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Remifentanil
Also known as: Ultiva, Remifentanil hcl, 132539-07-2, Gi 87084b, Gi-87084b, Remifentanil hydrochloride [usan]
Molecular Formula
C20H29ClN2O5
Molecular Weight
412.9  g/mol
InChI Key
WFBMIPUMYUHANP-UHFFFAOYSA-N
FDA UNII
5V444H5WIC

A piperidine-propionate derivative and opioid analgesic structurally related to FENTANYL. It functions as a short-acting MU OPIOID RECEPTOR agonist, and is used as an analgesic during induction or maintenance of general anesthesia, following surgery, during childbirth, and in mechanically ventilated patients under intensive care.
1 2D Structure

Remifentanil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl 1-(3-methoxy-3-oxopropyl)-4-(N-propanoylanilino)piperidine-4-carboxylate;hydrochloride
2.1.2 InChI
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
2.1.3 InChI Key
WFBMIPUMYUHANP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC(=O)OC)C(=O)OC.Cl
2.2 Other Identifiers
2.2.1 UNII
5V444H5WIC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(4-methoxycarbonyl-4-((1-oxopropyl)phenylamino)-1-piperidine)propanoic Acid Methyl Ester

2. Gi 87084b

3. Gi-87084b

4. Gi87084b

5. Remifentanil

6. Remifentanil Monohydrochloride

7. Ultiva

2.3.2 Depositor-Supplied Synonyms

1. Ultiva

2. Remifentanil Hcl

3. 132539-07-2

4. Gi 87084b

5. Gi-87084b

6. Remifentanil Hydrochloride [usan]

7. 5v444h5wic

8. 4-carboxy-4-(n-phenylpropionamido)-1-piperidine Propionic Acid, Dimethyl Ester, Monohydrochloride

9. 132539-07-2 (hcl)

10. Ultiva (tn)

11. Methyl 1-(3-methoxy-3-oxopropyl)-4-(n-propanoylanilino)piperidine-4-carboxylate;hydrochloride

12. 1-piperidinepropanoic Acid, 4-(methoxycarbonyl)-4-((1-oxopropyl)phenylamino)-, Methyl Ester, Monohydrochloride

13. Chebi:32091

14. Unii-5v444h5wic

15. Schembl41242

16. Chembl1201120

17. Dtxsid50157614

18. Remifentanil Hydrochloride (jan/usan)

19. Remifentanil Hydrochloride [mi]

20. Sb17332

21. Remifentanil Hydrochloride [jan]

22. Remifentanil Hydrochloride [mart.]

23. Remifentanil Hydrochloride [vandf]

24. Remifentanil Hydrochloride [who-dd]

25. D01177

26. Remifentanil Hydrochloride [orange Book]

27. Remifentanil Hydrochloride [ep Monograph]

28. Remifentanil Hydrochloride (1.0 Mg/ml Acetonitrile)

29. Remifentanil Hydrochloride, >=97% (hplc), Powder

30. Q27114780

31. Remifentanil Hydrochloride, European Pharmacopoeia (ep) Reference Standard

32. Remifentanil Hydrochloride Solution, 100 Mug/ml In Methanol (as Free Base), Certified Reference Material

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 412.9 g/mol
Molecular Formula C20H29ClN2O5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass412.1764997 g/mol
Monoisotopic Mass412.1764997 g/mol
Topological Polar Surface Area76.2 Ų
Heavy Atom Count28
Formal Charge0
Complexity523
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameUltiva
PubMed HealthRemifentanil (Injection)
Drug ClassesAnalgesic, Anesthetic Adjunct
Drug LabelULTIVA (remifentanil hydrochloride) for Injection is a -opioid agonist chemically designated as a 3-[4-methoxycarbonyl-4-[(1-oxopropyl)phenylamino]-1-piperidine]propanoic acid methyl ester, hydrochloride salt, C20H28N2O5HCl, with a molecular wei...
Active IngredientRemifentanil hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 1mg base/vial; eq 5mg base/vial; eq 2mg base/vial
Market StatusPrescription
CompanyMylan Institutional

2 of 2  
Drug NameUltiva
PubMed HealthRemifentanil (Injection)
Drug ClassesAnalgesic, Anesthetic Adjunct
Drug LabelULTIVA (remifentanil hydrochloride) for Injection is a -opioid agonist chemically designated as a 3-[4-methoxycarbonyl-4-[(1-oxopropyl)phenylamino]-1-piperidine]propanoic acid methyl ester, hydrochloride salt, C20H28N2O5HCl, with a molecular wei...
Active IngredientRemifentanil hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 1mg base/vial; eq 5mg base/vial; eq 2mg base/vial
Market StatusPrescription
CompanyMylan Institutional

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Analgesics, Opioid

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Opioid Agonist [EPC]; Full Opioid Agonists [MoA]
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