Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References
ChemicalBook > CAS DataBase List > Pentamidine

Pentamidine

Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References
Product Name
Pentamidine
CAS No.
100-33-4
Chemical Name
Pentamidine
Synonyms
NSC 9921;MP 601205;PENTAMIDINE;Pentamidine USP/EP/BP;4,4’-diamidinodiphenoxypentane;4,4’-(pentamethylenedioxy)di-benzamidin;p,p’-(pentamethylenedioxy)dibenzamidine;4,4’-(pentamethylenedioxy)dibenzamidine;Pentamidine DISCONTINUED, offer P272501;4,4'-(1,5-Pentanediylbisoxy)dibenzamidine
CBNumber
CB4476092
Molecular Formula
C19H24N4O2
Formula Weight
340.42
MOL File
100-33-4.mol
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Pentamidine Property

Melting point:
186 °C (dec.)
Boiling point:
476.22°C (rough estimate)
Density 
1.1805 (rough estimate)
refractive index 
1.6620 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
DMSO, Methanol (Sparingly)
form 
Solid
pka
pKa 11.4 (Uncertain)
color 
White to Off-White
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Safety

RIDADR 
3249
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
100-33-4(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
20679
Product name
Pentamidine
Purity
≥98%
Packaging
100mg
Price
$121
Updated
2024/03/01
Cayman Chemical
Product number
20679
Product name
Pentamidine
Purity
≥98%
Packaging
250mg
Price
$228
Updated
2024/03/01
Cayman Chemical
Product number
20679
Product name
Pentamidine
Purity
≥98%
Packaging
500mg
Price
$362
Updated
2024/03/01
Cayman Chemical
Product number
20679
Product name
Pentamidine
Purity
≥98%
Packaging
1g
Price
$543
Updated
2024/03/01
Usbiological
Product number
286712
Product name
Pentamidine
Packaging
2mg
Price
$319
Updated
2021/12/16
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Pentamidine Chemical Properties,Usage,Production

Pharmacology and mechanism of action

Pentamidine is a synthetic aromatic diamidine chemically related to the antidiabetic drug phenformin and was introduced into the treatment of trypanosomiasis and leishmaniasis in 1940. Pentamidine has also an established place in the treatment of Pneumocystis carinii pneumonia [1].
The mechanism of action of pentamidine is not known. The drug concentrates in trypanosomes via an energy-dependent, high affinity uptake system, which operates more rapidly in drug sensitive strains. Inside the cell, pentamidine interacts with nucleic acids thus affecting DNA biosynthesis [2]. It has also been shown that the drug inhibits the plasmamembrane Ca++-ATPase of the parasites [3]. In vitro, the drug causes ultra-structural disruptions of the mitochondrial structures of Leishmania mexicana and tropica [2, 4]. The drug has also been shown to inhibit trypanosomal S-adenosyl-L-methionine decarboxylase, thus reducing the synthesis of polyamines [5].

Indications

Trypanosomiasis
In the treatment of early-stage Trypanosoma brucei gambiense.
Leishmaniasis
In the treatment of patients with visceral, diffuse cutaneous, or mucocutaneous leishmaniasis due to L. aethiopica and L. guyanensis who are unresponsive or intolerant to antimony preparations.
Pneumocystis carinii pneumonia
Pentamidine is also used in the prophylaxis and treatment of Pneumocystis carinii pneumonia as a second choice.

Side effects

Following parenteral administration of pentamidine, about 45% of the patients may experience side effects some of which can be fatal . Rapid i.v. injection may cause sudden hypotension followed by breathlessness, tachycardia, dizziness, headache, vomiting and fainting which are due to histamine release. Local pain and sterile abscess may be formed after intramuscular injection [6]. Nephrotoxicity which is usually mild to moderate and reversible is the most common side effect. Hypoglycaemic reactions are also common. A few patients may develop hyperglycaemia and diabetes mellitus. This paradoxical effect is thought to be due to a cytolytic release of insulin followed by destruction of the beta-cells. Leucopenia, abnormal liver function, hypocalcaemia and Stevens-Johnson syndrome can also occur . There have been occasional reports of acute pancreatitis [7].
In two smaller studies conducted in Côte d’Ivoire, the most common subjective side effect reported was abdominal pain. A few patients complained of hypersalivation [8]. Pentamidine has been reported to possess anticholinesterase activity [9] and the abdominal pain and the hypersalivation reported in the former study may be due to this effect.

