Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H9NO6 |
| Molecular Weight | 191.139 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1[C@@]([H])([C@]2([H])[C@@]([H])([C@@]([H])(CO2)ON(=O)=O)O1)O
InChI
InChIKey=YWXYYJSYQOXTPL-SLPGGIOYSA-N
InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1
| Molecular Formula | C6H9NO6 |
| Molecular Weight | 191.139 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Isosorbide mononitrate (trade name Monoket), an organic nitrate, is a vasodilator with effects on both arteries and veins. It is used for the prevention of angina pectoris due to coronary artery disease and the treatment of acute and chronic angina pectoris, hypertension, and myocardial infarction. Isosorbide mononitrate is the major active metabolite of isosorbide dinitrate (ISDN), and most of the clinical activity of the dinitrate is attributable to the mononitrate. The principal pharmacological action of isosorbide mononitrate is relaxation of vascular smooth muscle and consequent dilatation of peripheral arteries and veins, especially the latter. Dilation of the veins promotes peripheral pooling of blood and decreases venous return to the heart, thereby reducing left ventricular end-diastolic pressure and pulmonary capillary wedge pressure (preload). Arteriolar relaxation reduces systemic vascular resistance, systolic arterial pressure, and mean arterial pressure (afterload). Dilatation of the coronary arteries also occurs. The relative importance of preload reduction, afterload reduction and coronary dilatation remains undefined. Similar to other nitrites and organic nitrates, Isosorbide Mononitrate is converted to nitric oxide (NO), an active intermediate compound that activates the enzyme guanylate cyclase. Isosorbide mononitrate is rapidly and completely absorbed from the gastrointestinal tract. In humans, is not subject to first pass metabolism in the liver.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2111348 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MONOKET Approved Usemonoket® is indicated for the prevention and treatment of angina pectoris due to coronary artery disease. The onset of action of oral isosorbide mononitrate is not sufficiently rapid for this product to be useful in aborting an acute anginal episode. Launch Date7.4139841E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1151 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/ |
120 mg 1 times / day steady-state, oral dose: 120 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
557 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
388 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
356 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
14241 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/ |
120 mg 1 times / day steady-state, oral dose: 120 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6979 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2524 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2647 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/ |
120 mg 1 times / day steady-state, oral dose: 120 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/ |
60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ISOSORBIDE MONONITRATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
240 mg 1 times / day steady, oral Highest studied dose Dose: 240 mg, 1 times / day Route: oral Route: steady Dose: 240 mg, 1 times / day Sources: |
unhealthy, adult n = 312 Health Status: unhealthy Condition: chronic stable angina pectoris Age Group: adult Sex: unknown Population Size: 312 Sources: |
Other AEs: Headache... |
60 mg 1 times / day steady, oral Recommended Dose: 60 mg, 1 times / day Route: oral Route: steady Dose: 60 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: chronic stable angina pectoris Age Group: adult Sex: unknown Population Size: 267 Sources: |
Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (6 patients) Sources: |
20 mg 1 times / day steady, oral Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult n = 159 Health Status: unhealthy Condition: myocardial infarction or congestive heart failure Age Group: adult Sex: unknown Population Size: 159 Sources: |
Disc. AE: Headache, Nausea... AEs leading to discontinuation/dose reduction: Headache (5%) Sources: Nausea (2%) |
5 mg 1 times / day steady, oral Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: |
unhealthy, adult n = 54 Health Status: unhealthy Condition: myocardial infarction or congestive heart failure Age Group: adult Sex: unknown Population Size: 54 Sources: |
Disc. AE: Rash, Pruritus... AEs leading to discontinuation/dose reduction: Rash (2%) Sources: Pruritus (2%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | 57% | 240 mg 1 times / day steady, oral Highest studied dose Dose: 240 mg, 1 times / day Route: oral Route: steady Dose: 240 mg, 1 times / day Sources: |
unhealthy, adult n = 312 Health Status: unhealthy Condition: chronic stable angina pectoris Age Group: adult Sex: unknown Population Size: 312 Sources: |
| Headache | 6 patients Disc. AE |
60 mg 1 times / day steady, oral Recommended Dose: 60 mg, 1 times / day Route: oral Route: steady Dose: 60 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: chronic stable angina pectoris Age Group: adult Sex: unknown Population Size: 267 Sources: |
| Nausea | 2% Disc. AE |
20 mg 1 times / day steady, oral Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult n = 159 Health Status: unhealthy Condition: myocardial infarction or congestive heart failure Age Group: adult Sex: unknown Population Size: 159 Sources: |
