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

Details

Stereochemistry ACHIRAL
Molecular Formula C20H28N2O5.ClH
Molecular Weight 412.908
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REMIFENTANIL HYDROCHLORIDE

SMILES

Cl.CCC(=O)N(C1=CC=CC=C1)C2(CCN(CCC(=O)OC)CC2)C(=O)OC

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 376.4467
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
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
[Total intravenous anesthesia (TIVA) and balanced anesthesia with short-acting anesthetics for ENT surgery in children].
1999
TIVA with propofol and remifentanil.
1999 May
Remifentanil, propofol or both for conscious sedation during eye surgery under regional anaesthesia.
1999 Nov
Bradycardia after administration of remifentanil.
2000 Mar
Asystole with propofol and remifentanil.
2000 May
Probable seizure after remifentanil in a 4-year-old boy.
2000 May
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
[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
Effect of the opioid remifentanil on cellular immune response in the rat.
2001 Apr
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 hemorrhagic shock on remifentanil: a pharmacokinetic and pharmacodynamic analysis.
2001 Feb
Assessment of depth of anesthesia and postoperative respiratory recovery after remifentanil- versus alfentanil-based total intravenous anesthesia in patients undergoing ear-nose-throat surgery.
2001 Feb
Sevoflurane--nitrous oxide anaesthesia supplemented with remifentanil: effect on recovery and cognitive function.
2001 Feb
The effect of remifentanil on the heat pain threshold in volunteers.
2001 Feb
The use of esmolol as an alternative to remifentanil during desflurane anesthesia for fast-track outpatient gynecologic laparoscopic surgery.
2001 Feb
Recovery and neurological examination after remifentanil-desflurane or fentanyl-desflurane anaesthesia for carotid artery surgery.
2001 Jan
Recirculatory pharmacokinetics and pharmacodynamics of rocuronium in patients: the influence of cardiac output.
2001 Jan
Remifentanil versus meperidine for monitored anesthesia care: a comparison study in older patients undergoing ambulatory colonoscopy.
2001 Jan
Opioid chronopharmacology.
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
Bispectral index monitoring in sevoflurane and remifentanil anesthesia. Analysis of drugs management and immediate recovery.
2001 Jun
Recovery profile and side effects of remifentanil-based anaesthesia with desflurane or propofol for laparoscopic cholecystectomy.
2001 Mar
[Anesthesia in extreme obesity].
2001 May
[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
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
Haemodynamic changes and vasopressin release are not consistently associated with carbon dioxide pneumoperitoneum in humans.
2001 May
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
A comparison of propofol and remifentanil for sedation and limitation of movement during periretrobulbar block.
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
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 Dec 15 15:30:12 UTC 2023
Edited
by admin
on Fri Dec 15 15:30:12 UTC 2023
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 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 [WHO-DD]
Common Name 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 Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
Code System Code Type Description
DAILYMED
5V444H5WIC
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL1005
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
MERCK INDEX
m9521
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY Merck Index
FDA UNII
5V444H5WIC
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
EVMPD
SUB04215MIG
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
RXCUI
236540
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID50157614
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
NCI_THESAURUS
C47702
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
PUBCHEM
60814
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
CHEBI
32091
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
SMS_ID
100000090469
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
CAS
132539-07-2
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
DRUG BANK
DBSALT001450
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
USAN
DD-66
Created by admin on Fri Dec 15 15:30:12 UTC 2023 , Edited by admin on Fri Dec 15 15:30:12 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY