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Details

Stereochemistry ACHIRAL
Molecular Formula C20H28N2O5.ClH
Molecular Weight 412.9084
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REMIFENTANIL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=WFBMIPUMYUHANP-UHFFFAOYSA-N
InChI=1S/C20H28N2O5.ClH/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;1H

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

Molecular Formula ClH
Molecular Weight 36.4609
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
[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
[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
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.
2001 Apr
Remifentanil.
2001 Aug
[Mastocytosis: general anesthesia with remifentanil and sevoflurane].
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
Recovery and neurological examination after remifentanil-desflurane or fentanyl-desflurane anaesthesia for carotid artery surgery.
2001 Jan
Use of remifentanil in a patient with peripartum cardiomyopathy requiring Caesarean section.
2001 Jan
Use of remifentanil for major abdominal surgery.
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
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
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
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
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
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
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
Effect of age on recovery from remifentanil anaesthesia.
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 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
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
Effects of remifentanil/propofol in comparison with isoflurane on dynamic cerebrovascular autoregulation in humans.
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
Effects of the opioid remifentanil on olfactory function in healthy volunteers.
2001 Sep 28
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 21:07:12 UTC 2021
Edited
by admin
on Fri Jun 25 21:07:12 UTC 2021
Record UNII
5V444H5WIC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REMIFENTANIL HYDROCHLORIDE
JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
REMIFENTANIL HYDROCHLORIDE [WHO-DD]
Common Name English
REMIFENTANIL HCL
Common Name English
REMIFENTANIL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
REMIFENTANIL HYDROCHLORIDE [JAN]
Common Name English
ULTIVA
Brand Name English
4-CARBOXY-4-(N-PHENYLPROPIONAMIDO)-1-PIPERIDINE PROPIONIC ACID, DIMETHYL ESTER, MONOHYDROCHLORIDE
Common Name English
REMIFENTANIL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
REMIFENTANIL HYDROCHLORIDE [MART.]
Common Name English
REMIFENTANIL HYDROCHLORIDE [USAN]
Common Name English
1-PIPERIDINEPROPANOIC ACID, 4-(METHOXYCARBONYL)-4-((1-OXOPROPYL)PHENYLAMINO)-, METHYL ESTER, MONOHYDROCHLORIDE
Common Name English
GI-87084B
Code English
REMIFENTANIL HYDROCHLORIDE [MI]
Common Name English
REMIFENTANIL HYDROCHLORIDE [VANDF]
Common Name English
GI 87084B
Code English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
NCI_THESAURUS C1506
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1005
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
MERCK INDEX
M9521
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY Merck Index
FDA UNII
5V444H5WIC
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
EVMPD
SUB04215MIG
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
RXCUI
236540
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY RxNorm
EPA CompTox
132539-07-2
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
NCI_THESAURUS
C47702
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
PUBCHEM
60814
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
CAS
132539-07-2
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
DRUG BANK
DBSALT001450
Created by admin on Fri Jun 25 21:07:12 UTC 2021 , Edited by admin on Fri Jun 25 21:07:12 UTC 2021
PRIMARY
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