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Tox | Related Drugs | 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:

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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	2.512		High	1
caco2-efflux	Caco-2 efflux ratio (BA/AB)	1.052		High	1
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	59.841	10^-6 cm/s	High	1
dh-clint	Dog hepatocyte intrinsic clearance	9.594	uL/min/10^6 cells	High	1
dppb	Dog plasma protein binding (% unbound)	0.830	%	High	1
fcs-ppb	Fetal calf serum protein binding (% unbound)	1.170	%	High	1
herg	hERG pIC50	4.673	pIC50	High	1
hh-clint	Human hepatocyte intrinsic clearance	12.882	uL/min/10^6 cells	High	1
hlm-clint	Human liver microsomal intrinsic clearance	51.761	uL/min/mg protein	High	1
hppb	Human plasma protein binding (% unbound)	0.300	%	High	1
kinase-safety-class	ACVR2B,EIF2AK3,GRK2,ITK,MAPK7,PDK1,PDK2,PDK4,PRKDC	9
mdck-mdr1-bcrp-efflux	MDCK-MDR1-BCRP efflux ratio	0.698		High	1
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	3.251		High	1
mh-clint	Mouse hepatocyte intrinsic clearance	70.307		High	1
mppb	Mouse plasma protein binding (% unbound)	0.720		High	1
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	12.677		High	1
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pld-class	Phospholipidosis risk class (1 = positive, 0 = negative)	0		High	1
pppb	Pig plasma protein binding (% unbound)	1.120	%	High	1
rat-kpuu-brain	Rat brain Kpuu	0.386	%	High	1
rh-clint	Rat hepatocyte intrinsic clearance	44.668	uL/min/10^6 cells	High	1
rh-fuinc	Rat hepatocyte fraction unbound in incubation	43.080	%	High	1
rppb	Rat plasma protein binding (% unbound)	0.280	%	High	1
solubility-dd	Solubility at pH 7.4 in DMSO	238.781	uM	High	1

Approvals:

Date	Agency	Company	Orphan
May 25, 1999	FDA	SB PHARMCO

FDA Adverse Event Reporting System (Female)

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	18541.88	177.13	4181	14765	94513	90514988
Myocardial infarction	15073.36	177.13	3593	15353	102379	90507122
Coronary artery disease	6803.29	177.13	1535	17411	32088	90577413
Cerebrovascular accident	6344.60	177.13	1890	17056	121643	90487858
Acute myocardial infarction	3082.02	177.13	821	18125	34069	90575432
Coronary arterial stent insertion	1886.59	177.13	350	18596	2490	90607011
Coronary artery bypass	1304.06	177.13	249	18697	2100	90607401
Angina unstable	1121.10	177.13	267	18679	6876	90602625
Myocardial ischaemia	860.81	177.13	248	18698	13566	90595935
Transient ischaemic attack	567.67	177.13	243	18703	42933	90566568
Vascular graft	558.79	177.13	104	18842	749	90608752
Angina pectoris	533.32	177.13	226	18720	38934	90570567
Cardio-respiratory arrest	502.96	177.13	251	18695	62889	90546612
Chest pain	437.13	177.13	428	18518	319217	90290284
Arteriosclerosis	427.55	177.13	137	18809	10716	90598785
Acute coronary syndrome	419.84	177.13	135	18811	10678	90598823
Atrial fibrillation	395.03	177.13	280	18666	133331	90476170
Cardiomyopathy	365.39	177.13	143	18803	20063	90589438
Arteriosclerosis coronary artery	360.99	177.13	117	18829	9486	90600015
Sudden cardiac death	352.87	177.13	84	18862	2148	90607353
Ischaemic cardiomyopathy	339.71	177.13	84	18862	2529	90606972
Cardiac arrest	291.80	177.13	212	18734	104723	90504778
Drug ineffective	258.46	177.13	7	18939	1384291	89225210
Cardiac disorder	258.02	177.13	156	18790	56716	90552785
Off label use	211.58	177.13	4	18942	1102248	89507253
Nausea	188.87	177.13	11	18935	1110305	89499196

