Moexipril

Identification

Summary

Moexipril is an angiotensin converting enzyme inhibitor prodrug used to treat hypertension.

Brand Names
Univasc
Generic Name
Moexipril
DrugBank Accession Number
DB00691
Background

Moexipril is a non-sulfhydryl containing precursor of the active angiotensin-converting enzyme (ACE) inhibitor moexiprilat. It is used to treat high blood pressure (hypertension). It works by relaxing blood vessels, causing them to widen. Lowering high blood pressure helps prevent strokes, heart attacks and kidney problems.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 498.5681
Monoisotopic: 498.236601452
Chemical Formula
C27H34N2O7
Synonyms
  • Moexipril
  • Moexiprilum
External IDs
  • RS-10085

Pharmacology

Indication

For the treatment of hypertension.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageHypertensionCombination Product in combination with: Hydrochlorothiazide (DB00999)••••••••••••
Management ofHypertension••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Moexipril is a non-sulfhydryl containing precursor of the active angiotensin-converting enzyme (ACE) inhibitor moexiprilat. It is used to treat high blood pressure (hypertension). It works by relaxing blood vessels, causing them to widen. Lowering high blood pressure helps prevent strokes, heart attacks and kidney problems.

Mechanism of action

Moexipril is a prodrug for moexiprilat, which inhibits ACE in humans and animals. The mechanism through which moexiprilat lowers blood pressure is believed to be primarily inhibition of ACE activity. ACE is a peptidyl dipeptidase that catalyzes the conversion of the inactive decapeptide angiotensin I to the vasoconstrictor substance angiotensin II. Angiotensin II is a potent peripheral vasoconstrictor that also stimulates aldosterone secretion by the adrenal cortex and provides negative feedback on renin secretion. ACE is identical to kininase II, an enzyme that degrades bradykinin, an endothelium-dependent vasodilator. Moexiprilat is about 1000 times as potent as moexipril in inhibiting ACE and kininase II. Inhibition of ACE results in decreased angiotensin II formation, leading to decreased vasoconstriction, increased plasma renin activity, and decreased aldosterone secretion. The latter results in diuresis and natriuresis and a small increase in serum potassium concentration (mean increases of about 0.25 mEq/L were seen when moexipril was used alone). Whether increased levels of bradykinin, a potent vasodepressor peptide, play a role in the therapeutic effects of moexipril remains to be elucidated. Although the principal mechanism of moexipril in blood pressure reduction is believed to be through the renin-angiotensin-aldosterone system, ACE inhibitors have some effect on blood pressure even in apparent low-renin hypertension.

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Humans
Absorption

Moexipril is incompletely absorbed, with bioavailability as moexiprilat of about 13% compared to intravenous (I.V.) moexipril (both measuring the metabolite moexiprilat), and is markedly affected by food, which reduces Cmax and AUC by about 70% and 40%, respectively, after the ingestion of a low-fat breakfast or by 80% and 50%, respectively, after the ingestion of a high-fat breakfast.

Volume of distribution
  • 183 L
Protein binding

Moexiprilat is approxomately 50% protein bound.

Metabolism

Rapidly converted to moexiprilat, the active metabolite. Conversion to the active metabolite is thought to require carboxyesterases and is likely to occur in organs or tissues, other than the gastrointestinal tract, in which carboxyesterases occur. The liver is thought to be one site of conversion, but not the primary site.

Hover over products below to view reaction partners

Route of elimination

Moexiprilat undergoes renal elimination.

Half-life

Moexipril elimination half-life is approximately 1 hour. Moexiprilat elimination half-life is 2 to 9 hours.

