Glimepiride

Details

• Internal ID: 1c676383-3216-4ad3-960d-b5c7f8f95d86
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzenesulfonamides
• IUPAC Name: 4-ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide
• SMILES (Canonical): CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
• SMILES (Isomeric): CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
• InChI: InChI=1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)
• InChI Key: WIGIZIANZCJQQY-UHFFFAOYSA-N
• Popularity: 4,253 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄N₄O₅S
• Molecular Weight: 490.60 g/mol
• Exact Mass: 490.22499137 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-(2-(4-(((((trans-4-methylcyclohexyl)amino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo-
• RefChem:439179
• 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-2-4-(trans-4-methylcyclohexyl)aminocarbonylaminosulfonylphenylethyl-2-oxo-
• glimepiride
• 93479-97-1
• Amaryl
• cis-Glimepiride
• 684286-46-2
• Glimepirida
• Glimepirid
• Glimepiridum
• Amarel
• Endial
• Glimepride
• Hoe-490
• HOE 490
• Glimepiride Impurity A
• Glimepiride, cis-
• 4-ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide
• CHEBI:5383
• MFCD00878417
• 1-((p-(2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl)phenyl)sulfonyl)-3-(trans-4-methylcyclohexyl)urea
• 261361-60-8
• NSC-759809
• 24T6XIR2MZ
• DTXSID5040675
• 6KY687524K
• NCGC00016960-03
• Glimepiridum [Latin]
• Glimepirida [Spanish]
• CAS-93479-97-1
• Glista OD
• 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-(2-(4-(((((4-methylcyclohexyl)amino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo-, trans-
• 3-Ethyl-4-methyl-N-(4-(N-((rel-(1r,4r)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
• 3-ethyl-4-methyl-N-[2-(4-{[(trans-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
• Ristomycin Monosulfate (90%)
• DTXCID3020675
• Glymepirid
• Glorion
• Glemax
• Glimer
• Roname
• Solosa
• Ristocetin Sulfate; Ristomycin Sulfate
• 1-[[4-[2-[[(3-Ethyl-4-methyl-2-oxo-2,3-dihydro-1H-pyrrol-1-yl)carbonyl]amino]ethyl]phenyl]sulphonyl]-3-(cis-4-methylcyclohexyl)urea (cis-Glimepiride)
• 3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide
• 3-ethyl-4-methyl-N-{2-[4-({[(4-methylcyclohexyl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
• SMR000466368
• SL-NH2 Trifluoroacetic Acid Salt (1:2)
• Amaryl (TN)
• CCRIS 7083
• SR-05000001508
• UNII-24T6XIR2MZ
• boxamide
• BRN 5365754
• gimepiride
• Niddaryl
• Sugral
• HOE490
• UNII-6KY687524K
• 1-[[P-[2-(3-ETHYL-4-METHYL-2-OXO-3-PYRROLINE-1-CARBOXAMIDO)ETHYL]PHENYL]SULFONYL]-3-(TRANS-4-METHYLCYCLOHEXYL)UREA
• Glimepiride [USAN:USP:INN:BAN]
• Glimepiride; 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl] 2-oxo-1H-pyrrole-1-carboxamide; Amaryl; Glimperide; HOE 490; trans-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl] 2-oxo-1H-pyrrole-1-carboxamide
• Amaryl, Glista OD
• Glimepiride (Standard)
• CPD000466368
• GLIMEPIRIDE [MI]
• Prestwick0_000651
• Prestwick1_000651
• Prestwick2_000651
• Prestwick3_000651
• GLIMEPIRIDE [INN]
• GLIMEPIRIDE [JAN]
• GLIMEPIRIDE [USAN]
• GLIMEPIRIDE [VANDF]
• CHEMBL1481
• GLIMEPIRIDE [MART.]
• Oprea1_382896
• SCHEMBL16084
• SCHEMBL16086
• BSPBio_000681
• GLIMEPIRIDE [USP-RS]
• GLIMEPIRIDE [WHO-DD]
• GLIMEPIRIDE CIS-ISOMER
• MLS000759495
• MLS001076674
• MLS001401419
• MLS003915622
• MLS006011260
• SPBio_002602
• GLIMEPIRIDE [EMA EPAR]
• BPBio1_000751
• CHEMBL149223
• GTPL6820
• orb1310911
• Glimepiride (JP18/USP/INN)
• Glimepiride - Bio-X trade mark
• SCHEMBL14965363
• CHEBI:92609
• HY-B0104R
• DTXSID20861130
• GLIMEPIRIDE [ORANGE BOOK]
• MSK7192
• Glimepiride for system suitability
