Avanafil
- CAS No.
- 330784-47-9
- Chemical Name:
- Avanafil
- Synonyms
- Stendra;vanafil;4-((3-chloro-4-Methoxybenzyl)aMino)-2-(2-(hydroxyMethyl)pyrrolidin-1-yl)-N-(pyriMidin-2-ylMethyl)pyriMidine-5-carboxaMide;(S)-4-((3-Chloro-4-Methoxybenzyl)aMino)-2-(2-(hydroxyMethyl)pyrrolidin-1-yl)-N-(pyriMidin-2-ylMethyl)pyriMidine-5-carboxaMide;U 53;U-53;D03217;avanfil;AVANAFE;Avanafil
- CBNumber:
- CB91503998
- Molecular Formula:
- C23H26ClN7O3
- Molecular Weight:
- 483.95
- MDL Number:
- MFCD11977961
- MOL File:
- 330784-47-9.mol
| 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 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302 | |||||||||
| Precautionary statements | P280-P305+P351+P338 | |||||||||
| HS Code | 29339900 | |||||||||
| NFPA 704 |
|
Avanafil price More Price(34)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML2799 | Avanafil ≥98% (HPLC) | 330784-47-9 | 100MG | $33.8 | 2023-06-20 | Buy |
| Sigma-Aldrich | SML2799 | Avanafil ≥98% (HPLC) | 330784-47-9 | 500MG | $127 | 2023-06-20 | Buy |
| Cayman Chemical | 23024 | Avanafil ≥98% | 330784-47-9 | 100mg | $32 | 2024-03-01 | Buy |
| Cayman Chemical | 23024 | Avanafil ≥98% | 330784-47-9 | 250mg | $70 | 2024-03-01 | Buy |
| Cayman Chemical | 23024 | Avanafil ≥98% | 330784-47-9 | 500mg | $116 | 2024-03-01 | Buy |
Avanafil Chemical Properties,Uses,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.
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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ZHEJIANG JIUZHOU CHEM CO., LTD | +86-0576225566889 +86-13454675544 | admin@jiuzhou-chem.com；jamie@jiuzhou-chem.com；alice@jiuzhou-chem.com | China | 20000 | 58 |
| Firsky International Trade (Wuhan) Co., Ltd | +8615387054039 | admin@firsky-cn.com | China | 436 | 58 |
| Wuhan Marco Pharmaceutical Technology Co., Ltd. | +86-86-18572802410 +8618572802410 | sales@marcopht.com | China | 55 | 58 |
| ANHUI WITOP BIOTECH CO., LTD | +8615255079626 | eric@witopchemical.com | China | 23556 | 58 |
| Wuhan Quanjinci New Material Co.,Ltd. | +8615271838296 | kyra@quanjinci.com | China | 1532 | 58 |
| Shaanxi Cuikang Pharmaceutical Technology Co., Ltd | +86-19164747840 +86-13119157289 | 13119157289@163.com | China | 2971 | 58 |
| Wuhan Mayue Longteng Technology Development Co., Ltd. | +undefined15171477138 | helen.yan@lantu-tech.com | China | 287 | 58 |
| Shanghai Getian Industrial Co., LTD | +86-15373193816 +86-15373193816 | mike@ge-tian.com | China | 272 | 58 |
| Dorne Chemical Technology co. LTD | +86-13583358881 +86-18560316533 | Ethan@dornechem.com | China | 294 | 58 |
| Wuhan Cell Pharmaceutical Co., Ltd | +86-13129979210 +86-13129979210 | sales@cellwh.com | China | 376 | 58 |
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- Avanafil occurs as white crystalline powder, molecular formula C23H26ClN7O3 and molecular weight of 483.95 and is slightly sol....
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View Lastest Price from Avanafil manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-24 | Avanafil
330784-47-9
|
US $27.00 / box | 1box | 99% | 10000box | Shanghai Getian Industrial Co., LTD | |
 |
2024-04-24 | Avanafil
330784-47-9
|
US $30.00 / Box | 1Box | 99.99% | 10000000000 | zhuzhou dingcheng meihei comestic co.,ltd | |
 |
2024-04-24 | Avanafil
330784-47-9
|
US $10.00-10.00 / ASSAYS | 1ASSAYS | 99% | 100kg | Dorne Chemical Technology co. LTD |