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 | C19H24N4O2 |
| Molecular Weight | 340.4195 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 Date4.82112012E11 |
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 |
|
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 unknown | 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 unknown | 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 unknown | 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 n = 1 Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Age Group: 17 Population Size: 1 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: Page: p.1167 |
unhealthy, 37.9 ± 7.5 n = 76 Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Age Group: 37.9 ± 7.5 Sex: M+F Population Size: 76 Sources: Page: p.1167 |
|
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: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Sources: Page: p.6 |
Disc. AE: Acute pancreatitis... AEs leading to discontinuation/dose reduction: Acute pancreatitis Sources: Page: p.6 |
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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 n = 1 Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Age Group: 17 Population Size: 1 Sources: |
|
| Hepatic impairment | 1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 n = 1 Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Age Group: 17 Population Size: 1 Sources: |
|
| Hypotension | 1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 n = 1 Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Age Group: 17 Population Size: 1 Sources: |
|
| Impaired renal function | 1600 mg single, intravenous Overdose Dose: 1600 mg Route: intravenous Route: single Dose: 1600 mg Sources: |
unhealthy, 17 n = 1 Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Age Group: 17 Population Size: 1 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: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Pneumonia due to Pneumocystis carinii Sources: Page: p.6 |
| 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 Condition: Pneumonia due to Pneumocystis carinii 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 |
|---|---|---|
| Efficacy of trimethoprim and sulfamethoxazole in the prevention and treatment of Pneumocystis carinii pneumonitis. | 1974 Mar |
|
| [Kidney failure during treatment of T. rhodesiense trypanosomiasis with pentamidin]. | 1977 |
|
| [Nephrotoxic effect of pentamidine in the treatment of interstitial pneumonia in 2 children with acute lymphoblastic leukemia]. | 1979 Dec |
|
| Visceral leishmaniasis unresponsive to antimonial drugs. II. Response to high dosage sodium stibogluconate or prolonged treatment with pentamidine. | 1985 |
|
| Pentamidine treatment of Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. Association with acute renal failure and myoglobinuria. | 1985 Dec |
|
| Extrapyramidal symptoms in AIDS patients given low-dose metoclopramide or chlorpromazine. | 1985 Nov 23 |
|
| Sciatic nerve damage associated with pentamidine. | 1985 Oct |
|
| Pentamidine-associated hypotension and route of administration. | 1985 Sep |
|
| Pentamidine and renal toxicity. | 1985 Sep 12 |
|
| Pentamidine and hematuria. | 1986 Jul |
|
| Torsade de pointes during administration of pentamidine isethionate. | 1987 Sep |
|
| Aggressive psychosis in AIDS patient on high-dose steroids. | 1987 Sep 26 |
|
| Trimethoprim-sulfamethoxazole compared with pentamidine for treatment of Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. A prospective, noncrossover study. | 1988 Aug 15 |
|
| Tremor induced by trimethoprim-sulfamethoxazole in patients with the acquired immunodeficiency syndrome (AIDS). | 1988 Jul 1 |
|
| Risk factors for hypoglycemia associated with pentamidine therapy for Pneumocystis pneumonia. | 1988 Jul 15 |
|
| Cationic antitrypanosomal and other antimicrobial agents in the therapy of experimental Pneumocystis carinii pneumonia. | 1988 Jun |
|
| Comparison of dosages, intervals, and drugs in the prevention of Pneumocystis carinii pneumonia. | 1988 May |
|
| Torsades de pointes during intravenous pentamidine isethionate therapy. | 1989 Jan 15 |
|
| Acute renal failure after nebulised pentamidine. | 1989 Jun 3 |
|
| Renal insufficiency with nebulised pentamidine. | 1989 Oct 28 |
|
| Nephrotoxicity and hyperkalemia in patients with acquired immunodeficiency syndrome treated with pentamidine. | 1989 Sep |
|
| Pentamidine-induced torsades de pointes in a renal transplant recipient with Pneumocystis carinii pneumonia. | 1990 Apr |
|
| Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia. | 1990 Apr |
|
| Novel pentamidine analogs in the treatment of experimental Pneumocystis carinii pneumonia. | 1990 Jun |
|
| Reye's syndrome in adult with AIDS. | 1990 Jun 16 |
|
| Acute, rapidly progressive renal failure with simultaneous use of amphotericin B and pentamidine. | 1990 Mar |
|
| Ventricular tachycardia and torsades de pointes complicating pentamidine therapy of Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. | 1990 Oct 1 |
|
| Symptomatic hypocalcemia and hypomagnesemia with renal magnesium wasting associated with pentamidine therapy in a patient with AIDS. | 1990 Sep |
|
| [Transitory acute kidney insufficiency and insulin-dependent after treatment of kala-azar with pentamidine and N-methylglucamine antimony]. | 1991 May |
|
| Pentamidine-associated nephrotoxicity and hyperkalemia in patients with AIDS. | 1991 Nov |
|
| Higher pentamidine levels in AIDS patients with hypoglycemia and azotemia during treatment of Pneumocystis carinii pneumonia. | 1992 Sep |
|
| Search of chemical scaffolds for novel antituberculosis agents. | 2005 Apr |
|
| A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
|
| Pentamidine-induced long QT syndrome and block of hERG trafficking. | 2005 Jan |
|
| Protein trafficking abnormalities: a new mechanism in drug-induced long QT syndrome. | 2005 May |
|
| In vitro selection and in vivo efficacy of piperazine- and alkanediamide-linked bisbenzamidines against Pneumocystis pneumonia in mice. | 2006 Jul |
|
| [Cutaneous leishmaniasis--an import from Belize]. | 2007 |
|
| Perioral numbness associated with intravenous pentamidine administration. | 2007 Jan |
|
| Cellulose biosynthesis pathway is a potential target in the improved treatment of Acanthamoeba keratitis. | 2007 May |
|
| Using the zebrafish lateral line to screen for ototoxicity. | 2008 Jun |
|
| Pentamidine dosage: a base/salt confusion. | 2008 May 28 |
|
| Two cases of visceral leishmaniasis in Colombia resistant to meglumine antimonial treatment. | 2009 Jul-Aug |
|
| The diamidine DB75 targets the nucleus of Plasmodium falciparum. | 2009 May 14 |
|
| Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 2010 Dec |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
| Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
|
| Synthesis and antiprotozoal activity of dicationic 2,6-diphenylpyrazines and aza-analogues. | 2013 Nov 1 |
|
| Synthesis and antiprotozoal activities of benzyl phenyl ether diamidine derivatives. | 2013 Sep |
|
| 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 Jun |
|
| Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
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
by
admin
on
Edited
Thu Jul 06 11:36:06 UTC 2023
by
admin
on
Thu Jul 06 11:36:06 UTC 2023
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| Record UNII |
HMB3ISP7OB
|
| Record Status |
Validated (UNII)
|
| Record Version |
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HMB3ISP7OB
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112667-20-6
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24834404
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DTXSID20150132
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