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Details

Stereochemistry ACHIRAL
Molecular Formula C20H28N2O5
Molecular Weight 376.4475
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REMIFENTANIL

SMILES

CCC(=O)N(c1ccccc1)C2(CCN(CCC(=O)OC)CC2)C(=O)OC

InChI

InChIKey=ZTVQQQVZCWLTDF-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H28N2O5
Molecular Weight 376.4475
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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. ULTIVA is a µ-opioid agonist with rapid onset and peak effect, and short duration of action. The µ-opioid activity of ULTIVA is antagonized by opioid antagonists such as naloxone. ULTIVA is indicated for IV administration: 1. As an analgesic agent for use during the induction and maintenance of general anesthesia for inpatient and outpatient procedures. 2. For continuation as an analgesic into the immediate postoperative period in adult patients under the direct supervision of an anesthesia practitioner in a postoperative anesthesia care unit or intensive care setting. 3. As an analgesic component of monitored anesthesia care in adult patients.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ULTIVA

Approved Use

ULTIVA is indicated for IV administration: 1.As an analgesic agent for use during the induction and maintenance of general anesthesia for inpatient and outpatient procedures. 2.For continuation as an analgesic into the immediate postoperative period in adult patients under the direct supervision of an anesthesia practitioner in a postoperative anesthesia care unit or intensive care setting. 3.As an analgesic component of monitored anesthesia care in adult patients.

Launch Date

8.371296E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
194 μg/mL
6 μg/kg/h 1 times / day other, intravenous
dose: 6 μg/kg/h
route of administration: Intravenous
experiment type: OTHER
co-administered:
REMIFENTANIL ACID blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14 ng/mL
6 μg/kg/h 1 times / day other, intravenous
dose: 6 μg/kg/h
route of administration: Intravenous
experiment type: OTHER
co-administered:
REMIFENTANIL blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
8080 μg × h/mL
6 μg/kg/h 1 times / day other, intravenous
dose: 6 μg/kg/h
route of administration: Intravenous
experiment type: OTHER
co-administered:
REMIFENTANIL ACID blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
745 ng × h/mL
6 μg/kg/h 1 times / day other, intravenous
dose: 6 μg/kg/h
route of administration: Intravenous
experiment type: OTHER
co-administered:
REMIFENTANIL blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.48 h
6 μg/kg/h 1 times / day other, intravenous
dose: 6 μg/kg/h
route of administration: Intravenous
experiment type: OTHER
co-administered:
REMIFENTANIL ACID blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11.4 min
6 μg/kg/h 1 times / day other, intravenous
dose: 6 μg/kg/h
route of administration: Intravenous
experiment type: OTHER
co-administered:
REMIFENTANIL blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
0.5 μg/kg/min 1 times / day other, intravenous
dose: 0.5 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
REMIFENTANIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Target controlled infusion of remifentanil and propofol for cesarean section in a patient with multivalvular disease and severe pulmonary hypertension.
2001
Use of remifentanil in combination with desflurane or propofol for ambulatory oral surgery.
2001
[Total intravenous anesthesia using remifentanil and propofol with midazolam co-induction in laparoscopic surgery of the gallbladder].
2001
[Stand-by and conscious sedation--possibilities and limits of anesthesiological management].
2001
Effects of fentanyl, alfentanil, remifentanil and sufentanil on loss of consciousness and bispectral index during propofol induction of anaesthesia.
2001 Apr
Rational use of opioids.
2001 Apr
Effect of the opioid remifentanil on cellular immune response in the rat.
2001 Apr
[Fiberoptic intubation during remifentanil propofol sedation].
2001 Apr
Influence of aortic blood flow velocity on changes of middle cerebral artery blood flow velocity during isoflurane and sevoflurane anaesthesia.
2001 Apr
Monitored anesthesia care in awake craniotomy for brain tumor surgery.
2001 Apr
Remifentanil.
2001 Aug
Target-controlled infusion or manually controlled infusion of propofol in high-risk patients with severely reduced left ventricular function.
2001 Aug
The use of remifentanil to facilitate the insertion of the laryngeal mask airway.
2001 Aug
Effects of combined methohexitone-remifentanil anaesthesia in electroconvulsive therapy.
2001 Aug
Influence of hypotensive and normotensive anesthesia on platelet aggregability and hemostatic markers in orthognathic surgery.
2001 Aug 1
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.
2001 Jan
Opioid chronopharmacology.
2001 Jul
Anaesthetic management of a child with a positive family history of malignant hyperthermia for posterior fossa surgery in the sitting position.
2001 Jul
Esmolol is not an alternative to remifentanil for fast-track outpatient gynecologic laparoscopic surgery.
2001 Jul
Monitored anesthesia care using remifentanil and propofol for awake craniotomy.
2001 Jul
Sevoflurane with remifentanil allows rapid tracheal intubation without neuromuscular blocking agents.
2001 Jul-Aug
Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome.
2001 Jun
Recovery after remifentanil and sufentanil for analgesia and sedation of mechanically ventilated patients after trauma or major surgery.
2001 Jun
Safety and efficacy of remifentanil infusion in craniosynostosis repair in infants.
2001 Jun
The effects of remifentanil on haemodynamic stability during rigid bronchoscopy.
2001 Jun
Intraoperative motor evoked potentials to transcranial electrical stimulation during two anaesthetic regimens.
2001 Jun
[Remifentanil for palliative abdominal surgery in a patient with myasthenia gravis].
2001 Jun-Jul
Recovery from propofol anaesthesia supplemented with remifentanil.
2001 Mar
[Alterations in left ventricular-arterial coupling and mechanical efficiency produced by remifentanil during cardiac anesthesia].
2001 Mar
[Esterase-metabolized remifentanil hydrochloride opioid (Ultiva-TM), a new step towards the solution of the problem of regulation of analgetic components of general anesthesia].
2001 Mar-Apr
[Droperidol and dimenhydrinate alone or in combination for prevention of postoperative nausea and vomiting].
2001 May
[General anesthesia with remifentanil in two cases of emergency cesarean section].
2001 May
[Sedation in spinal anesthesia. Comparison of remifentanil and propofol].
2001 May
A patient with hypertrophic obstructive cardiomyopathy presenting for total knee replacement.
2001 May
Propofol/remifentanil versus propofol alone for bone marrow aspiration in paediatric haemato-oncological patients.
2001 May
A preliminary investigation of remifentanil as a labor analgesic.
2001 May
Magnesium as part of balanced general anaesthesia with propofol, remifentanil and mivacurium: a double-blind, randomized prospective study in 50 patients.
2001 Nov
The bispectral index during an anaphylactic circulatory arrest.
2001 Oct
Goal oriented general anesthesia for Cesarean section in a parturient with a large intracranial epidermoid cyst.
2001 Oct
Threshold-level repetitive transcranial electrical stimulation for intraoperative monitoring of central motor conduction.
2001 Oct
A comparison of propofol and remifentanil for sedation and limitation of movement during periretrobulbar block.
2001 Sep
Hemodynamics and emergence profile of remifentanil versus fentanyl prospectively compared in a large population of surgical patients.
2001 Sep
Does functional ability in the postoperative period differ between remifentanil- and fentanyl-based anesthesia?
2001 Sep
Spontaneous movements, local reactions and pain on injection of rocuronium. A comparison between female and male patients.
2001 Sep
Remifentanil and fentanyl during anaesthesia for major abdominal and gynaecological surgery. An open, comparative study of safety and efficacy.
2001 Sep
Potential hazard with syringe infusion pump.
2001 Sep
Facilitation of laryngeal mask airway insertion: effects of remifentanil administered before induction with target-controlled propofol infusion.
2001 Sep
Quantitative EEG changes associated with loss and return of consciousness in healthy adult volunteers anaesthetized with propofol or sevoflurane.
2001 Sep
Effects of the opioid remifentanil on olfactory function in healthy volunteers.
2001 Sep 28
Effects of cerebrospinal fluid loss and epidural blood patch on cerebral blood flow in swine.
2001 Sep-Oct
Patents

