Repaglinide

Details

• Internal ID: ec2bfcf8-d14e-411a-9c7f-9db29cfd0cca
• Taxonomy: Organoheterocyclic compounds > Piperidines > Phenylpiperidines
• IUPAC Name: 2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
• InChI: InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1
• InChI Key: FAEKWTJYAYMJKF-QHCPKHFHSA-N
• Popularity: 2,571 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆N₂O₄
• Molecular Weight: 452.60 g/mol
• Exact Mass: 452.26750763 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.22
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

• 135062-02-1
• Prandin
• GlucoNorm
• Repaglinida
• AG-EE 623 ZW
• Repaglinidum
• AG-EE 388 ZW
• AGEE-623ZW
• AG-EE-623ZW
• NSC-759893
• AG-EE-623-ZW
• 2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
• DTXSID3023552
• A10BX02
• 668Z8C33LU
• 2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid
• DTXCID603552
• (+)-2-Ethoxy-alpha-(((S)-alpha-isobutyl-o-piperidinobenzyl)carbamoyl)-p-toluic acid
• Benzoic acid, 2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-, (S)-
• enyglid
• repa-glinide
• 2-ethoxy-4-(2-{[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino}-2-oxoethyl)benzoic acid
• AG-EE 388
• 2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid
• (+)-repaglinide
• 2-ethoxy-4-((((1S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)carbamoyl)methyl)benzoic acid
• 2-ethoxy-4-(2-(((1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl)amino)-2-oxoethyl)benzoic acid
• RefChem:56406
• 2-ethoxy-N-(alpha-(2-methyl-1-propyl)-2-piperidinobenzyl)-4-carbamoylmethylbenzoic acid
• (S)-2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)-phenyl)butyl)amino)-2-oxoethyl)-benzoic acid
• 629-921-1
• Benzoic Acid, 2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-,(S)-
• 2-ethoxy-4-(2-(((1R)-3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid
• repaglinide impurity E
• NovoNorm
• (S)-2-Ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid
• Repaglinidum [INN-Latin]
• Repaglinida [INN-Spanish]
• C27H36N2O4
• MFCD00906179
• AG-EE 623ZW
• CHEMBL1272
• (S)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid
• (S)-2-ethoxy-4-(2-(3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzoic acid
• NCGC00016978-01
• Repaglinide [USAN]
• CAS-135062-02-1
• 2-ethoxy-4-[2-({(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl}amino)-2-oxoethyl]benzoic acid
• Actulin
• Surepost
• (-)-Repaglinide
• Reglin
• (S)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid
• SMR000466305
• Prandin (TN)
• (S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid
• Repaglinide (JAN/USP/INN)
• UNII-668Z8C33LU
• AG-EE-623 ZW
• Novonorm;
• Repaglinide CRS
• AG-EE-388
• SMP-508
• Surepost (TN)
• (S)-2-Ethoxy-4-[2-[[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid;AG-EE-623;Novonorm
• BJX
• Repaglinide [USAN:USP:INN:BAN]
• NN-623
• Repaglinide (Standard)
• 111GE012
• REPAGLINIDE [MI]
• Prestwick0_001046
• Prestwick1_001046
• Prestwick2_001046
• Prestwick3_001046
• REPAGLINIDE [INN]
• REPAGLINIDE [JAN]
• REPAGLINIDE [VANDF]
• (S)-2-Ethoxy-4-(2-((methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-benzoic acid
• REPAGLINIDE [MART.]
• SCHEMBL16137
• BSPBio_000972
• REPAGLINIDE [USP-RS]
• REPAGLINIDE [WHO-DD]
• MLS000759407
• MLS001076684
• MLS001424111
• MLS006011560
• BIDD:GT0338
• SPBio_002906
• REPAGLINIDE [EMA EPAR]
• BPBio1_001070
• CHEBI:8805
• GTPL6841
• orb1309813
• Repaglinide - Bio-X trade mark
• SCHEMBL29373506
• SCHEMBL29392295
• MSK7195
• REPAGLINIDE [ORANGE BOOK]
• Repaglinide for system suitability
• GLXC-05202
• HMS1571A14
• HMS2051N08
• HMS2094C07
• HMS2098A14
• HMS2231M21
• HMS3414D09
• HMS3678D09
• HMS3715A14
• Pharmakon1600-01506035
• REPAGLINIDE [EP MONOGRAPH]
• REPAGLINIDE [USP MONOGRAPH]
• Tox21_110721
• AC-726
• BDBM50153520
• EBC-06064
• HB1106
• HY-15209R
• MSK7195-100A
• NSC759893
• s1426
• STK629501
• AKOS005561792
• MSK7195-1000A
• Repaglinide for system suitability CRS
• Repaglinide, >=98% (HPLC), solid
• BS-1010
• CCG-101013
• CS-0979
• DB00912
• FR27699
• NC00263
• NSC 759893
