Dipyridamole

Details

• Internal ID: f96faae1-6bbe-4581-8360-b33e8e677273
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Amines > Tertiary amines > Tertiary alkylarylamines > Dialkylarylamines
• IUPAC Name: 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
• SMILES (Canonical): C1CCN(CC1)C2=NC(=NC3=C2N=C(N=C3N4CCCCC4)N(CCO)CCO)N(CCO)CCO
• SMILES (Isomeric): C1CCN(CC1)C2=NC(=NC3=C2N=C(N=C3N4CCCCC4)N(CCO)CCO)N(CCO)CCO
• InChI: InChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2
• InChI Key: IZEKFCXSFNUWAM-UHFFFAOYSA-N
• Popularity: 19,173 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₀N₈O₄
• Molecular Weight: 504.60 g/mol
• Exact Mass: 504.31725179 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.02
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

• 58-32-2
• Persantin
• Dipyridamine
• Dipyridamol
• Dipyudamine
• Persantine
• Curantyl
• Stenocardil
• Stimolcardio
• Kurantil
• Cardioflux
• Cardoxin
• Dipiridamol
• Dipyridan
• Peridamol
• Anginal
• Apricor
• Coribon
• Corosan
• Coroxin
• Chilcolan
• Justpertin
• Permiltin
• Stenocardiol
• Agilease
• Piroan
• Cleridium 150
• Coronarine
• Gulliostin
• Prandiol
• Natyl
• Prandiol 75
• Usaf Ge-12
• Dypyridamol
• Iv Persantine
• Dipyridamolum
• 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol
• RA-8
• Dypyridamole
• RA 8
• NSC-515776
• Dipiridamol [INN-Spanish]
• Dipyridamolum [INN-Latin]
• NSC 515776
• EINECS 200-374-7
• UNII-64ALC7F90C
• BRN 0068373
• 64ALC7F90C
• CHEBI:4653
• MLS000028420
• 2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)pyrimido[5,4-d][1,3]diazin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol
• DTXSID6040668
• B01AC07
• Cleridium
• Dipyridamole (Persantine)
• NSC515776
• 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
• CHEMBL932
• 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido(5,4-d)pyrimidine
• SMR000058382
• Pyrimido(5,4-d)pyrimidine, 2,6-bis(bis(2-hydroxyethyl)amino)-4,8-dipiperidino-
• 2,2',2'',2'''-((4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetrakis(ethan-1-ol)
• Dipyramidole
• Cardoxil
• DTXCID4020668
• 4-26-00-03840 (Beilstein Handbook Reference)
• 2,2',2'',2'''-((4,8-Dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol
• AGGRENOX COMPONENT DIPYRIDAMOLE
• Ethanol, 2,2',2'',2'''-((4,8-di-1-piperidinylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetrakis-
• Ethanol, 2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-
• CAS-58-32-2
• Dipyridamole [USAN:USP:INN:BAN:JAN]
• NCGC00015385-12
• Coridil
• DIPYRIDAMOLE COMPONENT OF AGGRENOX
• Protangix
• 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine
• Dipiridamol (INN-Spanish)
• Dipyridamolum (INN-Latin)
• Ethanol, 2,2',2'',2'''-((4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetra-
• DIPYRIDAMOLE (MART.)
• DIPYRIDAMOLE [MART.]
• 2,2',2'',2'''-{[4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilo}tetraethanol
• DIPYRIDAMOLE (USP-RS)
• DIPYRIDAMOLE [USP-RS]
• C24H40N8O4
• Permole
• DIPYRIDAMOLE (EP MONOGRAPH)
• DIPYRIDAMOLE [EP MONOGRAPH]
• DIPYRIDAMOLE (USP MONOGRAPH)
• DIPYRIDAMOLE [USP MONOGRAPH]
• Persantine (TN)
• Dipyridamole (USAN:USP:INN:BAN:JAN)
• (3E)-3-[[(1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methylene]dihydro-5-methoxy-2(3H)3-[(1E)-2-[(1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]ethenyl]furan; (+)-Coronarin E-furanone; Coronarin D methyl ethe
• SR-01000003065
• dipiridamolo
• Dipridacot
• Dipridamole
• Curanty
• 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol
• 2,2',2'',2'''-((4,8-dipiperidin-1-ylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol
