ChemicalBook > CAS DataBase List > Dipyridamole

Dipyridamole

Product Name
Dipyridamole
CAS No.
58-32-2
Chemical Name
Dipyridamole
Synonyms
DIPYRIDAMOL;Dipiridamol;dypyridamole;Anginal;persantin;Persantine;Dipyridamole (200 mg);ra8;RA 8;Natyl
CBNumber
CB6731869
Molecular Formula
C24H40N8O4
Formula Weight
504.63
MOL File
58-32-2.mol
More
Less

Dipyridamole Property

Melting point:
165-166 °C (lit.)
Boiling point:
593.96°C (rough estimate)
Density 
1.2046 (rough estimate)
refractive index 
1.6910 (estimate)
storage temp. 
room temp
solubility 
DMSO: soluble
form 
powder
pka
pKa 6.4 (Uncertain)
color 
yellow
Water Solubility 
Soluble in chloroform, methanol, dilute acids, ethanol. Slightly soluble in water.
Merck 
14,3346
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
NIST Chemistry Reference
Pyrimidine, 2,6-bis(diethanolamino)-4,8-dipiperidino-pyrimido-(5,4-d)-(58-32-2)
More
Less

Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
KK7450000
HS Code 
29335990
Toxicity
LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D9766
Product name
Dipyridamole
Purity
≥98% (HPLC)
Packaging
1g
Price
$35.8
Updated
2024/03/01
Sigma-Aldrich
Product number
BP131
Product name
Dipyridamole
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$262
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1102
Product name
Dipyridamole impurity standard
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
25MG
Price
$238
Updated
2024/03/01
Sigma-Aldrich
Product number
1220506
Product name
Dipyridamole
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$242.4
Updated
2024/03/01
TCI Chemical
Product number
D2274
Product name
Dipyridamole
Packaging
5g
Price
$47
Updated
2024/03/01
More
Less

Dipyridamole Chemical Properties,Usage,Production

Description

Dipyridamole (58-32-2) is a phosphodiesterase inhibitor (IC50=0.37, 0.38, 0.45, 0.9 and 4.5 μM for PDE11, 6, 10, 5 and 8 respectively.1,2 Potent equilibrative nucleoside transporter 1 (ENT1) inhibitor Ki=8.2 nM vs. 144.8 nM for ENT1 and ENT2 respectively.3 Antiplatelet activity.4

Chemical Properties

Yellow Powder

Originator

Persantine,Boehringer Ingelheim,US,1961

Uses

Dipyridamole prevents platelets sticking to the replacement heart valve and causing a blood clot on the valve. It is used to dilate blood vessels in people with peripheral arterial disease and coronary artery disease. This compound has been shown to suppress high glucose-induced osteopontin mRNA expression and protein secretion, as well as inhibit cAMP and cGMP hydrolysis. Research indicates that Dipyridamole is a non-specific nucleoside transport inhibitor with the ability to increase the effects of adenosine in sinoatrial and atrioventricular nodes. Dipyridamole is an inhibitor of ENT1 and ENT2.

Uses

Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation

Uses

A phosphodiester, cGMP, and non-specific nucleoside transport inhibitor

Uses

Dipiridamol is known as a coronary vasodilating agent, although it also possesses specific antiaggregant activity. It is used for preventing thrombo-formation after cardiac valve replacement in combination with warfarin.

Definition

ChEBI: A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.

Manufacturing Process

Urea may be reacted with acetoacetic ester and that product nitrated to give 5-nitro-orotec acid. That is hydrogenated, then reacted with urea and potassium cyanate to give tetrahydroxypyrimidopyrimidine. The tetrahydroxy compound is converted to the tetrachloro compound POCl3. Reaction with diethanolamine and then with piperidine gives dipyridamole.

brand name

Persantine (Boehringer Ingelheim).

Therapeutic Function

Coronary vasodilator

General Description

Dipyridamole, 2,2',2',2'''-[(4,8-di-1piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]-tetrakisethanol (Persantine), may be used for coronary andmyocardial insufficiency. Its biggest use today, however, isas an antithrombotic in patients with prosthetic heart valves.It is a bitter, yellow, crystalline powder, soluble in diluteacids, methanol, or chloroform. A formulation containingdipyridamole and aspirin (Aggrenox) is currently beingmarketed as an antithromobotic.
Dipyridamole is a long-acting vasodilator. Its vasodilatingaction is selective for the coronary system; it is indicatedfor long-term therapy of chronic angina pectoris. Thedrug also inhibits adenosine deaminase in erythrocytesand interferes with the uptake of the vasodilator adenosineby erythrocytes. These actions potentiate the effect ofprostacyclin (PGI2), which acts as an inhibitor to plateletaggregation.

Biological Activity

Coronary vasodilator; adenosine transport inhibitor. Phosphodiesterase inhibitor (IC 50 values are 0.37, 0.38, 0.45, 0.9 and 4.5 μ M? for PDE11, 6, 10, 5 and 8 respectively).

Biochem/physiol Actions

Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation.

Mechanism of action

Dipyridamole exerts its antiplatelet function by increasing cellular concentrations of cAMP via its inhibition of the degradating enzyme, cyclic nucleotide PDE3. It also blocks adenosine uptake, which acts at A2 adenosine receptors to stimulate platelet adenyl cyclase. Less common uses for this drug include inhibition of embolization from prosthetic heart valves when used in combination with warfarin (the only currently recommended use) and reduction of thrombosis in patients with thrombotic disease when used in combination with aspirin. Alone, dipyridamole has little, if any, benefit in the treatment of thrombotic conditions.

Clinical Use

Dipyridamole is a pyrimidopyrimidine derivative with vasodilatory and antiplatelet properties.

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. Human systemic effects cardiomyopathy including infarction. Mutation data reported. Used as a coronary vasodilator. When heated to decomposition it e

Synthesis

Dipyridamole, 2,2',2'',2'''-[(4,8-dipiperidinopirimido[5,4-d]pirimidin-2,6- diyl)-diimino]-tetraethanol (19.4.13), is easily synthesized from 5-nitroorotic acid (19.4.8), easily obtained, in turn, by nitrating of 2,4-dihydroxy-6-methylpyrimidine, which is usually synthesized by the condensation of urea with acetoacetic ether. Reduction of the nitro group in 5-nitroorotic acid by various reducing agents gives 5-aminoorotic acid (19.4.9), which is reacted with urea or with potassium cyanide to give 2,4,6,8- tetrahydroxypyrimido[5,4-d]pyrimidine (19.4.10). This undergoes a reaction with a mixture of phosphorous oxychloride and phosphorous pentachloride, which forms 2,4,6,8- tetrachloropyrimido[ 5,4-d]pyrimidine (19.4.11). Reacting the resulting tetrachloride with piperidine replaces the chlorine atoms at C4 and C8 of the heterocyclic system with piperidine, giving 2,6-dichloropyrimido-4,8-dipiperidino[5,4-d]pyrimidine (19.4.12). Reacting the resulting product with diethanolamine gives dipyridamole (19.4.13).

Drug interactions

Potentially hazardous interactions with other drugs
Anti-arrhythmics: effects of adenosine enhanced and extended.
Anticoagulants: anticoagulant effect of coumarins, phenindione and heparin enhanced.

Metabolism

Dipyridamole is metabolised in the liver. Renal excretion of the parent compound is negligible (< 0.5%). Urinary excretion of the glucuronide metabolite is low (5%), the metabolites are mostly (about 95%) excreted via the bile into the faeces, with some evidence of entero-hepatic recirculation.

storage

Store at RT

References

1) Fujishige et al. (1999), Cloning and characterization of a novel human phosphodiesterase that hydrolyzes both cAMP and cGMP (PDE10A); J. Biol. Chem., 274 18438 2) Soderling et al. (1998), Cloning and characterization of a cAMP-specific cyclic nucleotide phosphodiesterase; Proc. Natl. Acad. Sci. USA, 95 8991 3) Lin and Buolamwini (2007), Synthesis, flow cytometric evaluation, and identification of highly potent dipyridamole analogues as equilibrative nucleoside transporter 1 inhibitors.; J. Med. Chem., 50 3906 4) Coccheri (2010), Antiplatelet drugs – do we need new options? With a reappraisal of direct thromboxane inhibitors; Drugs, 70 887