• GLIMEPIRIDE [EP MONOGRAPH]
• GLIMEPIRIDE [USP IMPURITY]
• GLXC-06551
• HMS1570C03
• HMS2052L03
• HMS2090K18
• HMS2097C03
• HMS2235L07
• HMS3269A09
• HMS3372O07
• HMS3394L03
• HMS3413K06
• HMS3654F17
• HMS3677K06
• HMS3714C03
• HMS5079H13
• Pharmakon1600-01504915
• GLIMEPIRIDE [USP MONOGRAPH]
• MSK7192-100AM
• BCP05331
• DRB80990
• DUETACT COMPONENT GLIMEPIRIDE
• HY-B0104
• MSK7192-1000AM
• Tox21_110713
• AC-476
• BDBM50237590
• NSC759809
• NSC813217
• s1344
• STL451059
• STL453194
• AKOS015894919
• AKOS015969663
• Glimepiride, >=98% (HPLC), solid
• Tox21_110713_1
• AB07644
• BCP9000728
• CCG-101156
• CS-1844
• DB00222
• FG23667
• FG23668
• KS-5238
• NC00406
• NSC 759809
• NSC-813217
• NCGC00016960-01
• NCGC00016960-02
• NCGC00016960-04
• NCGC00016960-05
• NCGC00016960-07
• NCGC00161404-01
• NCGC00161404-02
• NCGC00181757-01
• NCGC00371061-02
• NCGC00371061-06
• 1-{[4-(2-{[(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)carbonyl]amino}ethyl)phenyl]sulfonyl}-3-(trans-4-methylcyclohexyl)urea
• 1H-Pyrrole-1-carboxamide, 2,5-dihydro-3-ethyl-4-methyl-N-(2-(4-(((((4-methylcyclohexyl)amino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo-, trans-
• 3-ethyl-4-methyl-n-(4-(n-((1r,4r)-4-methylcyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro
• BG164507
• SMR001550123
• Glimepiride 100 microg/mL in Acetonitrile
• AB00513874
• CS-0165191
• G0395
• GLIMEPIRIDE IMPURITY A [EP IMPURITY]
• NS00004860
• SW196369-4
• C07669
• D00593
• H36404
• AB00513874-06
• AB00513874-08
• AB00513874-09
• AB00513874_10
• AB00513874_11
• 479G971
• EN300-19873446
• Q425027
• SR-05000001508-1
• SR-05000001508-2
• SR-05000001508-3
• BRD-K34776109-001-03-4
• BRD-K34776109-001-14-1
• BRD-K34776109-001-15-8
• BRD-K34776109-001-16-6
• BRD-K42693031-001-01-8
• Q27253874
• Glimepiride Solution in Acetonitrile/Methanol, 100ug/mL
• Z1501475009
• Glimepiride Solution in Acetonitrile/Methanol, 1000ug/mL
• Glimepiride, British Pharmacopoeia (BP) Reference Standard
• Glimepiride, European Pharmacopoeia (EP) Reference Standard
• Glimepiride, United States Pharmacopeia (USP) Reference Standard
• Glimepiride for system suitability, European Pharmacopoeia (EP) Reference Standard
• 1-((4-(2-(((3-ETHYL-4-METHYL-2-OXO-2,3-DIHYDRO-1H-PYRROL-1-YL)CARBONYL)AMINO)ETHYL)PHENYL)SULFONYL)-3-(CIS-4-METHYLCYCLOHEXYL)UREA
• 1H-PYRROLE-1-CARBOXAMIDE, 3-ETHYL-2,5-DIHYDRO-4-METHYL-N-(2-(4-(((((CIS-4-METHYLCYCLOHEXYL)AMINO)CARBONYL)AMINO)SULFONYL)PHENYL)ETHYL)-2-OXO-
• 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans- 4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-
• 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide
• 3-ethyl-4-methyl-N-(4-(N-(((1r,4r)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
• 3-ethyl-4-methyl-N-(4-(N-(((1s,4s)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide? (Glimepiride Impurity pound(c)
• 3-Ethyl-4-methyl-N-(4-[N-((1r,4r)-4-methylcyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
• 3-ethyl-4-methyl-N-[2-(4-{[(4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
• 3-ethyl-4-methyl-N-[2-(4-{[(cis-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-car
• 3-ethyl-4-methyl-N-[2-(4-{[(cis-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-car boxamide
• 3-Ethyl-4-Methyl-N-[2-(4-{[(Cis-4-Methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-Oxo-2,5-Dihydro-1h-Pyrrole-1-Carboxamide
• cis-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(cis-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1- carboxamide
• N'-{[4-(2-{[(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)carbonyl]amino}ethyl)phenyl]sulfonyl}-N-(4-methylcyclohexyl)carbamimidic acid