FDA Adverse Event Reporting System (Male)

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	19785.73	247.83	5712	20047	118297	42477279
Cardiac failure congestive	15227.55	247.83	4321	21438	81281	42514295
Coronary artery disease	9498.10	247.83	2719	23040	51001	42544575
Cerebrovascular accident	5560.84	247.83	2102	23657	95058	42500518
Acute myocardial infarction	3751.99	247.83	1379	24380	56786	42538790
Coronary artery bypass	2877.51	247.83	650	25109	4160	42591416
Coronary arterial stent insertion	2809.05	247.83	616	25143	3369	42592207
Angina unstable	1281.88	247.83	412	25347	11036	42584540
Myocardial ischaemia	928.25	247.83	363	25396	17399	42578177
Vascular graft	841.55	247.83	194	25565	1362	42594214
Ischaemic cardiomyopathy	669.69	247.83	220	25539	6302	42589274
Angina pectoris	538.34	247.83	301	25458	32595	42562981
Arteriosclerosis coronary artery	484.61	247.83	233	25526	18444	42577132
Transient ischaemic attack	472.59	247.83	279	25480	33460	42562116
Acute coronary syndrome	471.12	247.83	213	25546	14652	42580924
Arteriosclerosis	385.26	247.83	197	25562	17792	42577784
Cardio-respiratory arrest	384.06	247.83	303	25456	58333	42537243
Drug ineffective	366.14	247.83	3	25756	630194	41965382
Off label use	361.90	247.83	5	25754	638330	41957246
Cardiomyopathy	344.93	247.83	187	25572	19023	42576553
Atrial fibrillation	315.13	247.83	404	25355	139189	42456387
Sudden cardiac death	314.66	247.83	110	25649	3814	42591762
Cardiac arrest	264.97	247.83	328	25431	108992	42486584
Cardiac disorder	259.86	247.83	224	25535	48708	42546868
Chest pain	254.19	247.83	364	25395	139166	42456410

FDA Adverse Event Reporting System (Geriatric)

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	33223.78	271.50	8330	28810	183753	110368406
Cardiac failure congestive	30838.86	271.50	7502	29638	143498	110408661
Coronary artery disease	13150.71	271.50	3308	33832	68382	110483777
Cerebrovascular accident	11557.10	271.50	3656	33484	177628	110374531
Acute myocardial infarction	6917.15	271.50	2071	35069	81706	110470453
Coronary arterial stent insertion	4845.33	271.50	937	36203	4978	110547181
Coronary artery bypass	4251.38	271.50	843	36297	5199	110546960
Angina unstable	2129.84	271.50	580	36560	15852	110536307
Myocardial ischaemia	1434.79	271.50	478	36662	26206	110525953
Vascular graft	1405.93	271.50	282	36858	1843	110550316
Angina pectoris	926.60	271.50	441	36699	61854	110490305
Transient ischaemic attack	843.26	271.50	417	36723	63565	110488594
Cardio-respiratory arrest	810.87	271.50	497	36643	115339	110436820
Acute coronary syndrome	739.91	271.50	282	36858	22830	110529329
Arteriosclerosis	685.83	271.50	272	36868	24495	110527664
Chest pain	672.64	271.50	725	36415	375650	110176509
Sudden cardiac death	574.43	271.50	165	36975	5472	110546687
Ischaemic cardiomyopathy	550.39	271.50	173	36967	7838	110544321
Arteriosclerosis coronary artery	513.04	271.50	222	36918	24896	110527263
Off label use	483.87	271.50	4	37136	1500181	109051978
Drug ineffective	477.07	271.50	7	37133	1520533	109031626
Cardiac arrest	467.92	271.50	443	36697	196310	110355849
Atrial fibrillation	440.59	271.50	460	36680	229182	110322977
Cardiomyopathy	439.84	271.50	218	36922	33307	110518852
Nausea	373.75	271.50	9	37131	1235681	109316478
Fatigue	342.62	271.50	16	37124	1215942	109336217
Diarrhoea	338.13	271.50	10	37130	1139495	109412664
Vomiting	285.73	271.50	4	37136	910671	109641488
Pyrexia	277.36	271.50	5	37135	898260	109653899
Cardiac disorder	277.05	271.50	219	36921	76061	110476098

