Russia striker Pavel Pogrebnyak has lost his fitness battle to play in Euro 2008.
The 24-year-old suffered a cartilage injury to his left knee when he scored for his country in the 2-1 friendly win over Serbia.
Guus Hiddink had given the Zenit St Petersburg front man the maximum amount of time to recover from the problem, but on Saturday asked UEFA for permission to call up midfielder Oleg Ivanov in his place.
The 21-year-old Sovetov Samara man is yet to win a cap for his country.
Pogrebnyak's injury continues a run of bad luck for the striker, who missed Zenit's 2-0 UEFA Cup final victory over Rangers last month through suspension.
He finished as joint top-scorer in the tournament with 10 goals, a tally matched by Bayern Munich's Luca Toni.
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