Please Wait
Applying Filters...
menu
    • menu
    Granules India Limited has high volume world-class facilities for APIs, PFIs, & FDFs, serving customers in over 80 countries.

    Virtual Booth

    Contact Supplier

    Jai Radhe Sales is your partner for all your sourcing needs.

    Virtual Booth

    Contact Supplier

    xyz-pharma-m-2024-10-07

    Virtual Booth

    Contact Supplier

    Egis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

    Virtual Booth

    Contact Supplier

    Biophore is a research-driven global pharmaceutical company focused on niche APIs for the generic industry.

    Virtual Booth

    Contact Supplier

    xyz-pharma-m-2024-10-07

    Virtual Booth

    Contact Supplier

    Menu

    CAS-14636-12-5

    BUILDING BLOCK

    MARKET PLACE

    PharmaCompass
    Xls

    Filters

    clear-filterReset all filters
    2D Structure
    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

    2D Structure

    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 Weight 1227.4 g/mol
    Molecular Formula C52H74N16O15S2
    XLogP3-5.8
    Hydrogen Bond Donor Count16
    Hydrogen Bond Acceptor Count19
    Rotatable Bond Count25
    Exact Mass1226.49609806 g/mol
    Monoisotopic Mass1226.49609806 g/mol
    Topological Polar Surface Area563 Ų
    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

    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.