Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H24N4O2.CH4O3S |
| Molecular Weight | 436.525 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.NC(=N)C1=CC=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1
InChI
InChIKey=LCNPURURRXMYET-UHFFFAOYSA-N
InChI=1S/C19H24N4O2.CH4O3S/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;1-5(2,3)4/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23);1H3,(H,2,3,4)
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C19H24N4O2 |
| Molecular Weight | 340.4195 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00738
https://en.wikipedia.org/wiki/Pentamidine
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00738
https://en.wikipedia.org/wiki/Pentamidine
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 bruceigambiense (West African trypanosomiasis). Pentamidine is also used as a prophylactic against PCP in patients receiving chemotherapy and in some patients who have undergone organ transplantation, 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. Studies suggest that the pentamidine isethionate interferes with microbial nuclear metabolism by inhibition of DNA, RNA, phospholipid and protein synthesis. However, the mode of action is not fully understood.
CNS Activity
Curator's Comment: Pentamidine is able to cross the BBB, but a proportion is retained within the capillary endothelium. This may well explain its inability to treat well established CNS trypanosome infection. Furthermore, pentamidine movement into the CNS is a complex process involving multiple transporters.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: O14717 Gene ID: 1787.0 Gene Symbol: TRDMT1 Target Organism: Homo sapiens (Human) |
204.4 µM [EC50] | ||
Target ID: CHEMBL2366046 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | NEBUPENT Approved UsePentamidine Launch Date1985 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
751 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8056699 |
3.9 mg/kg 1 times / day multiple, intravenous dose: 3.9 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
PENTAMIDINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
612 ng/mL |
4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PENTAMIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
18.8 ng/mL |
4 mg/kg 1 times / day multiple, irrigation dose: 4 mg/kg route of administration: Irrigation experiment type: MULTIPLE co-administered: |
PENTAMIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6734 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8056699 |
3.9 mg/kg 1 times / day multiple, intravenous dose: 3.9 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
PENTAMIDINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.4 h |
4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PENTAMIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 Health Status: unhealthy Age Group: 17 Sources: |
Other AEs: Impaired renal function, Hepatic impairment... Other AEs: Impaired renal function Sources: Hepatic impairment Hypotension Cardiopulmonary arrest |
600 mg 1 times / month multiple, respiratory Highest studied dose Dose: 600 mg, 1 times / month Route: respiratory Route: multiple Dose: 600 mg, 1 times / month Sources: |
unhealthy, 37.9 ± 7.5 Health Status: unhealthy Age Group: 37.9 ± 7.5 Sex: M+F Sources: |
|
300 mg 1 times / month multiple, respiratory Recommended Dose: 300 mg, 1 times / month Route: respiratory Route: multiple Dose: 300 mg, 1 times / month Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Acute pancreatitis... AEs leading to discontinuation/dose reduction: Acute pancreatitis Sources: |
4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Hypotension, Hypoglycemia... Other AEs: Extravasation, Injection site ulceration... AEs leading to discontinuation/dose reduction: Hypotension (grade 3-5) Other AEs:Hypoglycemia (grade 5) Acute pancreatitis (grade 5) Cardiac arrhythmias (grade 5) Cardiac arrhythmias (grade 5) Extravasation Sources: Injection site ulceration Injection site necrosis Slough injection site |
4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Hypotension, Hypoglycemia... Other AEs: Extravasation, Injection site ulceration... AEs leading to discontinuation/dose reduction: Hypotension (grade 3-5) Other AEs:Hypoglycemia (grade 5) Acute pancreatitis (grade 5) Cardiac arrhythmias (grade 5) Cardiac arrhythmias (grade 5) Extravasation Sources: Injection site ulceration Injection site necrosis Slough injection site |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Cardiopulmonary arrest | 1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 Health Status: unhealthy Age Group: 17 Sources: |
|
| Hepatic impairment | 1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 Health Status: unhealthy Age Group: 17 Sources: |
|
| Hypotension | 1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 Health Status: unhealthy Age Group: 17 Sources: |
|
| Impaired renal function | 1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 Health Status: unhealthy Age Group: 17 Sources: |
|
| Acute pancreatitis | Disc. AE | 300 mg 1 times / month multiple, respiratory Recommended Dose: 300 mg, 1 times / month Route: respiratory Route: multiple Dose: 300 mg, 1 times / month Sources: |
unhealthy Health Status: unhealthy Sources: |
| Extravasation | 4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Injection site necrosis | 4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Injection site ulceration | 4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Slough injection site | 4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Hypotension | grade 3-5 Disc. AE |
4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Acute pancreatitis | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Cardiac arrhythmias | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Cardiac arrhythmias | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hypoglycemia | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intramuscular Recommended Dose: 4 mg/kg, 1 times / day Route: intramuscular Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Extravasation | 4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Injection site necrosis | 4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Injection site ulceration | 4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Slough injection site | 4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Hypotension | grade 3-5 Disc. AE |
