Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H24N4O2.2CH4O3S |
Molecular Weight | 532.631 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CS(O)(=O)=O.NC(=N)C1=CC=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1
InChI
InChIKey=WRXSODAXJSKMAW-UHFFFAOYSA-N
InChI=1S/C19H24N4O2.2CH4O3S/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;2*1-5(2,3)4/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23);2*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
Sources: http://jpet.aspetjournals.org/content/329/3/967.long
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.
Originator
Sources: https://www.google.ch/patents/EP0315467A2?cl=en
Curator's Comment: Pentamidine was first discovered by Ewins et al., as shown in U.S. Patent No. 2,277,861
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: O14717 Gene ID: 1787.0 Gene Symbol: TRDMT1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2275129/ |
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 |
|
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 |
---|---|---|
[Severe renal and pancreatic complications during treatment with pentamidine in African trypanosomiasis]. | 1975 Aug-Sep |
|
Pentamidine treatment of Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. Association with acute renal failure and myoglobinuria. | 1985 Dec |
|
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 |
|
Nephrotoxicity and hyperkalemia in patients with acquired immunodeficiency syndrome treated with pentamidine. | 1989 Sep |
|
Analogues of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia. | 1990 Apr |
|
Effects of pentamidine alone and in combination with ketoconazole or itraconazole on the growth of Candida albicans. | 1990 Dec |
|
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model. | 1991 Nov-Dec |
|
Inhibition of topoisomerases from Pneumocystis carinii by aromatic dicationic molecules. | 1991 Nov-Dec |
|
Hematuria associated with pentamidine therapy for Pneumocystis carinii pneumonia. | 1992 Jun |
|
Prophylactic effect of FK463, a novel antifungal lipopeptide, against Pneumocystis carinii infection in mice. | 2000 Sep |
|
Pentamidine isethionate as treatment and secondary prophylaxis for disseminated cutaneous leishmaniasis during HIV infection: case report. | 2001 Dec |
|
[Rhabdomyolysis induced by pentamidine (Pentacarinat) during treatment of cutaneous leishmaniasis: 2 cases]. | 2002 Jan |
|
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species. | 2002 Jun |
|
Pentamidine, the drug of choice for the treatment of cutaneous leishmaniasis in Surinam. | 2002 Nov |
|
T wave alternans and Torsades de Pointes after the use of intravenous pentamidine. | 2002 Sep |
|
Antileishmanial drugs cause up-regulation of interferon-gamma receptor 1, not only in the monocytes of visceral leishmaniasis cases but also in cultured THP1 cells. | 2003 Apr |
|
Novel bisbenzamidines as potential drug candidates for the treatment of Pneumocystis carinii pneumonia. | 2004 Sep 6 |
|
Early-onset pentamidine-associated second-degree heart block and sinus bradycardia: case report and review of the literature. | 2005 Jun |
|
Use of Leishmania donovani field isolates expressing the luciferase reporter gene in in vitro drug screening. | 2005 Sep |
|
Novel synthesis of nicotinamide derivatives of cytotoxic properties. | 2006 Jul 1 |
|
Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs. | 2006 Mar |
|
Perioral numbness associated with intravenous pentamidine administration. | 2007 Jan |
|
Using the zebrafish lateral line to screen for ototoxicity. | 2008 Jun |
|
Pentamidine dosage: a base/salt confusion. | 2008 May 28 |
|
The diamidine DB75 targets the nucleus of Plasmodium falciparum. | 2009 May 14 |
|
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 activities of benzyl phenyl ether diamidine derivatives. | 2013 Sep |
|
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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/22005072
Pentamidine was found to be active against T. whipplei strains both in axenic medium and in cell culture, with minimum inhibitory concentration ranges of 0.125-0.25mg/L.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:13:42 GMT 2023
by
admin
on
Fri Dec 15 15:13:42 GMT 2023
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Record UNII |
863QBB4D0A
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Record Status |
Validated (UNII)
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Record Version |
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SUB32093
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DTXSID50987751
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m8497
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PENTAMIDINE MESYLATE
Created by
admin on Fri Dec 15 15:13:42 GMT 2023 , Edited by admin on Fri Dec 15 15:13:42 GMT 2023
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PRIMARY | Description: A white or light pink, granular powder; almost odourless. Solubility: Slightly soluble in water and ethanol (~750 g/l) TS; practically insoluble in ether R and acetone R. Category: Antitrypanosomal drug; antileishmaniasis drug. Storage: Pentamidine mesilate should be kept in a well-closed container.Definition: Pentamidine mesilate contains not less than 98.5% and not more than 102.5% of C19H24N4O2,2CH4O3S, calculatedwith reference to the dried substance. Manufacture: The production method must be evaluated to determine the potential for formation of alkyl mesilates, which isparticularly likely to occur if the reaction medium contains lower alcohols. Where necessary, the production method is validated todemonstrate that alkyl mesilates are not detectable in the final product. |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |