Pentamidine

Pentamidine

Clinical data
Trade names	Nebupent, Pentam, others
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	IV, IM, inhalation
ATC code	P01CX01 (WHO) QP51AF02 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Protein binding	69%
Biological half-life	6.4-9.4 hours
Identifiers
IUPAC name 4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide
Synonyms	pentamidine diisethionate, pentamidine dimesilate
CAS Number	100-33-4 Y
PubChem (CID)	4735
DrugBank	DB00738 Y
ChemSpider	4573 Y
UNII	673LC5J4LQ Y
KEGG	D08333 Y
ChEBI	CHEBI:45081 Y
ChEMBL	CHEMBL55 Y
ECHA InfoCard	100.002.583
Chemical and physical data
Formula	C19H24N4O2
Molar mass	340.42 g/mol
3D model (Jmol)	Interactive image
SMILES O(c1ccc(cc1)C(=[N@H])N)CCCCCOc2ccc(C(=[N@H])N)cc2
InChI InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23) Y Key:XDRYMKDFEDOLFX-UHFFFAOYSA-N Y

Pentamidine is an antimicrobial medication used to treat African trypanosomiasis, leishmaniasis, babesiosis, and to prevent and treat pneumocystis pneumonia (PCP) in people with poor immune function. In African trypanosomiasis it is used for early disease before central nervous system involvement, as a second line option to suramin. It is an option for both visceral leishmaniasis and cutaneous leishmaniasis. Pentamidine can be given by injection into a vein or muscle or by inhalation.

Common side effects of the injectable form include low blood sugar, pain at the site of injection, nausea, vomiting, low blood pressure, and kidney problems. Common side effects of the inhaled form include wheezing, cough, and nausea. It is unclear if doses should be changed in those with kidney or liver problems. Pentamidine is not recommended in early pregnancy but may be used in later pregnancy. Its safety during breastfeeding is unclear. While how the medication works is not entirely clear, it is believed to involve decreasing the making of DNA, RNA, and protein.

Pentamidine came into medical use in 1937. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. In regions of the world where the disease is common pentamidine is provided for free by the World Health Organization. In the United States as of 2016 the inhalation powder costs 122.84 USD and a vial for injection costs 45.31 USD a dose. Since it was found useful for PCP pneumonia the price has been increased greater than ten times.