Terlipressin acetateProduct ingredient for Terlipressin

Name
Terlipressin acetate
Drug Entry
Terlipressin

Terlipressin is a synthetic analogue of vasopressin, which is an endogenous neurohormone that acts as a vasoconstrictor.1 It is a prodrug of lypressin, or lysine vasopressin. Compared to endogenous vasopressin, terlipressin has a longer half life and increased selectivity for the V1 receptor.8 As a potent vasopressor, terlipressin has been investigated in various shock states and conditions with diminished vasomotor tone.1,2,3,4,5 It was also studied in hepatorenal syndrome (HRS) and variceal bleeding.6 The drug was first approved by the FDA in September 2022.8

Accession Number
DBSALT002332
Structure
Synonyms
Not Available
UNII
4U092XZF0K
CAS Number
Not Available
Weight
Average: 1437.56
Monoisotopic: 1436.591180254
Chemical Formula
C56H92N16O24S2
InChI Key
MLECZWUGJYWVAV-NSECCGHPSA-N
InChI
InChI=1S/C52H74N16O15S2.2C2H4O2.5H2O/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;2*1-2(3)4;;;;;/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);2*1H3,(H,3,4);5*1H2/t31-,32-,33-,34-,35-,36-,37-,38-;;;;;;;/m0......./s1
IUPAC Name
(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-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide bis(acetic acid) pentahydrate
SMILES
O.O.O.O.O.CC(O)=O.CC(O)=O.NCCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@@H](CC2=CC=C(O)C=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
ChemSpider
32697620
Predicted Properties
PropertyValueSource
Water Solubility0.167 mg/mLALOGPS
logP-1.6ALOGPS
logP-10Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.43Chemaxon
pKa (Strongest Basic)10.26Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count17Chemaxon
Hydrogen Donor Count16Chemaxon
Polar Surface Area512.85 Å2Chemaxon
Rotatable Bond Count25Chemaxon
Refractivity305.18 m3·mol-1Chemaxon
Polarizability121.49 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon