Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H40N8O4 |
Molecular Weight | 504.6256 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCN(CCO)C1=NC2=C(N=C(N=C2C(=N1)N3CCCCC3)N(CCO)CCO)N4CCCCC4
InChI
InChIKey=IZEKFCXSFNUWAM-UHFFFAOYSA-N
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
Molecular Formula | C24H40N8O4 |
Molecular Weight | 504.6256 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00975Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/012836s057lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00975
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/012836s057lbl.pdf
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. Dipyridamole likely inhibits both adenosine deaminase and phosphodiesterase, preventing the degradation of cAMP, an inhibitor of platelet function. This elevation in cAMP blocks the release of arachidonic acid from membrane phospholipids and reduces thromboxane A2 activity. Dipyridamole also directly stimulates the release of prostacyclin, which induces adenylate cyclase activity, thereby raising the intraplatelet concentration of cAMP and further inhibiting platelet aggregation. Used 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.
CNS Activity
Sources: https://web.archive.org/web/20170215181448/http://files.boehringer.com.au/files/PI/Persantin%20100%20PI.pdf
Curator's Comment: Dipyridamole does not cross the blood brain barrier.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17636949 |
144.8 nM [IC50] | ||
Target ID: CHEMBL4409 Sources: http://www.drugbank.ca/drugs/DB00975 |
1.2 µM [IC50] | ||
Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8254606 |
0.52 µM [IC50] | ||
Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873613 |
0.5 µM [IC50] | ||
Target ID: CHEMBL1910 Sources: http://www.drugbank.ca/drugs/DB00975 |
45.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Persantine Approved UsePersantine (dipyridamole USP) tablets are indicated as an adjunct to coumarin anticoagulants in the prevention
of postoperative thromboembolic complications of cardiac valve replacement. Launch Date1961 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1881 ng/mL |
200 mg 2 times / 2 weeks multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
475 ng/mL |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2781 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2825745 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15030 ng × h/mL |
200 mg 2 times / 2 weeks multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2492 ng × h/mL |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
15779 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2825745 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.74 h |
200 mg 2 times / 2 weeks multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.3 h |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPYRIDAMOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
DIPYRIDAMOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Disc. AE: Loss of consciousness, Respiratory distress... AEs leading to discontinuation/dose reduction: Loss of consciousness Sources: Page: p.75Respiratory distress Apnea Coma |
8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Disc. AE: Tachycardia, Hypotension... AEs leading to discontinuation/dose reduction: Tachycardia Sources: Page: e15Hypotension Multi-organ failure Delirium Anuria Renal failure |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Disc. AE: Headache, Diarrhoea... AEs leading to discontinuation/dose reduction: Headache (9.1%) Sources: Page: p.1786Diarrhoea (3.5%) Nausea (1.5%) Vomiting (2%) Dyspepsia (1.5%) |
5 g single, oral Overdose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: Page: p.62 |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Angina pectoris Age Group: 62 Sex: F Population Size: 1 Sources: Page: p.62 |
Disc. AE: Myocardial infarction... AEs leading to discontinuation/dose reduction: Myocardial infarction Sources: Page: p.62 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Apnea | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Coma | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Loss of consciousness | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Respiratory distress | Disc. AE | 1750 mg single, oral Overdose Dose: 1750 mg Route: oral Route: single Dose: 1750 mg Sources: Page: p.75 |
healthy, 23 n = 1 Health Status: healthy Age Group: 23 Sex: F Population Size: 1 Sources: Page: p.75 |
Anuria | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Delirium | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Hypotension | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Multi-organ failure | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Renal failure | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Tachycardia | Disc. AE | 8 g single, oral Overdose Dose: 8 g Route: oral Route: single Dose: 8 g Co-administed with:: paracetamol, p.o(8 g, single) Sources: Page: e15 |
