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
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
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
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
Remifentanil.
2001 Aug
[Mastocytosis: general anesthesia with remifentanil and sevoflurane].
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
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.
2001 Jan
Use of remifentanil in a patient with peripartum cardiomyopathy requiring Caesarean section.
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
Postoperative reading speed does not indicate implicit memory in elderly cardiac patients after propofol and remifentanyl anaesthesia.
2001 Jul
Sevoflurane with remifentanil allows rapid tracheal intubation without neuromuscular blocking agents.
2001 Jul-Aug
Recovery after remifentanil and sufentanil for analgesia and sedation of mechanically ventilated patients after trauma or major surgery.
2001 Jun
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
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- 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
Recovery from propofol anaesthesia supplemented with remifentanil.
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
[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
A patient with hypertrophic obstructive cardiomyopathy presenting for total knee replacement.
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
The bispectral index during an anaphylactic circulatory arrest.
2001 Oct
Effect of age on recovery from remifentanil anaesthesia.
2001 Oct
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
The in vitro effects of remifentanil, sufentanil, fentanyl, and alfentanil on isolated human right atria.
2001 Sep
Quantitative EEG changes associated with loss and return of consciousness in healthy adult volunteers anaesthetized with propofol or sevoflurane.
2001 Sep
Patient-controlled analgesia for labour using remifentanil: a feasibility study.
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.
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
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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
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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