Contraindications and precautions

Patients should remain supine during pentamidine administration and their blood pressure and blood glucose levels monitored. It is advisable to have adrenaline ready in case of a sudden collapse. Where possible, kidney and liver function tests should be assessed regularly during the treatment.
Pentamidine is not recommended for use in patients with late-stage trypanosomiasis.

Interactions

There have been no reports.

Preparations

Available as pentamidine isethionate (174 mg isethionate is equivalent to 100 mg base).
• Pentacarinat® (Rhône-Poulenc Rorer). Vials containing 300 mg pentamidine isethionate powder which is dissolved with 2–3 ml of sterile water.
• Pentam-300® (LyphoMed, USA). Vials containing 300 mg pentamidine isethionate
powder which is dissolved with 2–3 ml of sterile water.

References

1. Goa KL, Campoli-Richards D (1987). Pentamidine Isethionate. A review of its antiprotozoal activity, pharmacokinetic properties and therapeutic use in Pneumocystis carinii pneumonia. Drugs, 33, 242–258.
2. Sands M, Kron MA, Brown RB (1985). Pentamidine: A review. Rev Infect Dis, 7, 625–634.
3. Benaim G, Lopez-Estrano C, Docampo R, Moreno SNJ (1993). A calmodulin-stimulated Ca2+ pump in plasma-membrane vesicles from Trypanosoma brucei; selective inhibition by pentamidine. Biochem J, 296, 756–763.
4. Steck EA, Kinnamon KE, Rane DS, Hanson WL (1981). Leishmania donovani, Plasmodium berghei, Trypanosoma rhodesiense: antiprotozoal effects of some amidine types. Exp Parasitol, 52, 404–413.
5. Bitonti AJ, Dumont JA, McCann PP (1986). Characterisation of Trypanosoma brucei brucei SadenosylL-methionine decarboxylase and its inhibition by Berenil, pentamidine and methylglyoxal bis(quanylhydrazone). Biochem J, 237, 518–521.
6. Navin TR, Fontaine RE (1984). Intravenous versus intramuscular administration of pentamidine. N Engl J Med, 311, 1701–1702.
7. Murphey SA, Josephs AS (1981). Acute pancreatitis associated with pentamidine therapy. Arch Intern Med, 141, 56–58.
8. Bronner U, Gustafsson LL, Doua F, Ericsson Ö, Miézan T, Rais M, Rombo L (1995). Pharmacokinetics and adverse reactions of a single dose of pentamidine in patients with
9. Alston TA (1988). Inhibition of cholinesterase by pentamidine. Lancet, ii, 1423.

Description

Pentamidine is an aromatic diamine that is effective against protozoal diseases, such as amoebic dysentery, malaria, trypanosomiasis, and leishmaniasis. In clinical studies, it has also been shown to be an effective prophylaxis against pneumocystis pneumonia.

Chemical Properties

Crystalline Solid

Originator

Nebupent,Fujisawa Healthcare Inc ,USA

Uses

Has 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).

Uses

antiprotozoal, inhibits nucleic acid & protein synthesis

Definition

ChEBI: Pentamidine is a diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease. It has a role as a trypanocidal drug, an antifungal agent, a NMDA receptor antagonist, an anti-inflammatory agent, a chemokine receptor 5 antagonist, an EC 2.3.1.48 (histone acetyltransferase) inhibitor, a calmodulin antagonist, a S100 calcium-binding protein B inhibitor and a xenobiotic. It is a carboxamidine, a diether and an aromatic ether. It is a conjugate base of a pentamidinium(2+).

Indications

Pentamidine (Pentam 300) binds to DNA and may inhibit kinetoplast DNA replication and function. It also may act by inhibiting dihydrofolate reductase and interfering with polyamine metabolism. An effect on organism respiration, especially at high doses, also may play a role.

