Identification
- Summary
Pentamidine is an antifungal agent used to treat Pneumocystis pneumonia in patients infected with HIV.
- Brand Names
- Nebupent, Pentam
- Generic Name
- Pentamidine
- DrugBank Accession Number
- DB00738
- Background
Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of pneumocystis pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Pentamidine (DB00738)
- Weight
- Average: 340.4195
Monoisotopic: 340.189926032 - Chemical Formula
- C19H24N4O2
- Synonyms
- 1,5-bis(4-amidinophenoxy)pentane
- 4,4'-(1,5-pentanediylbis(oxy))bis-benzenecarboximidamide
- 4,4'-(pentamethylenedioxy)dibenzamidine
- 4,4'-Diamidinodiphenoxypentane
- p,p'-(pentamethylenedioxy)dibenzamidine
- Pentamidin
- Pentamidina
- Pentamidine
- Pentamidinum
- External IDs
- MB 800
- RP 2512
Pharmacology
- Indication
For the treatment of pneumonia due to Pneumocystis carinii.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Pneumocystis carinii pneumonia •••••••••••• ••••••••• Prophylaxis of Pneumocystis jirovecii pneumonia •••••••••••• •••••••••• •••• •••••••••• ••••• • •••••••• ••• •••••••• •••••••• Prophylaxis of Pneumocystis jirovecii pneumonia •••••••••••• ••••••• •• ••• •• •••• •••••••• •• •••••••••••• •••••••• •••••••••• ••• •••••••• •••••••• Prophylaxis of Pneumocystis jirovecii pneumonia •••••••••••• •••••••••• •••• •••••••••• ••••• • •••••••• ••• ••••••••• ••••••• •• ••• •• •••• •••••••• •• •••••••••••• •••••••• ••••••••• •••••••• Treatment of Trypanosomiasis ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Pentamidine is an antiprotozoal agent. It is an aromatic diamidine, and is known to have activity against Pneumocystis carinii. The exact nature of its antiprotozoal action is unknown. in vitro studies with mammalian tissues and the protozoan Crithidia oncopelti indicate that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids and proteins. Little is known about the drug's pharmacokinetics. The medication is also useful in Leishmaniasis and in prophylaxis against sleeping sickness caused by Trypanosoma brucei gambiense. Hydration before treatment lessens the incidence and severity of side effects, which include liver or kidney dysfunction, hypertension, hypotension, hypoglycemia, hypocalemia, leukopenia, thrombcytopenia, anemia, and allergic reaction. It is generally well-tolerated.
- Mechanism of action
The mode of action of pentamidine is not fully understood. It is thought that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids, and proteins.
Target Actions Organism UtRNA (cytosine(38)-C(5))-methyltransferase otherHumans UDNA intercalationHumans - Absorption
Absorbed poorly through the gastrointestinal tract and is usually administered parenterally.
- Volume of distribution
Not Available
- Protein binding
69%
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
9.1-13.2 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include pain, nausea, anorexia, hypotension, fever, rash, bad taste in mouth, confusion/hallucinations, dizziness, and diarrhea.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Pentamidine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept The metabolism of Pentamidine can be increased when combined with Abatacept. Abiraterone The metabolism of Pentamidine can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Pentamidine. Acalabrutinib The metabolism of Pentamidine can be decreased when combined with Acalabrutinib. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pentamidine gluconate B0WU872RIR 123245-08-9 JAVCHNFPSHBZAF-UUPCJSQJSA-N Pentamidine isethionate V2P3K60DA2 140-64-7 YBVNFKZSMZGRAD-UHFFFAOYSA-N Pentamidine mesylate 863QBB4D0A 6823-79-6 WRXSODAXJSKMAW-UHFFFAOYSA-N - International/Other Brands
- Pentacarinat (Sanofi-Aventis) / Pentacrinat (Abbot) / Pentam (Abbot) / Pneumopent
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image NebuPent Inhalant 300 mg/6mL Respiratory (inhalation) Physicians Total Care, Inc. 1994-06-09 2010-06-30 US 
