Terlipressin

Terlipressin is a synthetic triglycyllysine derivative of vasopressin with vasoconstrictive, antihemorrhagic, and antidiuretic properties. Upon intravenous administration, terlipressin, an inactive prodrug, is biotransformed to its active moiety, lysine vasopressin (LVP), a nonselective vasopressin analogue with affinity for vasopressin receptors V1 (V1a), V2 and V3 (V1b). As a V1 agonist, terlipressin increases systemic vascular resistance, particularly in the splanchnic area, resulting in a decrease of portal pressure. V1 binding also promotes platelet aggregation and glycogenolysis, while V3 binding induces adrenocorticotropic hormone (ACTH) secretion. Compared to vasopressin, terlipressin has a minimal effect on V2 receptors, which are responsible for promotion of water reabsorption in the collecting ducts of the kidney via stimulation of cyclic AMP production.

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CAT No: 10-101-342

CAS No: 14636-12-5

Synonyms/Alias: Terlipressin;14636-12-5;glypressin;Terlipressin acetate;glycylpressin;Terlipressine;Terlipressina;Terlipressinum;Lucassin;Terlipressine [INN-French];Terlipressinum [INN-Latin];Terlipressina [INN-Spanish];N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin;Terlipresina;Variquel;EINECS 238-680-8;UNII-7Z5X49W53P;DTXSID7048952;(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;DTXCID0028878;7Z5X49W53P;Terlivaz;NCGC00185754-01;Terlipressine (INN-French);Terlipressinum (INN-Latin);Terlipressina (INN-Spanish);glycyl-glycyl-glycyl-L-cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparagyl-L-cysteinyl-L-prolyl-L-lysyl-glycinamide (4->9)-disulfide;terlypressin;triglycylvasopressin;TGLVP;914453-96-6;triglycyl lysine vasopressin;Terlipressin?;Terlipressin [USAN:INN:BAN];Lucassin (TN);HS-2028;Terlipressin (USAN/INN);SCHEMBL22699;TERLIPRESSIN (MART.);CHEMBL2135460;GTPL11241;H01BA04;BENFXAYNYRLAIU-QSVFAHTRSA-N;CHEBI:135905;TERLIPRESSIN (EP MONOGRAPH);EX-A3116;Tox21_113374;AKOS015994637;CCG-270662;CS-5769;DB02638;DA-58411;HY-12554;CAS-14636-12-5;NS00024791;C72780;D06672;GLYCYLGLYCYLGLYCYL(8-L-LYSINE)VASOPRESSIN;N-(N-(N-glycylglycyl)glycyl)-L-lysinevasopressin;Q324147;BRD-K73451719-001-01-2;VASOPRESSIN, N-(GLYCYLGLYCYLGLYCYL)-8-L-LYSINE-;GLY-GLY-GLY-CYS-TYR-PHE-GLN-ASN-CYS-PRO-LYS-GLY-NH2 (4-9 DISULFIDE);(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;238-680-8;

Chemical 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

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC52H74N16O15S2
M.W/Mr.1227.4
SequenceOne Letter Code:GGGCYFQNCPKG
Three Letter Code:H-Gly-Gly-Gly-Cys(1)-Tyr-Phe-Gln-Asn-Cys(1)-Pro-Lys-Gly-NH2
ActivityAgonist
Biological ActivityTerlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension which has been found to be effective when norepinephrine fails.
TargetVasopressin Receptor
Long-term Storage ConditionsDMF: 20 mg/ml
DMSO: 25 mg/ml
Ethanol: Partially soluble
PBS (pH 7.2): 10 mg/ml
InChIInChI=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
InChI KeyBENFXAYNYRLAIU-QSVFAHTRSA-N
Canonical SMILESC1CC(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
Isomeric SMILESC1C[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

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