132539-07-2 Usage
Description
Ultiva was launched in Germany and the US for use in general anesthesia
and immediate post-operative pain management. This compound can be prepared
via the Michael addition of a 4,4-disubstituted piperidine to methyl acrylate. It
behaves as a specific μ-opiod agonist that is about 30 times more potent than its
chemical relative alfentanil. While its pharmacodynamic properties are similar to
other μ agonists, remifentanil has unique pharmacokinetic properties. It has a rapid
onset (1.6 min) and a rapid offset (5.4 min) independent of duration of administration.
This has been attributed to its rapid catabolism by general esterases to the
corresponding acrylic acid derivative. The metabolite has 0.01 to 0.0005 times the
activity of remifentanil and is excreted via the kidneys (80% recovery).
Chemical Properties
White Solid
Originator
Glaxo Wellcome (UK)
Uses
Labelled synthetic mu-opioid agonist. This is a controlled substance (opiate)
Brand name
Ultiva (Abbott).
Biochem/physiol Actions
Remifentanil hydrochloride is a mu opioid receptor agonist, anesthetic, and analgesic compound. Remifentanil was developed as an ultra-short-acting mu opioid receptor agonist with improved pharmacodynamic properties.
Pharmacokinetics
Remifentanil is much like alfentanil in its pharmacodynamic effects. It is a selective μ opioid agonist
with 15 to 20 times greater potency than alfentanil. Remifentanil has an onset of
action of 1 to 3 minutes when given intravenously. Its unique property is its rapid
offset of action, which is independent of the duration of administration of the compound. Thus, it is
very useful for titration of antinociceptive effect, followed by a rapid and predictable recovery time
of 3 to 5 minutes. The short duration of action is a result of the ester group, which has been
rationally designed into the substituent on the piperidine nitrogen. This ester group is rapidly
hydrolyzed to the inactive carboxylic acid by serum and tissue esterases, making the drug's
duration of action essentially independent of the liver or renal function of the patient. Remifentanil
is used extensively for analgesia associated with general anesthesia procedures. It often is used in
combination with injectable general anesthetic agents, such as midazolam or propofol.
Check Digit Verification of cas no
The CAS Registry Mumber 132539-07-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,2,5,3 and 9 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 132539-07:
(8*1)+(7*3)+(6*2)+(5*5)+(4*3)+(3*9)+(2*0)+(1*7)=112
112 % 10 = 2
So 132539-07-2 is a valid CAS Registry Number.
InChI:InChI=1/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
132539-07-2Relevant articles and documents
INTERMEDIATES FOR THE PREPARATION OF REMIFENTANIL HYDROCHLORIDE
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, (2020/05/14)
A new intermediate for synthesizing 1-substituted-4-[phenyl(propanoyl)amino]piperidine-4-carbonitrile derivatives is laid open. Specifically set out is a method for use of this intermediate in the preparation of remifentanil. The enclosed shorter process offers a greater yield of products with higher purity as compared to methods reported in the prior art.
Alternate Process for Remifentanil Preparation
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Page/Page column 9, (2010/05/13)
An alternate process for synthesizing opiate or opioid analgesics and anesthetics, and intermediates thereof is provided. In particular, a process of synthesizing synthetic opiate or opioid compounds such as, for example, remifentanil, carfentanil, sufentanil, fentanyl, and alfentanil are disclosed.
CRYSTALLINE FORM OF REMIFENTANIL HYDROCHLORIDE
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Page/Page column 3, (2008/06/13)
The present invention relates to a crystalline polymorphic form of remifentanil hydrochloride. The invention also describes methods of preparing a polymorphic form of remifentanil hydrochloride.
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