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58-32-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:850 http://www.chembase.cn/molecule-850.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
58-32-2
EC Number
200-374-7
MDL Number
MFCD00010555
PubChem SID
46506292
24277705
160964313
24857223
PubChem CID
3108

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.971636  H Acceptors 12 
H Donor LogD (pH = 5.5) 1.8017116 
LogD (pH = 7.4) 1.8063301  Log P 1.8063892 
Molar Refractivity 142.7794 cm3 Polarizability 53.02881 Å3
Polar Surface Area 145.44 Å2 Rotatable Bonds 12 
Lipinski's Rule of Five false 
Log P 1.52  LOG S -2.74 
Solubility (Water) 9.22e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO: soluble expand Show data source
ethanol: soluble expand Show data source
Slightly expand Show data source
Apperance
yellow powder expand Show data source
Melting Point
163 expand Show data source
165 - 166°C expand Show data source
165-166 °C(lit.) expand Show data source
Hydrophobicity(logP)
1.411 expand Show data source
1.5 expand Show data source
Storage Condition
-20°C expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
KK7450000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
room temp expand Show data source
Gene Information
human ... CYP1A2(1544), PDE10A(10846), PDE5A(8654), SLC29A1(2030)mouse ... Slc29a1(63959) expand Show data source
human ... CYP1A2(1544), PDE10A(10846), SLC29A1(2030)mouse ... Slc29a1(63959) expand Show data source
Mechanism of Action
Adenosine uptake inhibitor causing indirect adenosine receptor activation expand Show data source
Vasodilator expand Show data source
Purity
≥98% (TLC) expand Show data source
95% expand Show data source
95+% expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Coronary vasodilator expand Show data source
Enhances effects of anticoagulants expand Show data source
Empirical Formula (Hill Notation)
C24H40N8O4 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02153722 external link
Selective inhibitor of cGMP phosphodiesterase and inhibits
DrugBank - DB00975 external link
Item Information
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 external link
Related research area: Cardiovascular Disease
Sigma Aldrich - D9766 external link
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 external link
Biochem/physiol Actions
Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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