Coadministration is contraindicated as it results in increased plasma concentrations of oral midazolam, thereby increasing the risk of extreme sedation and respiratory depression. Coadministration with Kaletra increased the AUC of oral midazolam by 13-fold and increased the AUC of parenteral midazolam by 4-fold due to CYP3A inhibition by Kaletra. Kaletra must not be coadministered with ORALLY administered midazolam, whereas caution should be used with coadministration of Kaletra and PARENTERAL midazolam. If Kaletra is coadministered with parenteral midazolam, it should be done in an intensive care unit (ICU) or similar setting which ensures close clinical monitoring and appropriate medical management in case of respiratory depression and/or prolonged sedation. Dosage adjustment for midazolam should be considered especially if more than a single dose of midazolam is administered.
Kaletra Summary of Product Characteristics, AbbVie Ltd, January 2021.

Coadministration of lopinavir and ORALLY administered midazolam is contraindicated due to the potential for prolonged or increased sedation or respiratory depression. Kaletra is contraindicated with drugs that are highly dependent on CYP3A for clearance and for which elevated plasma concentrations are associated with serious and/or life-threatening reactions. Midazolam is extensively metabolized by CYP3A4. Increases in the concentration of midazolam are expected to be significantly higher with oral than parenteral administration. If lopinavir is coadministered with PARENTERAL midazolam, close clinical monitoring for respiratory depression and/or prolonged sedation should be exercised and dosage adjustment should be considered.
Kaletra Prescribing Information, AbbVie Ltd, October 2020.