Clearance
  • 441 mL/min
Adverse Effects
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Toxicity

Human overdoses of moexipril have not been reported. In case reports of overdoses with other ACE inhibitors, hypotension has been the principal adverse effect noted. Single oral doses of 2 g/kg moexipril were associated with significant lethality in mice. Rats, however, tolerated single oral doses of up to 3 g/kg. Common adverse effects include cough, dizziness, diarrhea, flu syndrome, fatigue, pharyngitis, flushing, rash, and myalgia

Pathways
PathwayCategory
Moexipril Action PathwayDrug action
Moexipril Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Moexipril is combined with Abaloparatide.
AcebutololMoexipril may increase the hypotensive activities of Acebutolol.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Moexipril.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Moexipril.
Acetylsalicylic acidThe therapeutic efficacy of Moexipril can be decreased when used in combination with Acetylsalicylic acid.
Food Interactions
  • Avoid hypertensive herbs (e.g. bayberry, blue cohosh, cayenne, ephedra, and licorice).
  • Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
  • Limit salt intake. Salt may attenuate the antihypertensive effect.
  • Take separate from meals. Take 1 hour before meals.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Moexipril HydrochlorideQ1UMG3UH4582586-52-5JXRAXHBVZQZSIC-JKVLGAQCSA-N
Active Moieties
NameKindUNIICASInChI Key
MoexiprilatprodrugH3753190JS103775-14-0CMPAGYDKASJORH-YSSFQJQWSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Moexipril hydrochlorideTablet, film coated15 mg/1OralCobalt Laboratories2006-12-152013-05-31US flag
Moexipril hydrochlorideTablet, film coated7.5 mg/1OralCobalt Laboratories2006-12-152013-02-28US flag
UnivascTablet, film coated7.5 mg/1OralPhysicians Total Care, Inc.2003-04-032011-06-30US flag
UnivascTablet, film coated15 mg/1OralUcb Inc1995-07-152015-08-31US flag
UnivascTablet, film coated7.5 mg/1OralUcb Inc1995-07-15Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Moexipril HydrochlorideTablet, film coated15 mg/1OralGlenmark Pharmaceuticals Inc., USA2010-12-31Not applicableUS flag
Moexipril HydrochlorideTablet, film coated7.5 mg/1OralTeva Pharmaceuticals USA, Inc.2003-05-08Not applicableUS flag
Moexipril HydrochlorideTablet, coated15 mg/1OralPaddock Laboratories, Inc.2006-11-302014-07-31US flag
Moexipril HydrochlorideTablet7.5 mg/1OralApotex Corp.2008-06-092012-03-31US flag
Moexipril HydrochlorideTablet, film coated7.5 mg/1OralGlenmark Pharmaceuticals Inc., USA2010-12-31Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FEMIPRES PLUSMoexipril (7.5 mg) + Hydrochlorothiazide (12.5 mg)Tablet, film coatedOralTeofarma S.R.L.2014-07-082019-05-08Italy flag
FEMIPRES PLUSMoexipril Hydrochloride (15 MG) + Hydrochlorothiazide (25 MG)Tablet, coatedOralTeofarma S.R.L.2014-07-08Not applicableItaly flag
FEMPRESS PLUS 15MG/25MGMoexipril Hydrochloride (15 mg) + Hydrochlorothiazide (25 mg)Tablet, film coatedOral2010-09-012020-12-15Germany flag
Moexipril Hydrochloride and HydrochlorothiazideMoexipril Hydrochloride (7.5 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralHeritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc.2014-03-072014-03-08US flag
Moexipril Hydrochloride and HydrochlorothiazideMoexipril Hydrochloride (15 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, coatedOralPaddock Laboratories, Inc.2009-07-012013-08-31US flag

Categories

ATC Codes
C09AA13 — MoexiprilC09BA13 — Moexipril and diuretics
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Alpha amino acid esters / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Tetrahydroisoquinolines / Anisoles / Alkyl aryl ethers / Aralkylamines / Fatty acid esters / Benzene and substituted derivatives / Dicarboxylic acids and derivatives
show 10 more
Substituents
Alkyl aryl ether / Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Anisole / Aralkylamine
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
peptide (CHEBI:6960)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
WT87C52TJZ
CAS number
103775-10-6
InChI Key
UWWDHYUMIORJTA-HSQYWUDLSA-N
InChI
InChI=1S/C27H34N2O7/c1-5-36-27(33)21(12-11-18-9-7-6-8-10-18)28-17(2)25(30)29-16-20-15-24(35-4)23(34-3)14-19(20)13-22(29)26(31)32/h6-10,14-15,17,21-22,28H,5,11-13,16H2,1-4H3,(H,31,32)/t17-,21-,22-/m0/s1
IUPAC Name
(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC(OC)=C(OC)C=C2C[C@H]1C(O)=O

References

General References
  1. Asmar R, Sayegh F, Tracz W, Hlawaty M, Olszowska M, Jourde M, Vincent M, Goujoun B, Maldonado J: Reversal of left ventricular hypertrophy with the ACE inhibitor moexipril in patients with essential hypertension. Acta Cardiol. 2002 Feb;57(1):31-2. [Article]
  2. Blacher J, Raison J, Amah G, Schiemann AL, Stimpel M, Safar ME: Increased arterial distensibility in postmenopausal hypertensive women with and without hormone replacement therapy after acute administration of the ACE inhibitor moexipril. Cardiovasc Drugs Ther. 1998 Sep;12(4):409-14. [Article]
  3. Brogden RN, Wiseman LR: Moexipril. A review of its use in the management of essential hypertension. Drugs. 1998 Jun;55(6):845-60. [Article]
  4. Cawello W, Boekens H, Waitzinger J, Miller U: Moexipril shows a long duration of action related to an extended pharmacokinetic half-life and prolonged ACE inhibition. Int J Clin Pharmacol Ther. 2002 Jan;40(1):9-17. [Article]
  5. Chrysant SG, Chrysant GS: Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol. 2004 Aug;44(8):827-36. [Article]
  6. Chrysant SG, Chrysant GS: Pharmacological profile and clinical use of moexipril. Expert Rev Cardiovasc Ther. 2003 Sep;1(3):345-52. [Article]
  7. Chrysant GS, Nguyen PK: Moexipril and left ventricular hypertrophy. Vasc Health Risk Manag. 2007;3(1):23-30. [Article]
  8. Grass GM, Morehead WT: Evidence for site-specific absorption of a novel ACE inhibitor. Pharm Res. 1989 Sep;6(9):759-65. [Article]
  9. Kalasz H, Petroianu G, Tekes K, Klebovich I, Ludanyi K, Gulyas Z: Metabolism of moexipril to moexiprilat: determination of in vitro metabolism using HPLC-ES-MS. Med Chem. 2007 Jan;3(1):101-6. [Article]
  10. Persson B, Stimpel M: Evaluation of the antihypertensive efficacy and tolerability of moexipril, a new ACE inhibitor, compared to hydrochlorothiazide in elderly patients. Eur J Clin Pharmacol. 1996;50(4):259-64. [Article]
  11. Spinar J, Vitovec J: MORE--MOexipril and REgression of left ventricle hypertrophy in combination therapy A multicentric open label clinical trial. Int J Cardiol. 2005 Apr 20;100(2):199-206. [Article]
  12. Stimpel M, Koch B, Oparil S: Antihypertensive treatment in postmenopausal women: results from a prospective, randomized, double-blind, controlled study comparing an ACE inhibitor (moexipril) with a diuretic (hydrochlorothiazide). Cardiology. 1998 May;89(4):271-6. [Article]
  13. White CM: Pharmacologic, pharmacokinetic, and therapeutic differences among ACE inhibitors. Pharmacotherapy. 1998 May-Jun;18(3):588-99. [Article]
  14. White WB, Whelton A, Fox AA, Stimpel M, Kaihlanen PM: Tricenter assessment of the efficacy of the ACE inhibitor, moexipril, by ambulatory blood pressure monitoring. J Clin Pharmacol. 1995 Mar;35(3):233-8. [Article]
Human Metabolome Database
HMDB0014829
KEGG Compound
C07704
PubChem Compound
91270
PubChem Substance
46508441
ChemSpider
82418
BindingDB
50084673
RxNav
30131
ChEBI
6960
ChEMBL
CHEMBL1165
ZINC
ZINC000003812306
Therapeutic Targets Database
DAP000586
PharmGKB
PA164769059
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Moexipril

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentInduction of Intraoperative Hypotension1
2CompletedTreatmentPrimary Biliary Cholangitis1
1CompletedNot AvailableHealthy Volunteers (HV)2
1CompletedTreatmentHealthy Volunteers (HV)2
Not AvailableCompletedNot AvailableCoronavirus Disease 2019 (COVID‑19) / COVID / Hypertension1

Pharmacoeconomics

Manufacturers
  • Apotex inc
  • Glenmark generics ltd
  • Paddock laboratories inc
  • Teva pharmaceuticals usa inc
  • Schwarz pharma inc
Packagers
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Cobalt Pharmaceuticals Inc.
  • Glenmark Generics Ltd.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Paddock Labs
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Resource Optimization and Innovation LLC
  • Schwarz Pharma Inc.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
TabletOral
TabletOral
Tablet, film coatedOral
TabletOral15 mg/1
TabletOral7.5 mg/1
Tablet, coatedOral15 mg/1
Tablet, coatedOral7.5 mg/1
Tablet, coatedOral
TabletOral7.500 mg
Tablet, film coatedOral
Tablet, film coatedOral15 mg/1
Tablet, film coatedOral7.5 mg/1
Tablet, film coatedOral15 mg
Tablet, film coatedOral7.5 mg
Prices
Unit descriptionCostUnit
Univasc 15 mg tablet2.44USD tablet
Univasc 7.5 mg tablet2.13USD tablet
Moexipril hcl 15 mg tablet1.48USD tablet
Moexipril hcl 7.5 mg tablet1.41USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySoluble (about 10% weight-to-volume) in distilled water at room temperature as HCl salt.Not Available
logP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00585 mg/mLALOGPS
logP1.52ALOGPS
logP1.5Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)3.46Chemaxon
pKa (Strongest Basic)5.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area114.4 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity132.88 m3·mol-1Chemaxon
Polarizability53.55 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5775
Blood Brain Barrier-0.9022
Caco-2 permeable-0.7313
P-glycoprotein substrateSubstrate0.9085
P-glycoprotein inhibitor IInhibitor0.5919
P-glycoprotein inhibitor IIInhibitor0.8157
Renal organic cation transporterNon-inhibitor0.8146
CYP450 2C9 substrateNon-substrate0.8588
CYP450 2D6 substrateNon-substrate0.8369
CYP450 3A4 substrateSubstrate0.7014
CYP450 1A2 substrateNon-inhibitor0.8205
CYP450 2C9 inhibitorNon-inhibitor0.5961
CYP450 2D6 inhibitorNon-inhibitor0.8261
CYP450 2C19 inhibitorNon-inhibitor0.6592
CYP450 3A4 inhibitorNon-inhibitor0.5935
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6861
Ames testNon AMES toxic0.8358
CarcinogenicityNon-carcinogens0.9378
BiodegradationNot ready biodegradable0.9762
Rat acute toxicity2.5131 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9715
hERG inhibition (predictor II)Inhibitor0.8751
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004i-2321900000-ca0e1fd0441e1f76dfdc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0130900000-80bd1c1fe9badb399c41
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0142900000-ee1d1fc4470d92f31e75
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0561-0223900000-33e5316dad9dbe650bd3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ko-5292500000-da4f33ec24cf3065c8b4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-3920100000-f53b71a145cc5eb96bcf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0940100000-6acde9eb8a51e9c5a0f6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-249.3687858
predicted
DarkChem Lite v0.1.0
[M-H]-203.26231
predicted
DeepCCS 1.0 (2019)
[M+H]+250.9179858
predicted
DarkChem Lite v0.1.0
[M+H]+205.65787
predicted
DeepCCS 1.0 (2019)
[M+Na]+249.2286858
predicted
DarkChem Lite v0.1.0
[M+Na]+211.57039
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Chrysant SG, Chrysant GS: Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol. 2004 Aug;44(8):827-36. [Article]
  3. Edling O, Bao G, Feelisch M, Unger T, Gohlke P: Moexipril, a new angiotensin-converting enzyme (ACE) inhibitor: pharmacological characterization and comparison with enalapril. J Pharmacol Exp Ther. 1995 Nov;275(2):854-63. [Article]
  4. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:32