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

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

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
[Stand-by and conscious sedation--possibilities and limits of anesthesiological management].	2001	11367878
Rational use of opioids.	2001 Apr	11376535
[Fiberoptic intubation during remifentanil propofol sedation].	2001 Apr	11355421
Monitored anesthesia care in awake craniotomy for brain tumor surgery.	2001 Apr	11344849
Propofol/remifentanil in neurosurgery.	2001 Apr	11314843
Ultra-fast-track anesthetic technique facilitates operating room extubation in patients undergoing off-pump coronary revascularization surgery.	2001 Apr	11312471
[Mastocytosis: general anesthesia with remifentanil and sevoflurane].	2001 Aug	11530751
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
Small doses of remifentanil or sufentanil for blunting cardiovascular changes induced by tracheal intubation: a double-blind comparison.	2001 Feb	11270019
[Fastrach laryngeal mask, sevoflurane and remifentanil: an anesthetic alternative for the myasthenic patient].	2001 Feb	11257957
[Computer simulation and pharmacoeconomics. Computer simulation as an aid for the analysis of operating room efficiency: an example].	2001 Feb	11252577
Patient-controlled intravenous analgesia using remifentanil in the parturient.	2001 Feb	11220427
Recovery and neurological examination after remifentanil-desflurane or fentanyl-desflurane anaesthesia for carotid artery surgery.	2001 Jan	11575408
Comparative analysis of costs of total intravenous anaesthesia with propofol and remifentanil vs. balanced anaesthesia with isoflurane and fentanyl.	2001 Jan	11270005
A comparison of remifentanil and fentanyl in patients undergoing carotid endarterectomy.	2001 Jan	11270004
Anaesthetic management of a child with a positive family history of malignant hyperthermia for posterior fossa surgery in the sitting position.	2001 Jul	11442873
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
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- and fentanyl-based anesthesia for intraoperative monitoring of somatosensory evoked potentials.	2001 Jun	11375835
[Remifentanil for palliative abdominal surgery in a patient with myasthenia gravis].	2001 Jun-Jul	11446948
[Alterations in left ventricular-arterial coupling and mechanical efficiency produced by remifentanil during cardiac anesthesia].	2001 Mar	11337645
Intravenous anaesthesia with remifentanil in a preterm infant.	2001 Mar	11240891
A comparison of two constant-dose continuous infusions of remifentanil for severe postoperative pain.	2001 Mar	11226107
[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
[Droperidol and dimenhydrinate alone or in combination for prevention of postoperative nausea and vomiting].	2001 May	11413698
[Sedation in spinal anesthesia. Comparison of remifentanil and propofol].	2001 May	11412730
Dose-dependent regional cerebral blood flow changes during remifentanil infusion in humans: a positron emission tomography study.	2001 May	11388521
A patient with hypertrophic obstructive cardiomyopathy presenting for total knee replacement.	2001 May	11385898
Propofol/remifentanil versus propofol alone for bone marrow aspiration in paediatric haemato-oncological patients.	2001 May	11359587
A preliminary investigation of remifentanil as a labor analgesic.	2001 May	11323383
Remifentanil is a valuable alternative to contraindicated neuraxial analgesia in the parturients.	2001 May	11323377
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	11323327
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
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
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
Facilitation of laryngeal mask airway insertion: effects of remifentanil administered before induction with target-controlled propofol infusion.	2001 Sep	11531680
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:30:12 GMT 2023` Edited by `admin` on `Fri Dec 15 15:30:12 GMT 2023`
Record UNII	5V444H5WIC
Record Status	`Validated (UNII)`
Record Version

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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