Manufacturing Process

2.5 g of p,p'-dicyano-1,5-diphenoxy-pentane (obtained by the interaction of phydroxybenzonitrile and pentamethylene-dibromide in aqueous alkaline solution, melting point 114°C) are dissolved in 15 cc of nitrobenzene and 2.5 cc of absolute ethyl alcohol added. The solution is saturated with dry hydrochloric acid gas at 0°C and allowed to stand for 48 h. It is then diluted with dry ether and the precipitated 1,5-diphenoxypentane, 4,4'di(ethoxycarbonimidoyl) dihydrochlorid is filtered and washed with ether.
4 g of 1,5-diphenoxypentane, 4,4'-di(ethoxycarbonimidoyl) dihydrochloride are mixed with 30 cc. of 6 % ethyl alcoholic ammonia and heated in a closed vessel at 50°C for 5 h. The alcohol is removed and the residual 1,5diphenoxypentane, 4,4'-diamidino dihydrochloride is twice recrystallised fromdilute hydrochloric acid and finally purifled by dissolving in water and precipitating with acetone. Its melts at 236°C, dec.
Pentamidine isetionate salt may be produced by the reaction pentamidine base with isethionic acid.

brand name

Nebupent [as isethionate] (Fujisawa); Pentacarinat [as isethionate] (Rhone-Poulenc Rorer); Pentam 300 [as isethionate] (Fujisawa).

Therapeutic Function

Antiprotozoal

Antimicrobial activity

Pentamidine has broad activity in experimental models against P. falciparum, Toxoplasma gondii, Leishmania spp., Trypanosoma spp. and Babesia spp. It also has activity against Pn. jirovecii.

Acquired resistance

Relapse rates of 7–16% have been reported in the treatment of human African trypanosomiasis in West Africa. Patients usually respond to a subsequent course of treatment with melarsoprol. A membrane transporter is involved in crossresistance of arsenic-resistant T. brucei to diamidines, affecting diminazene and stilbamidine more than pentamidine.

Pharmaceutical Applications

A synthetic diamidine, available as the isethionate (2-hydroxymethane sulfonate) salt for parenteral use. It is also administered by instillation of a nebulized solution directly into the lungs.

Mechanism of action

Pentamidine is not well absorbed from the intestinal tract after oral administration and generally is given by intramuscular injection. The drug binds to tissues, particularly the kidney, and is slowly excreted, mostly as the unmodified drug. It does not enter the central nervous system (CNS). Its sequestration in tissues accounts for its prophylactic use in trypanosomiasis.

Pharmacokinetics

Oral absorption: Negligible
Cmax 4 mg/kg intramuscular: c. 0.5 mg/L after 1 h
Plasma half-life: c. 6.5 h
Volume of distribution: 3 L/kg
Plasma protein binding: c. 70%
Pentamidine is rapidly and extensively metabolized by rat liver, and high concentrations are retained in renal and hepatic tissue for up to 6 months after administration. In humans distribution is mainly in the liver, kidney, adrenal glands and spleen, with lower accumulation in the lung. This tissue retention is the basis for its prophylactic use. Although transport across the blood–brain barrier has been demonstrated in experimental models, it is probably unable to cross the blood–brain barrier in sufficient quantity to be trypanocidal: <1% of the plasma concentration has been measured in the CSF of sleeping sickness patients. About 15–20% of the dose is excreted in the urine but because of retention in tissues there is an extremely long terminal half-life (>12 days).

Clinical Use

Human African trypanosomiasis (early stages before CNS involvement) Prophylaxis and therapy of Pn. jirovecii pneumonia
Visceral leishmaniasis unresponsive to pentavalent antimonials and cutaneous leishmaniasis caused by L. guyanensis
There is limited evidence for its use in the treatment of babesiosis.

Clinical Use

Pentamidine is active against Pneumocystis carinii, trypanosomes, and leishmaniasis unresponsive to pentavalent antimonials. It is an alternative agent for the treatment of P. carinii pneumonia. Although it is more toxic than trimethoprim–sulfamethoxazole, it has been widely used in patients with acquired immunodeficiency syndrome (AIDS), in whom P. carinii infection is common.
Pentamidine is an alternative drug for visceral leishmaniasis, especially when sodium stibogluconate has failed or is contraindicated. Pentamidine is also a reserve agent for the treatment of trypanosomiasis before the CNS is invaded. This characteristic largely restricts its use to Gambian trypanosomiasis.

Side effects

Adverse reactions occur frequently. Rapid drug infusion may produce tachycardia, vomiting, shortness of breath, headache, and a fall in blood pressure. Changes in blood sugar (hypoglycemia or hyperglycemia) necessitate caution in its use, particularly in patients with diabetes mellitus. Renal function should be monitored and blood counts checked for dyscrasias.

