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N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin structure
N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin structure

N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin

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
CAS No.: 14636-12-5
Molecular Weight:1227.37216
Modify Date.: 2022-11-22 16:56
Introduction: N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is used norepinephrine-resistant septic shock and hepatorenal syndrome. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is also used in the treatment of acute variceal bleeding. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressinSupplier View more+
1. Names and Identifiers
1.1 Name
N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin
1.2 Synonyms

(2S)-1-{[(4R,7S,10S,13S,16S,19R)-19-{[({[(Aminoacetyl)amino]acetyl}amino)acetyl]amino}-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-N-{(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxo-2-hexanyl}-2-pyrrolidinecarboxamide (2S)-1-{[(4R,7S,10S,13S,16S,19R)-19-{[({[(Aminoacetyl)amino]acetyl}amino)acetyl]amino}-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-N-{(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl}pyrrolidine-2-carboxamide (non-preferred name) [N-α-Triglycyl-8-lysine]-vasopressin 130: PN: WO2010033207 SEQID: 171 claiMed protein 1-Triglycyl-8-lysine Vasopressin EINECS 238-680-8 MFCD00155450 Nα-Glycyl-glycyl-glycyl-[8-lysine]-vasopressin Nα-Glycyl-glycyl-glycyl-lysine-vasopressin Nα-Glycylglycylglycyl-vasopressin Nα-Gly-Gly-Gly-8-Lys-vasopressin Terlipressin Terlipressin Acetate Terlipressin, Terlipressine, Terlipressina, Terlipressinum

1.3 CAS No.
14636-12-5
1.4 CID
72081
1.5 EINECS(EC#)
238-680-8
1.6 Molecular Formula
C52H74N16O15S2 (isomer)
1.7 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
1.8 InChkey
BENFXAYNYRLAIU-QSVFAHTRSA-N
1.9 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
1.10 Isomers 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. Properties
3.1 Density
1.46
3.1 Boiling point
1824 °C at 760 mmHg
3.1 Refractive index
1.664
3.1 Flash Point
1056.9 °C
3.1 Precise Quality
1226.50000
3.1 PSA
563.45000
3.1 logP
0.05740
3.1 Solubility
1.67e-01 g/L
3.2 Appearance
Solid
3.3 Chemical Properties
N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin isWhite Solid
3.4 pKa
9.90±0.15(Predicted)
3.5 Water Solubility
1.67e-01 g/L
3.6 StorageTemp
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
3. Use and Manufacturing
4.1 Usage
N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is used norepinephrine-resistant septic shock and hepatorenal syndrome. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is also used in the treatment of acute variceal bleeding. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressinSupplier
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

5. Precursor and Product
6. Other Information
6.0 靶点

Vasopressin V1 receptor

6.1 Cell Line:
IEC-6 cells induced by oxygen and glucose deprivation/re-oxygenation (OGD/R)
6.2 Concentration:
25 nM
6.3 Incubation Time:
24 hours, 48 hours, 72 hours
6.4 Result:
Significantly increased the proliferation of IEC-6 cells.
6.5 体内研究

Using a mouse nonlethal hepatic ischemia-reperfusion (IR) model, Terlipressin administration significantly ameliorates IR-induced liver apoptosis, necrosis and inflammation.

