Dipyridamole | 58-32-2

Dipyridamole Properties

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.
FDA UNII	64ALC7F90C
NCI Dictionary of Cancer Terms	dipyridamole
NCI Drug Dictionary	dipyridamole
ATC code	B01AC07
NIST Chemistry Reference	Pyrimidine, 2,6-bis(diethanolamino)-4,8-dipiperidino-pyrimido-(5,4-d)-(58-32-2)

Pharmacokinetic data

Protein binding	97-99%
Excreted unchanged in urine	1-5%
Volume of distribution	1.33-3.53(L/kg)
Biological half-life	9-12 / Unch

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS07

Signal word

Warning

Hazard statements

H315-H319-H335

Precautionary statements

P261-P264-P271-P280-P302+P352-P305+P351+P338

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)

NFPA 704

	0
2		0

Dipyridamole price More Price(54)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	D9766	Dipyridamole ≥98% (HPLC)	58-32-2	1g	$35.8	2024-03-01	Buy
Sigma-Aldrich	BP131	Dipyridamole British Pharmacopoeia (BP) Reference Standard	58-32-2	100MG	$262	2024-03-01	Buy
Sigma-Aldrich	BP1102	Dipyridamole impurity standard British Pharmacopoeia (BP) Reference Standard	58-32-2	25MG	$238	2024-03-01	Buy
Sigma-Aldrich	1220506	Dipyridamole United States Pharmacopeia (USP) Reference Standard	58-32-2	200mg	$242.4	2024-03-01	Buy
TCI Chemical	D2274	Dipyridamole	58-32-2	5g	$47	2024-03-01	Buy

Product number	Packaging	Price	Buy
D9766	1g	$35.8	Buy
BP131	100MG	$262	Buy
BP1102	25MG	$238	Buy
1220506	200mg	$242.4	Buy
D2274	5g	$47	Buy

Dipyridamole Chemical Properties,Uses,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

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

Uses

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

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

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).

Synthesis_58-32-2

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 synthesis

Synthesis of Dipyridamole from 2,6-Dichloro-4,8-dipiperidinopyrimidino[5,4-d]pyrimidine and Diethanolamine

Dipyridamole Preparation Products And Raw materials

Raw materials

5-AMINOOROTIC ACID Nitric acid Hydrogen Potassium cyanate Diethanolamine

Phosphorus oxychloride Piperidine Ethyl acetoacetate Phosphorus oxychloride

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Preparation Products

Dipyridamole Suppliers

Global( 463)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Huadong Medicine (Xi'an)Bodyguard Pharmaceutical Co.,Ltd.	+86-029-86185165 +8618629664246	guoyuan@eastchinapharm.com	China	1615	58
Hebei Mojin Biotechnology Co., Ltd	+8613288715578	sales@hbmojin.com	China	12453	58
Changzhou Rokechem Technology Co., Ltd.	18758118018	sales001@rokechem.com	China	255	58
Shanghai Affida new material science and technology center	+undefined15081010295	2691956269@qq.com	China	359	58
Beijing Cooperate Pharmaceutical Co.,Ltd	010-60279497	sales01@cooperate-pharm.com	CHINA	1811	55
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21695	55
Nanjing ChemLin Chemical Industry Co., Ltd.	025-83697070	product@chemlin.com.cn	CHINA	3012	60
Shanghai Yingrui Biopharma Co., Ltd.	+86-21-33585366 - 03@	sales03@shyrchem.com	CHINA	738	60
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Zhejiang ZETian Fine Chemicals Co. LTD	18957127338	stella@zetchem.com	China	2141	58

Supplier	Advantage
Huadong Medicine (Xi'an)Bodyguard Pharmaceutical Co.,Ltd.	58
Hebei Mojin Biotechnology Co., Ltd	58
Changzhou Rokechem Technology Co., Ltd.	58
Shanghai Affida new material science and technology center	58
Beijing Cooperate Pharmaceutical Co.,Ltd	55
Henan Tianfu Chemical Co.,Ltd.	55
Nanjing ChemLin Chemical Industry Co., Ltd.	60
Shanghai Yingrui Biopharma Co., Ltd.	60
career henan chemical co	58
Zhejiang ZETian Fine Chemicals Co. LTD	58

View Lastest Price from Dipyridamole manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-03-19	Dipyridamole 58-32-2	US $0.00-0.00 / KG	1KG	99	10 tons	Shanghai Affida new material science and technology center
2024-03-16	Dipyridamole 58-32-2	US $0.00 / KG	100g	98%+	100kg	WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2023-08-18	Dipyridamole 58-32-2	US $0.00 / KG	1KG	99%	50000KG/month	Hebei Mojin Biotechnology Co., Ltd

Dipyridamole
58-32-2
US $0.00-0.00 / KG
99
Shanghai Affida new material science and technology center

Dipyridamole
58-32-2
US $0.00 / KG
98%+
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD

Dipyridamole
58-32-2
US $0.00 / KG
99%
Hebei Mojin Biotechnology Co., Ltd

Dipyridamole Spectrum

Dipyridamole(58-32-2)MS Dipyridamole(58-32-2)¹HNMR Dipyridamole(58-32-2)¹³CNMR Dipyridamole(58-32-2)IR1 Dipyridamole(58-32-2)IR2 Dipyridamole(58-32-2)Raman

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2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetraet Corosan Coroxin Curantyl 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 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 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 Apricor Cardioflux Cardoxil Chilcolan Cleridium Cleridium 150 cleridium150 Coribon Coridil Coronarine pyrimido(5,4-d)pyrimidine,2,6-bis(bis(2-hydroxyethyl)amino)-4,8-dipiperidino RA 8 ra8 Stenocardil