Close
4
World-Pharmacists-Day-Insert
X

Overview

Client Email Product
CAS 14636-12-5
PharmaCompass
  • Chemistry
CAS 14636-12-5
Also known as: 14636-12-5, Glypressin, Terlipressina, Terlipressine, Terlipressinum, Terlipressine [inn-french]
Molecular Formula
C52H74N16O15S2
Molecular Weight
1227.381  g/mol
InChI Key
BENFXAYNYRLAIU-QSVFAHTRSA-N
FDA UNII
7Z5X49W53P

Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. It has been found to be effective when norepinephrine does not help. [Wikipedia]
1 2D Structure

CAS 14636-12-5

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 Other Identifiers
2.2.1 UNII
7Z5X49W53P
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 14636-12-5

2. Glypressin

3. Terlipressina

4. Terlipressine

5. Terlipressinum

6. Terlipressine [inn-french]

7. Terlipressinum [inn-latin]

8. Terlipressina [inn-spanish]

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

10. Lucassin

11. Terlipressin [ban:inn]

12. Einecs 238-680-8

13. Hs-2028

14. Glycylpressin

15. Ncgc00185754-01

16. Unii-7z5x49w53p

17. Terlipressin [usan:inn:ban]

18. Glypressin (tn)

19. Lucassin (tn)

20. C52h74n16o15s2

21. Ac1l2hdp

22. Terlipressin (usan/inn)

23. D0p4vx

24. Ac1q5jb2

25. Dsstox_cid_28878

26. Dsstox_rid_83146

27. Dsstox_gsid_48952

28. Schembl22699

29. Triglycyl-8-lysine-vasopressin

30. Chembl2135460

31. Dtxsid7048952

32. Chebi:135905

33. Molport-006-167-813

34. (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

35. Tox21_113374

36. Akos015994637

37. Cs-5769

38. Db02638

39. Am016547

40. An-11837

41. Dr003713

42. Hy-12554

43. Sc-47098

44. Cas-14636-12-5

45. Ls-161411

46. Ft-0630417

47. 36t125

48. D06672

49. J-008213

50. (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-[[2-[[2-[(2-aminoacetyl)amino]acetyl]amino]acetyl]amino]-7-(2-amino-2-oxo-ethyl)-10-(3-amino-3-oxo-propyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbon

51. (2s)-1-[(4s,7s,10s,13s,16s,19s)-19-[[2-[[2-[(2-aminoacetyl)amino]acetyl]amino]acetyl]amino]-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-pentazacycloicosane-4-carbonyl]-n-[(1s)-5-amino-1-(carbamoylmethylcarbamoyl)pentyl]pyrrolidine-2-carboxamide

52. (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

53. (s)-n-((s)-6-amino-1-((2-amino-2-oxoethyl)amino)-1-oxohexan-2-yl)-1-((4r,7s,10s,13s,16s,19r)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-19-(2-(2-(2-aminoacetamido)acetamido)a

54. Cetamido)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 1227.381 g/mol
Molecular Formula C52H74N16O15S2
Hydrogen Bond Donor Count16
Hydrogen Bond Acceptor Count19
Rotatable Bond Count25
Exact Mass1226.496 g/mol
Monoisotopic Mass1226.496 g/mol
Topological Polar Surface Area563 A^2
Heavy Atom Count85
Formal Charge0
Complexity2380
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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

Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels.


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.


5.3 ATC Code

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.


Ask Us for Pharmaceutical Supplier and Partner
Ask Us, Find A Supplier / Partner
No Commissions, No Strings Attached, Get Connected for FREE

What are you looking for?

How can we help you?

The request can't be empty

Please read our Privacy Policy carefully

You must agree to the privacy policy

The name can't be empty
The company can't be empty.
The email can't be empty Please enter a valid email.
The mobile can't be empty

Advertise With Us

Advertise With Us