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Chemistry

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Also known as: 14636-12-5, Terlipressin acetate, Glypressin, Glycylpressin, Terlipressine [inn-french], Terlipressinum [inn-latin]

Molecular Formula

C₅₂H₇₄N₁₆O₁₅S₂

Molecular Weight

1227.4 g/mol

InChI Key

BENFXAYNYRLAIU-QSVFAHTRSA-N

An inactive peptide prodrug that is slowly converted in the body to lypressin. It is used to control bleeding of ESOPHAGEAL VARICES and for the treatment of HEPATORENAL SYNDROME.

1 2D Structure

Terlipressin Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C52H74N16O15S2/c53-17-5-4-9-31(45(76)60-23-41(57)72)63-51(82)38-10-6-18-68(38)52(83)37-27-85-84-26-36(61-44(75)25-59-43(74)24-58-42(73)22-54)50(81)65-34(20-29-11-13-30(69)14-12-29)48(79)64-33(19-28-7-2-1-3-8-28)47(78)62-32(15-16-39(55)70)46(77)66-35(21-40(56)71)49(80)67-37/h1-3,7-8,11-14,31-38,69H,4-6,9-10,15-27,53-54H2,(H2,55,70)(H2,56,71)(H2,57,72)(H,58,73)(H,59,74)(H,60,76)(H,61,75)(H,62,78)(H,63,82)(H,64,79)(H,65,81)(H,66,77)(H,67,80)/t31-,32-,33-,34-,35-,36-,37-,38-/m0/s1

2.1.3 InChI Key

BENFXAYNYRLAIU-QSVFAHTRSA-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=C(C=C4)O)NC(=O)CNC(=O)CNC(=O)CN)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=C(C=C4)O)NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Glipressin

2. Gly Gly Gly 8 Lys Vasopressin

3. Gly-gly-gly-8-lys-vasopressin

4. Glycylpressin

5. Glypressin

6. N-(alpha)-glycyl-glycyl-glycyl-8-lysine Vasopressin

7. Remestyp

8. Terlypressin

9. Tglvp

10. Tri-gly-8-lys- Vasopressin

11. Triglycyl Lysine Vasopressin

12. Triglycyl-(8-lysine)vasopressin

13. Triglycylvasopressin

14. Vasopressin, Tri-gly-8-lys-

2.2.2 Depositor-Supplied Synonyms

1. 14636-12-5

2. Terlipressin Acetate

3. Glypressin

4. Glycylpressin

5. Terlipressine [inn-french]

6. Terlipressinum [inn-latin]

7. Terlipressina [inn-spanish]

8. N-(n-(n-glycylglycyl)glycyl)-8-l-lysinevasopressin

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

10. Ncgc00185754-01

11. Terlipressina

12. Terlipressine

13. Terlipressinum

14. Lucassin

15. Einecs 238-680-8

16. Terlivaz

17. Variquel

18. Unii-7z5x49w53p

19. Terlipressin [usan:inn:ban]

20. Lucassin (tn)

21. Hs-2028

22. Terlipressin (usan/inn)

23. Dsstox_cid_28878

24. Dsstox_rid_83146

25. Dsstox_gsid_48952

26. Schembl22699

27. Chembl2135460

28. Dtxsid7048952

29. Gtpl11241

30. Chebi:135905

31. 7z5x49w53p

32. Amy25370

33. Ex-a3116

34. Glycyl-glycyl-glycyl-l-cysteinyl-l-tyrosyl-l-phenylalanyl-l-glutaminyl-l-asparagyl-l-cysteinyl-l-prolyl-l-lysyl-glycinamide (4->9)-disulfide

35. Tox21_113374

36. Akos015994637

37. Ccg-270662

38. Cs-5769

39. Db02638

40. Hy-12554

41. Cas-14636-12-5

42. 36t125

43. C72780

44. D06672

45. Q324147

46. J-008213

47. (2s)-6-amino-2-{[(2s)-1-{[(4r,7s,10s,13s,16s,19r)-19-{2-[2-(2-aminoacetamido)acetamido]acetamido}-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}pyrrolidin-2-yl]formamido}-n-(carbamoylmethyl)hexanamide

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₅₂H₇₄N₁₆O₁₅S₂
Molecular Weight	1227.4 g/mol
XLogP3	-5.8
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	25
Exact Mass	1226.49609806 g/mol
Monoisotopic Mass	1226.49609806 g/mol
Topological Polar Surface Area	563 Å²
Heavy Atom Count	85
Formal Charge	0
Complexity	2380
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

Commonly used to stop bleeding of varices in the food pipe (oesophagus).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Terlipressin is a medicine similar to a naturally occurring hormone present in the body, known as antidiuretic hormone (ADH) or vasopressin. ADH has two main effects in the body. Firstly, it causes narrowing of blood vessels (vasoconstriction), thereby limiting blood flow to a particular area of the body. It also acts on receptors in the kidney to retain water in the body, which helps to prevent excessive loss of water in the urine.

5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Vasoconstrictor Agents

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

5.3 ATC Code

H01BA04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

H - Systemic hormonal preparations, excl. sex hormones and insulins

H01 - Pituitary and hypothalamic hormones and analogues

H01B - Posterior pituitary lobe hormones

H01BA - Vasopressin and analogues

H01BA04 - Terlipressin

5.4 Mechanism of Action

Terlipressin, an analogue of vasopressin, acts on three different receptors, vasopressin receptor V1a (which initiates vasoconstriction, liver gluconeogenesis, platelet aggregation and release of factor VIII), vasopressin receptor V1b (which mediates corticotrophin secretion from the pituitary) and vasopressin receptor V2 which controls free water reabsorption in the renal medullar. The binding of terlipressin to the V2 receptor activates adenylate cyclase which causes the release of aquaporin 2 channels into the cells lining the renal medullar duct. This allows water to be reabsorbed down an osmotic gradient so the urine is more concentrated.

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