Verapamil

Details

• Internal ID: c8b7bf63-5f55-4479-854d-f11c091073d8
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylbutylamines
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
• SMILES (Canonical): CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
• SMILES (Isomeric): CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
• InChI: InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3
• InChI Key: SGTNSNPWRIOYBX-UHFFFAOYSA-N
• Popularity: 21,458 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈N₂O₄
• Molecular Weight: 454.60 g/mol
• Exact Mass: 454.28315770 g/mol
• Topological Polar Surface Area (TPSA): 64.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 5.09
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 13

Synonyms

• 52-53-9
• Iproveratril
• Dilacoran
• Vasolan
• Isoptimo
• Isoptin
• Verapamilo
• Verapamilum
• Falicard
• Finoptin
• Isoptine
• Cordilox
• Calan
• D-365
• Lekoptin
• Verapamilum [INN-Latin]
• Verapamilo [INN-Spanish]
• Isotopin
• Calcan
• Tarka
• CP-16533-1
• dl-Verapamil
• (+/-)-VERAPAMIL
• r,s-verapamil
• Verelan
• Verapamil [USAN:INN:BAN]
• Verapamil slow release
• CCRIS 6749
• Covera-HS
• 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
• 5-((3,4-dimethoxyphenethyl)(methyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile
• 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
• Ansyr
• EINECS 200-145-1
• UNII-CJ0O37KU29
• Verapamil [USAN:BAN:INN]
• (+-)-Verapamil
• CJ0O37KU29
• Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
• NSC 272306NA
• C27H38N2O4
• CP-16,533-1
• Verapamil (USAN/INN)
• EINECS 260-462-6
• alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
• 2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
• alpha-Isopropyl-alpha-((N-methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
• CP-165331
• Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-
• alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)-methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile
• RS-Verapamil
• CP 16533-1
• D 365
• DTXSID9041152
• CHEBI:77733
• NSC-272306NA
• Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino) propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
• HSDB 3928
• NCGC00016083-09
• Verelan (TN)
• Covera-hs (TN)
• Calan (TN)
• 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
• Benzeneacetonitrile, .alpha.-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-.alpha.-(1-methylethyl)-
• (+/-)-Verapamil hydrochlorid
• DTXCID7021152
• ()-Verapamil hydrochlorid
• Drosteakard
• Arpamyl
• Veracim
• Veraptin
• Verexamil
• (+/-)-Verapamil;CP-16533-1
• (1)-3-(3,4-Dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrile
• CAS-52-53-9
• (+/-)-5-((3,4-DIMETHOXYPHENETHYL)METHYLAMINO)-2-(3,4-DIMETHOXYPHENYL)-2-ISOPROPYLVALERONITRILE
• 2-(3,4-Dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methyl-amino]-2-(1-methylethyl) pentanenitrile
• 56949-77-0
• NSC272366
• verapamil-
• ?Verapamil
• C27-H38-N2-O4
• Bosoptin (TN)
• Benzeneacetonitrile, alpha-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-alpha-(1-methylethyl)-
• Isoptin (TN)
• Calan (Salt/Mix)
• Akilen (Salt/Mix)
• Verapamilum (Latin)
