia
ristaben
sitagliptin phosphate hydrate
sitagliptin phosphate monohydrate
MK-0431
MK 0431
sitagliptin monophosphate monohydrate
sitagliptin phosphate anhydrous
sitagliptin hydrochloride monohydrate

A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES.

Molecular weight: 407.32
Formula: C16H15F6N5O
CLOGP: 0.69
LIPINSKI: 0
HAC: 6
HDO: 1
TPSA: 77.04
ALOGS: -4.08
ROTB: 5

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.10	g	O

ADMET properties:

Show entries

Search:

Property	Value	Reference
BA (Bioavailability)	87 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	78 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	6 mL/min/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	50 mg/mL	Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	2.80 L/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	12 hours	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.62 %	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.35 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Showing 1 to 9 of 9 entries

Previous1Next

Approvals:

Date	Agency	Company	Orphan
March 20, 2007	EMA	MERCK SHARP DOHME
Oct. 16, 2006	FDA	MERCK SHARP DOHME

FDA Adverse Event Reporting System (Female)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Blood glucose increased	860.04	10.98	699	63910	83057	63341356
Hypoglycaemia	658.18	10.98	521	64088	59544	63364869
Pancreatitis	601.68	10.98	455	64154	48600	63375813
Diabetes mellitus inadequate control	554.00	10.98	282	64327	14844	63409569
Pancreatic carcinoma	444.88	10.98	196	64413	7432	63416981
Carotid artery thrombosis	350.88	10.98	125	64484	2669	63421744
Neurologic neglect syndrome	335.16	10.98	120	64489	2601	63421812
Lactic acidosis	325.55	10.98	287	64322	38000	63386413
Glycosylated haemoglobin increased	313.93	10.98	181	64428	12217	63412196
Personality disorder	302.75	10.98	138	64471	5673	63418740

Showing 1 to 10 of 316 entries

Previous1 2 3 4 5…32Next

FDA Adverse Event Reporting System (Male)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Pancreatitis	634.20	10.95	516	56080	38375	34861960
Hypoglycaemia	552.74	10.95	554	56042	54086	34846249
Blood glucose increased	437.07	10.95	539	56057	66179	34834156
Pancreatic carcinoma	419.17	10.95	229	56367	8672	34891663
Diabetes mellitus inadequate control	401.84	10.95	258	56338	13206	34887129
Pancreatic carcinoma metastatic	338.32	10.95	140	56456	2800	34897535
Glycosylated haemoglobin increased	237.86	10.95	175	56421	11185	34889150
Pancreatitis acute	221.53	10.95	250	56346	27891	34872444
Lactic acidosis	188.37	10.95	256	56340	34516	34865819
Diabetic ketoacidosis	182.30	10.95	183	56413	17849	34882486

Showing 1 to 10 of 275 entries

Previous1 2 3 4 5…28Next

FDA Adverse Event Reporting System (Geriatric)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypoglycaemia	998.04	10.32	885	94342	100709	79548452
Blood glucose increased	893.18	10.32	879	94348	114096	79535065
Diabetes mellitus inadequate control	682.34	10.32	401	94826	23863	79625298
Pancreatitis	650.45	10.32	586	94641	67989	79581172
Lactic acidosis	522.03	10.32	525	94702	69834	79579327
Diabetic ketoacidosis	418.31	10.32	338	94889	33784	79615377
Glycosylated haemoglobin increased	381.76	10.32	255	94972	19005	79630156
Pancreatic carcinoma	364.94	10.32	218	95009	13359	79635802
Pancreatitis acute	322.57	10.32	345	94882	49259	79599902
Carotid artery thrombosis	317.04	10.32	124	95103	2929	79646232

Showing 1 to 10 of 391 entries

Previous1 2 3 4 5…40Next

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Show entries

Search:

Source	Code	Description
ATC	A10BD07	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Combinations of oral blood glucose lowering drugs
ATC	A10BD12	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Combinations of oral blood glucose lowering drugs
ATC	A10BD24	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Combinations of oral blood glucose lowering drugs
ATC	A10BH01	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Dipeptidyl peptidase 4 (DPP-4) inhibitors
ATC	A10BH51	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Dipeptidyl peptidase 4 (DPP-4) inhibitors
CHEBI has role	CHEBI:35526	antidiabetic
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:48353	serine proteinase inhibitors
CHEBI has role	CHEBI:68612	dipeptidyl peptidase-4 inhibitors
CHEBI has role	CHEBI:78298	environmental contaminants

Showing 1 to 10 of 18 entries

Previous1 2Next

Drug Use | Suggest Off label Use Form| |View source of the data|

Show entries

Search:

Disease	Relation	SNOMED_ID	DOID
Diabetes mellitus type 2	indication	44054006	DOID:9352
Alcoholism	contraindication	7200002
Asthenia	contraindication	13791008
Myocardial infarction	contraindication	22298006	DOID:5844
Acute vomiting	contraindication	23971007
Alcohol intoxication	contraindication	25702006
Shock	contraindication	27942005
Dehydration	contraindication	34095006
Infectious disease	contraindication	40733004
Ketoacidosis	contraindication	56051008