Side effects

Side effects range from local irritation and sterile abscess at the site of injection to transient effects (vomiting, abdominal discomfort) and serious systemic effects (hypotension, effects on the heart, hypoglycemia and hyperglycemia, leukopenia, thrombocytopenia). In a study of the treatment of South American cutaneous leishmaniasis, 17% of patients prematurely terminated treatment due to toxicity and another 30% reported side effects.

Synthesis

Pentamidine, 4-4??-(pentamethylendioxy)dibenzamidine (37.4.2), is made by reacting 4-hydroxybenzonitrile with 1,5-dibromopentane in the presence of sodium hydroxide to make 1,5-bis-(4-cyanophenoxy)pentane (37.4.1). Subsequent reaction of this with an ethanol solution of hydrogen chloride with the intermediate formation of an iminoester, and then with an ethanol solution of ammonia gives the desired pentamidine.

Pentamidine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Pentamidine manufacturers

Hebei Duling International Trade Co. LTD
Product
Pentamidine 100-33-4
Price
US $25.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2022-12-28
Hebei Zhanyao Biotechnology Co. Ltd
Product
Pentamidine 100-33-4
Price
US $10.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
20 Tons
Release date
2021-11-17
Dideu Industries Group Limited
Product
Pentamidine 100-33-4
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-06-18

100-33-4, PentamidineRelated Search:

4-Methoxyphenylacetic acid 2-Phenoxyethanol 4-Methoxybenzoic acid p-Anisaldehyde m-Anisyl alcohol BENZAMIDINE Benzoyl peroxide 3-Phenoxybenzaldehyde (Trifluoromethoxy)benzene Anisole pentamidine isetionate,PENTAMIDINE ISETHIONATE NMDA ANTAGONIST, NEUR,PENTAMIDINE ISETHIONATE SALT,PENTAMIDINE ISETHIONATE,PENTAMIDINE DIISETHIONATE N-hydroxypentamidine PENTAMIDINE DIMETHANESULFONATE,pentamidine mesylate N,N'-dihydroxypentamidine PENTAMIDINE DIISETIONATE Pentamidine cis-platinum pentamidine bromide cis-platinum pentamidine seleniocyanate

  • 4,4’-(pentamethylenedioxy)dibenzamidine
  • 4,4’-diamidino-alpha,omega-diphenoxypentane
  • 4,4’-diamidinodiphenoxypentane
  • p,p’-(pentamethylene-dioxy)bis-benzamidine
  • p,p’-(pentamethylenedioxy)dibenzamidine
  • 4,4'-[1,5-PENTANEDIYLBIS(OXY)]BIS-BENZENECARBOXIMIDAMIDE
  • PENTAMIDINE
  • 4,4’-(1,5-pentanediylbis(oxy))bis-benzenecarboximidamid
  • 4,4’-(pentamethylenedioxy)di-benzamidin
  • 3-(1,3-Benzothiazol-2-yl)-7-diethylaminochromen-2-one
  • 4,4'-(1,5-Pentanediylbisoxy)dibenzamidine
  • 4,4'-(Pentane-1,5-diylbisoxy)bisbenzamidine
  • 4,4'-(Pentane-1,5-diyldioxy)bis(benzenecarboxamidine)
  • 4,4'-[1,5-Pentanediylbis(oxy)]bisbenzamidine
  • 4,4'-[Pentamethylenebis(oxy)]bis(benzamidine)
  • 4-[5-(4-amidinophenoxy)pentoxy]benzamidine
  • 4-[5-(4-carbamimidoylphenoxy)pentoxy]benzenecarboximidamide
  • 4,4'-(Pentane-1,5-diylbis(oxy))dibenziMidaMide
  • MP 601205
  • NSC 9921
  • Benzenecarboximidamide, 4,4'-[1,5-pentanediylbis(oxy)]bis-
  • Pentamidine USP/EP/BP
  • Pentamidine DISCONTINUED, offer P272501
  • 4,4'-(Pentane-1,5-diylbis(oxy))dibenzimidamide
  • 100-33-4
  • C19H24N4O2
  • NEBUPENT
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Amines
  • Aromatics