1-{[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-lysylglycinamide

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1-{[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-lysylglycinamide

Also known as: Plv-2, 56-59-7, Felypressine, Felypressinum, 2-(l-phenylalanine)-8-l-lysinevasopressin, Felipresina

Molecular Formula

C₄₆H₆₅N₁₃O₁₁S₂

Molecular Weight

1040.2 g/mol

InChI Key

SFKQVVDKFKYTNA-DZCXQCEKSA-N

A synthetic analog of LYPRESSIN with a PHENYLALANINE substitution at residue 2. Felypressin is a vasoconstrictor with reduced antidiuretic activity.

1 2D Structure

1-{[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-lysylglycinamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C46H65N13O11S2/c47-18-8-7-14-29(40(64)52-23-38(51)62)54-45(69)35-15-9-19-59(35)46(70)34-25-72-71-24-28(48)39(63)55-31(20-26-10-3-1-4-11-26)43(67)56-32(21-27-12-5-2-6-13-27)42(66)53-30(16-17-36(49)60)41(65)57-33(22-37(50)61)44(68)58-34/h1-6,10-13,28-35H,7-9,14-25,47-48H2,(H2,49,60)(H2,50,61)(H2,51,62)(H,52,64)(H,53,66)(H,54,69)(H,55,63)(H,56,67)(H,57,65)(H,58,68)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1

2.1.3 InChI Key

SFKQVVDKFKYTNA-DZCXQCEKSA-N

2.1.4 Canonical SMILES

C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=CC=C4)N)C(=O)NC(CCCCN)C(=O)NCC(=O)N

2.1.5 Isomeric SMILES

C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=CC=C4)N)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Lysine Vasopressin, Phenylalanine

2. Octapressin

3. Octopressin

4. Phelypressin

5. Phenylalanine Lysine Vasopressin

6. Phenylalanyl-lysyl Vasopressin

7. Plv-2

8. Vasopressin, Phenylalanine Lysine

9. Vasopressin, Phenylalanyl Lysyl

10. Vasopressin, Phenylalanyl-lysyl

2.2.2 Depositor-Supplied Synonyms

1. Plv-2

2. 56-59-7

3. Felypressine

4. Felypressinum

5. 2-(l-phenylalanine)-8-l-lysinevasopressin

6. Felipresina

7. Phe(2)-lys(8)-vasopressin

8. Chebi:60564

9. (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide

10. L-cysteinyl-l-phenylalanyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-lysylglycinamide Cyclic (1-6)disulfide

11. 1-{[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-l-prolyl-l-lysylglycinamide

12. Felipresina [inn-spanish]

13. Felypressine [inn-french]

14. Felypressinum [inn-latin]

15. Unii-17n2918v6g

16. Ncgc00182033-01

17. Einecs 200-282-7

18. Vasopressin, 2-l-phenylalanine-8-l-lysine-

19. Dsstox_cid_28525

20. Dsstox_rid_82797

21. Dsstox_gsid_48599

22. Schembl33291

23. Chembl3185126

24. Dtxsid6048599

25. Hy-a0182

26. Tox21_112932

27. 17n2918v6g

28. Cs-5837

29. Db00093

30. Cas-56-59-7

31. L-cysteinyl-l-phenylalanyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-lysylglycinamide Cyclic (1->6)disulfide

32. H-[cys-phe-phe-gln-asn-cys]-pro-lys-gly-nh2

33. A913370

34. (s)-n-((s)-6-amino-1-((2-amino-2-oxoethyl)amino)-1-oxohexan-2-yl)-1-((4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide

2.3 Create Date

2007-02-09

3 Chemical and Physical Properties

Molecular Formula	C₄₆H₆₅N₁₃O₁₁S₂
Molecular Weight	1040.2 g/mol
XLogP3	-3.5
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	19
Exact Mass	1039.43679229 g/mol
Monoisotopic Mass	1039.43679229 g/mol
Topological Polar Surface Area	456 Å²
Heavy Atom Count	72
Formal Charge	0
Complexity	1920
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For use as an alternative to adrenaline as a localising agent, provided that local ischaemia is not essential.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Felypressin is a synthetic analog of lypressin or vasopressin with a greater vasoconstrictor activity than antidiuretic action. It is used primarily as a hemostatic.

5.2 MeSH Pharmacological Classification

Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

5.3 Mechanism of Action

Felypressin binds to the vasopressin receptor V1a. This causes contraction of the smooth muscle in the vascular bed, especially capillaries, small arterioles and venules.