Terlipressin acetate

Pharmacological effects Mechanism of Action Adverse Drug Reactions

Product Name: Terlipressin acetate
CAS No.: 14636-12-5
Chemical Name: Terlipressin acetate
Synonyms: TERLIPRESSIN;Terlipressin for NMR identification;H-Gly-Gly-Gly-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2;Glypressin;Glycylpressin;Terilipressin;TerlipressinuM;Terlipressin CRS;Terlipressin(net);Terlipressin, >99%
CBNumber: CB4266213
Molecular Formula: C52H74N16O15S2
Formula Weight: 1227.37
MOL File: 14636-12-5.mol

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Terlipressin acetate Property

Melting point:: >170°C (dec.)
Boiling point:: 1824.0±65.0 °C(Predicted)
Density: 1.46±0.1 g/cm3(Predicted)
storage temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 9.90±0.15(Predicted)
color: White
Sequence: Gly-Gly-Gly-c[Cys-Tyr-Phe-Gln-Asn-Cys]-Pro-Lys-Gly-NH2，(Disulfide bridge: Cys-Cys)
InChI: InChI=1/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-/s3
InChIKey: BENFXAYNYRLAIU-ITQMCZIINA-N
SMILES: N1(CCC[C@H]1C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N)C(=O)[C@@H]1CSSC[C@H](NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@H](C(N[C@@H](CC2C=CC=CC=2)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)N1)=O)CC1=CC=C(O)C=C1 |&1:4,8,23,28,45,48,59,68,r|
CAS DataBase Reference: 14636-12-5(CAS DataBase Reference)

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Safety

HS Code: 3504009000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 27027
Product name: Terlipressin
Packaging: 100mg
Price: $245
Updated: 2021/12/16

Cayman Chemical

Product number: 27027
Product name: Terlipressin
Packaging: 250mg
Price: $548
Updated: 2021/12/16

Cayman Chemical

Product number: 27027
Product name: Terlipressin
Packaging: 50mg
Price: $129
Updated: 2021/12/16

Usbiological

Product number: 021377
Product name: Terlipressin Diacetate Salt
Packaging: 10mg
Price: $425
Updated: 2021/12/16

Usbiological

Product number: T2735-25
Product name: Terlipressin
Packaging: 50mg
Price: $545
Updated: 2021/12/16

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Terlipressin acetate Chemical Properties,Usage,Production

Pharmacological effects

Terlipressin acetate 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.

Mechanism of Action

Terlipressin acetate, 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.

Adverse Drug Reactions

Abdominal cramps, cardiac arrhythmias, headache, transient blanching, increased arterial pressure.
Potentially Fatal: MI, cardiac failure.

Description

Terlipressin acetate is a novel synthetic long-acting vasopressin preparation. It is a kind of prodrug, which is inactive by itself. After the action of aminopeptidase in the body, after removing the three glycyl residues at its N-terminus, it slowly "releases" the active lysine vasopressin. Therefore, terlipressin acts as a reservoir that releases lysine vasopressin at a steady rate.

Chemical Properties

N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin (Terlipressin acetate) is White Solid

Uses

Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. It is used norepinephrine-resistant septic shock and hepatorenal syndrome. It is also used in the treatment of acute variceal bleeding. Terlipressin Acetate 1 mg solution for injection is used for the treatment of: bleeding from dilated (widening) veins in the food pipe leading to your stomach (called bleeding oesophageal varices).

Definition

ChEBI: Terlipressin is a polypeptide.

Clinical Use

Treatment of bleeding oesophageal varices

Side effects

In clinical trials, the most common side effects of terlipressin administration were paleness, increased blood pressure, peripheral ischemia, abdominal pain, nausea, diarrhea, and headache.
Terlipressin related adverse events are common and most of terlipressin related adverse events were mild or moderate, which can be resolved spontaneously without any intervention. As terlipressin acts mainly on the splanchnic vessels, the incidence of severe ischemic complications is lower with terlipressin than with vasopressin. However, it may cause serious complications such as myocardial infarction, intestinal ischemia, peripheral cyanosis, and skin necrosis[1].

