A Russian missile has killed 19 people including five children in an apartment block in northern Ukraine, destroying 30 flats as families slept.

Three of the children were one-year-olds in the attack on Pryluky, east of Kyiv, early on Wednesday, and one of the boys died with his mother and grandmother, officials said.

Ukraine’s Volodymyr Zelensky said it was one of Russia’s “most vile strikes”, and suggested the Russian military had carried it out as a “birthday gift” to Vladimir Putin, who turned 74 on Wednesday.

Moscow made no mention of the attack on Pryluky but said its “massive strike” had targeted military industries in Kyiv and elsewhere.

Across the country, the death toll on Wednesday climbed to 25, as Russian strikes claimed two lives in the capital, two in Kremenchuk, and two more in Oleksandriya. More than 430 apartments and private homes were damaged and dozens of people were injured in the attack on the central city of Kremenchuk, the regional leader said.

Rescue teams in Pryluky spent hours searching for victims in the rubble of a five-storey block of flats.

Late in the afternoon rescuers said the body of a fifth child had been found at the scene. More than 50 residents were wounded in the attack that also damaged other residential buildings as well as a youth centre.

Chernihiv regional head Vyacheslav Chaus said the town was hit by five cruise missiles, one of which slammed into the apartment building.

Zelensky named the one-year-old victims as Oleksandr, Kyrylo, and Serhii, and said a boy of eight called Maxsym had also been killed.

Prime Minister Serhii Koretskyi said a boy called Sasha had died with his mother, Kateryna and her mother Viktoriia, and only the boy’s elder sister Olha had survived.

Local reports said they had lived on the fifth floor and that Viktoriia had been looking after her grandson while her daughter worked in a factory.

“The Russians wanted to strike painfully and demonstratively,” Zelensky said, adding that 70 missiles were fired in total.

Zelensky added that Ukraine had itself struck targets in attacks on Russia’s Perm, Samara and Astrakhan regions in the past 24 hours, adding there was “also a response in the Black Sea”, without providing further details.

In Kyiv, many residents spent the night in underground stations to escape the Russian barrage. Mayor Vitaly Klitschko said last week the capital was being torn apart by Russian attacks.

Ukraine’s national police posted pictures online showing what it says is an unexploded Russian Iskander missile in the middle of a Kyiv district. BBC Verify has confirmed the images are genuine and the apparent missile fragments came down in an area of open land surrounded by high-rise apartment buildings.

Another verified video shows damage to cars and what appears to be rubble and a fallen tree in an area surrounded by apartment blocks in Kremenchuk.

Ukraine’s air force said it had succeeded in shooting down five ballistic missiles and 39 cruise missiles and more than 100 drones, including 46 of Russia’s jet-powered drones which have caused so much damage in recent weeks.

However, that would mean that as many as 26 cruise or ballistic missiles penetrated its defences, and Zelensky renewed a call for allies to provide air defence support packages to Ukraine.

According to Zelensky, one of the “key targets” of the attack was Ukraine’s energy infrastructure, which Moscow earlier said it would intensify strikes on following Ukraine’s strikes on Moscow’s energy facilities.

In a separate post on Wednesday, Zelensky said Ukraine had struck four targets in retaliatory attacks in the past 24 hours, including two oil facilities and a training ground as well as a target in the Black Sea.

On Tuesday evening, footage emerged showing a huge plume of smoke engulfing an oil tanker off the coast of Sochi, along the Black Sea in southern Russia.

The Russian transport ministry later said unmanned boats had attacked the Liberian-flagged Aframax Rio oil tanker. Authorities claim the crew was rescued.

Separately, Bulgaria has halted a search for the missing crew of a ship that sank after being hit by a drone on Tuesday, Vice-Admiral Rumen Nikolov from the Maritime Administration Executive Agency said, as reported by Bulgaria’s BTA news agency. No details of the crew are known, but Nikolov said it was assumed there were Syrians on board.

Tracking data shows the ship was anchored at the southern end of the Bosphorus strait until Monday when it entered the Black Sea heading north. Its last reported position on ship-tracking site MarineTraffic was at 23:43 GMT on Monday in what is known as the Bulgarian exclusive economic zone of the Black Sea.

Bulgarian specialist news outlet Maritime.bg reported the Alfa Watan was attacked by a drone and sank 70nm (130km) east of Byala.

As well as the civilian cargo ship, a second vessel – carrying grain – was also hit within Bulgaria’s exclusive economic zone, its Prime Minister Rumen Radev said on Tuesday. The 18 crew members on the second vessel were rescued.

Bulgaria has not said who it believes was behind the attacks, and Moscow has not commented on the incident.

Russia has intensified strikes in the Black Sea, particularly the eastern side, as part of its war against Ukraine. In an evening address on Tuesday, Zelensky claimed Russia was responsible for the attacks.

Additional reporting by BBC Verify