• Isoptin (Salt/Mix)
• Cordilox (Salt/Mix)
• delta-365
• alpha-isopropyl-alpha-
• VERAPAMIL [INN]
• VERAPAMIL [MI]
• Covera-HS (Salt/Mix)
• VERAPAMIL [USAN]
• Prestwick0_000141
• Prestwick1_000141
• Prestwick2_000141
• Prestwick3_000141
• Spectrum2_001740
• Spectrum4_000906
• Spectrum5_001786
• VERAPAMIL [VANDF]
• D0R0FE
• VERAPAMIL [WHO-DD]
• CHEMBL6966
• Lopac0_001237
• SCHEMBL16742
• BSPBio_000242
• BSPBio_001513
• BSPBio_002358
• KBioGR_000233
• KBioGR_001372
• KBioGR_002343
• KBioSS_000233
• KBioSS_002346
• MLS006011414
• DivK1c_000399
• SPBio_001820
• SPBio_002181
• BPBio1_000268
• CHEBI:9948
• GTPL2406
• CP 16533-1 (Verapamil)
• SCHEMBL13287282
• (A+/-)-Verapamil hydrochloride
• BDBM81939
• KBio1_000399
• KBio2_000233
• KBio2_002343
• KBio2_002801
• KBio2_004911
• KBio2_005369
• KBio2_007479
• KBio3_000465
• KBio3_000466
• KBio3_002823
• C08DA01
• ()-Verapamil;CP-16533-1
• cMAP_000023
• NINDS_000399
• Verapamil (Na-Ca chanel blocker)
• Bio1_000425
• Bio1_000914
• Bio1_001403
• Bio2_000233
• Bio2_000713
• HMS1791L15
• HMS1989L15
• HMS2089H17
• HMS3402L15
• Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-, (+)-
• Tox21_110300
• LS-174
• MFCD00056240
• NSC_62969
• STK538085
• AKOS005468962
• Tox21_110300_1
• CCG-205311
• DB00661
• SDCCGSBI-0051204.P005
• CAS_52-53-9
• IDI1_000399
• IDI1_033983
• NCGC00016083-04
• NCGC00016083-05
• NCGC00016083-06
• NCGC00016083-07
• NCGC00016083-08
• NCGC00016083-10
• NCGC00016083-11
• NCGC00016083-13
• NCGC00016083-14
• NCGC00016083-15
• NCGC00016083-16
• NCGC00016083-17
• NCGC00016083-18
• NCGC00016083-20
• NCGC00016083-25
• NCGC00016083-34
• NCGC00024710-04
• NCGC00024710-05
• NCGC00024710-06
• NCGC00024710-07
• NCGC00024710-08
• NCGC00024710-09
• NCGC00344584-01
• 2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methyl-amino]-2-isopropyl-pentanenitrile
• AC-16016
• BP-21223
• HY-14275
• NCI60_020143
• SMR001550201
• SBI-0051204.P003
• AB00053495
• CS-0002967
• FT-0603225
• FT-0675801
• C07188
• D02356
• E75969
• EN300-708774
• AB00053495-20
• AB00053495_21
• A829133
• CP-165331/CP-16533-1
• L001330
• Q410291
• BRD-A09533288-001-02-7
• BRD-A09533288-003-05-6
• CP-165331 / CP-16533-1
• F2173-0851
• VERAPAMIL, Dexverapamil, Verapamyl hydrochloride, VERAPAMIL HYDROCHLORIDE
• (+-)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile
• .alpha.-((N-Methyl-N-homoveratryl)-.gamma.-aminopropyl)-3,4-dimethoxyphenylacetonitrile
• (?)-alpha-[3-[[2-(3,4-Dimethoxyphenyl)ethyl](methyl)amino]propyl]-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile
• 2-(3,4-Dimethoxyphenyl)-5-((2-(3,4-dimethoxyphenyl)ethyl)(methyl)amino)-2-isopropylpentanenitrile, (+/-)-
• 2-(3,4-Dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]-2-isopropylpentanenitrile #
• alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino) propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-benzeneacetonitrile
• alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile
• Benzeneacetonitrilo, Alfa-[3-[[2-(3,4-dimetoxifenil) etilo] metilamino] propil]-3,4-dimetoxi-alfa-(1-metiletil)-
• rac-2-(3,4-dimethoxyphenyl)-5-((2-(3,4-dimethoxyphenyl)ethyl)(methyl)amino)-2-(propan-2-yl)pentanenitrile