4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Acute pancreatitis | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Cardiac arrhythmias | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Cardiac arrhythmias | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hypoglycemia | grade 5 Disc. AE |
4 mg/kg 1 times / day multiple, intravenous Recommended Dose: 4 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [IC50 0.097 uM] | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs. | 2015-06 |
|
| Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015-05-18 |
|
| Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013-12 |
|
| Synthesis and antiprotozoal activity of dicationic 2,6-diphenylpyrazines and aza-analogues. | 2013-11-01 |
|
| Synthesis and antiprotozoal activities of benzyl phenyl ether diamidine derivatives. | 2013-09 |
|
| The pharmacological profile of brain liver intestine Na+ channel: inhibition by diarylamidines and activation by fenamates. | 2011-11 |
|
| Synthetic chromanol derivatives and their interaction with complex III in mitochondria from bovine, yeast, and Leishmania. | 2011-10-17 |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 2010-12 |
|
| Bisbenzamidines as antifungal agents. are both amidine functions required to observe an anti-Pneumocystis carinii activity? | 2010-06-11 |
|
| Bisbenzamidine derivative, pentamidine represses DNA damage response through inhibition of histone H2A acetylation. | 2010-02-09 |
|
| Two cases of visceral leishmaniasis in Colombia resistant to meglumine antimonial treatment. | 2009-09-10 |
|
| Synthesis and antiprotozoal activity of pyridyl analogues of pentamidine. | 2009-08-13 |
|
| Effects of acute intravenous administration of pentamidine, a typical hERG-trafficking inhibitor, on the cardiac repolarization process of halothane-anesthetized dogs. | 2009-08 |
|
| Pentamidine-induced facial numbness. | 1991-04 |
|
| Effects of pentamidine alone and in combination with ketoconazole or itraconazole on the growth of Candida albicans. | 1990-12 |
|
| Ventricular tachycardia and torsades de pointes complicating pentamidine therapy of Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. | 1990-10-01 |
|
| Symptomatic hypocalcemia and hypomagnesemia with renal magnesium wasting associated with pentamidine therapy in a patient with AIDS. | 1990-09 |
|
| Structure-activity relationships of analogs of pentamidine against Plasmodium falciparum and Leishmania mexicana amazonensis. | 1990-07 |
|
| Reye's syndrome in adult with AIDS. | 1990-06-16 |
|
| Novel pentamidine analogs in the treatment of experimental Pneumocystis carinii pneumonia. | 1990-06 |
|
| Pentamidine-induced torsades de pointes in a renal transplant recipient with Pneumocystis carinii pneumonia. | 1990-04 |
|
| Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia. | 1990-04 |
|
| Acute, rapidly progressive renal failure with simultaneous use of amphotericin B and pentamidine. | 1990-03 |
|
| Renal insufficiency with nebulised pentamidine. | 1989-10-28 |
|
| Nephrotoxicity and hyperkalemia in patients with acquired immunodeficiency syndrome treated with pentamidine. | 1989-09 |
|
| Acute renal failure after nebulised pentamidine. | 1989-06-03 |
|
| Torsades de pointes during intravenous pentamidine isethionate therapy. | 1989-01-15 |
|
| Recurrent ventricular tachycardia due to pentamidine-induced cardiotoxicity. | 1988-12 |
|
| Trimethoprim-sulfamethoxazole compared with pentamidine for treatment of Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. A prospective, noncrossover study. | 1988-08-15 |
|
| Risk factors for hypoglycemia associated with pentamidine therapy for Pneumocystis pneumonia. | 1988-07-15 |
|
| Tremor induced by trimethoprim-sulfamethoxazole in patients with the acquired immunodeficiency syndrome (AIDS). | 1988-07-01 |
|
| Cationic antitrypanosomal and other antimicrobial agents in the therapy of experimental Pneumocystis carinii pneumonia. | 1988-06 |
|
| Ventricular tachycardia due to pentamidine isethionate. | 1988-05 |
|
| Comparison of dosages, intervals, and drugs in the prevention of Pneumocystis carinii pneumonia. | 1988-05 |
|
| Aggressive psychosis in AIDS patient on high-dose steroids. | 1987-09-26 |
|
| Torsade de pointes during administration of pentamidine isethionate. | 1987-09 |
|
| Adverse reactions associated with pentamidine isethionate in AIDS patients: recommendations for monitoring therapy. | 1986-11 |
|
| Hypoglycemic coma from pentamadine in an AIDS patient. | 1986-07 |
|
| Pentamidine and hematuria. | 1986-07 |
|
| Pentamidine-induced hypoglycemia in patients with the acquired immune deficiency syndrome. | 1986-03 |
|
| Pentamidine treatment of Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. Association with acute renal failure and myoglobinuria. | 1985-12 |
|
| Extrapyramidal symptoms in AIDS patients given low-dose metoclopramide or chlorpromazine. | 1985-11-23 |
|
| Sciatic nerve damage associated with pentamidine. | 1985-10 |
|
| Pentamidine and renal toxicity. | 1985-09-12 |
|
| Pentamidine-associated hypotension and route of administration. | 1985-09 |
|
| Visceral leishmaniasis unresponsive to antimonial drugs. II. Response to high dosage sodium stibogluconate or prolonged treatment with pentamidine. | 1985 |
|
| [Nephrotoxic effect of pentamidine in the treatment of interstitial pneumonia in 2 children with acute lymphoblastic leukemia]. | 1979-12 |
|
| [Kidney failure during treatment of T. rhodesiense trypanosomiasis with pentamidin]. | 1977 |
|
| Efficacy of trimethoprim and sulfamethoxazole in the prevention and treatment of Pneumocystis carinii pneumonitis. | 1974-03 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e2ad9d3c-b6c3-4f70-87e0-722a8ff94ccb
Curator's Comment: 300 mg once every four weeks administered via the Respirgard
The recommended adult dosage is 300 mg once every four weeks administered via the Respirgard® II nebulizer. The dose should be delivered until the nebulizer chamber is empty (approximately 30 to 45 minutes). The flow rate should be 5 to 7 liters per minute from a 40 to 50 pounds per square inch (PSI) air or oxygen source. Alternatively, a 40 to 50 PSI air compressor can be used with flow limited by setting the flowmeter at 5 to 7 liters per minute or by setting the pressure at 22 to 25 PSI. Low pressure (less than 20 PSI) compressors should not be used.
Route of Administration:
Irrigation
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
HMB3ISP7OB
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| Record Status |
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| Record Version |
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