Brifentanil

Synopsis, Chemistry

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Also known as: Brifentanil [inn], 101345-71-5, 6gdt77pqbw, N-[(3r,4s)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-(2-fluorophenyl)-2-methoxyacetamide, Brifentanilum, Brifentanyl

Molecular Formula

C₂₀H₂₉FN₆O₃

Molecular Weight

420.5 g/mol

InChI Key

KKMGCTVJCQYQPV-WBVHZDCISA-N

FDA UNII

6GDT77PQBW

Brifentanil (also known as A-3331) is an analog of fentanyl, a potent opioid. This drug is classified as an opioid analgesic and was developed in the early 1990s. The effects of brifentanil are very similar to those of alfentanil, with strong but short lasting analgesia and sedation, and particularly notable itching and respiratory depression.

1 2D Structure

Brifentanil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(3R,4S)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-N-(2-fluorophenyl)-2-methoxyacetamide

2.1.2 InChI

InChI=1S/C20H29FN6O3/c1-4-25-20(29)26(23-22-25)12-11-24-10-9-17(15(2)13-24)27(19(28)14-30-3)18-8-6-5-7-16(18)21/h5-8,15,17H,4,9-14H2,1-3H3/t15-,17+/m1/s1

2.1.3 InChI Key

KKMGCTVJCQYQPV-WBVHZDCISA-N

2.1.4 Canonical SMILES

CCN1C(=O)N(N=N1)CCN2CCC(C(C2)C)N(C3=CC=CC=C3F)C(=O)COC

2.1.5 Isomeric SMILES

CCN1C(=O)N(N=N1)CCN2CC[C@@H]([C@@H](C2)C)N(C3=CC=CC=C3F)C(=O)COC

2.2 Other Identifiers

2.2.1 UNII

6GDT77PQBW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2-(4-ethyl-4,5-dihydro-5-oxo1h-tetrazolyl)ethyl)-3-methyl-4-(n-(2-fluorophenyl)methoxyacetamido)piperidine

2. A 3331

3. A-3331

4. A-3331.hcl

5. Brifentanil Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. Brifentanil [inn]

2. 101345-71-5

3. 6gdt77pqbw

4. N-[(3r,4s)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-(2-fluorophenyl)-2-methoxyacetamide

5. Brifentanilum

6. Brifentanyl

7. N-[(3s,4r)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-3-methylpiperidin-4-yl]-n-(2-fluorophenyl)-2-methoxyacetamide

8. Brifentanilo

9. Unii-6gdt77pqbw

10. Brifentanilum [inn-latin]

11. Brifentanilo [inn-spanish]

12. A-3331-

13. Brifentanil [who-dd]

14. Schembl488879

15. Dtxsid20143867

16. Db09172

17. Q4967117

18. (+/-)-cis-n-(1-(2-(4-ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-3-methyl-4-piperidyl)-2'-fluoro-2-methoxyacetanilide

19. Acetamide, N-((3r,4s)-1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-3-methyl-4-piperidinyl)-n-(2-fluorophenyl)-2-methoxy-, Rel-

20. Acetamide, N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-3-methyl-4-piperidinyl)-n-(2-fluorophenyl)-2-methoxy-, Cis-

21. Acetamide, N-(1-(2-(4-ethyl-4,5-dihydro-5-oxo-1h-tetrazol-1-yl)ethyl)-3-methyl-4-piperidinyl)-n-(2-fluorophenyl)-2-methoxy-, Cis-(+/-)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₉FN₆O₃
Molecular Weight	420.5 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	420.22851697 g/mol
Monoisotopic Mass	420.22851697 g/mol
Topological Polar Surface Area	81 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	636
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1