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9735	97.35%
Caco-2	+	0.5463	54.63%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5532	55.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.7532	75.32%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	+	0.9390	93.90%
P-glycoprotein inhibitior	+	0.9674	96.74%
P-glycoprotein substrate	+	0.9291	92.91%
CYP3A4 substrate	+	0.7963	79.63%
CYP2C9 substrate	-	0.5000	50.00%
CYP2D6 substrate	+	0.6427	64.27%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9553	95.53%
CYP2C8 inhibition	+	0.6246	62.46%
CYP inhibitory promiscuity	-	0.9181	91.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7623	76.23%
Carcinogenicity (trinary)	Non-required	0.6565	65.65%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9582	95.82%
Skin irritation	-	0.7995	79.95%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9552	95.52%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	II	0.7343	73.43%
Estrogen receptor binding	+	0.7477	74.77%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.7590	75.90%
Glucocorticoid receptor binding	-	0.8183	81.83%
Aromatase binding	+	0.7197	71.97%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.6206	62.06%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9798	97.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	579 nM	IC50	via CMAUP
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	524807.46 nM	IC50	PMID: 18678495
CHEMBL3622	P33261	Cytochrome P450 2C19	21800 nM	IC50	PMID: 23033255
CHEMBL3721	P10632	Cytochrome P450 2C8	17500 nM	Ki	PMID: 16248836
CHEMBL289	P10635	Cytochrome P450 2D6	43300 nM	IC50	PMID: 23033255
CHEMBL3491	P51589	Cytochrome P450 2J2	22000 nM	IC50	PMID: 23033255
CHEMBL340	P08684	Cytochrome P450 3A4	12000 nM; 17600 nM; 4700 nM	IC50; IC50; IC50	PMID: 23033255; PMID: 22328583; PMID: 12699389
CHEMBL234	P35462	Dopamine D3 receptor	186 nM	IC50	via CMAUP
CHEMBL240	Q12809	HERG	143 nM; 143 nM; 143 nM; 141.25 nM; 144.54 nM; 10 nM; 141.25 nM; 141.25 nM; 144.54 nM; 141.25 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 12729675; PMID: 12190308; PMID: 21300721; PMID: 21185626; PMID: 19110341; via Super-PRED; PMID: 12873512; PMID: 18448342; PMID: 15745831; PMID: 15911273
CHEMBL1941	P25021	Histamine H2 receptor	2590 nM	IC50	via CMAUP
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	3500 nM; 6800 nM; 113 nM; 35 nM; 9660 nM	IC50; IC50; Kd; Kd; IC50	PMID: 25093931; PMID: 22112208; via Super-PRED; via Super-PRED; PMID: 18707884
CHEMBL4302	P08183	P-glycoprotein 1	1600 nM; 3100 nM; 29 nM; 740 nM; 38 nM; 1700 nM; 12000 nM; 6300 nM; 4570.88 nM; 5800 nM; 4570.88 nM; 6606.93 nM; 4570.88 nM; 6606.93 nM; 8440 nM; 400 nM; 6300 nM; 5754.4 nM; 400 nM; 4780 nM; 2210 nM; 2110 nM; 1480 nM; 6500 nM; 4700 nM; 4200 nM; 5420 nM; 2100 nM; 4200 nM; 575.44 nM; 500 nM; 9800 nM; 14000 nM; 5200 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 23245571; PMID: 10386932; PMID: 25282263; PMID: 25282263; PMID: 25985195; DOI: 10.1039/C2MD20286G; DOI: 10.1039/C2MD20286G; PMID: 12699389; PMID: 18678495; PMID: 18083034; PMID: 18083034; PMID: 18083034; PMID: 17890094; PMID: 17890094; PMID: 15359574; PMID: 15240100; PMID: 12699389; PMID: 18083034; PMID: 12699389; PMID: 12569305; PMID: 12569305; PMID: 12477351; PMID: 12477351; PMID: 11716514; PMID: 11716514; PMID: 11716514; PMID: 18707884; PMID: 10820137; PMID: 11454724; PMID: 22452412; PMID: 22112208; PMID: 21354800; PMID: 19402665; PMID: 19250834
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	442 nM	IC50	via CMAUP
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	165 nM	IC50	via CMAUP
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	297 nM	IC50	via CMAUP
CHEMBL228	P31645	Serotonin transporter	240 nM	IC50	via CMAUP
CHEMBL1980	Q14524	Sodium channel protein type V alpha subunit	41500 nM	IC50	PMID: 21300721
CHEMBL5685	O15245	Solute carrier family 22 member 1	6800 nM	IC50	PMID: 18788725
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	32000 nM; 64000 nM	IC50; IC50	PMID: 22587986; PMID: 22587986
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	50000 nM; 150 nM; 23500 nM; 24000 nM; 47000 nM	IC50; IC50; IC50; IC50; IC50	PMID: 22761000; PMID: 8474099; PMID: 22761000; PMID: 22761000; PMID: 22761000
CHEMBL4633	P22001	Voltage-gated potassium channel subunit Kv1.3	8000 nM	IC50	PMID: 23084278

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.29%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	96.11%	85.31%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.22%	99.17%
CHEMBL2535	P11166	Glucose transporter	93.86%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.29%	86.33%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.93%	92.68%
CHEMBL4581	P52732	Kinesin-like protein 1	88.85%	93.18%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	88.80%	87.16%
CHEMBL1255126	O15151	Protein Mdm4	88.79%	90.20%
CHEMBL3837	P07711	Cathepsin L	88.51%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.25%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.20%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.07%	93.65%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.76%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	84.79%	93.31%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	83.64%	96.25%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.52%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.49%	89.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.34%	90.71%
CHEMBL5747	Q92793	CREB-binding protein	82.63%	95.12%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.42%	100.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	81.03%	96.86%
CHEMBL249	P25103	Neurokinin 1 receptor	80.58%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.49%	91.11%

Plants that contains it

• Piper nigrum

Cross-Links

• PubChem: 2520
• NPASS: NPC42793
• ChEMBL: CHEMBL6966