Pharmacological effects Mechanism of Action Adverse Drug Reactions
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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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Terlipressin acetate Suppliers

Shenzhen JYMed Technology Co., Ltd.
Tel
755-755-26612112 15013529272;
Fax
+86 (755) 8635-0488
Email
jymed@jymedtech.com
Country
China
ProdList
81
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58
Hangzhou Peptide Biochem Co.,Ltd
Tel
0571-89197072; 18668118770
Fax
0571-89197072
Email
linda@peptide-china.com
Country
China
ProdList
248
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Hangzhou Peptidego Biotech Co.,Ltd.
Tel
0571-87213919
Fax
0571-87213919
Email
Eric@peptidego.com
Country
China
ProdList
6756
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58
Hangzhou Xinhai Pharmaceutical Technology Co., Ltd.
Tel
0571-86758863 13867485072
Fax
0571-86758863
Email
lulu@thinheal.com
Country
China
ProdList
302
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Nanjing Pusheng Biomedical Technology Co., Ltd
Tel
02557628056 15150681880
Email
order@pushengmedical.com
Country
China
ProdList
267
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58
Hangzhou Go Top Peptide Biotech
Tel
0571-88211921 13355716090
Email
Sales@gotopbio.com
Country
China
ProdList
2857
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58
Zhongke Huayao (Jiangsu) Biotechnology Co., Ltd
Tel
18014456767 18014456767
Email
wenxi@jszkhy.com
Country
China
ProdList
1350
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58
Nanjing Yuanpeptide Biotech Co.,Ltd.
Tel
18168071971
Email
support@yuan-peptide.com
Country
China
ProdList
2978
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58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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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
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
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

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