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阿伐那非
Tier C — Watch / tradeAvanafil · all drugs expiring in 2028 →
田边三菱制药株式会社
Originator
2011
First approval
2028
Expiry (public)
$0.03B ▲
Peak sales
化学药
Type
Targets：PDE5A
Brand：Spedra、Stendra、海驰、Zepeed、Stendra/Spedra
Indications (approved)：勃起功能障碍
Regional status
US
批准上市
2012-04-27
EU
批准上市
2013-06-20
China
批准上市
2021-03-23
Japan
-
Synthetic routes & intermediates7 routes
Originator routes × 1Optimised (non-patent) × 6Process routes × 0
Routes are ordered originator first, then optimised / process (non-patent) routes; each lists steps, overall yield and the intermediate table (code / CAS / name) — ready for supplier sourcing and RFQ. Rendered by this site from structured data; no third-party route graphics used.
OriginatorRoute 1Steps 7 · Total yield 145 g
| Code | CAS No. | Intermediate |
|---|---|---|
| AVAN-001 | 87-13-8 | diethyl 2-(ethoxymethylene)malonate |
| AVAN-002 | 2986-19-8 | methyl carbamimidothioate |
| AVAN-003 | 53554-29-3 | ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate |
| AVAN-004 | 5909-24-0Available | ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate |
| AVAN-005 | 41965-95-1 | (3-chloro-4-methoxyphenyl)methanamine hydrochloride |
| AVAN-006 | 330785-81-4 | ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate |
| AVAN-007 | 330785-82-5 | ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate |
| AVAN-008 | 23356-96-9 | (S)-pyrrolidin-2-ylmethanol |
| AVAN-009 | 330785-83-6 | ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate |
| AVAN-010 | 330785-84-7 | (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid |
| AVAN-011 | 372118-67-7 | pyrimidin-2-ylmethanamine hydrochloride |
OptimisedRoute 2Steps 5 · Total yield 2.9 g
| Code | CAS No. | Intermediate |
|---|---|---|
| AVAN-004 | 5909-24-0Available | ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate |
| AVAN-006 | 330785-81-4 | ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate |
| AVAN-008 | 23356-96-9 | (S)-pyrrolidin-2-ylmethanol |
| AVAN-012 | 115514-77-7 | (3-chloro-4-methoxyphenyl)methanamine |
| AVAN-013 | 330786-34-0 | 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid |
| AVAN-014 | 75985-45-4 | pyrimidin-2-ylmethanamine |
| AVAN-015 | 1364671-62-4 | 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| AVAN-016 | 1364671-52-2 | 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
OptimisedRoute 3Steps 3 · Total yield 1.96 g
| Code | CAS No. | Intermediate |
|---|---|---|
| AVAN-008 | 23356-96-9 | (S)-pyrrolidin-2-ylmethanol |
| AVAN-017 | 320407-92-9 | 4-(bromomethyl)-2-chloro-1-methoxybenzene |
| AVAN-018 | 71-30-7 | 4-aminopyrimidin-2(1H)-one |
| AVAN-019 | - | 4-((3-chloro-4-methoxybenzyl)amino)pyrimidin-2(1H)-one |
| AVAN-020 | 1450983-42-2 | (S)-(1-(4-((3-chloro-4-methoxybenzyl)amino)pyrimidin-2-yl)pyrrolidin-2-yl)methanol |
| AVAN-021 | 1450983-43-3 | N-(pyrimidin-2-ylmethyl)formamide |
OptimisedRoute 4Steps 3 · Total yield 1.96 g
| Code | CAS No. | Intermediate |
|---|---|---|
| AVAN-008 | 23356-96-9 | (S)-pyrrolidin-2-ylmethanol |
| AVAN-017 | 320407-92-9 | 4-(bromomethyl)-2-chloro-1-methoxybenzene |
| AVAN-018 | 71-30-7 | 4-aminopyrimidin-2(1H)-one |
| AVAN-019 | - | 4-((3-chloro-4-methoxybenzyl)amino)pyrimidin-2(1H)-one |
| AVAN-021 | 1450983-43-3 | N-(pyrimidin-2-ylmethyl)formamide |
| AVAN-022 | - | 4-((3-chloro-4-methoxybenzyl)amino)-2-oxo-N-(pyrimidin-2-ylmethyl)-1,2-dihydropyrimidine-5-carboxamide |
OptimisedRoute 5Steps 3 · Total yield 39 g
| Code | CAS No. | Intermediate |
|---|---|---|
| AVAN-008 | 23356-96-9 | (S)-pyrrolidin-2-ylmethanol |
| AVAN-012 | 115514-77-7 | (3-chloro-4-methoxyphenyl)methanamine |
| AVAN-014 | 75985-45-4 | pyrimidin-2-ylmethanamine |
| AVAN-023a | 2972-52-3 | 2,4-dichloropyrimidine-5-carbonyl chloride |
| AVAN-023b | 55084-66-7 | 4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride |
| AVAN-023d | 1534330-76-1 | 2,4-bis(methylthio)pyrimidine-5-carbonyl chloride |
| AVAN-023c | 1534330-77-2 | 4-bromo-2-(methylthio)pyrimidine-5-carbonyl chloride |
| AVAN-024b | 1534330-75-0 | 4-chloro-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| AVAN-024a | 1534330-72-7 | 2,4-dichloro-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| AVAN-024d | 1534330-74-9 | 2,4-bis(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| AVAN-024 | 1534330-75-0 | 4-chloro-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| AVAN-025a | 1364671-62-4 | 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| AVAN-025b | 1534330-73-8 | 2-chloro-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| AVAN-024c | - | 4-bromo-2-(methylthio)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
OptimisedRoute 6Steps 8 · Total yield 519 mg
| Code | CAS No. | Intermediate |
|---|---|---|
| AVAN-001 | 87-13-8 | diethyl 2-(ethoxymethylene)malonate |
| AVAN-005 | 41965-95-1 | (3-chloro-4-methoxyphenyl)methanamine hydrochloride |
| AVAN-008 | 23356-96-9 | (S)-pyrrolidin-2-ylmethanol |
| AVAN-014 | 75985-45-4 | pyrimidin-2-ylmethanamine |
| AVAN-026 | 62-56-6Available | thiourea |
| AVAN-027 | - | - |
| AVAN-028 | - | - |
| AVAN-029 | - | - |
| AVAN-030 | - | - |
| AVAN-031 | - | - |
| AVAN-032 | - | - |
| AVAN-033 | - | - |
OptimisedRoute 7Steps 5 · Total yield 1.74 g
| Code | CAS No. | Intermediate |
|---|---|---|
| AVAN-008 | 23356-96-9 | (S)-pyrrolidin-2-ylmethanol |
| AVAN-009 | 330785-83-6 | ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate |
| AVAN-014 | 75985-45-4 | pyrimidin-2-ylmethanamine |
| AVAN-034 | 105-56-6Available | ethyl 2-cyanoacetate |
| AVAN-035 | 57-13-6 | urea |
| AVAN-036 | 61679-83-2 | ethyl (E)-2-cyano-3-ureidoacrylate |
| AVAN-037 | 20187-46-6 | ethyl 6-amino-2-oxo-1,2-dihydropyrimidine-5-carboxylate |
| AVAN-038 | 13719-57-8 | 2-chloro-4-(chloromethyl)-1-methoxybenzene |
| AVAN-039 | 330785-99-4 | ethyl 6-((3-chloro-4-methoxybenzyl)amino)-2-oxo-1,2-dihydropyrimidine-5-carboxylate |
Frequently asked questions
What are the approved indications of Avanafil?
Approved indications include: 勃起功能障碍.
When does the Avanafil patent expire?
Based on public sources, the Avanafil patent expires in 2028.
How many synthesis routes are recorded for Avanafil?
7 synthesis routes are recorded; the shortest is 3 steps with 1.96 g total yield. Intermediates in each route carry codes and CAS numbers.
Where can I buy Avanafil intermediates?
3 intermediate CAS of Avanafil are available through the Unibest supply network — see the route tables on this page and request a quote per CAS.
How do I get a quote for Avanafil intermediates?
Open the CAS profile of the target intermediate from this page, or submit an RFQ directly — the CAS enters the matching flow automatically and the supply network responds with quotes.
Source: cross-verified data (structured fields only) · 2026-09-24