diff --git a/pyproject.toml b/pyproject.toml
index 94270634..9f45a831 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "sap-cloud-sdk"
-version = "0.58.0"
+version = "0.58.1"
 description = "SAP Cloud SDK for Python"
 readme = "README.md"
 license = "Apache-2.0"
diff --git a/src/sap_cloud_sdk/core/_tenant.py b/src/sap_cloud_sdk/core/_tenant.py
index 1bb4b1ec..4bf3dbb0 100644
--- a/src/sap_cloud_sdk/core/_tenant.py
+++ b/src/sap_cloud_sdk/core/_tenant.py
@@ -1,4 +1,5 @@
 import re
+from urllib.parse import urlparse, urlunparse
 
 
 _SUBDOMAIN_RE = re.compile(r"^[A-Za-z0-9](?:[A-Za-z0-9\-]{0,61}[A-Za-z0-9])?$")
@@ -18,3 +19,34 @@ def _validate_tenant_subdomain(tenant_subdomain: str | None) -> None:
         return
     if not _SUBDOMAIN_RE.fullmatch(tenant_subdomain):
         raise ValueError(f"Invalid tenant_subdomain: {tenant_subdomain!r}")
+
+
+def _derive_tenant_token_url(
+    token_url: str,
+    identityzone: str,
+    tenant_subdomain: str,
+) -> str:
+    """Return *token_url* with the first hostname label replaced by *tenant_subdomain*.
+
+    Only the leading DNS label of the hostname is replaced when it equals
+    *identityzone*.  All other URL components (scheme, port, path, query,
+    fragment) are preserved verbatim.  If the first label does not match
+    *identityzone*, the original URL is returned unchanged.
+
+    Args:
+        token_url: The configured OAuth2 token endpoint URL.
+        identityzone: Provider identity zone label from the service binding.
+        tenant_subdomain: Validated single-label tenant identifier.
+
+    Returns:
+        The derived token URL with only the first hostname label swapped.
+    """
+    parsed = urlparse(token_url)
+    host = parsed.hostname or ""
+    first_label, sep, rest = host.partition(".")
+    if sep and first_label == identityzone:
+        new_netloc = f"{tenant_subdomain}.{rest}"
+        if parsed.port is not None:
+            new_netloc = f"{new_netloc}:{parsed.port}"
+        return urlunparse(parsed._replace(netloc=new_netloc))
+    return token_url
diff --git a/src/sap_cloud_sdk/core/protocol/http/models.py b/src/sap_cloud_sdk/core/protocol/http/models.py
index e8e68014..f5e0e09f 100644
--- a/src/sap_cloud_sdk/core/protocol/http/models.py
+++ b/src/sap_cloud_sdk/core/protocol/http/models.py
@@ -13,7 +13,10 @@
 from oauthlib.oauth2 import BackendApplicationClient
 from requests_oauthlib import OAuth2Session
 
-from sap_cloud_sdk.core._tenant import _validate_tenant_subdomain
+from sap_cloud_sdk.core._tenant import (
+    _validate_tenant_subdomain,
+    _derive_tenant_token_url,
+)
 
 logger = logging.getLogger(__name__)
 
@@ -112,7 +115,9 @@ def _fetch_token(self, tenant_subdomain: Optional[str]) -> OAuth2Session:
             and token_url is not None
         ):
             _validate_tenant_subdomain(tenant_subdomain)
-            token_url = str(token_url).replace(str(identityzone), tenant_subdomain)
+            token_url = _derive_tenant_token_url(
+                str(token_url), str(identityzone), tenant_subdomain
+            )
 
         client = BackendApplicationClient(client_id=str(self._config.client_id))
         oauth = OAuth2Session(client=client)
diff --git a/tests/core/unit/test_http_client.py b/tests/core/unit/test_http_client.py
index 46c7fd4d..83d4c997 100644
--- a/tests/core/unit/test_http_client.py
+++ b/tests/core/unit/test_http_client.py
@@ -284,3 +284,25 @@ def test_valid_subdomain_replaces_identityzone_in_token_url(self):
             provider._fetch_token("tenant-123")
         call_kwargs = mock_session.fetch_token.call_args[1]
         assert call_kwargs["token_url"] == "https://tenant-123.authentication.region/oauth/token"
+
+    def test_identityzone_in_path_is_not_replaced(self):
+        """str.replace would corrupt the URL if identityzone appears in the path too."""
+        cfg = MagicMock()
+        # token_url whose path also contains the identityzone value
+        cfg.token_url = "https://provider-zone.authentication.region/provider-zone/token"
+        cfg.identityzone = "provider-zone"
+        cfg.client_id = "cid"
+        cfg.client_secret = "csecret"
+        factory = MagicMock(return_value=cfg)
+        factory.has_changed = MagicMock(return_value=False)
+        provider = XsuaaAuthProvider(factory)
+
+        with patch("sap_cloud_sdk.core.protocol.http.models.OAuth2Session") as mock_oauth_cls:
+            mock_session = MagicMock()
+            mock_oauth_cls.return_value = mock_session
+            mock_session.fetch_token.return_value = {"access_token": "tok", "expires_in": 3600}
+            provider._fetch_token("tenant-abc")
+
+        call_kwargs = mock_session.fetch_token.call_args[1]
+        # Only the first hostname label must be replaced; path segment untouched
+        assert call_kwargs["token_url"] == "https://tenant-abc.authentication.region/provider-zone/token"
diff --git a/tests/core/unit/test_tenant.py b/tests/core/unit/test_tenant.py
index b1d259d4..8839b829 100644
--- a/tests/core/unit/test_tenant.py
+++ b/tests/core/unit/test_tenant.py
@@ -2,7 +2,7 @@
 
 import pytest
 
-from sap_cloud_sdk.core._tenant import _validate_tenant_subdomain
+from sap_cloud_sdk.core._tenant import _validate_tenant_subdomain, _derive_tenant_token_url
 
 
 class TestValidateTenantSubdomain:
@@ -36,3 +36,42 @@ def test_invalid_subdomains_raise_value_error(self, invalid, description):
 
     def test_none_is_a_no_op(self):
         _validate_tenant_subdomain(None)  # must not raise
+
+
+class TestDeriveTenantTokenUrl:
+    BASE = "https://provider-zone.authentication.eu10.hana.ondemand.com/oauth/token"
+    IZ = "provider-zone"
+
+    def test_replaces_first_label_only(self):
+        result = _derive_tenant_token_url(self.BASE, self.IZ, "tenant-123")
+        assert result == "https://tenant-123.authentication.eu10.hana.ondemand.com/oauth/token"
+
+    def test_scheme_preserved(self):
+        result = _derive_tenant_token_url(self.BASE, self.IZ, "tenant-123")
+        assert result.startswith("https://")
+
+    def test_path_preserved(self):
+        result = _derive_tenant_token_url(self.BASE, self.IZ, "tenant-123")
+        assert result.endswith("/oauth/token")
+
+    def test_identityzone_in_path_not_replaced(self):
+        # Even if identityzone value appears in the path, it must not be touched
+        url = f"https://provider-zone.auth.region/{self.IZ}/token"
+        result = _derive_tenant_token_url(url, self.IZ, "tenant-abc")
+        assert result == f"https://tenant-abc.auth.region/{self.IZ}/token"
+
+    def test_port_preserved_when_present(self):
+        url = "https://provider-zone.authentication.region:8443/oauth/token"
+        result = _derive_tenant_token_url(url, self.IZ, "tenant-123")
+        assert result == "https://tenant-123.authentication.region:8443/oauth/token"
+
+    def test_no_match_returns_original_url(self):
+        url = "https://other-zone.authentication.region/oauth/token"
+        result = _derive_tenant_token_url(url, self.IZ, "tenant-123")
+        assert result == url
+
+    def test_single_label_hostname_returns_original(self):
+        # token_url with no dots in host — nothing to replace
+        url = "https://provider-zone/oauth/token"
+        result = _derive_tenant_token_url(url, self.IZ, "tenant-123")
+        assert result == url
diff --git a/uv.lock b/uv.lock
index f392fca5..f7db0eff 100644
--- a/uv.lock
+++ b/uv.lock
@@ -4363,7 +4363,7 @@ wheels = [
 
 [[package]]
 name = "sap-cloud-sdk"
-version = "0.58.0"
+version = "0.58.1"
 source = { editable = "." }
 dependencies = [
     { name = "cryptography" },