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

Stem definition	Drug id	CAS RN
peroxisome proliferator activating receptor-gamma (PPAR-gamma) agonists, thiazolidinedione derivatives	2405	122320-73-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: rosiglitazone rosiglitazone maleate rosiglizole rosiglitazone hydrochloride rosiglitazone HCl	A thiazolidinedione that functions as a selective agonist for PPAR GAMMA. It improves INSULIN SENSITIVITY in adipose tissue, skeletal muscle, and the liver of patients with TYPE 2 DIABETES MELLITUS. Molecular weight: 357.43 Formula: C18H19N3O3S CLOGP: 3.02 LIPINSKI: 0 HAC: 6 HDO: 1 TPSA: 71.53 ALOGS: -3.97 ROTB: 7 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

rosiglitazone
rosiglitazone maleate
rosiglizole
rosiglitazone hydrochloride
rosiglitazone HCl

A thiazolidinedione that functions as a selective agonist for PPAR GAMMA. It improves INSULIN SENSITIVITY in adipose tissue, skeletal muscle, and the liver of patients with TYPE 2 DIABETES MELLITUS.

Molecular weight: 357.43
Formula: C18H19N3O3S
CLOGP: 3.02
LIPINSKI: 0
HAC: 6
HDO: 1
TPSA: 71.53
ALOGS: -3.97
ROTB: 7

Status: OFM

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

Drug dosage:

Dose	Unit	Route
6	mg	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	3.90 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ
CL (Clearance)	0.65 mL/min/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.37 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.20 L/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.03 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.00 %	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	0 %	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
May 25, 1999	FDA	SB PHARMCO

FDA Adverse Event Reporting System (Female)

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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
Cardiac failure congestive	17336.53	163.83	4181	14752	88252	63381837
Myocardial infarction	14015.79	163.83	3593	15340	96300	63373789
Coronary artery disease	6318.46	163.83	1535	17398	30842	63439247
Cerebrovascular accident	5932.63	163.83	1890	17043	106134	63363955
Acute myocardial infarction	2860.40	163.83	821	18112	31303	63438786
Coronary arterial stent insertion	1763.87	163.83	350	18583	2479	63467610
Coronary artery bypass	1213.71	163.83	249	18684	2120	63467969
Angina unstable	1028.68	163.83	267	18666	6828	63463261
Myocardial ischaemia	791.41	163.83	248	18685	12611	63457478
Vascular graft	523.64	163.83	104	18829	735	63469354

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FDA Adverse Event Reporting System (Male)

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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
Myocardial infarction	18813.21	279.25	5712	19997	115373	34815849
Cardiac failure congestive	14507.41	279.25	4321	21388	78949	34852273
Coronary artery disease	9256.30	279.25	2719	22990	45586	34885636
Cerebrovascular accident	5437.49	279.25	2102	23607	82709	34848513
Acute myocardial infarction	3595.15	279.25	1379	24330	52340	34878882
Coronary artery bypass	2738.29	279.25	650	25059	4252	34926970
Coronary arterial stent insertion	2666.90	279.25	616	25093	3513	34927709
Angina unstable	1195.32	279.25	412	25297	11241	34919981
Myocardial ischaemia	866.34	279.25	363	25346	17045	34914177
Vascular graft	807.94	279.25	194	25515	1328	34929894

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FDA Adverse Event Reporting System (Geriatric)

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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
Myocardial infarction	30885.07	302.72	8330	28745	175799	79531514
Cardiac failure congestive	28852.58	302.72	7502	29573	134900	79572413
Coronary artery disease	12380.90	302.72	3308	33767	62166	79645147
Cerebrovascular accident	10944.35	302.72	3656	33419	151636	79555677
Acute myocardial infarction	6424.65	302.72	2071	35004	74965	79632348
Coronary arterial stent insertion	4521.18	302.72	937	36138	5107	79702206
Coronary artery bypass	3975.20	302.72	843	36232	5219	79702094
Angina unstable	1940.00	302.72	580	36495	15947	79691366
Vascular graft	1327.20	302.72	282	36793	1749	79705564
Myocardial ischaemia	1303.53	302.72	478	36597	25041	79682272