• 2,2',2'',2'''-[(4,8-dipiperidin-1-ylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol
• Dipyridamole; 2,2',2'',2'''-[[4,8-Di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilo]tetraethanol
• H9F
• Prestwick_145
• MFCD00010555
• Spectrum_001004
• Tocris-0691
• Opera_ID_494
• Prestwick0_000142
• Prestwick1_000142
• Prestwick2_000142
• Prestwick3_000142
• Spectrum2_000972
• Spectrum3_000402
• Spectrum4_000522
• Spectrum5_000839
• DIPYRIDAMOLE [MI]
• Lopac-D-9766
• DIPYRIDAMOLE [INN]
• DIPYRIDAMOLE [JAN]
• UPCMLD-DP072
• D 9766
• DIPYRIDAMOLE [USAN]
• cid_3108
• DIPYRIDAMOLE [VANDF]
• Lopac0_000464
• SCHEMBL16119
• BSPBio_000244
• BSPBio_001554
• BSPBio_001924
• KBioGR_001123
• KBioSS_001484
• MLS001076306
• MLS001333724
• MLS002548866
• DIPYRIDAMOLE [WHO-DD]
• DivK1c_000696
• SPECTRUM1500259
• SPBio_001003
• SPBio_002183
• BPBio1_000270
• GTPL4807
• Thymidine,6-dihydro-6-methoxy-
• UPCMLD-DP072:001
• BDBM23620
• Dipyridamole (JP17/USP/INN)
• HMS502C18
• IZEKFCXSFNUWAM-UHFFFAOYSA-
• KBio1_000696
• KBio2_001484
• KBio2_004052
• KBio2_006620
• KBio3_001144
• NINDS_000696
• BCPP000256
• DIPYRIDAMOLE [ORANGE BOOK]
• HMS1568M06
• HMS1791N16
• HMS1920I10
• HMS1989N16
• HMS2089N15
• HMS2091O18
• HMS2095M06
• HMS2232E19
• HMS3259C03
• HMS3261M10
• HMS3266J17
• HMS3371J03
• HMS3402N16
• HMS3411B03
• HMS3655I20
• HMS3675B03
• HMS3712M06
• HMS3742O03
• HMS3867F13
• Pharmakon1600-01500259
• AMY40468
• BCP26947
• HY-B0312
• Tox21_110133
• Tox21_500464
• 2,6-Bis(diethanolamine)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine
• CCG-40190
• NSC756743
• s1895
• AKOS000509426
• Tox21_110133_1
• BCP9000613
• DB00975
• Dipyridamole, >=98% (TLC), powder
• HS-0041
• LP00464
• NC00448
• NSC-619103
• NSC-756743
• SDCCGSBI-0050449.P005
• IDI1_000696
• SMP2_000208
• NCGC00015385-01
• NCGC00015385-02
• NCGC00015385-03
• NCGC00015385-04
• NCGC00015385-05
• NCGC00015385-06
• NCGC00015385-07
• NCGC00015385-08
• NCGC00015385-09
• NCGC00015385-10
• NCGC00015385-11
• NCGC00015385-13
• NCGC00015385-14
• NCGC00015385-15
• NCGC00015385-16
• NCGC00015385-17
• NCGC00015385-18
• NCGC00015385-29
• NCGC00023914-02
• NCGC00023914-04
• NCGC00023914-05
• NCGC00023914-06
• NCGC00023914-07
• NCGC00023914-08
• NCGC00023914-09
• NCGC00023914-10
• NCGC00023914-11
• NCGC00261149-01
• 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol
• 2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)-[1,3]diazino[5,4-d]pyrimidin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol
• 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-bis(1-piperidyl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
• AC-18100
• AC-30804
• Ethanol,2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-
• NCI60_005689
• SBI-0050449.P004
• 2,8-dipiperidinopyrimido[5,4-d]pyrimidine
• AB00051974
• EU-0100464
• FT-0603242
• SW196456-3
• EN300-70723
• BIM-0050449.0001
• D00302
• O10551
• AB00051974-18
• AB00051974-19
• AB00051974_20
• AB00051974_21
• A828156
• A831828
• Q419374
• SR-01000003065-2
• SR-01000003065-4
• SR-01000003065-5
• SR-01000003065-7
• W-105400
• BRD-K86301799-001-04-1
• BRD-K86301799-001-19-9
• BRD-K86301799-001-24-9
• Z1137167676
• Dipyridamole, British Pharmacopoeia (BP) Reference Standard
• Dipyridamole, European Pharmacopoeia (EP) Reference Standard
• 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido-[5,4-d]pyrimidin
• Dipyridamole, United States Pharmacopeia (USP) Reference Standard
• Pyrimido(5, 2,6-bis[bis(2-hydroxyethyl)amino]-4,8-diperidino-
• 2,2'',2'''-[4,8-Dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilotetraethanol
• 2,2',2'',2'''-(4,8-Dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilotetraethanol
• 2-[[2-(bis(2-hydroxyethyl)amino)-4,8-di(piperidin-1-yl)pyrimido[6,5-e]pyrimidin-
• Dipyridamole for peak identification, European Pharmacopoeia (EP) Reference Standard
• Ethanol,2',2'',2'''-(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetra-
• WLN: T66 BN DN GN INJ CCN HCN E- AT6NTJ B2Q F2Q& J- AT6NTJ B2Q F2Q
• 2,2',2'',2''''-((4,8-Dipiperidinopyrimido-(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol
• 2,2',2'',2'''-(4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl)tetraethanol
• 2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol
• 2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakisethanol
• 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-bis(1-piperidinyl)-6-pyrimido[5,4-d]pyrimidinyl]-(2-hydroxyethyl)amino]ethanol
• Ethanol, 2,2',2'',2'''-(4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyldinitrilo)tetra-
• Ethanol, 2,2',2',2'''-((4,8-di-1-iperidinylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetrakis-
• Ethanol,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-
• Ethanol,2',2'',2'''-[(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetra-
• InChI=1/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	-	0.7397	73.97%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7622	76.22%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	+	0.9566	95.66%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.8000	80.00%
BSEP inhibitior	+	0.7689	76.89%
P-glycoprotein inhibitior	-	0.8319	83.19%
P-glycoprotein substrate	-	0.7916	79.16%
CYP3A4 substrate	-	0.5804	58.04%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	+	0.3501	35.01%
CYP3A4 inhibition	+	0.6789	67.89%
CYP2C9 inhibition	+	0.8045	80.45%
CYP2C19 inhibition	-	0.9570	95.70%
CYP2D6 inhibition	+	0.7201	72.01%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9743	97.43%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	-	0.9000	90.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6415	64.15%
Eye corrosion	-	0.9821	98.21%
Eye irritation	-	0.7343	73.43%
Skin irritation	-	0.7731	77.31%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4541	45.41%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9077	90.77%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7197	71.97%
Acute Oral Toxicity (c)	III	0.7781	77.81%
Estrogen receptor binding	+	0.6028	60.28%
Androgen receptor binding	+	0.5226	52.26%
Thyroid receptor binding	-	0.5269	52.69%
Glucocorticoid receptor binding	-	0.5088	50.88%
Aromatase binding	+	0.5255	52.55%
PPAR gamma	+	0.5254	52.54%
Honey bee toxicity	-	0.9612	96.12%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	-	0.7577	75.77%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1997	Q99808	Equilibrative nucleoside transporter 1	0.49 nM; 0.86 nM; 8.18 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	400 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	4 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	95.30%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.62%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.84%	98.95%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	87.08%	98.46%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.37%	90.08%
CHEMBL3105	P09874	Poly [ADP-ribose] polymerase-1	83.92%	93.90%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	81.69%	96.25%
CHEMBL237	P41145	Kappa opioid receptor	81.56%	98.10%

Plants that contains it

• Heracleum candicans
• Prangos ferulacea

Cross-Links

• PubChem: 3108
• LOTUS: LTS0051783
• wikiData: Q419374