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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
FDA CS	M0447306	Thiazolidinediones
FDA MoA	N0000175377	Peroxisome Proliferator-activated Receptor gamma Agonists
MeSH PA	D007004	Hypoglycemic Agents
FDA EPC	N0000180186	Peroxisome Proliferator Receptor gamma Agonist
FDA EPC	N0000180190	Thiazolidinedione
CHEBI has role	CHEBI:35526	hypoglycemic agent
CHEBI has role	CHEBI:35554	cardiovascular drug
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:50864	insulin-sensitizing drug
CHEBI has role	CHEBI:64946	anti-HIV agent
CHEBI has role	CHEBI:145947	antiatherosclerotic agent
CHEBI has role	CHEBI:35620	vasodilator agent
CHEBI has role	CHEBI:35674	antihypertensive agent
CHEBI has role	CHEBI:35842	antirheumatic drug
CHEBI has role	CHEBI:38068	antimalarial
CHEBI has role	CHEBI:50919	antiemetic
CHEBI has role	CHEBI:65023	anti-asthmatic agent
CHEBI has role	CHEBI:67079	anti-inflammatory agent
CHEBI has role	CHEBI:75835	anti-anaemic agent
CHEBI has role	CHEBI:83157	EC 6.2.1.3 (long-chain-fatty-acid—CoA ligase) inhibitor
CHEBI has role	CHEBI:173084	ferroptosis inhibitor

Related Drugs by ATC class:

A10BD Combinations of oral blood glucose lowering drugs 19 drugs

acarbose alogliptin canagliflozin dapagliflozin empagliflozin ertugliflozin evogliptin gemigliptin glimepiride linagliptin lobeglitazone metformin show all 19 →

A10BG Thiazolidinediones 3 drugs

lobeglitazone pioglitazone troglitazone

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

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
Macular retinal edema	contraindication	37231002	DOID:4449
Infectious disease	contraindication	40733004
Body fluid retention	contraindication	43498006
Chronic heart failure	contraindication	48447003
Hepatic porphyria	contraindication	55056006	DOID:3133
Ketoacidosis	contraindication	56051008
Metabolic acidosis	contraindication	59455009
Hemolytic anemia	contraindication	61261009	DOID:583
Glucose-6-phosphate dehydrogenase deficiency anemia	contraindication	62403005
Osteoporosis	contraindication	64859006	DOID:11476
Hypopituitarism	contraindication	74728003	DOID:9406
Cardiogenic shock	contraindication	89138009
Kidney disease	contraindication	90708001	DOID:557
Lactic acidosis	contraindication	91273001	DOID:3650
Fracture of bone	contraindication	125605004
Autonomic dysreflexia	contraindication	129618003
Liver function tests abnormal	contraindication	166603001
Cobalamin deficiency	contraindication	190634004
Angina pectoris	contraindication	194828000
Decompensated cardiac failure	contraindication	195111005
Cerebrovascular accident	contraindication	230690007
Disease of liver	contraindication	235856003	DOID:409
Drug-induced hepatitis	contraindication	235876009
Hypoglycemic disorder	contraindication	237630007
Sepsis syndrome	contraindication	238150007
Osteopenia	contraindication	312894000
Primary adrenocortical insufficiency	contraindication	373662000
Adrenal cortical hypofunction	contraindication	386584007	DOID:10493
Fever	contraindication	386661006
Surgical procedure	contraindication	387713003
Severe diarrhea	contraindication	409587002
Breastfeeding (mother)	contraindication	413712001
Disorder of coronary artery	contraindication	414024009
Myocardial ischemia	contraindication	414795007	DOID:3393
Traumatic injury	contraindication	417746004
Fever greater than 100.4 Fahrenheit	contraindication	426000000
Radiography with IV Iodinated Contrast Agent	contraindication
Severe Hypoxemia	contraindication