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A10BD03	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Combinations of oral blood glucose lowering drugs
ATC	A10BD04	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Combinations of oral blood glucose lowering drugs
ATC	A10BG02	ALIMENTARY TRACT AND METABOLISM DRUGS USED IN DIABETES BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS Thiazolidinediones
CHEBI has role	CHEBI:50864	insulin sensitizers
CHEBI has role	CHEBI:83157	EC 6.2.1.3 inhibitors
CHEBI has role	CHEBI:173084	ferroptosis inhibitors
FDA CS	M0199114	PPAR gamma
FDA CS	M0447306	Thiazolidinediones
FDA EPC	N0000180186	Peroxisome Proliferator Receptor gamma Agonist
FDA EPC	N0000180190	Thiazolidinedione

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

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Disease	Relation	SNOMED_ID	DOID
Treatment Refractory Type 2 Diabetes Mellitus	indication
Alcoholism	contraindication	7200002
Weight gain finding	contraindication	8943002
Asthenia	contraindication	13791008
Pulmonary edema	contraindication	19242006	DOID:11396
Myocardial infarction	contraindication	22298006	DOID:5844
Acute vomiting	contraindication	23971007
Alcohol intoxication	contraindication	25702006
Shock	contraindication	27942005
Dehydration	contraindication	34095006

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	6.5	acidic
pKa2	5.84	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Peroxisome proliferator-activated receptor gamma	Nuclear hormone receptor	P37231	PPARG_HUMAN	AGONIST	EC50	7.04	WOMBAT-PK	CHEMBL
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	4.53	CHEMBL
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN		IC50	5.39	DRUG MATRIX
Amine oxidase [flavin-containing] B	Enzyme	P27338	AOFB_HUMAN		Ki	5.38	CHEMBL
Amine oxidase [flavin-containing] A	Enzyme	P21397	AOFA_HUMAN		Ki	4.56	CHEMBL
Peroxisome proliferator-activated receptor alpha	Nuclear hormone receptor	Q07869	PPARA_HUMAN		EC50	7.41	CHEMBL
Retinoic acid receptor RXR-alpha	Nuclear hormone receptor	P19793	RXRA_HUMAN		Kd	4.82	CHEMBL
Retinoic acid receptor gamma	Nuclear hormone receptor	P13631	RARG_HUMAN		Ki	5	CHEMBL
Thromboxane-A synthase	Enzyme	P24557	THAS_HUMAN		IC50	5.45	DRUG MATRIX
Peroxisome proliferator-activated receptor delta	Nuclear hormone receptor	Q03181	PPARD_HUMAN		EC50	5.44	CHEMBL

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External reference:

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ID	Source
BRL	PDB_CHEM_ID
007789	NDDF
007790	NDDF
05V02F2KDG	UNII
1056	IUPHAR_LIGAND_ID
116096001	SNOMEDCT_US
155141-29-0	SECONDARY_CAS_RN
253198	RXNORM
302543-62-0	SECONDARY_CAS_RN
326053005	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
AVANDAMET	HUMAN PRESCRIPTION DRUG LABEL	2	54868-4965	TABLET, FILM COATED	2 mg	ORAL	NDA	30 sections
AVANDAMET	HUMAN PRESCRIPTION DRUG LABEL	2	54868-5157	TABLET, FILM COATED	4 mg	ORAL	NDA	30 sections
AVANDAMET	HUMAN PRESCRIPTION DRUG LABEL	2	54868-5262	TABLET, FILM COATED	4 mg	ORAL	NDA	30 sections
AVANDAMET	HUMAN PRESCRIPTION DRUG LABEL	2	54868-5376	TABLET, FILM COATED	2 mg	ORAL	NDA	30 sections
Avandia	HUMAN PRESCRIPTION DRUG LABEL	1	54868-4198	TABLET, FILM COATED	4 mg	ORAL	NDA	19 sections
Avandia	HUMAN PRESCRIPTION DRUG LABEL	1	54868-4221	TABLET, FILM COATED	8 mg	ORAL	NDA	19 sections
Avandia	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5249	TABLET, FILM COATED	2 mg	ORAL	NDA	19 sections

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