Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:52:02 UTC |
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HMDB ID | HMDB0015569 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Terlipressin |
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Description | Terlipressin is only found in individuals that have used or taken this drug. It is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. It has been found to be effective when norepinephrine does not help. [Wikipedia ]Terlipressin acts on three different receptors, vasopressin receptor V1a (which initiates vasoconstriction, liver gluconeogenesis, platelet aggregation and release of factor VIII), vasopressin receptor V1b (which mediates corticotrophin secretion from the pituitary) and vasopressin receptor V2 which controls free water reabsorption in the renal medullar. The binding of terlipressin to the V2 receptor activates adenylate cyclase which causes the release of aquaporin 2 channels into the cells lining the renal medullar duct. This allows water to be reabsorbed down an osmotic gradient so the urine is more concentrated. |
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Structure | 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 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 |
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Synonyms | Value | Source |
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N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin | HMDB | Glycylpressin | HMDB | Gly-gly-gly-8-lys-vasopressin | HMDB | Triglycylvasopressin | HMDB | N-(alpha)-Glycyl-glycyl-glycyl-8-lysine vasopressin | HMDB | