Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H24N2O5 |
| Molecular Weight | 396.4364 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CN1C2=CC=CC=C2CC[C@H](N[C@@H](CCC3=CC=CC=C3)C(O)=O)C1=O
InChI
InChIKey=MADRIHWFJGRSBP-ROUUACIJSA-N
InChI=1S/C22H24N2O5/c25-20(26)14-24-19-9-5-4-8-16(19)11-13-17(21(24)27)23-18(22(28)29)12-10-15-6-2-1-3-7-15/h1-9,17-18,23H,10-14H2,(H,25,26)(H,28,29)/t17-,18-/m0/s1
| Molecular Formula | C22H24N2O5 |
| Molecular Weight | 396.4364 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdfhttps://www.google.com/patents/WO2006084761A1 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf | http://usp35.infostar.com.cn/uspnf/pub/data/v35300/usp35nf30s0_m7495.htmlCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/benazepril.html | DOI: 10.1111/j.1527-3466.1990.tb00432.x
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdfhttps://www.google.com/patents/WO2006084761A1 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019851s042lbl.pdf | http://usp35.infostar.com.cn/uspnf/pub/data/v35300/usp35nf30s0_m7495.html
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/benazepril.html | DOI: 10.1111/j.1527-3466.1990.tb00432.x
BENAZEPRIL, (±)- is an impurity referred to as Related Compound B, which is a diastereomer of benazepril, an ACE inhibitor, under the brand name Lotensin used primarily in treatment of hypertension, congestive heart failure, and heart attacks, and also in preventing the renal and retinal complications of diabetes. BENAZEPRIL, (±)- is used as USP Reference Standard.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1808 |
14.0 nM [IC50] | ||
Target ID: CHEMBL1808 |
0.1 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | LOTENSIN Approved UseAmlodipine besylate and benazepril hydrochloride capsules is a combination capsule of amlodipine, a dihydropyridine calcium channel blocker (DHP CCB) and benazepril, an angiotensin converting enzyme (ACE) inhibitor. Amlodipine besylate and benazepril hydrochloride capsules are indicated for the treatment of hypertension in patients not adequately controlled on monotherapy with either agent (1) 1.1 Hypertension Amlodipine besylate and benazepril hydrochloride capsules are indicated for the treatment of hypertension in patients not adequately controlled on monotherapy with either agent. Launch Date1991 |
|||
| Primary | BENAZEPRIL HYDROCHLORIDE Approved UseBenazepril hydrochloride tablets are indicated for the treatment of hypertension. They
may be used alone or in combination with thiazide diuretics. Launch Date1991 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
437 pmol/g EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENAZEPRIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
334 pmol × h/g EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENAZEPRIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2344861 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENAZEPRIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
Other AEs: Headache, Back pain... Other AEs: Headache (8.6%) Sources: Back pain (2.6%) Diarrhoea (0.9%) Upper respiratory tract infection (3.4%) Peripheral oedema (1.7%) Sinusitis (1.7%) Fatigue (0.9%) Cough (1.7%) Arthralgia (0.9%) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (9%) Sources: Fatigue (2%) Nausea (2%) Dizziness (2%) Cough increased (2%) |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (3%) Sources: Fatigue (2%) Nausea (1%) Dizziness (3%) Dizziness postural (1%) Cough increased (2%) |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (3%) Sources: Fatigue (2%) Nausea (1%) Dizziness (2%) Dizziness postural (1%) Cough increased (1%) |
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Dizziness... Other AEs: Headache (6%) Sources: Dizziness (2%) Dizziness postural (2%) |
80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
Other AEs: Headache, Fatigue... Other AEs: Headache (2%) Sources: Fatigue (5%) Nausea (1%) Cough increased (1%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Arthralgia | 0.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Diarrhoea | 0.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Fatigue | 0.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Cough | 1.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Peripheral oedema | 1.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Sinusitis | 1.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Back pain | 2.6% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Upper respiratory tract infection | 3.4% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Headache | 8.6% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult |
| Cough increased | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
| Dizziness | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
| Fatigue | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
| Nausea | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
| Headache | 9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy |
| Dizziness postural | 1% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
| Nausea | 1% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
| Cough increased | 2% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
| Fatigue | 2% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
| Dizziness | 3% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
| Headache | 3% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy |
| Cough increased | 1% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
| Dizziness postural | 1% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
| Nausea | 1% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
| Dizziness | 2% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
| Fatigue | 2% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
| Headache | 3% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy |
| Dizziness postural | 2% | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
| Dizziness | 2% | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
| Headache | 6% | 5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy |
| Cough increased | 1% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
| Nausea | 1% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
| Headache | 2% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
| Fatigue | 5% | 80 mg 1 times / day multiple, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: |
unhealthy |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of co-administration of urokinase and benazepril on severe IgA nephropathy. | 2004-04 |
|
| Hypertensive patients from two rural Chinese counties respond differently to benazepril: the Anhui Hypertension Health Care Study. | 2004-02 |
|
| Combined treatment with an AT1 receptor blocker and angiotensin converting enzyme inhibitor has an additive effect on inhibiting neointima formation via improvement of nitric oxide production and suppression of oxidative stress. | 2004-02 |
|
| Low-dose dual blockade of the renin-angiotensin system in patients with primary glomerulonephritis. | 2004-02 |
|
| Stampidine prevents mortality in an experimental mouse model of viral hemorrhagic fever caused by lassa virus. | 2004-01-13 |
|
| Effect of antihypertensive monotherapy and combination therapy on arterial distensibility and left ventricular mass. | 2004-01 |
|
| Systemic contact dermatitis due to captopril without cross-sensitivity to fosinopril, quinapril and benazepril. | 2004 |
|
| Adherence to antihypertensive therapy with fixed-dose amlodipine besylate/benazepril HCl versus comparable component-based therapy. | 2003-12-23 |
|
| Gene expression profile revealed different effects of angiotensin II receptor blockade and angiotensin-converting enzyme inhibitor on heart failure. | 2003-12 |
|
| Relationship between polymorphism of the angiotensin-converting enzyme gene and the response to angiotensin-converting enzyme inhibition in hypertensive patients. | 2003-11 |
|
| [Vasopressin analogue injection as ultimate measure for counteracting severe catecholamine-refractory poisoning by several vasodilators taken with suicidal intent]. | 2003-10-17 |
|
| Investigation of pimobendan versus benazepril in canine myxomatous valvular disease. | 2003-10-04 |
|
| By the way, doctor. After a recent blood pressure check, my doctor bumped up my dose of Lotensin [an ACE inhibitor] from 10 milligrams to 20. I had been taking the 10-mg pill in the morning, but my doctor advised me to take the new, higher dose in the evening. He said most strokes and heart attacks happen in the morning, and that I could get better protection by taking the drug right before. But I read in the Health Letter a couple of months ago that you recommend morning intake, so I am confused. | 2003-10 |
|
| Angiotensin II inhibition increases cellular glucose transport during reperfusion but not ischemia in pig hearts. | 2003-09 |
|
| The first hypertension trial comparing the effects of two fixed-dose combination therapy regimens on cardiovascular events: Avoiding Cardiovascular events through Combination therapy in Patients Living with Systolic Hypertension (ACCOMPLISH). | 2003-08-28 |
|
| Rationale for combination therapy as initial treatment for hypertension. | 2003-08-28 |
|
| Using the electronic medical record to enhance the use of combination drugs. | 2003-08-26 |
|
| Sialic acid 9-O-acetylesterase catalyzes the hydrolyzing reaction from alacepril to deacetylalacepril. | 2003-08 |
|
| Effect of benazepril amlodipine combination on fibrinolysis in hypertensive diabetic patients. | 2003-08 |
|
| Argyria associated with colloidal silver supplementation. | 2003-07 |
|
| Achieving goal blood pressure in patients with type 2 diabetes: conventional versus fixed-dose combination approaches. | 2003-06-27 |
|
| An angiotensin converting enzyme inhibitor, benazepril can be transformed to an active metabolite, benazeprilat, by the liver of dogs with ascitic pulmonary heartworm disease. | 2003-06 |
|
| Results of a pilot pharmacotherapy quality improvement program using fixed-dose, combination amlodipine/benazepril antihypertensive therapy in a long-term care setting. | 2003-06 |
|
| [Study on candidate genes of benazepril related cough in Chinese hypertensives]. | 2003-06 |
|
| Pharmacokinetic/pharmacodynamic modelling of the disposition and effect of benazepril and benazeprilat in cats. | 2003-06 |
|
| [Postmarketing surveillance of benazepril-related cough and related risk factors analysis on hypertensives]. | 2003-05 |
|
| Effects of valsartan with or without benazepril on blood pressure, angiotensin II, and endoxin in patients with essential hypertension. | 2003-04 |
|
| Additive effect of ACE inhibition and angiotensin II receptor blockade in type I diabetic patients with diabetic nephropathy. | 2003-04 |
|
| Combination is better than monotherapy with ACE inhibitor or angiotensin receptor antagonist at recommended doses. | 2003-03 |
|
| Correlation of Angiotensin-converting enzyme gene polymorphism with effect of antihypertensive therapy by Angiotensin-converting enzyme inhibitor. | 2003-03 |
|
| Effects of combined ACE inhibitor and angiotensin II antagonist treatment in human chronic nephropathies. | 2003-03 |
|
| Effect of benazepril addition to amlodipine on ankle oedema and subcutaneous tissue pressure in hypertensive patients. | 2003-03 |
|
| [Effect of the compound of traditional Chinese drugs on gene expression of renal endothelin and its receptor of experimental diabetic nephropathy]. | 2003-02 |
|
| Linear IgA dermatosis induced by a new angiotensin-converting enzyme inhibitor. | 2003-02 |
|
| Quantitative determination of benazepril and benazeprilat in human plasma by gas chromatography-mass spectrometry using automated 96-well disk plate solid-phase extraction for sample preparation. | 2003-01-05 |
|
| Effects of antihypertensive drugs on peritoneal vessels in hypertensive dogs with mild renal insufficiency. | 2003 |
|
| ACE Inhibition with moexipril: a review of potential effects beyond blood pressure control. | 2003 |
|
| [The use of angiotensin-converting enzyme inhibitor benazepril in acute period of myocardial infarction]. | 2003 |
|
| [Comparative effectiveness of lotensin and capoten in patients with chronic cardiac failure]. | 2003 |
|
| Optimisation by experimental design of a capillary electrophoretic method for the separation of several inhibitors of angiotensin-converting enzyme using alkylsulphonates. | 2002-11-29 |
|
| Reoptimization of MDL keys for use in drug discovery. | 2002-11-26 |
|
| [Non-immunologic factor: immunosuppressive drug-induced nephrotoxicity]. | 2002-11 |
|
| The effects of antihypertensive agents on the survival rate of polycystic kidney disease in Han:SPRD rats. | 2002-11 |
|
| Selection of the dose of angiotensin converting enzyme inhibitor for patients with diabetic nephropathy depends on the presence or absence of left ventricular hypertrophy. | 2002-11 |
|
| [Effects of benazepril on apoptosis in the kidney of diabetic rats]. | 2002-06 |
|
| [Clinical observation on effect of shenle capsule in treating mesangial proliferating glomerulonephritis]. | 2002-05 |
|
| [CEA comprehensive evaluation for Western and traditional Chinese hypotensive drugs]. | 2001-09 |
|
| [Serological study on inhibitory function of shenkang injection on glomerular mesangial cell]. | 2001-07 |
|
| Short-term metabolic effects of the ACE-inhibitor benazepril in type 2 diabetes mellitus associated with arterial hypertension. | 1992-07-01 |
|
| Sympathomoderating influence of benazepril in essential hypertension. | 1992-04 |
Patents
Sample Use Guides
The recommended initial dose for patients not receiving a diuretic is 10 mg once a day. The usual maintenance dosage range is 20-40 mg per day administered as a single dose or in two equally divided doses. A dose of 80 mg gives an increased response, but experience with this dose is limited.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3140614
Curator's Comment: In the isolated rabbit aorta the vasocontraction induced by PGF2 alpha was competitively antagonized at 10(-5)-10(-4) mol/l, while vascular responses induced by PGE1, PGE2 or PGI2 was inhibited at 3 x 10(-4) mol/l of benazepril. https://www.ncbi.nlm.nih.gov/pubmed/2080946
Benazepril inhibited both adrenaline-stimulated aortic PGI2 synthesis (25 pg mg -1 min-1) and carbachol-stimulated urinary bladder PGI2 synthesis (20 pg mg -1 min-1) in dose-dependent manners. IC50 (concentrations of antagonist at which agonist-stimulated PGI2 synthesis was inhibited by 50%) was 8 x 10-5.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:31:26 GMT 2025
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on
Mon Mar 31 18:31:26 GMT 2025
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| Record UNII |
JRM708L703
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Validated (UNII)
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N0000175562
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NCI_THESAURUS |
C247
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N0000178477
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PRIMARY | Decreased Blood Pressure [PE] | ||
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88200
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DTXSID501024701
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m2303
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SUB05701MIG
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TARGET -> INHIBITOR |
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PRODRUG -> METABOLITE ACTIVE |
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
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