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Avanafil

Avanafil Structure
Avanafil
  • CAS No.330784-47-9
  • Chemical Name:Avanafil
  • CBNumber:CB91503998
  • Molecular Formula:C23H26ClN7O3
  • Formula Weight:483.95
  • MOL File:330784-47-9.mol
Avanafil Property
  • Melting point 150-152°C
  • Density 1.372
  • storage temp. Sealed in dry,Store in freezer, under -20°C
  • solubility DMSO (Slightly), Methanol (Slightly, Heated)
  • form Solid
  • pka 11.84±0.46(Predicted)
  • color White to Off-White
  • InChIKey WEAJZXNPAWBCOA-INIZCTEOSA-N
  • SMILES C1(N2CCC[C@H]2CO)=NC=C(C(NCC2=NC=CC=N2)=O)C(NCC2=CC=C(OC)C(Cl)=C2)=N1
  • CAS DataBase Reference 330784-47-9(CAS DataBase Reference)
  • FDA UNII DR5S136IVO
  • NCI Drug Dictionary avanafil
  • ATC code G04BE10
  • UNSPSC Code 12352200
  • NACRES NA.77
Safety
  • HS Code  :29339900
  • NFPA 704:
    0
    2 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H302
  • Precautionary statements P280-P305+P351+P338
Avanafil Price More Price(2)
  • Brand: Sigma-Aldrich(India)
  • Product number: SML2799
  • Product name : Avanafil
  • Purity: ≥98% (HPLC)
  • Packaging: 100MG
  • Price: ₹3163.5
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: SML2799
  • Product name : Avanafil
  • Purity: ≥98% (HPLC)
  • Packaging: 500MG
  • Price: ₹11888.1
  • Updated: 2022/06/14
  • Buy: Buy

Avanafil Chemical Properties,Usage,Production

  • Description Avanafil (Zepeed) was approved by the Korean Health Ministry for the treatment of erectile dysfunction (ED) in August 2011. Avanafil is a highly selective type 5 phosphodiesterase (PDE5) inhibitor. Avanafil is reported to be the most selective PDE5 inhibitor on the market. The onset of Tmax and half-life also varies among the marketed PDE5 inhibitors. Sildenafil has a Tmax at 1 h and a half-life of 3–5 h. Vardenafil is somewhat similar with a Tmax of 0.6 h and a half-life of 4–6 h. Tadalafil has the longest half-life among the marketed drugs with a half-life of 17 h. Avanafil has a fast onset of action reaching Tmax in 0.6 h with a half-life of 1.2 h. A synthesis of avanafil (TA-1790) is described in the patent literature. The main elimination route of avanafil is through the bile and feces. Avanafil was also found to be reabsorbed through enterohepatic recirculation.
  • Chemical Properties White Solid
  • Originator Mitsubishi Tanabe Pharma Corporation (Japan)
  • Uses A phosphodiesterase (PDE5) inhibitor, used to treat erectile dysfunction.
  • Uses Avanafil is a highly selective PDE5 inhibitor with IC50 of 1 nM.
  • Definition ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-[(3-chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid with the amino group of pyrimidin-2-ylmethylamine Used for treatment of erectile dysfunction.
  • brand name Zepeed
  • Clinical Use Avanafil was originally discovered at Tanabe Seiyaku (now Mitsubishi Tanabe). JW Pharmaceutical (previously Choongwae Pharma) and VIVUS have since developed and launched avanafil, which is an oral PDE5 inhibitor for the treatment of erectile dysfunction (ED). Although many marketed PDE5 inhibitors (e.g. sildenafil, vardenafil and tadalafil) are available for the treatment of ED, many patients are still unable to achieve the desired results and experience undesired side-effects with these existing medications. As such, second-generation PDE5 inhibitors with enhanced PDE5 selectivity, shorter systemic half-lives, and improved tolerability are desired. Developed to meet these criteria, Avanafil exhibited good oral bioavailability and PDE5 selectivity in both preclinical studies and clinical trials. Avanafil had a short onset of action (35 min) and short half-life (1.5 h).
  • Synthesis The synthesis presented is based on the published patent procedure and is outlined in the scheme. Commercially available 4-chloro-2-(methylsulfanyl)pyrimidine- 5-carboxylic acid ethyl ester (25) was treated with 3- chloro-4-methoxybenzylamine (26) and triethylamine at room temperature to give 4-benzylaminopyrimidine derivative 27 in 96% yield. Sulfide 27 was then oxidized with m-chloroperbenzoic acid (m-CPBA), followed bytreatment with L-prolinol and triethylamine to afford ethyl pyrimidinate 28 in 83% yield. This ester was then saponified with 10% sodium hydroxide to give pyrimidine- 5-carboxylic acid 29 in 80% yield, which then underwent conventional amide bond formation using 2-(aminomethyl) pyrimidine (29a), N-(3-dimethylaminopropal)-N0-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxybenzotriazole hydrate (HOBt) to give avanafil (IV) in 83% yield.

    Synthesis_330784-47-9

  • Drug interactions Potentially hazardous interactions with other drugs
    Alpha-blockers: enhanced hypotensive effect - maximum dose 50 mg.
    Antibacterials: concentration possibly increased by clarithromycin and telithromycin - avoid; concentration increased by erythromycin - reduce avanafil dose; concentration reduced by rifampicin - avoid.
    Antifungals: concentration increased by ketoconazole - avoid and fluconazole - reduce avanafil dose; concentration possibly increased by itraconazole and voriconazole - avoid.
    Antivirals: concentration possibly increased by atazanavir, indinavir and saquinavir - avoid; concentration possibly reduced by efavirenz - avoid; concentration possibly increased by fosamprenavir - reduce avanafil dose; concentration significantly increased by ritonavir - avoid.
    Aprepitant: concentration possibly increased by aprepitant - reduce avanafil dose.
    Calcium channel blockers: concentration possibly increased by diltiazem and verapamil - reduce avanafil dose.
    Cobicistat: concentration of avanafil possibly increased - avoid.
    Nicorandil: possibly enhanced hypotensive effect - avoid.
    Nitrates: enhanced hypotensive effect - avoid.
    Riociguat: possibly enhanced hypotensive effect - avoid.
  • Metabolism Avanafil is metabolised in the liver mainly by the cytochrome P450 isoenzyme CYP3A4 and to a minor extent by the CYP2C isoform. Two major metabolites are produced, one of which is active. Avanafil is excreted as metabolites mainly in the faeces (approximately 63%) in the urine (approximately 21%).
  • References [1] kotera j, mochida h, inoue h, noto t, fujishige k, sasaki t, kobayashi t, kojima k, yee s, yamada y, kikkawa k, omori k. avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction. j urol. 2012 aug;188(2):668-74.
    [2] cui ys, li n, zong ht, yan hl, zhang y. avanafil for male erectile dysfunction: a systematic review and meta-analysis. asian j androl. 2014 may-jun;16(3):472-7.
Avanafil Preparation Products And Raw materials
Raw materials
Preparation Products
Avanafil Suppliers
Global(457)Suppliers
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  • Tel：+86-86-13583358881<br/>+8618560316533
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Avanafil Spectrum
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  • 原料药【仅供科研】
  • C23H26ClN7O3
  • 阿伐那非,10 MM DMSO 溶液
  • 阿伐那非标准品
  • 阿伐那非-[13C,D5]/精确称量
  • 阿伐那非|||TA1790
  • 阿伐那非 开票名称:4-[[(3-氯-4-甲氧基苯基)甲基]氨基]-2-[(2S)-2-羟甲基-1-吡咯烷基]-5-嘧啶羧酸乙酯
  • 2-[(S)-2-(羟甲基)-1-吡咯烷基]-4-[(3-氯-4-甲氧基苄基)氨基]-N-[(2-嘧啶基)甲基]-5-嘧啶甲酰胺
  • 阿伐那非-D4
  • 便携式多参数水质分析仪
  • AVANAFIL; (S)-4-CHLORO-6-((3-CHLORO-4-METHOXYBENZYL)AMINO)-2-(2-(HYDROXYMETHYL)PYRROLIDIN-1-YL)-N-(PYRIMIDIN-2-YLMETHYL)PYRIMIDINE-6-CARBOXAMIDE

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