N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide

• ChemBase ID: 589
• Molecular Formular: C22H30N2O2S
• Molecular Mass: 386.5508
• Monoisotopic Mass: 386.20279921
• SMILES: s1c(CCN2CCC(N(c3ccccc3)C(=O)CC)(CC2)COC)ccc1
• Canonical SMILES: COCC1(CCN(CC1)CCc1cccs1)N(c1ccccc1)C(=O)CC
• InChI: InChI=1S/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3
• InChIKey: GGCSSNBKKAUURC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide
• IUPAC Traditional name: sufentanil
• Brand Name: Chronogesic; Sufenta
• Synonyms: Sufentanil Citrate; Sufentanilum [INN-Latin]; Sufentanyl; Sulfentanil Citrate; sufentanil; Sufentanil

Database IDs

• CAS Number: 56030-54-7
• PubChem SID: 46504737; 160964052
• PubChem CID: 41693
• CHEBI ID: 9316
• ATC CODE: N01AH03
• CHEMBL: 658
• Chemspider ID: 38043
• DrugBank ID: DB00708
• IUPHAR ligand ID: 3534
• KEGG ID: D05938
• Unique Ingredient Identifier: AFE2YW0IIZ
• Wikipedia Title: Sufentanil

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.47834045
• LogD (pH = 7.4): 2.129825
• Log P: 3.605173
• Molar Refractivity: 111.4159 cm^3
• Polarizability: 43.275696 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.4
• LOG S: -4.51
• Solubility (Water): 1.20e-02 g/l

PROPERTIES

Physical Property

• Solubility: 76 mg/L
• Melting Point: 97°C (206.6°F)
• Hydrophobicity(logP): 2.8

Pharmacology Properties

• Admin Routes: Injection
• Half Life: 265 minutes
• Legal Status: Class A (UK); Schedule II (US)

DETAILS

DrugBank - DB00708

• Drug Groups: approved; investigational
• Description: An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. [PubChem]
• Indication: Used as an analgesic adjunct in anesthesia and as a primary anesthetic drug in procedures requiring assisted ventilation and in the relief of pain.
• Pharmacology: Sufentanil is a synthetic opioid analgesic. Sufentanil 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, sufentanil exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Sufentanil 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. Sufentanil depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
• Toxicity: LD₅₀: 18.7 mg/kg (IV in mice)
• Affected Organisms: Humans and other mammals
• Half Life: 265 minutes
• External Links: Wikipedia; Drugs.com