NebuPent Inhalant 300 mg/6mL Respiratory (inhalation) Fresenius Kabi USA, LLC 2011-02-15 Not applicable US Pentacarinat 300 Inj Pws 300mg/vial Powder, for solution 300 mg / vial Intramuscular; Intravenous; Respiratory (inhalation) Aventis Pharma Ltd. 1989-12-31 2005-08-01 Canada 
Pentam 300 Injection, powder, lyophilized, for solution 300 mg/3mL Intramuscular; Intravenous Fresenius Kabi USA, LLC 2001-01-16 Not applicable US Pentamidine Isethionate Inj 300mg/vial BP Powder, for solution 300 mg / vial Intramuscular; Intravenous David Bull Laboratories (Pty) Ltd. 1990-12-31 1998-08-13 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Pentamidine Isethionate Injection, powder, lyophilized, for solution 300 mg/3mL Intramuscular; Intravenous XGen Pharmaceuticals DJB, Inc. 2023-04-04 Not applicable US Pentamidine Isethionate Injection, powder, lyophilized, for solution 300 mg/300mg Intramuscular; Intravenous Seton Pharmaceuticals 2018-04-01 Not applicable US Pentamidine Isethionate Injection, powder, lyophilized, for solution 300 mg/300mg Intramuscular; Intravenous Heritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc. 2021-01-08 Not applicable US Pentamidine Isethionate Inhalant 300 mg/6mL Respiratory (inhalation) XGen Pharmaceuticals DJB, Inc. 2023-04-04 Not applicable US Pentamidine Isethionate Inhalant 300 mg/300mg Respiratory (inhalation) Seton Pharmaceuticals 2019-10-14 Not applicable US
Categories
- ATC Codes
- P01CX01 — Pentamidine isethionate
- Drug Categories
- Agents Against Leishmaniasis and Trypanosomiasis
- Agents causing hyperkalemia
- Amidines
- Anti-Infective Agents
- Antibiotics for Pneumocystis Pneumonia
- Antifungal Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Benzamidines
- Blood Glucose Lowering Agents
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Substrates
- Hyperglycemia-Associated Agents
- Hypoglycemia-Associated Agents
- Miscellaneous Antiprotozoals
- Moderate Risk QTc-Prolonging Agents
- Nephrotoxic agents
- QTc Prolonging Agents
- Trypanocidal Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Alkyl aryl ethers / Carboximidamides / Carboxamidines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amidine / Aromatic homomonocyclic compound / Carboximidamide / Carboxylic acid amidine / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- carboxamidine, diether (CHEBI:45081)
- Affected organisms
- Pneumocystis carinii
Chemical Identifiers
- UNII
- 673LC5J4LQ
- CAS number
- 100-33-4
- InChI Key
- XDRYMKDFEDOLFX-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide
- SMILES
- NC(=N)C1=CC=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1
References
- General References
- Nguewa PA, Fuertes MA, Cepeda V, Iborra S, Carrion J, Valladares B, Alonso C, Perez JM: Pentamidine is an antiparasitic and apoptotic drug that selectively modifies ubiquitin. Chem Biodivers. 2005 Oct;2(10):1387-400. [Article]
- External Links
- Human Metabolome Database
- HMDB0014876
- KEGG Compound
- C07420
- PubChem Compound
- 4735
- PubChem Substance
- 46508562
- ChemSpider
- 4573
- BindingDB
- 45440
- 7994
- ChEBI
- 45081
- ChEMBL
- CHEMBL55
- ZINC
- ZINC000001530775
- Therapeutic Targets Database
- DAP000764
- PharmGKB
- PA450850
- PDBe Ligand
- PNT
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Pentamidine
- PDB Entries
- 1d64 / 1rkw / 3cr4 / 3cr5 / 3ey0 / 3gy3 / 3hii / 7wp3
- MSDS
- Download (50.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Withdrawn Treatment Pneumocystis Jirovecii Pneumonia 1 3 Completed Prevention Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Visceral Leishmaniosis 1 3 Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Pneumocystis Jirovecii Pneumonia 6 3 Terminated Treatment Human Immunodeficiency Virus (HIV) Infections / Pneumocystis Jirovecii Pneumonia 1 2 Completed Treatment Cutaneous Leishmaniases 1
Pharmacoeconomics
- Manufacturers
- App pharmaceuticals llc
- Armour pharmaceutical co
- Baxter healthcare corp anesthesia and critical care
- Hospira inc
- Watson laboratories inc
- Packagers
- APP Pharmaceuticals
- APPD
- Baxter International Inc.
