U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H28N2O5
Molecular Weight 376.4467
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REMIFENTANIL

SMILES

CCC(=O)N(C1=CC=CC=C1)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 376.4467
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

1996
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
[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
Rational use of opioids.
2001 Apr
Effect of the opioid remifentanil on cellular immune response in the rat.
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
Propofol/remifentanil in neurosurgery.
2001 Apr
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.
2001 Apr
[Mastocytosis: general anesthesia with remifentanil and sevoflurane].
2001 Aug
Small doses of remifentanil or sufentanil for blunting cardiovascular changes induced by tracheal intubation: a double-blind comparison.
2001 Feb
[Fastrach laryngeal mask, sevoflurane and remifentanil: an anesthetic alternative for the myasthenic patient].
2001 Feb
Patient-controlled intravenous analgesia using remifentanil in the parturient.
2001 Feb
Sevoflurane--nitrous oxide anaesthesia supplemented with remifentanil: effect on recovery and cognitive function.
2001 Feb
Use of remifentanil in a patient with peripartum cardiomyopathy requiring Caesarean section.
2001 Jan
Use of remifentanil for major abdominal surgery.
2001 Jan
Comparative analysis of costs of total intravenous anaesthesia with propofol and remifentanil vs. balanced anaesthesia with isoflurane and fentanyl.
2001 Jan
A comparison of remifentanil and fentanyl in patients undergoing carotid endarterectomy.
2001 Jan
Remifentanil and controlled hypotension; comparison with nitroprusside or esmolol during tympanoplasty.
2001 Jan
Recirculatory pharmacokinetics and pharmacodynamics of rocuronium in patients: the influence of cardiac output.
2001 Jan
Effect of remifentanil on pain and secondary hyperalgesia associated with the heat--capsaicin sensitization model in healthy volunteers.
2001 Jan
Remifentanil versus meperidine for monitored anesthesia care: a comparison study in older patients undergoing ambulatory colonoscopy.
2001 Jan
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
Postoperative reading speed does not indicate implicit memory in elderly cardiac patients after propofol and remifentanyl anaesthesia.
2001 Jul
Bispectral index monitoring in sevoflurane and remifentanil anesthesia. Analysis of drugs management and immediate recovery.
2001 Jun
Safety and efficacy of remifentanil infusion in craniosynostosis repair in infants.
2001 Jun
Effect of tracheal intubation or laryngeal mask airway insertion on intraocular pressure using balanced anesthesia with sevoflurane and remifentanil.
2001 Jun
Intraoperative motor evoked potentials to transcranial electrical stimulation during two anaesthetic regimens.
2001 Jun
Remifentanil- and fentanyl-based anesthesia for intraoperative monitoring of somatosensory evoked potentials.
2001 Jun
[Remifentanil for palliative abdominal surgery in a patient with myasthenia gravis].
2001 Jun-Jul
[Alterations in left ventricular-arterial coupling and mechanical efficiency produced by remifentanil during cardiac anesthesia].
2001 Mar
Recovery profile and side effects of remifentanil-based anaesthesia with desflurane or propofol for laparoscopic cholecystectomy.
2001 Mar
Clonidine decreases propofol requirements during anaesthesia: effect on bispectral index.
2001 May
[Anesthesia in extreme obesity].
2001 May
[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
Dose-dependent regional cerebral blood flow changes during remifentanil infusion in humans: a positron emission tomography study.
2001 May
Propofol and remifentanil pharmacodynamic interaction during orthopedic surgical procedures as measured by effects on bispectral index.
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
Remifentanil is a valuable alternative to contraindicated neuraxial analgesia in the parturients.
2001 May
The efficacy and resource utilization of remifentanil and fentanyl in fast-track coronary artery bypass graft surgery: a prospective randomized, double-blinded controlled, multi-center trial.
2001 May
A randomized double-blinded multicenter comparison of remifentanil versus fentanyl when combined with isoflurane/propofol for early extubation in coronary artery bypass graft surgery.
2001 May
A comparison of fentanyl, sufentanil, and remifentanil for fast-track cardiac anesthesia.
2001 Oct
Hemodynamics and emergence profile of remifentanil versus fentanyl prospectively compared in a large population of surgical patients.
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
The in vitro effects of remifentanil, sufentanil, fentanyl, and alfentanil on isolated human right atria.
2001 Sep
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 Sat Dec 16 17:13:30 GMT 2023
Edited
by admin
on Sat Dec 16 17:13:30 GMT 2023
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 Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
WHO-VATC QN01AH06
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
NDF-RT N0000175690
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
WHO-ATC N01AH06
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
DEA NO. 9739
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
NDF-RT N0000175684
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
NCI_THESAURUS C1506
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C66513
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
FDA UNII
P10582JYYK
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
DRUG BANK
DB00899
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL1005
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
MERCK INDEX
m9521
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2363
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
LACTMED
Remifentanil
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
CAS
132875-61-7
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
WEB RESOURCE
REMIFENTANIL
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
EVMPD
SUB10272MIG
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
CHEBI
8802
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
IUPHAR
7292
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
MESH
C071741
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
INN
6924
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
RXCUI
73032
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
REMIFENTANIL
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
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.
SMS_ID
100000089165
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID00157826
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
PUBCHEM
60815
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
DAILYMED
P10582JYYK
Created by admin on Sat Dec 16 17:13:31 GMT 2023 , Edited by admin on Sat Dec 16 17:13:31 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Potency higher than fentanyl (IC50=1.23 NM) fast onset and short duration of action.
IC50
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE INACTIVE -> PARENT
MINOR
METABOLITE INACTIVE -> PARENT
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC