REMIFENTANIL HYDROCHLORIDE

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20630se5-005_ultiva_lbl.pdf | https://www.drugbank.ca/drugs/DB00899 | https://www.ncbi.nlm.nih.gov/pubmed/16526829

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20630se5-005_ultiva_lbl.pdf	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20630se5-005_ultiva_lbl.pdf	Primary		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
194 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	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

Value	Dose	Co-administered	Analyte	Population
8080 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.48 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14766712	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
30% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020630s020lbl.pdf	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8802	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8802
ZINC	ZINC000000538283	http://zinc15.docking.org/substances/ZINC000000538283

PubMed

Title	Date	PubMed
Target controlled infusion of remifentanil and propofol for cesarean section in a patient with multivalvular disease and severe pulmonary hypertension.	2001	11534314
Use of remifentanil in combination with desflurane or propofol for ambulatory oral surgery.	2001	11534310
[Total intravenous anesthesia using remifentanil and propofol with midazolam co-induction in laparoscopic surgery of the gallbladder].	2001	11432253
Effects of fentanyl, alfentanil, remifentanil and sufentanil on loss of consciousness and bispectral index during propofol induction of anaesthesia.	2001 Apr	11573626
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.	2001 Apr	11312471
Remifentanil.	2001 Aug	11571418
[Mastocytosis: general anesthesia with remifentanil and sevoflurane].	2001 Aug	11530751
Target-controlled infusion or manually controlled infusion of propofol in high-risk patients with severely reduced left ventricular function.	2001 Aug	11505347
The use of remifentanil to facilitate the insertion of the laryngeal mask airway.	2001 Aug	11473861
Effects of combined methohexitone-remifentanil anaesthesia in electroconvulsive therapy.	2001 Aug	11472282
Influence of hypotensive and normotensive anesthesia on platelet aggregability and hemostatic markers in orthognathic surgery.	2001 Aug 1	11672580
Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients.	2001 Jan	11575417
Recovery and neurological examination after remifentanil-desflurane or fentanyl-desflurane anaesthesia for carotid artery surgery.	2001 Jan	11575408
Use of remifentanil in a patient with peripartum cardiomyopathy requiring Caesarean section.	2001 Jan	11575392
Opioid chronopharmacology.	2001 Jul	11531909
Anaesthetic management of a child with a positive family history of malignant hyperthermia for posterior fossa surgery in the sitting position.	2001 Jul	11442873
Esmolol is not an alternative to remifentanil for fast-track outpatient gynecologic laparoscopic surgery.	2001 Jul	11429376
Monitored anesthesia care using remifentanil and propofol for awake craniotomy.	2001 Jul	11426102
Postoperative reading speed does not indicate implicit memory in elderly cardiac patients after propofol and remifentanyl anaesthesia.	2001 Jul	11421835
Sevoflurane with remifentanil allows rapid tracheal intubation without neuromuscular blocking agents.	2001 Jul-Aug	11495870
Recovery after remifentanil and sufentanil for analgesia and sedation of mechanically ventilated patients after trauma or major surgery.	2001 Jun	11573581
Bispectral index monitoring in sevoflurane and remifentanil anesthesia. Analysis of drugs management and immediate recovery.	2001 Jun	11533541
Safety and efficacy of remifentanil infusion in craniosynostosis repair in infants.	2001 Jun	11455235
Effect of tracheal intubation or laryngeal mask airway insertion on intraocular pressure using balanced anesthesia with sevoflurane and remifentanil.	2001 Jun	11435050
[Remifentanil for palliative abdominal surgery in a patient with myasthenia gravis].	2001 Jun-Jul	11446948
Recovery from propofol anaesthesia supplemented with remifentanil.	2001 Mar	11573525
[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	11494899
Clonidine decreases propofol requirements during anaesthesia: effect on bispectral index.	2001 May	11575336
[Droperidol and dimenhydrinate alone or in combination for prevention of postoperative nausea and vomiting].	2001 May	11413698
[General anesthesia with remifentanil in two cases of emergency cesarean section].	2001 May	11412735
Haemodynamic changes and vasopressin release are not consistently associated with carbon dioxide pneumoperitoneum in humans.	2001 May	11308999
Magnesium as part of balanced general anaesthesia with propofol, remifentanil and mivacurium: a double-blind, randomized prospective study in 50 patients.	2001 Nov	11580778
The bispectral index during an anaphylactic circulatory arrest.	2001 Oct	11669440
Effect of age on recovery from remifentanil anaesthesia.	2001 Oct	11669432
Goal oriented general anesthesia for Cesarean section in a parturient with a large intracranial epidermoid cyst.	2001 Oct	11606346
Threshold-level repetitive transcranial electrical stimulation for intraoperative monitoring of central motor conduction.	2001 Oct	11599831
A comparison of fentanyl, sufentanil, and remifentanil for fast-track cardiac anesthesia.	2001 Oct	11574346
A comparison of propofol and remifentanil for sedation and limitation of movement during periretrobulbar block.	2001 Sep	11578885
Hemodynamics and emergence profile of remifentanil versus fentanyl prospectively compared in a large population of surgical patients.	2001 Sep	11578883
Does functional ability in the postoperative period differ between remifentanil- and fentanyl-based anesthesia?	2001 Sep	11578882
Spontaneous movements, local reactions and pain on injection of rocuronium. A comparison between female and male patients.	2001 Sep	11576052
Effects of remifentanil/propofol in comparison with isoflurane on dynamic cerebrovascular autoregulation in humans.	2001 Sep	11576048
Remifentanil and fentanyl during anaesthesia for major abdominal and gynaecological surgery. An open, comparative study of safety and efficacy.	2001 Sep	11553256
Potential hazard with syringe infusion pump.	2001 Sep	11531686
Facilitation of laryngeal mask airway insertion: effects of remifentanil administered before induction with target-controlled propofol infusion.	2001 Sep	11531680
The in vitro effects of remifentanil, sufentanil, fentanyl, and alfentanil on isolated human right atria.	2001 Sep	11524316
Quantitative EEG changes associated with loss and return of consciousness in healthy adult volunteers anaesthetized with propofol or sevoflurane.	2001 Sep	11517126
Patient-controlled analgesia for labour using remifentanil: a feasibility study.	2001 Sep	11517125
Effects of the opioid remifentanil on olfactory function in healthy volunteers.	2001 Sep 28	11669470
Effects of cerebrospinal fluid loss and epidural blood patch on cerebral blood flow in swine.	2001 Sep-Oct	11561258

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Remifentanil (10(-8) - 10(-4) mol/ L) caused a concentration-dependent vasorelaxation in the human being artery rings.

Name

Type

Language

REMIFENTANIL HYDROCHLORIDE

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