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Encyclopedia > Papaverine
Papaverine
Systematic (IUPAC) name
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline
Identifiers
CAS number 61-25-6
ATC code A03AD01 G04BE02
PubChem 4680
DrugBank APRD00628
Chemical data
Formula C20H21NO4[1]
Mol. mass 339.385 g/mol[1]
Pharmacokinetic data
Bioavailability 80%[3]
Protein binding ~90%
Metabolism Hepatic[3]
Half life 1.5-2 hours[3]
Excretion Renal[3]
Therapeutic considerations
Pregnancy cat.

USA: C[4] Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A03A Drugs for functional bowel disorders A03AA Synthetic anticholinergics, esters with tertiary amino group A03AA01 Oxyphencyclimine A03AA03 Camylofin A03AA04 Mebeverine A03AA05 Trimebutine A03AA06 Rociverine A03AA07 Dicycloverine A03AA08 Dihexyverine A03AA09 Difemerine A03AA30 Piperidolate A03AB Synthetic anticholinergics, quaternary... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... seadonkey rules =P ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes Oral, intravenous, intramuscular, rectal,[5] intracavernosal

Papaverine is an opium alkaloid used primarily in the treatment of visceral spasm, vasospasm (especially those involving the heart and the brain), and occasionally in the treatment of erectile dysfunction.[3] While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the other opium alkaloids (opiates). The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Intramuscular injection is an injection of a substance directly into a muscle. ... Opium is a narcotic produced from opium poppies. ... Diagram of Ephedrine An alkaloid, strictly speaking, is a naturally-occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... A spasm is a sudden, involuntary contraction of a muscle, a group of muscles, or a hollow organ, or a similarly sudden contraction of an orifice. ... Vasospasm refers to a condition in which blood vessels spasm, leading to constriction. ... The heart and lungs, from an older edition of Grays Anatomy. ... In animals the brain, or encephalon (Greek for in the head), is the control center of the central nervous system. ... Erectile dysfunction (ED) or impotence is a sexual dysfunction characterized by the inability to develop or maintain an erection of the penis. ... Binomial name Papaver somniferum L. The opium poppy, Papaver somniferum, is the type of poppy from which opium and all refined opiates such as morphine (up to 20%), thebaine (5%), codeine (1%), papaverine (1%), and noscapine (5-8%) are extracted. ... An opioid is any agent that binds to opioid receptors found principally in the central nervous system and gastrointestinal tract. ...

Contents

Uses

Papaverine is approved to treat spasms of the gastointestinal tract, bile ducts and ureter and for use as a cerebral and coronary vasodilator[3] in subarachnoid hemorrhage (combined with balloon angioplasty)[6] and coronary artery bypass surgery.[7] Papaverine may also be used as a smooth muscle relaxant in microsurgery where it is applied directly to blood vessels. X-Ray of the bile duct during a laprascopic cholecystectomy A bile duct is any of a number of long tube-like structures that carry bile. ... Transverse section of ureter. ... Wikipedia does not yet have an article with this exact name. ... A myocardial infarction occurs when an atherosclerotic plaque slowly builds up in the inner lining of a coronary artery and then suddenly ruptures, totally occluding the artery and preventing blood flow downstream. ... Vasodilation is where blood vessels in the body become wider following the relaxation of the smooth muscle in the vessel wall. ... A subarachnoid hemorrhage (SAH) is bleeding into the subarachnoid space surrounding the brain, i. ... Angioplasty is the mechanical dilation of an artery that have been obstructed, generally due to atheroma (the lesion of atherosclerosis). ... Early in a coronary artery bypass surgery during vein harvesting from the legs (left of image) and the establishment of bypass (placement of the aortic cannula) (bottom of image). ... Microsurgery is a type of surgery where an operation microscope is required in order to perform opératoire precision acts. ...


The in vivo mechanism of action is not entirely clear, but an inhibition of the enzyme phosphodiesterase causing elevation of cyclic AMP levels is significant. It may also alter mitochondrial respiration. Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... Cellular respiration is a process that describes the metabolic reactions and processes that take place in a cell to obtain chemical energy from fuel molecules. ...


It is also commonly used in cryopreservation of blood vessels along with other glycosaminoglycans and protein suspensions.[1] [2] Functions as a vasodilator during cryopreservation when used in conjunction with verapamil, phentolamine, nifedipine, tolazolines, or nitroprusside. [3] [4] Cryopreservation of plant shoots. ... The blood vessels are part of the circulatory system and function to transport blood throughout the body. ... Vasodilation is where blood vessels in the body become wider following the relaxation of the smooth muscle in the vessel wall. ... Verapamil (brand names: Isoptin®, Verelan®, Calan®) is a medical drug that acts as an L-type calcium channel blocker. ... Phentolamine is a competitive nonselective alpha adrenergic receptor antagonist. ... Nifedipine (brand name Adalat and Procardia) is a dihydropyridine calcium channel blocker. ... Sodium nitroprusside (Na2Fe(CN)5NO) is a potent peripheral vasodilator which affects both arterioles and venules. ...


Papaverine is also being investigated as a topical growth factor in tissue expansion with some success.


http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=15457029&dopt=Abstract


Side effects

Frequent side effects of papaverine treatment include polymorphic ventricular tachycardia, constipation, interference with sulphobromophthalein[8] retention test (used to determine hepatic function), increased transaminase levels, increased alkaline phosphatase levels, hyperbilirubinemia, somnolence, and vertigo.[3] Ventricular tachycardia (V-tach or VT) is a fast rhythm that originates in one of the ventricles of the heart. ... In biochemistry, a transaminase or an aminotransferase is an enzyme that catalyzes a type of reaction between an amino acid and an α-keto acid. ... Ball and stick model of alkaline phosphatase Alkaline phosphatase (ALP) (EC 3. ... Jaundice, technically known as icterus, is yellowing of the skin, sclera (eyes) and mucous membranes caused by increased levels of bilirubin in the system. ... Somnolence (or drowsiness) is a state of near-sleep, a strong desire for sleep, or sleeping for unusually long periods. ... Vertigo, sometimes called a headrush, is a major symptom of a balance disorder. ...


Rare side effects include flushing of the face, hyperhidrosis (excessive sweating), cutaneous eruption, arterial hypotension, tachycardia, lack of appetite, jaundice, eosinophilia, thrombopenia, mixed hepatitis, headache, allergic reaction, chronic active hepatitis,[3] and paradoxical aggravation of cerebral vasospasm.[9] Primary hyperhidrosis is the condition characterized by abnormally increased perspiration, in excess of that required for regulation of body temperature. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... Jaundice, also known as icterus (attributive adjective: icteric), is a yellowing of the skin, conjunctiva (clear covering over the sclera, or whites of the eyes) and mucous membranes caused by increased levels of bilirubin in the human body (or the body of another red blooded animal). ... Eosinophilia is the state of having high eosinophil granulocytes in the blood. ... Thrombocytopenia (or -paenia, or thrombopenia in short) is the presence of relatively few platelets in blood. ... Hepatitis is inflammation of the liver. ...


Formulations and Tradenames

Papaverine is available as a conjugate of hydrochloride, codecarboxylate, adenylate, and teprosylate.[10] It was also once available as a salt of hydrobromide, camsylate, cromesilate, nicotinate, and phenylglycolate. The hydrochloride salt is available for intramuscular, intravenous, rectal and oral administration.[5] The teprosylate is available in intravenous, intramuscular, and orally administered formulations.[11] The codecarboxylate is available in oral form, only,[12] as is the adenylate.[13] A chemically conjugated system, is a system of atoms covalently bonded with alternating single and double bonds (e. ... In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines). ... Pyridoxal-phosphate (PLP, pyridoxal-5-phosphate) is a cofactor of many enzymatic reactions. ... Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. ... Hydrobromic Acid is a chemical compound, with the chemical formula HBr. ... R-phrases 11-20/21/22-36/37/38 S-phrases 16-26-36 RTECS number EX1260000 (R) EX1250000 (S) Supplementary data page Structure and properties n, εr, etc. ... Niacin, also known as nicotinic acid or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH play essential roles in energy metabolism in the living cell. ...


The codecarboxylate is sold under the name Albatran®,[14] the adenylate as Dicertan®,[15] and the hydrochloride salt is sold variously as Artegodan® (Germany), Cardioverina® (countries outside Europe and the United States), Dispamil® (countries outside Europe and the United States), Opdensit® (Germany), Panergon® (Germany), Paverina Houde® (Italy, Belgium), Pavacap (United States), Pavadyl® (United States), Papaverin-Hamelin® (Germany), Paveron® (Germany), Spasmo-Nit® (Germany),[5] Cardiospan®, Papaversan®, Cepaverin®, Cerespan®, Drapavel®, Forpaven®, Papalease®, Pavatest®, Paverolan®, Therapav® (France[16]), Vasospan®, Cerebid®, Delapav®, Dilaves®, Durapav®, Dynovas®, Optenyl®, Pameion®, Papacon®, Pavabid®, Pavacen®, Pavakey®, Pavased®, Pavnell®, Alapav®, Myobid®, Vasal®, Pamelon®, Pavadel®, Pavagen®, Ro-Papav®, Vaso-Pav®, Papanerin-hcl®, Qua bid®, Papital T.R.®, Paptial T.R.®, Pap-Kaps-150®.[17]


References

  1. a  b  c  SID 544606 -- PubChem Substance Summary. Retrieved on 2005 September 25. National Center for Biotechnology Information.
  2. a  Papaverine Material Safety Data Sheet. Retrieved on 2005 September 25.
  3. a  b  c  d  e  f  g  h  Unknown (2000). PAPAVERINE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 2005 September 25. (French)
  4. a  Unknown (2004). Who should not take papaverine?. papaverine Consumer Drug Information. Cerner Multum, Inc. Retrieved on 2005 September 26.
  5. a  b  c  Unknown (1999). PAPAVERINE CHLORHYDRATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 2005 September 25. (French)
  6. a  Liu, James K.; Couldwell, William T (2005). "Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage". Neurocritical Care 2 (2): 124-32. PMID 16159054.  Fulltext options List of Library Holdings
  7. a  Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J (2004). "Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting". European Journal of Cardio-Thoracic Surgery 26 (5): 956-9. PMID 15519189.  Fulltext options List of Library Holdings
  8. a  SID 149219 -- PubChem Substance Summary. Retrieved on 2005 September 26. National Center for Biotechnology Information.
  9. a  Clyde BL, Firlik AD, Kaufmann AM, Spearman MP, Yonas H (1996). "Paradoxical aggravation of vasospasm with papaverine infusion following aneurysmal subarachnoid hemorrhage. Case report". Journal of Neurosurgery 84 (4): 690-5.  PubMed
  10. a  Molécule de base : PAPAVERINE. Retrieved on 2005 September 26. Biam.
  11. a  Unknown (1999). PAPAVERINE TEPROSILATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 2005 September 26. (French)
  12. a  Unknown (1998). PAPAVERINE CODECARBOXYLATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 2005 September 26. (French)
  13. a  Unknown (1998). PAPAVERINE ADENYLATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 2005 September 26. (French)
  14. a  SID 660773 PubChem Substance Summary. Retrieved on 2005 September 25. National Center for Biotechnology Information.
  15. a  SID 660767 -- PubChem Substance Summary. Retrieved on 2005 September 25. National Center for Biotechnology Information.
  16. a  THERAPAV (PRODUIT PUR) - Détail. Retrieved on 2005 September 26. CSST - Service du répertoire toxicologique. (French)
  17. a  SID 660767 -- PubChem Substance Summary - Depositor-Supplied Synonyms: All. Retrieved on 2005 September 26. National Center for Biotechnology Information.

2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 25 is the 268th day of the year (269th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 25 is the 268th day of the year (269th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 25 is the 268th day of the year (269th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 25 is the 268th day of the year (269th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 25 is the 268th day of the year (269th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 25 is the 268th day of the year (269th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... September 26 is the 269th day of the year (270th in leap years) in the Gregorian calendar. ...

External links

  • Links to external chemical sources
v • d • e
Urologicals (G04)
Acidifiers Ammonium chloride, Calcium chloride
Urinary antispasmodics Darifenacin, Emepronium, Flavoxate, Meladrazine, Oxybutynin, Propiverine, Solifenacin, Terodiline, Tolterodine, Trospium
For erectile dysfunction Alprostadil, Apomorphine, Avanafil, Moxisylyte, Papaverine, Phentolamine, Sildenafil, Tadalafil, Udenafil, Vardenafil, Vendafidel, Yohimbine
Other urologicals Acetohydroxamic acid, Collagen, Dimethyl sulfoxide, Magnesium hydroxide, Phenazopyridine, Phenyl salicylate, Succinimide
For benign prostatic hypertrophy 5α-reductase inhibitors: Dutasteride, Finasteride

Alpha blockers: Alfuzosin, Doxazosin, Tamsulosin, Terazosin
Urology is the field of medicine that focuses on the urinary tracts of males and females , and on the reproductive system of males. ... A section of the Anatomical Therapeutic Chemical Classification System. ... These are inorganic chemicals used to produce or become acid. ... Ammonium chloride or Sal Ammoniac (chemically ammonium chloride (NH4Cl); also nushadir salt, zalmiak, sal armagnac, sal armoniac, salmiakki, salmiak and salt armoniack) is, in its pure form, a clear white water-soluble crystalline salt with a biting taste. ... Calcium chloride is a chemical compound of calcium and chlorine. ... The urinary system is a system of organs, tubes, muscles, and nerves that work together to create, store, and carry, urine. ... An antispasmodic is a drug that suppresses smooth muscle contraction, especially in tubular organs. ... Darifenacin (Enablex®, Novartis) is a medication used to treat urinary incontinence. ... Flavoxate is an anticholinergic with antimuscarinic effects. ... Oxybutynin is an anti-cholinergenic pharmaceutical used to relieve urinary and bladder difficulties, including frequent urination and inability to control urination. ... Solifenacin (or Solifenacin succinate) is a urinary antispasmodic. ... Tolterodine is an antimuscarinic drug that is used to treat incontinence. ... Trospium is a urinary antispasmodic. ... Erectile dysfunction (ED) or impotence is a sexual dysfunction characterized by the inability to develop or maintain an erection of the penis. ... Alprostadil is a prostaglandin analogue used as a drug in the treatment of erectile dysfunction and has vasodilatory properties. ... Apomorphine is a type of dopaminergic agonist, a morphine derivative. ... Phentolamine is a competitive nonselective alpha adrenergic receptor antagonist. ... Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. ... Tadalafil is a drug used to treat male erectile dysfunction (impotence). ... Vardenafil (INN) is a PDE5 inhibitor used in the treatment of erectile dysfunction. ... Yohimbine, also known under the outdated names quebrachin, aphrodin, corynine, yohimvetol and hydroergotocin, is the principal alkaloid of the bark of the West-African tree Pausinystalia yohimbe Pierre (formerly Corynanthe yohimbe), family Rubiaceae (Madder family). ... Acetohydroxamic acid is a urological drug. ... Tropocollagen triple helix. ... Dimethyl sulfoxide (DMSO) is the chemical compound (CH3)2SO. This colorless liquid is an important dipolar aprotic solvent. ... Magnesium hydroxide, Mg(OH)2, otherwise known as milk of magnesia, is commonly used as an antacid or a laxative. ... Phenazopyridine is a chemical which, when secreted into the urine, has a specifical local analgesic effect. ... Phenyl Salicylate was introduced in 1886 by Marceli Nencki of Basel. ... Succinimides are drugs that can be used as anticonvulsants. ... Benign prostatic hyperplasia (BPH) is the increase in size of the prostate in middle_aged and elderly men. ... 5α-reductase inhibitors (or 5-alpha-reductase inhibitors) are a group of drugs with antiandrogenic activity, used in the treatment of benign prostatic hyperplasia and androgenic (or androgenetic) alopecia. ... Dutasteride inhibits the conversion of testosterone into dihydrotestosterone. ... Finasteride (marketed as Proscar, Propecia, Fincar, Finpecia, Finax, Finast, Finara, Finalo, Prosteride, Gefina, Finasterid IVAX) is an antiandrogen which acts by inhibiting 5-alpha reductase, the enzyme that converts testosterone to dihydrotestosterone. ... Alpha blockers (also called alpha-adrenergic blocking agents) constitute a variety of drugs which block alpha-adrenergic receptors in arteries and smooth muscles. ... Alfuzosin ((R,S)-N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl) methylamino] propyl] tetrahydro-2-furancarboxamide, provided as the hydrochloride salt) is an alpha-adrenergic blocker used to treat benign prostatic hyperplasia (BPH). ... Doxazosin mesylate, a quinazoline compound sold by Pfizer under the brand name Cardura, is used to treat high blood pressure and benign prostatic hyperplasia. ... Tamsulosin (rINN) (IPA: ) is an α1a-selective alpha blocker used in the symptomatic treatment of benign prostatic hyperplasia (BPH). ... Terazosin (Hytrin) is an alpha blocker used for treatment of symptoms of prostate enlargement (BPH). ...

Herbals: Pygeum africanum, Serenoa repens

  Results from FactBites:
 
UNODC - Bulletin on Narcotics - 1981 Issue 1 - 007 (3678 words)
Papaverine and papaverine hydrochloride and sulphate are described in the pharmacopoeiae of many countries.
To remove residual narcotine from the crude papaverine, 350 g sodium hydroxide were added to 600 g of grey coloured papaverine in 1.51 of water, and the mixture was digested for 2 h at 80-85°C under mechanical stirring, after which it was filtered.
Cryptopine is strongly basic, whereas papaverine is a weakly basic alkaloid and amongst the various grades of aluminium oxide available in India, the active neutral type (pH 6.5, 5% aqueous suspension) and the active acidic type (pH 5.2) were found to be very effective in removing the cryptopine in the papaverine.
UNODC - Bulletin on Narcotics - 1952 Issue 3 - 005 (2529 words)
Papaverine (1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline) is a member of the benzylisoquinoline sub-group of the opium alkaloids and is present in most varieties of opium to the extent of 0.5 to 1 per cent.
Papaverine, in the form of its hydrochloride, is administered intravenously in treating pulmonary arterial embolism and orally or by injection in treating renal or biliary colic.
Spath and Berger[12] synthesized papaverine in low yield by a route which is of interest because it employs intermediates which are likely to be the biogenetic precursors of the alkaloid.
  More results at FactBites »


 

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