- Hospira Inc.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Injection, powder, for solution Intravenous 300 mg Injection Inhalant Respiratory (inhalation) 300 mg/6mL Injection, powder, for solution Parenteral 300 MG Powder 300 mg/1vial Injection, powder, for solution Intramuscular; Intravenous; Respiratory (inhalation) 300 mg Powder, for solution Intramuscular; Intravenous; Respiratory (inhalation) 300 mg / vial Injection, powder, lyophilized, for solution Intramuscular; Intravenous 300 mg/3mL Inhalant Respiratory (inhalation) 300 mg/300mg Injection, powder, lyophilized, for solution Intramuscular; Intravenous 300 mg/300mg Powder, for solution Intramuscular; Intravenous 300 mg / vial - Prices
Unit description Cost Unit Nebupent 300 mg inhal powder 122.84USD each Pentam 300 vial 94.8USD vial Pentamidine 300 mg vial 45.31USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 186.0 °C (decomposes) Not Available water solubility Complete Not Available logP 4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0236 mg/mL ALOGPS logP 1.32 ALOGPS logP 2.32 Chemaxon logS -4.2 ALOGPS pKa (Strongest Basic) 12.13 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 118.2 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 120.53 m3·mol-1 Chemaxon Polarizability 38.85 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9416 Blood Brain Barrier + 0.9133 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.5352 P-glycoprotein inhibitor I Non-inhibitor 0.8571 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Inhibitor 0.6653 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Non-substrate 0.7339 CYP450 1A2 substrate Non-inhibitor 0.5272 CYP450 2C9 inhibitor Non-inhibitor 0.7439 CYP450 2D6 inhibitor Non-inhibitor 0.7676 CYP450 2C19 inhibitor Non-inhibitor 0.6581 CYP450 3A4 inhibitor Non-inhibitor 0.8661 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5621 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.8395 Biodegradation Not ready biodegradable 0.9818 Rat acute toxicity 2.2925 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7428 hERG inhibition (predictor II) Non-inhibitor 0.7711
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 201.7843025 predictedDarkChem Lite v0.1.0 [M-H]- 182.80579 predictedDeepCCS 1.0 (2019) [M+H]+ 201.5812025 predictedDarkChem Lite v0.1.0 [M+H]+ 185.3561 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.0150025 predictedDarkChem Lite v0.1.0 [M+Na]+ 193.36845 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other
- General Function
- Trna methyltransferase activity
- Specific Function
- Specifically methylates cytosine 38 in the anticodon loop of tRNA(Asp).
- Gene Name
- TRDMT1
- Uniprot ID
- O14717
- Uniprot Name
- tRNA (cytosine(38)-C(5))-methyltransferase
- Molecular Weight
- 44596.17 Da
References
- Sun T, Zhang Y: Pentamidine binds to tRNA through non-specific hydrophobic interactions and inhibits aminoacylation and translation. Nucleic Acids Res. 2008 Mar;36(5):1654-64. doi: 10.1093/nar/gkm1180. Epub 2008 Feb 7. [Article]
Unknown
Intercalation
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Shankar SM, Nania JJ: Management of Pneumocystis jiroveci pneumonia in children receiving chemotherapy. Paediatr Drugs. 2007;9(5):301-9. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Afrin LB, Afrin JB: Value of preemptive CYP2C19 genotyping in allogeneic stem cell transplant patients considered for pentamidine administration. Clin Transplant. 2011 May-Jun;25(3):E271-5. doi: 10.1111/j.1399-0012.2011.01399.x. Epub 2011 Feb 7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
- Kip AE, Schellens JHM, Beijnen JH, Dorlo TPC: Clinical Pharmacokinetics of Systemically Administered Antileishmanial Drugs. Clin Pharmacokinet. 2018 Feb;57(2):151-176. doi: 10.1007/s40262-017-0570-0. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Leukotriene-b4 20-monooxygenase activity
- Specific Function
- Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 2...
- Gene Name
- CYP4A11
- Uniprot ID
- Q02928
- Uniprot Name
- Cytochrome P450 4A11
- Molecular Weight
- 59347.31 Da
References
- Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54