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4-[5-(4-carbamimidoylphenoxy)pentoxy]benzenecarboximidamide

CAS number:100-33-4    molecular formula:C19H24N4O2

overview

compound introduction

戊脒是一种二醚,由戊烷-1,5-二醇构成,其中两个羟基氢被4-脒基苯基取代。一种抗锥虫药物,用于治疗皮肤利什曼病和查加斯病。它具有钙调蛋白拮抗剂、S100钙结合蛋白B抑制剂、外源性物质、抗真菌剂、抗锥虫药物、NMDA受体拮抗剂、趋化因子受体5拮抗剂、抗炎剂和EC 2.3.1.48(组蛋白乙酰转移酶)抑制剂的作用。它是一种脒、芳香醚和二醚。它是戊脒(2+)的共轭碱。

Specs

Chinese alias4,4'-(戊烷-1,5-二基双(氧基))二苯甲脒 | 戊脘脒 | 喷它咪 | 戊烷脒
English alias4,4'-Diamidinodiphenoxypentane | 4,4'-(Pentane-1,5-diylbis(oxy))dibenzimidamide
CAS number100-33-4molecular formulaC19H24N4O2
molecular weight340.4Exact mass≥98%
PSA118logp2.6

numbering system

CAS100-33-4
UNII673LC5J4LQ
RXCUI7994
HMDB IDHMDB0014876
KEGG IDD08333
ChEBI ID45081
WikidataQ416206
ChEMBL IDCHEMBL55
WikipediaPentamidine
NSC NumberNSC Number: NSC9921
AIDS Number000224
DrugBank IDDB00738
DrugCentral2090
PharmGKB IDPA450850
PubChem CID4735
Related CAS6823-79-6(DIMETHANESULFONATE)
Nikkaji NumberJ5.512C
Pharos Ligand IDZWTYU7KAJWPZ
NCI Thesaurus CodeC731
DSSTox Substance IDDTXSID7023431
Metabolomics Workbench ID43042
European Community (EC) Number202-841-0
PubChem Reference Collection SID483927673
International Nonproprietary Names (INN)PENTAMIDINE

physicochemical properties

LogP4
XLogP3XLogP3-AA: 2.6
Color/FormCrystallizes as colorless plates from water
Complexity376
Exact Mass340.18992602
Solubility2.36e-02 g/L
Human DrugsMedicines for the treatment of 1st stage African trypanosomiasis
Formal Charge0
Melting Point186.0 °C (decomposes)
Chemical ClassesOther Carboxylic Acid Derivatives
Heavy Atom Count25
Molecular Weight340.4
Monoisotopic Mass340.18992602
Isotope Atom Count0
Physical DescriptionSolid
Rotatable Bond Count10
Stability/Shelf LifeAfter reconstitution with sterile water, the Pentam solution is stable for 48 hours in the original vial at room temperature if protected from light.
Collision Cross Section176.9 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID7023431]
Hydrogen Bond Donor Count4
Covalently-Bonded Unit Count1
Hydrogen Bond Acceptor Count4
Other Experimental PropertiesMol wt 532.64. White powder /Dimethanesulfonate/
Topological Polar Surface Area118 Ų
Defined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Atom Stereocenter Count0
Undefined Bond Stereocenter Count0

Safety information

Hepatotoxicity:
Likelihood score: D (possible rare cause of clinically apparent liver injury).
Adverse Effects:
* Inhaled form - bronchospasm, wheezing, and cough
Cleanup Methods:
Spill Control. Manage hazardous drug spills according to the established, written policies and procedures for each workplace. Be aware that the size of the spill might determine who is authorized to conduct the cleanup and decontamination and how the cleanup is managed. Assure that the written policies and procedures address the protective equipment required for various spill sizes, the possible spreading of material, restricted access to hazardous drug spills, and signs to be posted. Assure that cleanup of a large spill is handled by workers who are trained in handling hazardous materials [29 CFR 1910.120]. Locate spill kits and other cleanup materials in the immediate area where exposures may occur. /Hazardous drugs/
Exposure Routes:
Absorbed poorly through the gastrointestinal tract and is usually administered parenterally.
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
FDA Requirements:
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl pentamidine isethionate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Pentamidine Isethionate/
Toxicity Summary:
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.
Signs and Symptoms:
Symptoms of overdose include pain, nausea, anorexia, hypotension, fever, rash, bad taste in mouth, confusion/hallucinations, dizziness, and diarrhea.
Medical Surveillance:
Employers should ensure that health care workers who are exposed to hazardous drugs are routinely monitored as part of a medical surveillance program. This includes workers who directly handle hazardous drugs such as nurses, pharmacists, and pharmacy technicians. In addition, other workers (e.g., nurses' aides, laundry workers) who may come directly into contact with patient wastes within 48 hours after a patient has received a hazardous drug should be included in a medical surveillance program. ... The elements of a medical surveillance program for hazardous drugs should include (at a minimum): Reproductive and general health questionnaires completed at the time of hire and periodically thereafter. Laboratory work, including complete blood count and urinalysis completed at the time of...
Carcinogen Classification:
No indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury:
References: DOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Values:
LD50 Mouse IV 15 mg/kg
Populations at Special Risk:
Pentamidine isethionate should be used with caution in patients with hypertension, hypotension, ventricular tachycardia, hypoglycemia, hyperglycemia, hypocalcemia, pancreatitis, leukopenia, thrombocytopenia, anemia, hepatic or renal dysfunction and Stevens-Johnson syndrome. /Pentamidine isethionate/
Hazard Classes and Categories:
STOT SE 3 (100%)
Antidote and Emergency Treatment:
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use...
Personal Protective Equipment (PPE):
... Some clinicians suggest that use of gowns, gloves, goggles, and masks by health-care personnel be considered, although the level of protection provided is not known. ... Use of surgical masks by health-care personnel caring for pentamidine-treated patients probably is unlikely to provide an effective means for reducing environmental exposure to the drug; therefore, if a face mask is used, alternative, appropriately designed (e.g., for adequate particle-size filtration) and well-fitted face masks (e.g., 3M Company model 9970 or 9920) should be employed since they are more likely to substantially reduce respiratory exposure levels.
Skin, Eye, and Respiratory Irritations:
Adverse effects ... include eye irritation (e.g., conjunctivitis); perioral and perinasal paresthesia; ... burning sensation of the eyes, nose, and throat; sinus irritation; ... nasal stuffiness; ... shortness of breath; ... acute bronchospasm ...

Production methods and uses

Production method
Saturating an anhydrous alcoholic solution of 4,4'-dicyanodiphenoxypentane with dry hydrogen chloride and allowing it to stand gives pentamidine.
purpose
For the treatment of pneumonia due to <i>Pneumocystis carinii</i>.

Related

upstream information
Methods of Manufacturing:
hydrogen chloride (CID:313); pentamidine (CID:4735)
downstream information

No downstream information yet

MSDS

Found 0 shareMSDS