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    Chemistry

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    Also known as: 330784-47-9, Stendra, Spedra, Ta 1790, Ta-1790, (s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
    Molecular Formula
    C23H26ClN7O3
    Molecular Weight
    483.9  g/mol
    InChI Key
    WEAJZXNPAWBCOA-INIZCTEOSA-N
    FDA UNII
    DR5S136IVO
    Avanafil
    Avanafil is an orally available phosphodiesterase type 5 (PDE5) inhibitor with vasodilatory activity. Avanafil selectively inhibits PDE5, thus inhibiting the degradation of cyclic guanosine monophosphate (cGMP) found in the smooth muscle of the corpus cavernosa of the penis. The inhibition of cGMP degradation results in prolonged muscle relaxation, vasodilation, and blood engorgement of the corpus cavernosa, thereby prolonging penile erection.
    Avanafil is a Phosphodiesterase 5 Inhibitor. The mechanism of action of avanafil is as a Phosphodiesterase 5 Inhibitor.
    1 2D Structure

    Avanafil

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
    2.1.2 InChI
    InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
    2.1.3 InChI Key
    WEAJZXNPAWBCOA-INIZCTEOSA-N
    2.1.4 Canonical SMILES
    COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCCC4CO)Cl
    2.1.5 Isomeric SMILES
    COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCC[C@H]4CO)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    DR5S136IVO
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)-1-pyrrolidinyl)-n-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide

    2. Stendra

    2.3.2 Depositor-Supplied Synonyms

    1. 330784-47-9

    2. Stendra

    3. Spedra

    4. Ta 1790

    5. Ta-1790

    6. (s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

    7. Chebi:66876

    8. Dr5s136ivo

    9. (s)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-pyrimidinylmethyl)carbamoyl]pyrimidine

    10. (s)-4-(3-chloro-4-methoxybenzylamino)-2-(2-hydroxymethylpyrrolidin-1-yl)-n-pyrimidin-2-ylmethyl-5-pyrimidinecarboxamide

    11. (s)-4-[(3-chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-n-(2pyrimidinylmethyl)-5-pyrimidinecarboxamide

    12. 4-[(3-chloro-4-methoxybenzyl)amino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

    13. 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

    14. 4-((3-chloro-4-methoxybenzyl)amino)-2-((2s)-2-(hydroxymethyl)pyrrolidin-1-yl)-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

    15. 5-pyrimidinecarboxamide, 4-(((3-chloro-4-methoxyphenyl)methyl)amino)-2-((2s)-2-(hydroxymethyl)-1-pyrrolidinyl)-n-(2-pyrimidinylmethyl)-

    16. Stendra (tn)

    17. Avanafil [usan:inn]

    18. Unii-dr5s136ivo

    19. Zepeed

    20. Ine-5-carboxamide

    21. Spedra (tn)

    22. Avanafil [usan]

    23. Avanafil (usan/inn)

    24. Avanafil [inn]

    25. Avanafil [mi]

    26. Avanafil [vandf]

    27. Avanafil [mart.]

    28. Avanafil [who-dd]

    29. Avanafil 100 Microg/ml In Acetonitrile:dimethylsulfoxide

    30. Schembl118799

    31. Avanafil [orange Book]

    32. Gtpl7448

    33. Chembl1963681

    34. Amy1794

    35. Dtxsid50186727

    36. 4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)-1-pyrrolidinyl)-n-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide

    37. Bdbm50036629

    38. Cs1566

    39. Mfcd11977961

    40. S4019

    41. Ta1790

    42. Zinc11677857

    43. Akos024462448

    44. Ccg-229896

    45. Db06237

    46. Vi-0162

    47. Ncgc00386241-01

    48. As-20106

    49. Hy-18252

    50. Sw219217-1

    51. D03217

    52. Ab01565827_02

    53. J-019006

    54. Q2873270

    55. Brd-k65781196-001-01-4

    56. (s)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[n-(2-pyrimidylmethyl)carbamoyl]-pyrimidine

    57. (s)-4-[(3-chlor-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1- Pyrrolidinyl]-n-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamid

    58. 4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimid

    59. 4-[(3-chloranyl-4-methoxy-phenyl)methylamino]-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-n-(pyrimidin-2-ylmethyl)pyrimid Ine-5-carboxamide

    60. Avanafil; (s)-4-chloro-6-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-n-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide

    61. E6l

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 483.9 g/mol
    Molecular Formula C23H26ClN7O3
    XLogP32.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count9
    Exact Mass483.1785654 g/mol
    Monoisotopic Mass483.1785654 g/mol
    Topological Polar Surface Area125 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity642
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameStendra
    PubMed HealthAvanafil (By mouth)
    Drug ClassesErectile Dysfunction Agent
    Drug LabelSTENDRA (avanafil) is a selective inhibitor of cGMP-specific PDE5.Avanafil is designated chemically as (S)-4-[(3-Chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide and has the following...
    Active IngredientAvanafil
    Dosage FormTablet
    RouteOral
    Strength200mg; 100mg; 50mg
    Market StatusPrescription
    CompanyVivus

    2 of 2  
    Drug NameStendra
    PubMed HealthAvanafil (By mouth)
    Drug ClassesErectile Dysfunction Agent
    Drug LabelSTENDRA (avanafil) is a selective inhibitor of cGMP-specific PDE5.Avanafil is designated chemically as (S)-4-[(3-Chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide and has the following...
    Active IngredientAvanafil
    Dosage FormTablet
    RouteOral
    Strength200mg; 100mg; 50mg
    Market StatusPrescription
    CompanyVivus

    4.2 Drug Indication

    Avanafil is indicated for the treatment of erectile dysfunction.

    FDA Label

    Treatment of erectile dysfunction in adult men.

    In order for Spedra to be effective, sexual stimulation is required.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Avanafil is a strong competitive inhibitor of phosphodiesterase 5 (PDE5) with a demonstrated _in vitro_ IC50 of 5.2 nM. Its inhibitory effects on PDE5 are 100-fold more potent than on PDE6 and >1000-fold more potent than on other PDE enzymes, meaning it is less likely to cause visual disturbances and cardiovascular adverse effects when compared with less selective PDE5 inhibitors such as [sildenafil] and [vardenafil]. It has a relatively quick onset of action allowing for administration as early as 15 minutes prior to sexual activity. PDE5 inhibitors like avanafil can cause significant drug interactions when administered alongside certain antihypertensive agents (e.g. alpha blockers, substantial amounts of alcohol). PDE5 inhibitors have also been associated with the development of non-arteritic anterior ischemic optic neuropathy (NAION), a rare condition that typically presents as sudden loss of vision in one or both eyes and appears to be more common in patients with a "crowded" optic disc. Patients presenting with any degree of vision loss should immediately discontinue use of all PDE5 inhibitors and seek medical attention. In some jurisdictions, a history of NAION or other degenerative retinal disorders is considered a contraindication to avanafil therapy.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    AVANAFIL
    5.2.2 FDA UNII
    DR5S136IVO
    5.2.3 Pharmacological Classes
    Phosphodiesterase 5 Inhibitors [MoA]; Phosphodiesterase 5 Inhibitor [EPC]
    5.3 ATC Code

    G04BE10

    G04BE10

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    G - Genito urinary system and sex hormones

    G04 - Urologicals

    G04B - Urologicals

    G04BE - Drugs used in erectile dysfunction

    G04BE10 - Avanafil

    5.4 Absorption, Distribution and Excretion

    Absorption

    Avanafil is rapidly absorbed following oral administration (Tmax of 30-45 minutes) and appears to have low to moderate oral bioavailability, though formal studies have not been conducted. Administration with a meal results in a mean delay in Tmax of 1.12 to 1.25 hours, a 39% mean reduction in Cmax, and a negligible effect on AUC.

    Route of Elimination

    Following oral administration, avanafil is extensively metabolized. Approximately 62% of a given dose is excreted as metabolites in the feces and approximately 21% as metabolites in the urine.

    Volume of Distribution

    The apparent volume of distribution of avanafil is 47 to 83 L.

    5.5 Metabolism/Metabolites

    Avanafil is extensively metabolized, primarily by CYP3A4 and to a lesser extent by CYP2C9. There are two major metabolites formed, M4 and M16, which exist in the plasma at concentrations 23% and 29% that of the parent compound, respectively. The M16 metabolite lacks pharmacologic effect, but the M4 metabolite has an inhibitory potency for PDE5 18% that of avanafil and accounts for approximately 4% of the observed pharmacologic activity of avanafil.

    5.6 Biological Half-Life

    Studies have demonstrated variability in the terminal elimination half-life of avanafil, with estimates ranging between 5 - 17 hours.

    5.7 Mechanism of Action

    Avanafil inhibits the cGMP-specific phosphodiesterase type 5 (PDE5) which is responsible for the degradation of cGMP in the corpus cavernosum located around the penis. Sexual arousal results in the local release of nitric oxide, which in turn stimulates the enzyme guanylate cyclase to produce cGMP. Elevated levels of cGMP result in local smooth muscle relaxation and increased blood flow to the penis (i.e. an erection). As PDE5 inhibitors like avanafil require the endogenous release of nitric oxide in order to exert their pharmacologic effect, they have no effect on the user in the absence of sexual stimulation/arousal.

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    07-Jan-2021
    19-Sep-2024
    KGS
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    DOSAGE - TABLET;ORAL - 100MG

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