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
- Molecular Weight:
- 340.42
- MOL File:
- 100-33-4.mol
- Modify Date:
- 2023/6/8 9:02:48
| 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 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H302-H335-H319 | |||||||||
| Precautionary statements | P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P | |||||||||
| RIDADR | 3249 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| NFPA 704 |
|
Pentamidine Chemical Properties,Uses,Production
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
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.
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
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
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.
Pentamidine Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | China | 29798 | 60 | Inquiry |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | China | 32760 | 60 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29900 | 58 | Inquiry |
| Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | China | 39916 | 58 | Inquiry |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | China | 49391 | 58 | Inquiry |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | United States | 19892 | 58 | Inquiry |
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