Dipyridamole Preparation Products And Raw materials

Raw materials

5-AMINOOROTIC ACID

Preparation Products

More
Less

Dipyridamole Suppliers

Americas 1 Belgium 2 Brazil 3 Canada 6 China 308 Europe 4 France 4 Germany 10 India 50 Italy 2 Japan 5 Jordan 1 Malaysia 1 Singapore 1 South Korea 1 Spain 4 Switzerland 2 Turkey 1 United Kingdom 20 United States 54 Venezuela 1 Global 481
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14055
Advantage
65
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
HBCChem, Inc.
Tel
+1-510-219-6317
Fax
+1-650-486-1361
Email
sales@hbcchem.com
Country
United States
ProdList
10648
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32161
Advantage
58
Alfa Chemistry
Tel
Fax
1-516-927-0118
Email
Info@alfa-chemistry.com
Country
United States
ProdList
24072
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
Alchem Pharmtech,Inc.
Tel
8485655694
Email
sales@alchempharmtech.com
Country
United States
ProdList
63687
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Wonda Science
Tel
--
Fax
--
Email
wonda@wondascience.com
Country
United States
ProdList
2192
Advantage
50
Focus Biomolecules
Tel
--
Fax
--
Email
sales@focusbiomolecules.com
Country
United States
ProdList
1284
Advantage
58
Abcam
Tel
--
Fax
--
Email
us.orders@abcam.com
Country
United States
ProdList
6001
Advantage
50
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
Rochem International Inc.
Tel
--
Fax
--
Email
gcadioli@rochemintl.com
Country
United States
ProdList
80
Advantage
58
Selleck Chemicals LLC
Tel
--
Fax
--
Email
sales@selleckchem.com
Country
United States
ProdList
1848
Advantage
58
MP Biomedicals, LLC. (Division of Valiant FC Co., Ltd.)
Tel
--
Fax
--
Email
serv@mpbio.com
Country
United States
ProdList
1854
Advantage
58
MilliporeSigma (Sigma-Aldrich Corp.)
Tel
--
Fax
--
Email
@sial.com
Country
United States
ProdList
5414
Advantage
58
MedKoo Biosciences, Inc.
Tel
--
Fax
--
Email
sales@medkoo.com
Country
United States
ProdList
126
Advantage
58
Kare Bay Biochem Inc.
Tel
--
Fax
--
Email
product@karebaybio.com
Country
United States
ProdList
110
Advantage
58
Chemica Inc.
Tel
--
Fax
--
Email
chemicainc@sbcglobal.net
Country
United States
ProdList
10
Advantage
58
Molcan Corporation
Tel
--
Fax
--
Email
info@molcan.com
Country
United States
ProdList
686
Advantage
60
Spectrum Chemical Mfg. Corp.
Tel
--
Fax
--
Email
marketing@spectrumchemical.com
Country
United States
ProdList
3113
Advantage
60
Moravek, Inc.
Tel
--
Fax
--
Email
info@moravek.com
Country
United States
ProdList
279
Advantage
58
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
MYLAN LABORATORIES LTD
Tel
--
Fax
--
Email
info@amstock.com
Country
United States
ProdList
179
Advantage
58
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Frontier Scientific, Inc.
Tel
--
Fax
--
Email
sales@frontiersci.com
Country
United States
ProdList
6222
Advantage
86
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
HBCChem Inc.
Tel
--
Fax
--
Email
sales@hbcchem-inc.com
Country
United States
ProdList
4569
Advantage
30
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
ECA International Corporation
Tel
--
Fax
--
Email
services@ecacorporation.com
Country
United States
ProdList
1062
Advantage
52
NetQem
Tel
--
Fax
--
Email
sales@netqem.us
Country
United States
ProdList
1641
Advantage
38
AerChem inc.
Tel
--
Fax
--
Email
laz18@aol.com
Country
United States
ProdList
364
Advantage
42
Advance Scientific & Chemical
Tel
--
Fax
--
Email
sales@advance-scientific.com
Country
United States
ProdList
6419
Advantage
71
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
SynFine Research
Tel
--
Fax
--
Email
research@synfine.com
Country
United States
ProdList
1024
Advantage
68
Sciencelab.com, Inc.
Tel
--
Fax
--
Email
accounting@sciencelab.com
Country
United States
ProdList
4159
Advantage
82
Aceto Corporation
Tel
--
Fax
--
Email
contact@aceto.com
Country
United States
ProdList
2619
Advantage
75
BIOMOL INTERNATIONAL, LP
Tel
--
Fax
--
Email
info@biomol.com
Country
United States
ProdList
1499
Advantage
77
EMD Biosciences, Inc.
Tel
--
Fax
--
Email
technical@calbiochem.com
Country
United States
ProdList
6529
Advantage
66
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
Spectrum Chemicals & Laboratory Products
Tel
--
Fax
--
Email
sales@spectrumchemical.com
Country
United States
ProdList
6699
Advantage
77
MP Biomedicals, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6561
Advantage
81
More
Less

