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

• ChemBase ID: 850
• Molecular Formular: C24H40N8O4
• Molecular Mass: 504.6256
• Monoisotopic Mass: 504.3172518
• SMILES: OCCN(c1nc(N2CCCCC2)c2nc(nc(N3CCCCC3)c2n1)N(CCO)CCO)CCO
• Canonical SMILES: OCCN(c1nc(N2CCCCC2)c2c(n1)c(nc(n2)N(CCO)CCO)N1CCCCC1)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
• InChIKey: IZEKFCXSFNUWAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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-({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
• IUPAC Traditional name: persantine; 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; dipyridamole
• Brand Name: Aggrenox; Agilease; Anginal; Apo-Dipyridamole Fc; Apo-Dipyridamole Sc; Apricor; Cardioflux; Cardoxil; Chilcolan; Cleridium; Cleridium 150; Coribon; Coridil; Coronarine; Corosan; Coroxin; Curantyl; Dipyridan; Gulliostin; IV Persantine; Justpertin; Kurantil; Natyl; Novo-Dipiradol; Peridamol; Permiltin; Persantin; Persantine; Piroan; Prandiol; Prandiol 75; Protangix; RA 8; RA-8; Stenocardil; Stenocardiol; Stimolcardio
• Synonyms: 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol; Permole; Persantine; Dipyridan; 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; Persantin; Curantyl; 2,2',2'',2'''-((4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol; Dipyridamole; 2,2',2'',2'''-(4,8-Dipiperidino-pyrimido [5,4-d] pyrimidine-2,6-diyldinitrilotetraethanol; Dipyridamol; Dipyridamine; Dypyridamol; Dipyudamine; Usaf Ge-12; Dipiridamol; Dipyridamole

Database IDs

• CAS Number: 58-32-2
• EC Number: 200-374-7
• MDL Number: MFCD00010555
• PubChem SID: 24277705; 46506292; 160964313; 24857223
• PubChem CID: 3108

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.971636
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): 1.8017116
• LogD (pH = 7.4): 1.8063301
• Log P: 1.8063892
• Molar Refractivity: 142.7794 cm^3
• Polarizability: 53.02881 Å^3
• Polar Surface Area: 145.44 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.52
• LOG S: -2.74
• Solubility (Water): 9.22e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; Slightly
• Apperance: yellow powder
• Melting Point: 163; 165 - 166°C; 165-166 °C(lit.)
• Hydrophobicity(logP): 1.411; 1.5

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: KK7450000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544), PDE10A(10846), PDE5A(8654), SLC29A1(2030)mouse ... Slc29a1(63959); human ... CYP1A2(1544), PDE10A(10846), SLC29A1(2030)mouse ... Slc29a1(63959)
• Mechanism of Action: Adenosine uptake inhibitor causing indirect adenosine receptor activation; Vasodilator

Product Information

• Purity: ≥98% (TLC); 95%; 95+%; 98%
• Salt Data: Free Base
• Application(s): Coronary vasodilator; Enhances effects of anticoagulants
• Empirical Formula (Hill Notation): C24H40N8O4

DETAILS

MP Biomedicals - 02153722

Selective inhibitor of cGMP phosphodiesterase and inhibits

DrugBank - DB00975

• Drug Groups: approved
• Description: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752)
• Indication: For as an adjunct to coumarin anticoagulants in the prevention of postoperative thromboembolic complications of cardiac valve replacement and also used in prevention of angina.
• Pharmacology: Dipyridamole, a non-nitrate coronary vasodilator that also inhibits platelet aggregation, is combined with other anticoagulant drugs, such as warfarin, to prevent thrombosis in patients with valvular or vascular disorders. Dipyridamole is also used in myocardial perfusion imaging, as an antiplatelet agent, and in combination with aspirin for stroke prophylaxis.
• Toxicity: Hypotension, if it occurs, is likely to be of short duration, but a vasopressor drug may be used if necessary. The oral LD₅₀ in rats is greater than 6,000 mg/kg while in the dogs, the oral LD₅₀ is approximately 400 mg/kg. LD₅₀=8.4g/kg (orally in rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: hepatic
• Absorption: 70%
• Half Life: 40 minutes
• Protein Binding: 99%
• Elimination: Dipyridamole is metabolized in the liver to the glucuronic acid conjugate and excreted with the bile.
• Distribution: * 1 to 2.5 L/kg
• Clearance: * 2.3-3.5 mL/min/kg
• References: Diener HC, Cunha L, Forbes C, Sivenius J, Smets P, Lowenthal A: European Stroke Prevention Study. 2. Dipyridamole and acetylsalicylic acid in the secondary prevention of stroke. J Neurol Sci. 1996 Nov;143(1-2):1-13. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1895

Related research area: Cardiovascular Disease

Sigma Aldrich - D9766

Biochem/physiol Actions
Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation.
包装
1, 5, 10, 25 g in glass bottle

Sigma Aldrich - 285676

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

REFERENCES

• Diener HC, Cunha L, Forbes C, Sivenius J, Smets P, Lowenthal A: European Stroke Prevention Study. 2. Dipyridamole and acetylsalicylic acid in the secondary prevention of stroke. J Neurol Sci. 1996 Nov;143(1-2):1-13. Pubmed
• www.bentham.org/prc/samples/prc1-1/Higashi.pdf
• Kadatz, R. et al., Arzneim.-Forsch., 1959, 9, 39, (pharmacol)
• U.K. Pat., 1959, 807 826; CA, 53, 12317, (synth, pharmacol)
• Beisenherz, G. et al., Arzneim.-Forsch., 1960, 10, 307, (metab)
• Takenaka, F. et al., Arzneim.-Forsch., 1972, 22, 892, (tox)
• Imai, K. et al., Yakugaku Zasshi, 1976, 96, 578; CA, 85, 108103, (synth)
• Adams, G.E., Adv. Med., 1980, 16, 171, (rev)
• Luger, P. et al., Acta Cryst. C, 1983, 39, 1454, (cryst struct)
• Rivey, M.D. et al., Drug Intell. Clin. Pharm., 1984, 18, 869, (rev, pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7225, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 225
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PCP250