• N-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-N'-4-methylcyclohexylurea
• trans-1-(4-(2-(3-ethyl-4-Me-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamido)ethyl)phenylsulfonyl)-3-(4-methylcyclohexyl)urea
• trans-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(4-methyl cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide
• Trans-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide
• trans-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole -1-carboxyamide;1-[[p-[2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenyl]sulfonyl]-3-(trans-4-methylcycloh
• trans-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole -1-carboxyamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	-	0.8122	81.22%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.9429	94.29%
Subcellular localzation	Lysosomes	0.3411	34.11%
OATP2B1 inhibitior	-	0.8332	83.32%
OATP1B1 inhibitior	+	0.9013	90.13%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9072	90.72%
P-glycoprotein inhibitior	+	0.7743	77.43%
P-glycoprotein substrate	+	0.7378	73.78%
CYP3A4 substrate	-	0.5594	55.94%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8985	89.85%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8599	85.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6700	67.00%
Carcinogenicity (trinary)	Non-required	0.6159	61.59%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9641	96.41%
Skin irritation	-	0.7437	74.37%
Skin corrosion	-	0.9183	91.83%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7091	70.91%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	-	0.8360	83.60%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.6061	60.61%
Estrogen receptor binding	-	0.6113	61.13%
Androgen receptor binding	+	0.5739	57.39%
Thyroid receptor binding	-	0.5270	52.70%
Glucocorticoid receptor binding	-	0.6514	65.14%
Aromatase binding	-	0.5548	55.48%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.9001	90.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3397	P11712	Cytochrome P450 2C9	316.2 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.63%	98.95%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	97.50%	95.34%
CHEMBL4072	P07858	Cathepsin B	97.14%	93.67%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.99%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.76%	95.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	91.92%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	91.21%	94.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.18%	96.38%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.63%	91.24%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.44%	93.03%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	88.17%	95.52%
CHEMBL255	P29275	Adenosine A2b receptor	87.68%	98.59%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.61%	94.45%
CHEMBL3437	Q16853	Amine oxidase, copper containing	87.14%	94.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.17%	91.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.99%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	83.91%	95.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.51%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.61%	89.00%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	82.16%	89.33%
CHEMBL221	P23219	Cyclooxygenase-1	80.65%	90.17%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	80.45%	81.88%

Plants that contains it

• Brassica juncea
• Capsicum annuum
• Changium smyrnioides
• Eleutherococcus senticosus
• Salvia miltiorrhiza
• Sinapis alba
• Terminalia chebula
• Viscum album
• Viscum coloratum
• Zingiber officinale

Cross-Links

• PubChem: 3476
• NPASS: NPC194857
• ChEMBL: CHEMBL149223