6.6 Pharmacological effects
Terlipressin is a novel long-acting synthetic vasopressin reagent,its chemical name is three glycyl lysine vasopressin, it is a prodrug, itself has no activity ,in vivo  , it removes three glycyl residues in its N-terminus by aminopeptidase, and slowly "releases" the active lysine vasopressin. It is this "slow release" mechanism that makes it maintain the smooth muscle contraction up to 10 hours after a single administration, whereas the same dose of vasopressin, it can maintain its activity for 20-40 minutes. On the other hand,because of the slow digestion,  lysine vasopressin in the circulation cannot reach toxic levels, and usage of  terlipressin is safer.
Pharmacological effect of terlipressin is splanchnic vascular smooth muscle contraction, and reduction of visceral blood flow (such as reducing blood flow in the mesentery, spleen, uterus, etc.), thereby reducing portal vein blood flow,and reducing portal pressure, on the other hand it may also reduce plasma renin concentration, thereby increasing the renal blood flow in patients with hepatorenal syndrome, to improve kidney function, and increase urine output. Terlipressin is currently the only drug which is able to increase mortality in patients with esophageal varices bleeding , it is previously mainly used in clinical for the treatment of variceal bleeding, in addition,terlipressin now has also been successfully used for liver and kidney integrated syndrome and refractory shock, it is also likely to play a useful role in the cardiopulmonary resuscitation . Compared with vasopressin, it has a lasting effect, and it does not cause dangerous complications, including promoting  fibrinolysis and severe complications in the cardiovascular systems, and the use of it is simple (available intravenous injection), it is more suitable for rescue and treatment of emergent and critical  patients.
6.7 Chemical Properties
N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is White Solid
6.8 Uses
N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is used norepinephrine-resistant septic shock and hepatorenal syndrome. N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin is also used in the treatment of acute variceal bleeding.
6.9 Pharmacological effects
Terlipressin is a novel long-acting synthetic vasopressin reagent,its chemical name is three glycyl lysine vasopressin, it is a prodrug, itself has no activity ,in vivo  , it removes three glycyl residues in its N-terminus by aminopeptidase, and slowly "releases" the active lysine vasopressin. It is this "slow release" mechanism that makes it maintain the smooth muscle contraction up to 10 hours after a single administration, whereas the same dose of vasopressin, it can maintain its activity for 20-40 minutes. On the other hand,because of the slow digestion,  lysine vasopressin in the circulation cannot reach toxic levels, and usage of  terlipressin is safer.
Pharmacological effect of terlipressin is splanchnic vascular smooth muscle contraction, and reduction of visceral blood flow (such as reducing blood flow in the mesentery, spleen, uterus, etc.), thereby reducing portal vein blood flow,and reducing portal pressure, on the other hand it may also reduce plasma renin concentration, thereby increasing the renal blood flow in patients with hepatorenal syndrome, to improve kidney function, and increase urine output. Terlipressin is currently the only drug which is able to increase mortality in patients with esophageal varices bleeding , it is previously mainly used in clinical for the treatment of variceal bleeding, in addition,terlipressin now has also been successfully used for liver and kidney integrated syndrome and refractory shock, it is also likely to play a useful role in the cardiopulmonary resuscitation . Compared with vasopressin, it has a lasting effect, and it does not cause dangerous complications, including promoting  fibrinolysis and severe complications in the cardiovascular systems, and the use of it is simple (available intravenous injection), it is more suitable for rescue and treatment of emergent and critical  patients.
6.10 Mechanism of Action
Terlipressin, a synthetic triglycyl-lysine derivative of vasopressin, is a inactive prodrug. It has pressor and antidiuretic effects. Following IV injection, lysine vasopressin are released following the enzymatic cleavage of 3 glycyl moieties.
Duration: 4-6 hr.
6.11 Adverse Drug Reactions
Abdominal cramps, cardiac arrhythmias, headache, transient blanching, increased arterial pressure.
Potentially Fatal: MI, cardiac failure.
6.12 Chemical Properties
White Solid
6.13 Uses
Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. Terlipressin is used norepinephrine-resistant septic shock and hepatorenal syndrome. Terlipressin is also used in the treatment of acute variceal bleeding.
6.14 Mesh
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.)|Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)
6.15 Mesh Entry Terms
glipressin
7. Computational chemical data
  • Molecular Weight: 1227.37216g/mol
  • Molecular Formula: C52H74N16O15S2
  • Compound Is Canonicalized: True
  • XLogP3-AA: -5.8
  • Exact Mass: 1226.49609806
  • Monoisotopic Mass: 1226.49609806
  • Complexity: 2380
  • Rotatable Bond Count: 25
  • Hydrogen Bond Donor Count: 16
  • Hydrogen Bond Acceptor Count: 19
  • Topological Polar Surface Area: 563
  • Heavy Atom Count: 85
  • Defined Atom Stereocenter Count: 8
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB//ABgAAAAAAAAAAAAAAAAAWAAAAAwYAAAAAAAAAABQAAAHgQQCAAADCzF2ASwBoPAAgCIAiFSEAACAAAgIAAIiIGOCIgIZjqC0TOUcAAk1hGImAedy6COIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==
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