The SS-N-3 Shaddock, Russian name P-5 Pyatyorka (Пятёрка) was the world's first long range anti-shipping cruise missile, and the third model of anti-ship missile to be produced by the USSR. The first two, the SS-N-1 Scrubber and SS-N-2 Styx were medium and short-range weapons, respectively. SS-N-3 was designed to be launched from ships, submarines and shore batteries against large warships; specifically the numerous aircraft carriers of the United States Navy and British Royal Navy. Its long range would allow a Soviet surface attack group to engage from beyond the effective combat range of carrier aircraft.

The Shaddock missile itself was a long (11.5 meter) cylindrical missile with swept wings and a pointed radome for a nose cone, protecting its active radar guidance system. It was launched by two solid-fueled rocket boosters, which brought it up to about 0.4 Mach, at which point a large turbojet engine took over for the cruise phase of flight. Under jet power, the missile would accelerate to 0.8 Mach, cruising at about 300-500 meters.

Its onboard inertial navigation system was programmed before launch with the location of its target, and would guide the missile to the general vicinity. A data link, which could be provided by ships, shore station or aircraft, updated the target coordinates while in flight. At a pre-determined point, the missile engaged its radar, searching a sector ahead of the weapon for targets. Once acquired, the missile would begin a shallow dive toward the target, detonating on impact, or at a predetermined range for nuclear-armed versions. Some of the early nuclear-tipped Shaddocks lacked the active radar altogether. The missile's payload consisted either of a 950kg semi-armor-piercing conventional explosive or a 350kt boosted fission nuclear warhead, likely the same type employed on the similar SS-N-12 Sandbox.

Launch platforms included the Kynda class cruiser, Kresta-I class cruiser and Whiskey class submarine. Three versions of the Whiskey existed, the 'single cylinder', 'twin cylinder' and 'long bin' versions, carrying one, two or four SS-N-3 missiles respectively. They had to surface to fire, and remain surfaced until the missiles had been handed off to a data link from another unit, greatly increasing the sub's vulnerability. None saw a terribly long service life. The SS-N-3 missile, however, remained in service until the late 1980s on the Kynda cruisers. Some shore-launched SS-N-3 missiles, all conventional-armed, may remain in service in Romania and several former Soviet republics.

While the SS-N-3 was regarded as a serious threat in the 1960s and early 1970s due to its sophisticated guidance and large warhead, by the late 1970s improved fire control systems for both guns and missiles rendered it quite easy to defend against. It also had no particular resistance to soft kill countermeasures like chaff and ECM. Even Soviet estimates suggested that the SS-N-3 would be considered no worse than a distraction against a US battle group with even a single Aegis or NTU escort, or against a British task force including several Type 42 destroyers. Against a modern air defense escort like a VLS-equipped Ticonderoga, a Type 45 destroyer or something like a Russian Slava class cruiser, it would be nearly useless.

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