| Headache | 5% Disc. AE |
20 mg 1 times / day steady, oral Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult n = 159 Health Status: unhealthy Condition: myocardial infarction or congestive heart failure Age Group: adult Sex: unknown Population Size: 159 Sources: |
| Pruritus | 2% Disc. AE |
5 mg 1 times / day steady, oral Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: |
unhealthy, adult n = 54 Health Status: unhealthy Condition: myocardial infarction or congestive heart failure Age Group: adult Sex: unknown Population Size: 54 Sources: |
| Rash | 2% Disc. AE |
5 mg 1 times / day steady, oral Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: |
unhealthy, adult n = 54 Health Status: unhealthy Condition: myocardial infarction or congestive heart failure Age Group: adult Sex: unknown Population Size: 54 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Clinical and cost-effective aspects of nitrate therapy in patients with ischemic heart disease after aortocoronary bypass surgery]. | 2001 |
|
| Efficiency of NO donors in substituting impaired endogenous NO production: a functional and morphological study. | 2001 |
|
| [Mononitrates in therapy of ischemic heart disease polycythemia vera]. | 2001 |
|
| [The effect of long-term administration of isosorbide 5-mononitrate (Mononit), nitric oxide donor, on gallbladder emptying in patients with chronic stable angina]. | 2001 |
|
| [Isosorbide-5-mononitrate (mono mac) in the prevention of bleeding from esophageal varicose veins in patients with liver cirrhosis]. | 2001 |
|
| Somatostatin plus isosorbide mononitrate versus somatostatin in the control of acute gastro-oesophageal variceal bleeding: a double blind, randomised, placebo controlled trial. | 2001 Aug |
|
| Endoscopic ligation compared with combined treatment with nadolol and isosorbide mononitrate to prevent recurrent variceal bleeding. | 2001 Aug 30 |
|
| Tolerance to nitroglycerin induced by isosorbide-5-mononitrate infusion in vivo. | 2001 Dec |
|
| Circadian variation of heart rate variability and the rate of autonomic change in the morning hours in healthy subjects and angina patients. | 2001 Jun |
|
| Potential usefulness of solubility index for prediction of the skin permeation rate of 5-ISMN from pressure-sensitive adhesive tape. | 2001 Jun 15 |
|
| Effect of long-acting isosorbide-5-mononitrate administration on large artery distensibility in patients with essential hypertension. | 2001 May |
|
| The prescription pattern of oral nitrates in coronary artery disease. Appropriateness and cost considerations. | 2001 Oct |
|
| Synthesis, hydrolysis kinetics and anti-platelet effects of isosorbide mononitrate derivatives of aspirin. | 2001 Oct |
|
| Nitric oxide induced cervical ripening in the human: Involvement of cyclic guanosine monophosphate, prostaglandin F(2 alpha), and prostaglandin E(2). | 2002 Apr |
|
| Massive choroidal hemorrhage associated with low molecular weight heparin therapy. | 2002 Apr |
|
| Pharmacologic efficacy in gastric variceal rebleeding and survival: including multivariate analysis. | 2002 Aug |
|
| [Therapy of portal hypertension]. | 2002 Dec |
|
| Topical mononitrate treatment in patients with anal fissure. | 2002 Jan |
|
| Mechanisms of nitric oxide generation from nitroglycerin and endogenous sources during hypoxia in vivo. | 2002 Jan |
|
| Pharmacokinetic profile of a new controlled-release isosorbide-5-mononitrate 60 mg scored tablet (Monoket Multitab). | 2002 Jan |
|
| [Effect of isosorbide mononitrate on hypotensive action of enalapril in patients with mild and moderate hypertension]. | 2002 Jul |
|
| Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery. | 2002 Jul |
|
| [Endoscopic ligation compared with combined treatment with nadolol and isosorbide mononitrate to prevent recurrent variceal bleeding]. | 2002 Jul |
|
| [Coronary artery disease observed in general hospitals: ETTIC study. Comparison between trimetazidine and mononitrate isosorbide for patients receiving betablockers]. | 2002 Nov |
|
| [How is antianginal therapy with pentaerythritol tetranitrate executed?]. | 2002 Nov 15 |
|
| A validated high performance liquid chromatographic method for analysis of isosorbide mononitrate in bulk material and extended release formulations. | 2002 Oct 15 |
|
| Dimethylarginine dimethylaminohydrolase I enhances tumour growth and angiogenesis. | 2002 Sep 9 |
|
| Effects of 5-isosorbide mononitrate and propranolol on subclinical hepatic encephalopathy and renal function in patients with liver cirrhosis. | 2002 Sep-Oct |
|
| [The impact of nitrates and mono-therapy and nitrates combined with angiotensin converting enzyme inhibitors on left ventricular remodeling and exercise capacity in patients after acute myocardial infarction]. | 2003 |
|
| [Various forms of mononitrates in treating patients with stress angina]. | 2003 |
|
| Hemodynamic response to pharmacological treatment of portal hypertension and long-term prognosis of cirrhosis. | 2003 Apr |
|
| Band ligation versus propanolol and isosorbide mononitrate for primary prophylaxis of variceal bleeding. | 2003 Aug |
|
| Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. | 2003 Aug |
|
| Simultaneous determination of aspirin and isosorbide 5-mononitrate in formulation by reversed phase high pressure liquid chromatography. | 2003 Aug 21 |
|
| Intercommunity and temporal variation of eleven essential and five toxic elements in human placentas from deliveries in thirteen arctic and sub-arctic areas of Russia and Norway. | 2003 Feb |
|