Showing 1 to 10 of 30 entries

Previous1 2 3Next

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.1	Basic
pKa2	2.67	Basic

Orange Book patent data (new drug applications)

Show entries

Search:

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
10MG;EQ 100MG BASE Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons	JUVISYNC	MERCK SHARP DOHME	N202343	Oct. 7, 2011	DISCN	TABLET	ORAL	7326708	April 11, 2026	METHOD OF TREATING TYPE 2 DIABETES MELLITUS IN PATIENTS FOR WHOM TREATMENT WITH BOTH SITAGLIPTIN AND SIMVASTATIN IS APPROPRIATE
10MG;EQ 50MG BASE Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons	JUVISYNC	MERCK SHARP DOHME	N202343	Sept. 18, 2012	DISCN	TABLET	ORAL	7326708	April 11, 2026	METHOD OF TREATING TYPE 2 DIABETES MELLITUS IN PATIENTS FOR WHOM TREATMENT WITH BOTH SITAGLIPTIN AND SIMVASTATIN IS APPROPRIATE
15MG;EQ 100MG BASE	STEGLUJAN	MSD SUB MERCK	N209805	Dec. 19, 2017	RX	TABLET	ORAL	7326708	Nov. 24, 2026	AN ADJUNCT TO DIET AND EXERCISE TO IMPROVE GLYCEMIC CONTROL IN ADULTS WITH TYPE 2 DIABETES
15MG;EQ 100MG BASE	STEGLUJAN	MSD SUB MERCK	N209805	Dec. 19, 2017	RX	TABLET	ORAL	8080580	July 13, 2030	AN ADJUNCT TO DIET AND EXERCISE TO IMPROVE GLYCEMIC CONTROL IN ADULTS WITH TYPE 2 DIABETES
15MG;EQ 100MG BASE	STEGLUJAN	MSD SUB MERCK	N209805	Dec. 19, 2017	RX	TABLET	ORAL	9439901	Oct. 21, 2030	AN ADJUNCT TO DIET AND EXERCISE TO IMPROVE GLYCEMIC CONTROL IN ADULTS WITH TYPE 2 DIABETES
1GM;EQ 100MG BASE	JANUMET XR	MERCK SHARP DOHME	N202270	Feb. 2, 2012	RX	TABLET, EXTENDED RELEASE	ORAL	7326708	Nov. 24, 2026	METHOD OF TREATING TYPE 2 DIABETES MELLITUS IN PATIENTS FOR WHOM TREATMENT WITH BOTH SITAGLIPTIN AND METFORMIN HCL EXTENDED RELEASE IS APPROPRIATE
1GM;EQ 50MG BASE	JANUMET	MSD SUB MERCK	N022044	March 30, 2007	RX	TABLET	ORAL	7326708	Nov. 24, 2026	METHOD OF TREATING TYPE 2 DIABETES MELLITUS BY ADMINISTERING A DIPEPTIDYL PEPTIDASE-IV INHIBITOR
1GM;EQ 50MG BASE	JANUMET XR	MERCK SHARP DOHME	N202270	Feb. 2, 2012	RX	TABLET, EXTENDED RELEASE	ORAL	7326708	Nov. 24, 2026	METHOD OF TREATING TYPE 2 DIABETES MELLITUS IN PATIENTS FOR WHOM TREATMENT WITH BOTH SITAGLIPTIN AND METFORMIN HCL EXTENDED RELEASE IS APPROPRIATE
1GM;EQ 50MG BASE	JANUMET	MSD SUB MERCK	N022044	March 30, 2007	RX	TABLET	ORAL	8414921	July 21, 2028	METHOD OF TREATING TYPE 2 DIABETES MELLITUS BY ADMINISTERING A DIPEPTIDYL PEPTIDASE-4 INHIBITOR IN COMBINATION WITH INSULIN
20MG;EQ 100MG BASE Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons	JUVISYNC	MERCK SHARP DOHME	N202343	Oct. 7, 2011	DISCN	TABLET	ORAL	7326708	April 11, 2026	METHOD OF TREATING TYPE 2 DIABETES MELLITUS IN PATIENTS FOR WHOM TREATMENT WITH BOTH SITAGLIPTIN AND SIMVASTATIN IS APPROPRIATE

Showing 1 to 10 of 22 entries

Previous1 2 3Next

Orange Book exclusivity data (new drug applications)

Show entries

Search:

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
15MG;EQ 100MG BASE	STEGLUJAN	MSD SUB MERCK	N209805	Dec. 19, 2017	RX	TABLET	ORAL	Sept. 17, 2024	REVISION TO THE LABELING TO INCLUDE RESULTS FROM CLINICAL STUDY, MK-8835-004/B1521021, VERTIS CV
1GM;EQ 100MG BASE	JANUMET XR	MERCK SHARP DOHME	N202270	Feb. 2, 2012	RX	TABLET, EXTENDED RELEASE	ORAL	Feb. 12, 2023	PEDIATRIC EXCLUSIVITY
1GM;EQ 50MG BASE	JANUMET	MSD SUB MERCK	N022044	March 30, 2007	RX	TABLET	ORAL	Feb. 12, 2023	PEDIATRIC EXCLUSIVITY
1GM;EQ 50MG BASE	JANUMET XR	MERCK SHARP DOHME	N202270	Feb. 2, 2012	RX	TABLET, EXTENDED RELEASE	ORAL	Feb. 12, 2023	PEDIATRIC EXCLUSIVITY
1GM;EQ 50MG BASE	JANUMET	MSD SUB MERCK	N022044	March 30, 2007	RX	TABLET	ORAL	Dec. 4, 2023	ADDITION OF CLINICAL INFORMATION OBTAINED FROM A PEDIATRIC TRIAL TO SECTION 8.4 OF THE LABELING
1GM;EQ 50MG BASE	JANUMET XR	MERCK SHARP DOHME	N202270	Feb. 2, 2012	RX	TABLET, EXTENDED RELEASE	ORAL	Dec. 4, 2023	ADDITION OF CLINICAL INFORMATION OBTAINED FROM A PEDIATRIC TRIAL TO SECTION 8.4 OF THE LABELING
1GM;EQ 50MG BASE	JANUMET	MSD SUB MERCK	N022044	March 30, 2007	RX	TABLET	ORAL	June 4, 2024	PEDIATRIC EXCLUSIVITY
1GM;EQ 50MG BASE	JANUMET XR	MERCK SHARP DOHME	N202270	Feb. 2, 2012	RX	TABLET, EXTENDED RELEASE	ORAL	June 4, 2024	PEDIATRIC EXCLUSIVITY
500MG;EQ 50MG BASE	JANUMET	MSD SUB MERCK	N022044	March 30, 2007	RX	TABLET	ORAL	Feb. 12, 2023	PEDIATRIC EXCLUSIVITY
500MG;EQ 50MG BASE	JANUMET XR	MERCK SHARP DOHME	N202270	Feb. 2, 2012	RX	TABLET, EXTENDED RELEASE	ORAL	Feb. 12, 2023	PEDIATRIC EXCLUSIVITY

Showing 1 to 10 of 24 entries

Previous1 2 3Next

Bioactivity Summary:

Show entries

Search:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Dipeptidyl peptidase 4	Enzyme	P27487	DPP4_HUMAN	INHIBITOR	Ki	7.77	WOMBAT-PK	CHEMBL
Angiotensin-converting enzyme	Enzyme	P12821	ACE_HUMAN		IC50	4.96	CHEMBL
Prolyl endopeptidase FAP	Enzyme	Q12884	SEPR_HUMAN		IC50	5.23	CHEMBL
Dipeptidyl peptidase 8	Enzyme	Q6V1X1	DPP8_HUMAN		IC50	4.96	CHEMBL
Dipeptidyl peptidase 9	Enzyme	Q86TI2	DPP9_HUMAN		IC50	4.70	CHEMBL
Dipeptidyl peptidase 2	Enzyme	Q9UHL4	DPP2_HUMAN		IC50	4.22	CHEMBL
Dipeptidyl peptidase 4	Enzyme		DPP4_MOUSE		IC50	7.16	CHEMBL
Dipeptidyl peptidase 4	Enzyme		DPP4_RAT		IC50	7.48	CHEMBL
Dipeptidyl peptidase IV	Unclassified		O31048_PORGN		IC50	4.75	CHEMBL

Showing 1 to 9 of 9 entries

Previous1Next

External reference:

Show entries

Search:

ID	Source
715	PDB_CHEM_ID
011790	NDDF
011791	NDDF
22317	MMSL
23649	MMSL
4025780	VUID
4025780	VANDF
4025781	VANDF
423307000	SNOMEDCT_US
424106006	SNOMEDCT_US

Showing 1 to 10 of 30 entries

Previous1 2 3Next

Pharmaceutical products:

Show entries

Search:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
JANUMET	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0575	TABLET, FILM COATED	50 mg	ORAL	NDA	29 sections
JANUMET	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0575	TABLET, FILM COATED	50 mg	ORAL	NDA	29 sections
JANUMET	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0575	TABLET, FILM COATED	50 mg	ORAL	NDA	29 sections
JANUMET	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0577	TABLET, FILM COATED	50 mg	ORAL	NDA	29 sections
JANUMET	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0577	TABLET, FILM COATED	50 mg	ORAL	NDA	29 sections
JANUMET	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0577	TABLET, FILM COATED	50 mg	ORAL	NDA	29 sections
JANUMET XR	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0078	TABLET, FILM COATED, EXTENDED RELEASE	50 mg	ORAL	NDA	30 sections
JANUMET XR	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0078	TABLET, FILM COATED, EXTENDED RELEASE	50 mg	ORAL	NDA	30 sections
JANUMET XR	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0078	TABLET, FILM COATED, EXTENDED RELEASE	50 mg	ORAL	NDA	30 sections
JANUMET XR	HUMAN PRESCRIPTION DRUG LABEL	2	0006-0080	TABLET, FILM COATED, EXTENDED RELEASE	50 mg	ORAL	NDA	30 sections

Showing 1 to 10 of 30 entries

Previous1 2 3Next