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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:

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
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN		IC50	5.39	DRUG MATRIX
Bile salt export pump	Transporter	O95342	ABCBB_HUMAN		IC50	5.19	CHEMBL
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
Free fatty acid receptor 1	GPCR	O14842	FFAR1_HUMAN	AGONIST	EC50	5.60	IUPHAR
Short transient receptor potential channel 5	Ion channel	Q9UL62	TRPC5_HUMAN	ACTIVATOR	EC50	4.51	IUPHAR
Sodium/bile acid cotransporter	Transporter	Q14973	NTCP_HUMAN		IC50	5.29	CHEMBL
CDGSH iron-sulfur domain-containing protein 1	Membrane other	Q9NZ45	CISD1_HUMAN		Ki	7.51	CHEMBL
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	4.53	CHEMBL
CDGSH iron-sulfur domain-containing protein 2	Membrane other	Q8N5K1	CISD2_HUMAN		IC50	5.64	CHEMBL
Amine oxidase [flavin-containing] B	Enzyme		AOFB_RAT		Ki	5.24	CHEMBL
Amine oxidase [flavin-containing] A	Enzyme		AOFA_RAT		Ki	4.49	CHEMBL
Peroxisome proliferator-activated receptor alpha	Transcription factor		PPARA_MOUSE		IC50	7.10	CHEMBL
Peroxisome proliferator-activated receptor gamma	Transcription factor		PPARG_MOUSE		EC50	7.52	CHEMBL
Type-1A angiotensin II receptor	GPCR		AGTRA_RAT		Ki	9.64	CHEMBL
Bile salt export pump	Transporter		ABCBB_RAT		IC50	4.40	CHEMBL
CDGSH iron-sulfur domain-containing protein 1	Membrane other		CISD1_RAT		IC50	5.96	CHEMBL

External reference:

ID	Source
4021162	VUID
N0000148613	NUI
D00596	KEGG_DRUG
155141-29-0	SECONDARY_CAS_RN
4021162	VANDF
4021163	VANDF
C0289313	UMLSCUI
CHEBI:50122	CHEBI
BRL	PDB_CHEM_ID
CHEMBL121	ChEMBL_ID
CHEMBL843	ChEMBL_ID
DB00412	DRUGBANK_ID
D000077154	MESH_DESCRIPTOR_UI
77999	PUBCHEM_CID
1056	IUPHAR_LIGAND_ID
7662	INN_ID
302543-62-0	SECONDARY_CAS_RN
05V02F2KDG	UNII
253198	RXNORM
8221	MMSL
d04434	MMSL
007789	NDDF
007790	NDDF
116096001	SNOMEDCT_US
326053005	SNOMEDCT_US
395869000	SNOMEDCT_US
05V02F2KDG	INXIGHT DRUGS

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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
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
Avandia	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5249	TABLET, FILM COATED	2 mg	ORAL	NDA	19 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

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rosiglitazone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Description:

Drug dosage:

ADMET properties:

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Approvals:

FDA Adverse Event Reporting System (Female)

FDA Adverse Event Reporting System (Male)

FDA Adverse Event Reporting System (Geriatric)

FDA Adverse Event Reporting System (Pediatric)

Pharmacologic Action:

Related Drugs by ATC class:

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

🐶 Veterinary Drug Use

🐶 Veterinary products

Acid dissociation constants calculated using MoKa v3.0.0

Orange Book patent data (new drug applications)

Orange Book exclusivity data (new drug applications)

Bioactivity Summary:

External reference:

Pharmaceutical products: