Systematic (IUPAC) name
4,4'-[pentane- 1,5-diylbis(oxy)]dibenzenecarboximidamide
Clinical data
Trade names Nebupent
AHFS/ monograph
Pregnancy cat. C(US)
Legal status Prescription only
Routes IV, IM, inhalation
Pharmacokinetic data
Protein binding 69%
Half-life 6.4-9.4 hours
CAS number 100-33-4 YesY
ATC code P01CX01 QP51AF02
PubChem CID 4735
DrugBank DB00738
ChemSpider 4573 YesY
KEGG D08333 YesY
Chemical data
Formula C19H24N4O2 
Mol. mass 340.42 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Pentamidine (formulated as a salt, pentamidine diisethionate or dimesilate) is an antimicrobial medication given for prevention and treatment of Pneumocystis pneumonia (PCP) caused by Pneumocystis jirovecii (formerly known as Pneumocystis carinii), a severe interstitial type of pneumonia often seen in patients with HIV infection. The drug is also the mainstay of treatment for stage I infection with Trypanosoma brucei gambiense (West African Trypanosomiasis).



Pentamidine is also used as a prophylactic against PCP in patients receiving chemotherapy, as they also have a depressed immune system as a direct side-effect of the drugs used. The mortality of untreated PCP is very high. Additionally, pentamidine has good clinical activity in treating leishmaniasis, and yeast infections caused by the organism Candida albicans. Pentamidine is also used as a prophylactic antibiotic for children undergoing treatment for leukemia.

The exact mechanism of its anti-protozoal action is unknown (though it may involve reactions with ubiquitin[1]), despite the fact that it is a basic therapeutic modality (in concurrence with multiple antifungal medications) when treating Acanthamoeba infections in the immunocompromised patients. In the United States, pentamidine is currently designated an orphan drug by the U.S. Food and Drug Administration.

Treatment of acute PCP

In the acute treatment of PCP, pentamidine is considered equally or slightly less active than co-trimoxazole (brand names Bactrim, Septrin, or Septra). Clinical evidence suggests that pentamidine is often better tolerated than co-trimoxazole because a high dose of co-trimoxazole is needed, which is associated with a high incidence and severity of side effects such as hepatitis, bone-marrow-damage, renal-damage, and life threatening skin disease (Lyell-syndrome). Moreover, many patients are or become allergic to co-trimoxazole. For treatment of PCP, 4 milligrams of pentamidine per kilogram of body weight is given intravenously once daily for 14 to 21 days. Treatment exceeding 21 days may be necessary, but is associated with increased toxicity. Intramuscular injection is not recommended. The effect of pentamidine often becomes evident within the first 2 days of treatment, with reduction in fever and improvement of respiratory function. In any case, improvements of chest x-ray studies occur within 6 to 8 days, provided therapy is successful. Pentamidine therapy cures 50 to 70% of all patients treated.

Primary and secondary prophylaxis of PCP

Primary prophylaxis of severely immunocompromised patients can be indicated where PCP has not yet been diagnosed. Secondary prophylaxis aims to prevent recurrent infections by PCP. For both forms of prophylaxis, an aerosolized formulation of pentamidine given by nebulizer once monthly in a dose of 300 mg is used. In primary prophylaxis, this reduces the long term likelihood of PCP by 70% when compared to no prophylaxis. The aerosolized route of administration is particularly suited for pregnant women in their first trimester (when TMP-SMX is contraindicated). Aerosolized administration may lead to an atypical PCP infection involving the upper lobes.


For other indications, such as leishmaniasis or sleeping sickness, special treatment schedules developed by the WHO or CDC exist.

Use as an antitumor drug has also been proposed.[2]


  • Severe allergy; no others in PCP patients in whom a proper diagnosis has been made


The mechanism is not well characterized, but there is some evidence that it may involve mitochondrial function.[3]

Side effects

Pentamidine can cause allergic and toxic side effects, most commonly having effects on the pancreas, which in part depend on the daily and/or cumulative dose:

Drug Interactions

The additional or sequential use of other nephrotoxic drugs like aminoglycosides, amphotericin B, capreomycin, colistin, polymyxin B, vancomycin, foscarnet, or cisplatin should be closely monitored, or whenever possible completely avoided.

Brand names and dose forms

  • For oral inhalation: NebuPent 300 mg Nebulizer
  • For parenteral treatment: Pentacrinat, Pentam 300, and Pentamidine isethionate for injection (Abbot); all containing 300 mg of Pentamidine

See also


  1. ^ Nguewa PA, Fuertes MA, Cepeda V, et al. (2005). "Pentamidine is an antiparasitic and apoptotic drug that selectively modifies ubiquitin". Chem. Biodivers. 2 (10): 1387–400. doi:10.1002/cbdv.200590111. PMID 17191940. 
  2. ^ Lee MS, Johansen L, Zhang Y, et al. (December 2007). "The novel combination of chlorpromazine and pentamidine exerts synergistic antiproliferative effects through dual mitotic action". Cancer Res. 67 (23): 11359–67. doi:10.1158/0008-5472.CAN-07-2235. PMID 18056463. 
  3. ^ Sun T, Zhang Y (March 2008). "Pentamidine binds to tRNA through non-specific hydrophobic interactions and inhibits aminoacylation and translation". Nucleic Acids Res. 36 (5): 1654–64. doi:10.1093/nar/gkm1180. PMC 2275129. PMID 18263620. 
  4. ^ C. P. Thakur, et al. (1991). "Comparison of regimes of treatment of antimony-resistant kala-azar patients: a randomized study". American Journal of Tropical Medicine and Hygiene 45 (4): 435–441. PMID 1659239. 

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Look at other dictionaries:

  • Pentamidine — Général Nom IUPAC 4,4 [pentane 1,5 diylbis(oxy)]dibenzènecarboximidamide No CAS …   Wikipédia en Français

  • pentamidine — ● pentamidine nom féminin Médicament de synthèse, utilisé en injection intramusculaire dans le traitement des trypanosomiases et des leishmanioses. pentamidine n. f. MED Médicament utilisé pour traiter la maladie du sommeil et les leishmanioses …   Encyclopédie Universelle

  • pentamidine — [ī΄sə thī′ə nāt΄pen tam′ə dēn΄] n. a white, crystalline substance, C23H36N4O10S2, used as a drug to treat AIDS related pneumonia or protozoan diseases, esp. trypanosomiasis: in full pentamidine isethionate [ī΄sə thī′ə nāt΄] …   English World dictionary

  • pentamidine — noun Date: 1941 a drug C23H36N4O10S2 used especially to treat protozoal infections (as leishmaniasis) and to prevent AIDS related pneumonia …   New Collegiate Dictionary

  • pentamidine — /pen tam i deen , din/, n. Pharm. an antiprotozoal substance, C19H24N4O2, used in the treatment of leishmaniasis, trypanosomiasis, and pneumonia due to Pneumocystis carinii. [1941; PENT(ANE) + AMIDINE] * * * …   Universalium

  • pentamidine — noun An antimicrobial medication used to prevent or treat pneumocystosis …   Wiktionary

  • pentamidine — pent·am·i·dine pen tam ə .dēn, dən n a diamidine used chiefly in the form of its salt C23H36N4O10S2 to treat protozoal infections (as leishmaniasis) and to prevent Pneumocystis carinii pneumonia in HIV infected individuals * * * n. a drug… …   Medical dictionary

  • pentamidine — [pɛn tamɪdi:n] noun Medicine a synthetic antibiotic drug used chiefly to treat PCP infection. Origin 1940s: from pentane + amide + ine4 …   English new terms dictionary

  • pentamidine — pent·am·i·dine …   English syllables

  • pentamidine — n. a drug effective against protozoans and used in the treatment of Pneumocystis pneumonia in AIDS patients and leishmaniasis. It is administered by injection or from an inhaler. Possible side effects include low blood pressure, heart… …   The new mediacal dictionary

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