The capital of the Paeonian dynasty was probably located in the area of Astibus (Astivos, Άστιβος in ancient Greek). The Paeonians lived in the region west of the fertile Axius river basin in the 5th and 4th centuries BC. The two tribes that lived along the river Astibo, a mouth of the Axius, were the Derrons, named after their healing god Darron, and the Laians, who, following the example of the Greek city-states in Chalkidiki, minted their own heavy coins as a sign of their sovereignty. Although these tribes were severely weakened by the Persian invasion of 480 BC under the leadership of King Xerxes I, they remained a formidable power and a well-organized people known for the production of their exceptionally heavy coins with emblems, including domesticated specimens of the wild aurochs, for which Paeonia was also famous. They were incorporated into the Macedonian Empire by Alexander I before 360 BC.
The area itself is first mentioned in the writings of the 3rd century BC historian Polien, who speaks of a river called ‘Astibo’, which is believed to be today’s Bregalnica River. Polien also states that the Paeonian emperors were crowned in Astibo.
The first mention of a settlement dates back to the reign of the Roman emperor Tiberius (14-37 AD).), when Estipeon is mentioned as an important settlement in the Roman province of Paeonia and as a second stop on the Roman road from Stobi to Pautalia.
In the 6th century, the Slavs invaded the Balkans and destroyed the Byzantine settlement, whereupon the Slavic tribe of Sagudats settled the area permanently.