healthy, 58 n = 1 Health Status: healthy Age Group: 58 Sex: F Population Size: 1 Sources: Page: e15 |
Dyspepsia | 1.5% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Nausea | 1.5% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Vomiting | 2% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Diarrhoea | 3.5% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Headache | 9.1% Disc. AE |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: Page: p.1786 |
unhealthy, 61 n = 198 Health Status: unhealthy Condition: Angina pectoris Age Group: 61 Sex: M+F Population Size: 198 Sources: Page: p.1786 |
Myocardial infarction | Disc. AE | 5 g single, oral Overdose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: Page: p.62 |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Angina pectoris Age Group: 62 Sex: F Population Size: 1 Sources: Page: p.62 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [Activation 27.71665 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
yes [Activation 1.2589 uM] | ||||
yes [Activation 10 uM] | ||||
yes [Activation 10 uM] | ||||
yes [Activation 5.0119 uM] | ||||
yes [IC50 2.6 uM] | ||||
yes [IC50 26 uM] | ||||
yes [IC50 30 uM] | ||||
yes [IC50 4 uM] | ||||
yes [IC50 4.8 uM] | ||||
yes [IC50 40 uM] | ||||
yes [IC50 74 uM] | ||||
yes [IC50 8.3 uM] | ||||
yes [IC50 81 uM] | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Page: 7.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Antithrombotic drugs for secondary stroke prophylaxis. | 2001 Apr |
|
Repeated thromboembolic and bleeding events after mechanical aortic valve replacement. | 2001 Apr |
|
Heterogeneity of resting and hyperemic myocardial blood flow in healthy humans. | 2001 Apr |
|
Safety, feasibility, and prognostic implications of pharmacologic stress echocardiography in 1482 patients evaluated in an ambulatory setting. | 2001 Apr |
|
Incremental prognostic value of stress echocardiography as an adjunct to exercise electrocardiography after uncomplicated myocardial infarction. | 2001 Apr |
|
Prognostic value of pharmacologic stress echocardiography in patients with left bundle branch block. | 2001 Apr 1 |
|
Adenosine permeation of a dynamic in vitro blood-brain barrier inhibited by dipyridamole. | 2001 Apr 13 |
|
Antiplatelet agents in tissue factor-induced blood coagulation. | 2001 Apr 15 |
|
Assessment of the effect of revascularization early after CABG using ECG-gated perfusion single-photon emission tomography. | 2001 Feb |
|
Preoperative dipyridamole-thallium scanning, selective coronary revascularization and long-term survival in patients with critical lower limb ischemia. | 2001 Feb |
|
The use of L-arginine [correction of F-arginine] and phosphodiesterase inhibitor (dipyridamole) to wean from inhaled nitric oxide. | 2001 Feb |
|
Newer antiplatelet therapies in stroke prevention. | 2001 Feb |
|
Antiplatelet therapy in the elderly. Aspirin, ticlopidine-clopidogrel, and GPIIb/GPIIIa antagonists. | 2001 Feb |
|
Antithrombotic therapy in valvular heart disease. | 2001 Feb |
|
Risks and benefits of adding anti-platelet therapy to warfarin among patients with prosthetic heart valves: a meta-analysis. | 2001 Feb |
|
Enhanced detection of reversible perfusion defects by Tc-99m sestamibi compared to Tc-99m tetrofosmin during vasodilator stress SPECT imaging in mild-to-moderate coronary artery disease. | 2001 Feb |
|
Quantification of myocardial perfusion in human subjects using 82Rb and wavelet-based noise reduction. | 2001 Feb |
|
Use of wavelet transforms in analysis of time-activity data from cardiac PET. | 2001 Feb |
|
Automated assessment of dipyridamole 201Tl myocardial SPECT perfusion scintigraphy by case-based reasoning. | 2001 Feb |
|
Predictive value of cardiac autonomic neuropathy in diabetic patients with or without silent myocardial ischemia. | 2001 Feb |
|
Paravertebral venous plexus distention (Batson's): an inciting etiologic agent in lumbar radiculopathy as observed by venous angiography. | 2001 Feb |
|
Serial evaluation of coronary flow reserve by transesophageal doppler echocardiography after angioplasty of proximal left anterior descending coronary artery: a 6-month follow-up study. | 2001 Feb |
|
Hypoxanthine transport in human tumour cell lines: relationship to the inhibition of hypoxanthine rescue by dipyridamole. | 2001 Feb 15 |
|
Extracellular adenosine-induced apoptosis in mouse neuroblastoma cells: studies on involvement of adenosine receptors and adenosine uptake. | 2001 Feb 15 |
|
Aggrenox and stress testing. | 2001 Feb 27 |
|
Peripheral flow response to transient arterial forearm occlusion does not reflect myocardial perfusion reserve. | 2001 Feb 27 |
|
Effect of dipyridamole on ischemia and reperfusion injury of canine liver. | 2001 Feb-Mar |
|
Inhibitors of the Cl-/HCO3- exchanger activate an apical anion conductance with similar features in the epithelial cells of rabbit gallbladder: analysis in intact epithelium. | 2001 Jan |
|
Myocardial contrast echocardiography: a new gold standard for perfusion imaging? | 2001 Jan |
