methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate

• ChemBase ID: 775
• Molecular Formular: C20H28N2O5
• Molecular Mass: 376.44672
• Monoisotopic Mass: 376.19982201
• SMILES: O(C(=O)C1(N(c2ccccc2)C(=O)CC)CCN(CC1)CCC(=O)OC)C
• Canonical SMILES: COC(=O)C1(CCN(CC1)CCC(=O)OC)N(c1ccccc1)C(=O)CC
• InChI: InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3
• InChIKey: ZTVQQQVZCWLTDF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
• IUPAC Traditional name: remifentanil
• Brand Name: Ultiva
• Synonyms: Remifentanyl; Remifentanil

Database IDs

• CAS Number: 132875-61-7
• PubChem SID: 160964238; 46504538
• PubChem CID: 60815

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.48355016
• LogD (pH = 7.4): 1.1568937
• Log P: 1.5152788
• Molar Refractivity: 100.5615 cm^3
• Polarizability: 39.659138 Å^3
• Polar Surface Area: 76.15 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.75
• LOG S: -2.8
• Solubility (Water): 5.91e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.4

DETAILS

DrugBank - DB00899

• Drug Groups: approved
• Description: Remifentanil (marketed by Abbott as Ultiva) is a potent ultra short-acting synthetic opioid analgesic drug. It is given to patients during surgery to relieve pain and as an adjunct to an anaesthetic. Remifentanil is a specific mu-type-opioid receptor agonist. Hence, it causes a reduction in sympathetic nervous system tone, respiratory depression and analgesia.
• Indication: For use during the induction and maintenance of general anesthesia.
• Pharmacology: Remifentanil is an opioid agonist with rapid onset and peak effect and ultra-short duration of action. The opioid activity of remifentanil is antagonized by opioid antagonists such as naloxone. The analgesic effects of remifentanil are rapid in onset and offset. Its effects and side effects are dose dependent and similar to other opioids. Remifentanil in humans has a rapid blood-brain equilibration half-time of 1 ± 1 minutes (mean ± SD) and a rapid onset of action.
• Affected Organisms: Humans and other mammals
• Biotransformation: By hydrolysis of the propanoic acid-methyl ester linkage by nonspecific blood and tissue esterases.
• Half Life: 1-20 minutes
• Protein Binding: 70% (bound to plasma proteins)
• Elimination: Remifentanil is an esterase-metabolized opioid. The carboxylic acid metabolite is essentially inactive (1/4600 as potent as remifentanil in dogs) and is excreted by the kidneys with an elimination half-life of approximately 90 minutes.
• Distribution: * 350 mL/kg; * 452 ± 144 mL/kg [neonates]; * 223 ± 30.6 mL/kg [adolescents]
• Clearance: * 40 mL/min/kg [young, healthy adults]
• External Links: Wikipedia; RxList; Drugs.com