View Lastest Price from Dipyridamole manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Dipyridamole 58-32-2
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%-101.5%;EP
Supply Ability
500KGS
Release date
2021-07-06
Apeloa production Co.,Limited
Product
Dipyridamole 58-32-2
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
10000
Release date
2024-06-04
Hebei Weibang Biotechnology Co., Ltd
Product
Dipyridamole 58-32-2
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-12-06

58-32-2, DipyridamoleRelated Search:

Cyprodinil DROPERIDOL Haloperidol Pyrimethanil 2,2-Bis(hydroxymethyl)propionic acid Flumetsulam Dipyridamole Mono-O-b-D-glucuronide 2,4,6,8-TETRACHLOROPYRIMIDO[5,4-D]PYRIMIDINE 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-bis(2,2,3,3,4,4,5,5,6,6-decadeuteriopiperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol CYT997 QUINACRINE DIHYDROCHLORIDE Vinpocetine Topotecan hydrochloride Methotrexate Temozolomide 2,6-Dichloro-4,8-dipiperidinopyrimidino[5,4-d]pyrimidine 6-Des(diethanolamino)-6-chloro Dipyridamole 2,4,6,8-Tetrahydroxy-Pyrimido-(5,4D)Pyrimidine

  • Dipyridamole (200 mg)
  • 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetraet
  • Corosan
  • Coroxin
  • Curantyl
  • Dipiridamol
  • Dipyridamine
  • Dipyridan
  • Dipyudamine
  • 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-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-
  • ethanol,2,2’,2’’,2’’’-((4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)din
  • etraethanol
  • Gulliostin
  • itrilo)tetra-
  • Justpertin
  • Kurantil
  • Natyl
  • NSC-515776
  • Peridamol
  • Permiltin
  • Persantine
  • Piroan
  • Prandiol
  • Prandiol 75
  • Protangix
  • Pyrimido(5,4-d)pyrimidine, 2,6-bis(bis(2-hydroxyethyl)amino)-4,8-diperidino-
  • 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))tetraethanol
  • DypyridaMole API
  • 2,6-Bis(diethanolamine)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine 2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakisethanol
  • 2,6-BIS(DIETHANOLAMINE)-4,8-DIPIPERIDINOPYRIMIDO[5,4-D]PYRIMIDINE
  • 2,6-bis(diethanolamino)-4,8-dipiperidinopyrimido-[5,4-d]pyrimidin
  • 2,6-BIS(DIETHANOLAMINO)-4,8-DIPIPERIDINOPYRIMIDO[5,4-D]PYRIMIDINE
  • 2,2',2'',2'''-4,8-DIPIPERIDINO-PYRIMIDO [5,4-D] PYRIMIDINE-2,6-DIYLDINITRILOTETRAETHANOL
  • 2,2',2'',2'''-[(4,8-DIPIPERIDINYLPYRIMIDO[5,4-D]PYRIMIDINE-2,6-DIYL)DINITRILO]TETRAKISETHANOL
  • persantin
  • Dipyridamole (FDA)
  • Dipyridamole,98%
  • Dypyridamol
  • DIPYRIDAMOLE CORONARY VASODILATOR
  • DIPYRIDAMOLE,USP
  • Dipyrdamole
  • 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetr
  • 2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol
  • 2,2’,2’’,2’’’-(4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyldinitrilo)t
  • 2,2’,2’’,2’’’-[(4,8-Di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakisethanol
  • Agilease
  • Anginal
  • Apricor
  • Cardioflux
  • Cardoxil
  • Chilcolan
  • Cleridium
  • Cleridium 150
  • cleridium150
  • Coribon
  • Coridil