Sample Use Guides

Usual Adult Dose for Anesthesia Induction of Anesthesia: Continuous IV infusion: 0.5 to 1 mcg/kg/min. If endotracheal intubation is to occur in less than 8 minutes, an initial dose of 1 mcg/kg may be administered over 30 to 60 seconds. Maintenance of Anesthesia: With Nitrous Oxide, 0.4 mg/kg/min by continuous IV infusion. Infusion dose range: 0.1 to 2 mcg/kg/min. Supplemental IV bolus: 1 mcg/kg every 2 to 5 minutes.
Route of Administration: Intravenous
Remifentanil (10(-8) - 10(-4) mol/ L) caused a concentration-dependent vasorelaxation in the human being artery rings.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:30:10 UTC 2021
Edited
by admin
on Fri Jun 25 22:30:10 UTC 2021
Record UNII
P10582JYYK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REMIFENTANIL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
GI 87084X
Code English
RAMIFENTANYL
Common Name English
REMIFENTANIL [WHO-DD]
Common Name English
REMIFENTANIL [MI]
Common Name English
ULTIVA-
Common Name English
REMIFENTANIL [INN]
Common Name English
REMIFENTANYL
Common Name English
REMIFENTANIL [VANDF]
Common Name English
IDS-NR-005
Code English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
WHO-VATC QN01AH06
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
NDF-RT N0000175690
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
WHO-ATC N01AH06
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
DEA NO. 9739
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
NDF-RT N0000175684
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
NCI_THESAURUS C1506
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C66513
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
FDA UNII
P10582JYYK
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
DRUG BANK
DB00899
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL1005
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
MERCK INDEX
M9521
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2363
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
LACTMED
Remifentanil
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
CAS
132875-61-7
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
WEB RESOURCE
REMIFENTANIL
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
EVMPD
SUB10272MIG
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
IUPHAR
7292
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
MESH
C071741
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
INN
6924
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
RXCUI
73032
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
REMIFENTANIL
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY Remifentanil is used for sedation as well as combined with other medications for use in general anesthesia. Remifentanil is used as an opioid analgesic that has a rapid onset and rapid recovery time. It has been used effectively during craniotomies, spinal surgery, cardiac surgery, and gastric bypass surgery. While opiates function similarly, with respect to analgesia, the pharmacokinetics of remifentanil allows for quicker post-operative recovery.
EPA CompTox
132875-61-7
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
PUBCHEM
60815
Created by admin on Fri Jun 25 22:30:10 UTC 2021 , Edited by admin on Fri Jun 25 22:30:10 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
METABOLITE -> PARENT
MAJOR
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ACTIVE MOIETY