Pentamidine

Pentamidine
Clinical data
Trade namesNebupent, Pentam, others[1]
Other namespentamidine diisethionate, pentamidine dimesilate
AHFS/Drugs.comMonograph
Routes of
administration		IV, IM, inhalation
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding69%
Elimination half-life6.4-9.4 hours
Identifiers
IUPAC name
  • 4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.583
Chemical and physical data
FormulaC19H24N4O2
Molar mass340.427 g·mol−1
3D model (JSmol)
Melting point186 °C (367 °F) (dec.)
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
  (verify)

Pentamidine is an antimicrobial medication used to treat African trypanosomiasis, leishmaniasis, Balamuthia infections,[2] babesiosis, and to prevent and treat pneumocystis pneumonia (PCP) in people with poor immune function.[1] In African trypanosomiasis it is used for early disease before central nervous system involvement, as a second line option to suramin.[1] It is an option for both visceral leishmaniasis and cutaneous leishmaniasis.[1] Pentamidine can be given by injection into a vein or muscle or by inhalation.[1]

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.[1] Common side effects of the inhaled form include wheezing, cough, and nausea.[1] It is unclear if doses should be changed in those with kidney or liver problems.[1] Pentamidine is not recommended in early pregnancy but may be used in later pregnancy.[1] Its safety during breastfeeding is unclear.[3] Pentamidine is in the aromatic diamidine family of medications.[4] While the way the medication works is not entirely clear, it is believed to involve decreasing the production of DNA, RNA, and protein.[1]

Pentamidine came into medical use in 1937.[5] It is on the World Health Organization's List of Essential Medicines.[6] It is available as a generic medication.[1] In regions of the world where trypanosomiasis is common pentamidine is provided for free by the World Health Organization (WHO).[7]

  1. ^ a b c d e f g h i j k "Pentamidine Isethionate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 3 December 2016.
  2. ^ "Treatment | Balamuthia | Parasites | CDC". 5 September 2019.
  3. ^ "Pentamidine Use During Pregnancy". www.drugs.com. Archived from the original on 9 November 2016. Retrieved 3 December 2016.
  4. ^ Cohen J, Powderly WG, Opal SM (2016). Infectious Diseases. Elsevier Health Sciences. p. 1368. ISBN 9780702063381. Archived from the original on 2017-03-08.
  5. ^ Magill AJ, Strickland GT, Maguire JH, Ryan ET, Solomon T (2012). Hunter's Tropical Medicine and Emerging Infectious Disease (9 ed.). Elsevier Health Sciences. p. 723. ISBN 978-1455740437. Archived from the original on 2016-12-20.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ "Trypanosomiasis, human African (sleeping sickness)". World Health Organization. February 2016. Archived from the original on 4 December 2016. Retrieved 7 December 2016.
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