Metabolism

Terlipressin is metabolised by tissue peptidases resulting in the slow release of lypressin. Terlipressin is almost completely metabolised in the kidneys and liver, with less than 1% of terlipressin and less than 0.1% of lypressin excreted in the urine.

References

[1] Chiang C, et al. Terlipressin-Induced Peripheral Cyanosis in a Patient with Liver Cirrhosis and Hepatorenal Syndrome. American Journal of Case Reports, 2019.

Terlipressin acetate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Terlipressin acetate manufacturers

Dorne Chemical Technology co. LTD

Product: Terlipressin acetate 14636-12-5
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 100kg
Release date: 2024-03-26

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Terlipressin acetate 14636-12-5
Price: US $0.00/g
Min. Order: 1g
Purity: 98%min
Supply Ability: 1000g
Release date: 2023-01-11

hebei hongtan Biotechnology Co., Ltd

Product: Terlipressin 14636-12-5
Price: US $30.00/box
Min. Order: 1box
Purity: 98%
Supply Ability: 5000box
Release date: 2024-03-20

14636-12-5, Terlipressin acetateRelated Search:

Teriparatideacetate Lecirelin Liraglutide Ornipressin Triptorelin Amyloid β-Peptide (1-42) (human) CRF (HUMAN, RAT) Abarelix FERTIRELIN Octreotide 15-28-Somatostatin-28 Teriparatide acetate Cosyntropin Carbetocin Oxytocin Vasopressin Terlipressin acetate Lypressin

[N-α-Triglycyl-8-lysine]-vasopressin

130: PN: WO2010033207 SEQID: 171 claiMed protein

1-Triglycyl-8-lysine Vasopressin

Nα-Glycyl-glycyl-glycyl-[8-lysine]-vasopressin

Nα-Glycyl-glycyl-glycyl-lysine-vasopressin

Nα-Glycylglycylglycyl-vasopressin

Nα-Gly-Gly-Gly-8-Lys-vasopressin

Terlipressin, Terlipressine, Terlipressina, Terlipressinum

H-Gly-Gly-Gly-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH(Disulfide bond)

Terlipressin Acetate salt

Terlipressin, >99%

(2S)-N-[6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[[(4R,7S,10S,13S,16S,19R)-7-(2-amino-2-oxoethyl)-19-[[2-[[2-[(2-amino-1-oxoethyl)amino]-1-oxoethyl]amino]-1-oxoethyl]amino]-10-(3-amino

Triglycyl-8-lysine-vasopressin

H-Gly-Gly-Gly-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2

TerlipressinuM

Terlipressin acetate, >=98%

Terlipressin Diacetate Salt

Thymosin al Acetate

TERLIPRESSIN

TERLIPRESSIN ACETATE

Gly-Gly-Gly-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2 (disulfide bridge 4:9)

(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

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

N-(GLYCYLGLYCYLGLYCYL)-8-L-LYSINE-VASOPRESSIN

H-Gly-Gly-Gly-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2 acetate salt (Disulfide bond)

Glypressin

L-Cys(1)-L-Tyr-L-Phe-L-Gln-L-Asn-L-Cys(1)-L-Pro-L-Lys-Gly-N-(Gly-Gly-Gly-)-NH2

Glycylpressin

Gly-Gly-Gly-[Lys8]vasopressin

Gly-Gly-Gly-L-Cys(1)-L-Tyr-L-Phe-L-Gln-L-Asn-L-Cys(1)-L-Pro-L-Lys-Gly-NH2

Terilipressin

Gly-Gly-Gly-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2

Terlipressin for NMR identification

Terlipressin CRS

Vasopressin, N-(glycylglycylglycyl)-8-L-lysine-

N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin USP/EP/BP

TerlipressinuM Glycylpressin

N-α-Triglycyl-8-lysine]-vasopressin

Terlipressin-15N3-13C6

TerlipressinQ: What is Terlipressin Q: What is the CAS Number of Terlipressin Q: What is the storage condition of Terlipressin Q: What are the applications of Terlipressin

Thymosin α1 Acetate 14636-12-5

Terlipressin(net)

L-α-amino-n-Butyric acid

14636-12-5

146363-12-5

156-1-3

C52H74N16O15S2

C52H74N16O15S2C2H4O2

hormones

Peptide

Amino Acid Derivatives

14636-12-5