N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide

• ChemBase ID: 681
• Molecular Formular: C21H32N6O3
• Molecular Mass: 416.51718
• Monoisotopic Mass: 416.25358891
• SMILES: O(CC1(N(c2ccccc2)C(=O)CC)CCN(CC1)CCn1nnn(c1=O)CC)C
• Canonical SMILES: COCC1(CCN(CC1)CCn1nnn(c1=O)CC)N(c1ccccc1)C(=O)CC
• InChI: InChI=1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3
• InChIKey: IDBPHNDTYPBSNI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide
• IUPAC Traditional name: alfentanil
• Brand Name: Alfenta
• Synonyms: Alfentanilum [INN-Latin]; Alfentanyl; Alfentanil

Database IDs

• CAS Number: 71195-58-9
• PubChem SID: 160964144; 46505618
• PubChem CID: 51263
• CHEBI ID: 2569
• ATC CODE: N01AH02
• CHEMBL: 634
• Chemspider ID: 46451
• DrugBank ID: DB00802
• KEGG ID: D07122
• Unique Ingredient Identifier: 1N74HM2BS7
• Wikipedia Title: Alfentanil
• Medline Plus: a601130

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.8123757
• LogD (pH = 7.4): 2.4512272
• Log P: 2.8073738
• Molar Refractivity: 118.592 cm^3
• Polarizability: 43.97878 Å^3
• Polar Surface Area: 81.05 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -3.22
• Solubility (Water): 2.52e-01 g/l

PROPERTIES

Physical Property

• Solubility: 34.6 mg/L
• Melting Point: 140.8°C (285.44°F)
• Hydrophobicity(logP): 0.2

Pharmacology Properties

• Admin Routes: Intravenous
• Bioavailability: 100%
• Half Life: 90–111 minutes
• Metabolism: Hepatic
• Protein Bound: 92%
• Legal Status: Class A (UK); Schedule II (US)

DETAILS

DrugBank - DB00802

• Drug Groups: illicit; approved
• Description: A short-acting opioid anesthetic and analgesic derivative of fentanyl. It produces an early peak analgesic effect and fast recovery of consciousness. Alfentanil is effective as an anesthetic during surgery, for supplementation of analgesia during surgical procedures, and as an analgesic for critically ill patients. [PubChem]
• Indication: For the management of postoperative pain and the maintenance of general anesthesia.
• Pharmacology: Alfentanil is a synthetic opioid analgesic. Alfentanil interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, alfentanil exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Alfentanil may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Alfentanil depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
• Toxicity: Symptoms of overexposure include characteristic rigidity of the skeletal muscles, cardiac and respiratory depression, and narrowing of the pupils.
• Affected Organisms: Humans and other mammals
• Biotransformation: The liver is the major site of biotransformation.
• Absorption: For intravenous injection or infusion only.
• Half Life: 90-111 minutes
• Protein Binding: 92%
• Elimination: Only 1.0% of the dose is excreted as unchanged drug; urinary excretion is the major route of elimination of metabolites.
• Distribution: * 0.4 to 1 L/kg
• Clearance: * 5 mL/kg/min
• External Links: Wikipedia; RxList