Pentamidine Isethionate
Basic information
- CAS
140-64-7- Standard SMILES
N=C(N)c1ccc(OCCCCCOc2ccc(C(=N)N)cc2)cc1.O=S(=O)(O)CCO.O=S(=O)(O)CCO- InChIKey
YBVNFKZSMZGRAD-UHFFFAOYSA-N- Molecular formula
- C19H24N4O2.2C2H6O4S
- Average molar mass
- 592.7 g/mol
- Monoisotopic mass
- 592.18728571
Overview
Pentamidine isethionate appears as odorless white or almost white crystals or powder. Odor also reported as a slight butyric odor. Very bitter taste. pH (5% aqueous solution) 4.5-6.5. (NTP, 1992)
Names & identifiers
- Preferred name
- Pentamidine Isethionate
- IUPAC
- 4-[5-(4-carbamimidoylphenoxy)pentoxy]benzenecarboximidamide;bis(2-hydroxyethanesulfonic acid)
- English name
- Pentamidine isethionate
- Molecular formula
- C23H36N4O10S2
- Molecular weight
- 592.68
Names & synonyms
PENTAMIDINE ISETHIONATE140-64-7Pentamidine diisethionate4,4'-(Pentane-1,5-diylbis(oxy))dibenzimidamide bis(2-hydroxyethanesulfonate)Pentamidine isetionatePentacarinatPentamidine diisetionateNebupentLomidinPneumopentDiamidineLomidine isoethionate
Show more names
2512RPM&B-800RP-2512BenambaxAeropentBanaMbax
PENTAMUSAF XR-10DTXSID5023796RP 2512OCZ103-OSPentamidini isetionasWR 4931V2P3K60DA2
Database identifiers
- CAS
140-64-7- PubChem CID
- 8813
- DTXSID
DTXSID5023796- ChEMBL
CHEMBL361506- ChEBI
CHEBI:7977- UNII
- V2P3K60DA2
- EC Number
- 205-424-1
Properties
Computed structural properties
- Topological polar surface area
- 284 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 14
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 493
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Pharmaceuticals
Solubility
greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)
Water > 30 (mg/mL)
Acetate buffer, pH 4 ~2.5 (mg/mL)
Carbonate buffer, pH 9 < 1 (mg/mL)
0.1 N HCl ~2.5 (mg/mL)
0.1 NaOH < 1 (mg/mL)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point370 to 378 °F (NTP, 1992)
Physical DescriptionPentamidine isethionate appears as odorless white or almost white crystals or powder. Odor also reported as a slight butyric odor. Very bitter taste. pH (5% aqueous solution) 4.5-6.5. (NTP, 1992)
Stability/Shelf Life
Bulk: The compound was found to be stable in the bulk form when exposed to light at ambient or 60 ° C temperature for 90 days. Solution: Pentamidine isethionate was found to be stable as a solution in normal saline at room temperature over a 72 hour period.
Collision Cross Section174.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 70 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound include fall in blood pressure, hypotension, hypoglycemia, dizziness, tachycardia, flushing, itching and an increase in blood urea. Other symptoms include pain and abscess formation at the site of injection, hyperglycemia, hematological disturbances, vomiting, liver and kidney dysfunction, dizziness, headache, breathlessness and fainting. It has caused local reactions and reversible uremia in an infant. It has also caused fever and profound fatal acidosis in a teen. It can cause hemorrhage and dermatitis via intramuscular routes. Other symptoms include cardiac arrhythmias, leukopenia, hypocalcemia, Stevens-Johnson syndrome, thrombocytopenia, confusion and hallucinations. Symptoms of exposure to a related compound include convulsions and liver and kidney damage. Other symptoms include pancreatitis. It may also cause diabetes mellitus.
Hazards SummaryImmunological contact urticaria documented in pharmaceutical and healthcare workers; [Kanerva, p. 219]
Reactive GroupAlcohols and Polyols
Reactivity Profile
Chemistry & industry
Pharmacology
ATC Code
P01CX01
P - Antiparasitic products, insecticides and repellents
Metabolism/MetabolitesHepatic.
Half Life: 9.1-13.2 hours
FDA Pharmacological Classification
PENTAMIDINE ISETHIONATE
Antiprotozoal [EPC]
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances that are destructive to protozoans.
Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA.
Uses & manufacturing
UsesFor the treatment of pneumonia due to <i>Pneumocystis carinii</i>.
Applications
UsesPentamidine isethionate salt has been used:as a positive control for anti-leishmanial, anti-plasmodial and cytotoxic assaysas a prototypical compound to analyse the inhibitor effect on human ether-a-go-go-related gene (HERG) K+ channel traffickingas an anti-leishmanial agent in promastigotes
UsesHas been widely used as a drug to treat protozoal diseases, such as malaria, amoebic dysentery and trypanosomiasis. It has also been shown to be effective for both prophylaxis of pneumocystic carinii pneumonia (PCC).
UsesAntiparasitic
General DescriptionOdorless white or almost white crystals or powder. Odor also reported as a slight butyric odor. Very bitter taste. pH (5% aqueous solution) 4.5-6.5.
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Compound notes
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