|
Echocardiographic assessment of viable myocardium. | 2001 Jan-Feb |
|
Stress echocardiography: technical considerations. | 2001 Jan-Feb |
|
Saphenous vein endothelial cell viability: a comparative study of endoscopic and open saphenectomy for coronary artery bypass grafting. | 2001 Jan-Mar |
|
Action of dipyridamole and warfarin on growth of human endothelial cells cultured in serum-free media. | 2001 Mar |
|
[Reporting echocardiography exams with the G8-Cardio ANMCO software]. | 2001 Mar |
|
Progressive intracranial vascular disease with strokes and seizures in a boy with progeria. | 2001 Mar |
|
Dipyridamole-atropine stress echocardiography versus exercise SPECT scintigraphy for detection of coronary artery disease in hypertensives with positive exercise test. | 2001 Mar |
|
Use of dobutamine stress echocardiography in determination of myocardial viability. | 2001 Mar |
|
An abnormal dipyridamole thallium/sestamibi fails to predict long-term cardiac events in vascular surgery patients. | 2001 Mar |
|
Abnormal renal vascular responses to dipyridamole-induced vasodilation in spontaneously hypertensive rats. | 2001 Mar |
|
Global myocardial blood flow and global flow reserve measurements by MRI and PET are comparable. | 2001 Mar |
|
Myocardial flow reserve parametric map, assessed by first-pass MRI compartmental analysis at the chronic stage of infarction. | 2001 Mar |
|
Coronary flow reserve in angiographically normal coronary arteries with one-vessel coronary artery disease without traditional risk factors. | 2001 Mar |
|
Antiarrhythmic effects of adenosine on ischemia-induced ventricular fibrillation. | 2001 Mar |
|
Safety, feasibility, and diagnostic accuracy of accelerated high-dose dipyridamole stress echocardiography. | 2001 Mar 1 |
|
Usefulness of oral dipyridamole therapy for angiographic slow coronary artery flow. | 2001 Mar 15 |
|
Activation of glutamate uptake by guanosine in primary astrocyte cultures. | 2001 Mar 26 |
|
Preliminary clinical results of photon energy recovery in simultaneous rest Tl-201/stress Tc-99m sestamibi myocardial SPECT. | 2001 Mar-Apr |
|
Prognostic value of dipyridamole SPECT imaging in low-risk patients after myocardial infarction. | 2001 Mar-Apr |
|
Dipyridamole myocardial SPECT with low heart rate response indicates cardiac autonomic dysfunction in patients with diabetes. | 2001 Mar-Apr |
|
Effect of power Doppler and digital subtraction techniques on the comparison of myocardial contrast echocardiography with SPECT. | 2001 May |
Sample Use Guides
Adjunctive Use in Prophylaxis of Thromboembolism after Cardiac Valve Replacement. The recommended dose is 75-100 mg four times daily as an adjunct to the usual warfarin therapy.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16103157
Mengovirus plaque formation in HeLa or L cells was inhibited nearly 100% by the presence of 80 uM dipyridamole.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:21:21 GMT 2023
by
admin
on
Sat Dec 16 16:21:21 GMT 2023
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Record UNII |
64ALC7F90C
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C744
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NDF-RT |
N0000008832
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NDF-RT |
N0000175578
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NDF-RT |
N0000008832
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WHO-ATC |
B01AC07
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WHO-VATC |
QB01AC07
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CHEMBL932
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C445
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DB00975
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4807
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200-374-7
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4653
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64ALC7F90C
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1220506
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64ALC7F90C
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D004176
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924
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SUB07229MIG
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m4658
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3521
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515776
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1545
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3108
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58-32-2
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DIPYRIDAMOLE
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100000091735
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Dipyridamole
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DTXSID6040668
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Related Record | Type | Details | ||
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ACTIVE MOIETY |