• NCGC00016978-02
• NCGC00016978-04
• NCGC00016978-05
• NCGC00016978-15
• 2-ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidyl)phenyl]butyl]amino]-2-oxo-ethyl]benzoic acid
• BR164332
• HY-15209
• SY046828
• SBI-0206942.P001
• AB00514019
• R0179
• SW197344-4
• 62R021
• C07670
• D00594
• F15001
• Repaglinide Solution in Acetonitrile, 100ug/mL
• AB00514019-09
• AB00514019_10
• AB00514019_11
• Repaglinide Solution in Acetonitrile, 1000ug/mL
• SR-01000759404
• Q2195995
• SR-01000759404-4
• BRD-K82846253-001-03-0
• BRD-K82846253-001-14-7
• BRD-K82846253-001-15-4
• BRD-K82846253-001-16-2
• Z1501485370
• Repaglinide, European Pharmacopoeia (EP) Reference Standard
• Repaglinide, United States Pharmacopeia (USP) Reference Standard
• (s)-(+)-2-ethoxy-4-(2-oxo-2-[(alpha-isobutyl-2-piperidinobenzyl)amino]ethyl)-benzoic acid
• Repaglinide for system suitability, European Pharmacopoeia (EP) Reference Standard
• (+)-2-ETHOXY-.ALPHA.-(((S)-.ALPHA.-ISOBUTYL-O-PIPERIDINOBENZYL)CARBAMOYL)-P-TOLUIC ACID
• (S)-2-Ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoicacid
• (S)-2-ETHOXY-4-(2-(METHYL-1-(2-(1-PIPERIDINYL)PHENYL)BUTYLAMINO)-2-OXOETHYL)-BENZOIC ACID
• (S)-2-Ethoxy-4-[2-[[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid
• (S)-2-Ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]-benzoic acid
• 2-Ethoxy-4-{[(S)-3-methyl-1-(2-piperidin-1-yl-phenyl)-butylcarbamoyl]-methyl}-benzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	-	0.7491	74.91%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8319	83.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9207	92.07%
OATP1B3 inhibitior	+	0.9232	92.32%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9480	94.80%
P-glycoprotein inhibitior	+	0.8549	85.49%
P-glycoprotein substrate	+	0.6268	62.68%
CYP3A4 substrate	+	0.7147	71.47%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.7944	79.44%
CYP3A4 inhibition	-	0.9264	92.64%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9206	92.06%
CYP2C8 inhibition	+	0.4543	45.43%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.6519	65.19%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9665	96.65%
Skin irritation	-	0.8224	82.24%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6820	68.20%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.9375	93.75%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7608	76.08%
Acute Oral Toxicity (c)	III	0.7284	72.84%
Estrogen receptor binding	+	0.7296	72.96%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5532	55.32%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.8676	86.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9733	97.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	398.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.76%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.42%	96.09%
CHEMBL2535	P11166	Glucose transporter	97.16%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.21%	85.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	95.16%	93.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.67%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.24%	99.17%
CHEMBL4208	P20618	Proteasome component C5	92.90%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	92.32%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.32%	95.56%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	92.21%	91.65%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.66%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.07%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.73%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.35%	95.17%
CHEMBL3902	P09211	Glutathione S-transferase Pi	87.03%	93.81%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.38%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.72%	95.89%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.39%	96.09%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	81.36%	87.50%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.03%	100.00%

Plants that contains it

• Salvia regla

Cross-Links

• PubChem: 65981
• LOTUS: LTS0035200
• wikiData: Q2195995