| Low doses of isosorbide mononitrate attenuate the postprandial increase in portal pressure in patients with cirrhosis. | 2003 Feb |
|
| The critically ill liver patient: the variceal bleeder. | 2003 Jan |
|
| Randomized, double-blind, placebo-controlled long-term study of isosorbide-5-mononitrate therapy in patients with left ventricular dysfunction after acute myocardial infarction. | 2003 Jan |
|
| Serum profile of isosorbide mononitrate after vaginal administration in the third trimester. | 2003 Jan |
|
| Comparative study of the use of diltiazem as an antispasmodic drug in coronary angiography via the transradial approach. | 2003 Jul |
|
| Beneficial effects of angiotensin-converting enzyme inhibitor and nitrate association on left ventricular remodeling in patients with large acute myocardial infarction: the Delapril Remodeling after Acute Myocardial Infarction (DRAMI) trial. | 2003 Jul |
|
| Optimal use of propranolol. | 2003 Jun |
|
| "A la carte" treatment of portal hypertension or just "hors d'oeuvres". | 2003 Jun |
|
| Propranolol plus placebo versus propranolol plus isosorbide-5-mononitrate in the prevention of a first variceal bleed: a double-blind RCT. | 2003 Jun |
|
| Amelioration of nitrate tolerance: matching strategies with mechanisms. | 2003 Jun 4 |
|
| Preserved endothelial function after long-term eccentric isosorbide mononitrate despite moderate nitrate tolerance. | 2003 Jun 4 |
|
| Severe portopulmonary hypertension in congenital hepatic fibrosis. | 2003 Mar |
|
| Mercury content and speciation in the plankton and benthos of Lake Superior. | 2003 Mar 20 |
|
| Isosorbide-5-mononitrate treatment prevents cyclosporin A-induced platelet hyperactivation and the underlying nitric oxide-cyclic guanosine-3',5'-monophosphate disturbances. | 2003 May 1 |
|
| Effect of nitric oxide on exercise-induced proteinuria in rats. | 2003 Nov |
Sample Use Guides
The recommended regimen of monoket (isosorbide mononitrate) tablets, is 20 mg twice daily, with the doses seven hours apart. A starting dose of 5 mg (½ tablet of the 10 mg dosing strength) might be appropriate for persons of particularly small stature but should be increased to at least 10 mg by the second or third day of therapy. Dosage adjustments are not necessary for elderly patients or patients with altered hepatic or renal function.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 22:11:56 UTC 2021
by
admin
on
Fri Jun 25 22:11:56 UTC 2021
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| Record UNII |
LX1OH63030
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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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NDF-RT |
N0000009909
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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NDF-RT |
N0000007647
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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WHO-ATC |
C01DA14
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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NCI_THESAURUS |
C29707
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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NDF-RT |
N0000007647
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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NDF-RT |
N0000175415
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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NDF-RT |
N0000007647
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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NDF-RT |
N0000007647
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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WHO-VATC |
QC01DA14
Created by
admin on Fri Jun 25 22:11:57 UTC 2021 , Edited by admin on Fri Jun 25 22:11:57 UTC 2021
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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240-197-2
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28004
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PRIMARY | RxNorm | ||
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5177
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M6541
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PRIMARY | Merck Index | ||
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SUB08336MIG
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LX1OH63030
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C030397
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1353102
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SUB30087
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27661
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C47575
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DB01020
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1506
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ISOSORBIDE MONONITRATE
Created by
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16051-77-7
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16051-77-7
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SUB12087MIG
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ALTERNATIVE | |||
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CHEMBL1311
Created by
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PRIMARY | |||
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7052
Created by
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PRIMARY |
| Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG | |||
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PARENT -> METABOLITE ACTIVE |
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PARENT -> IMPURITY |
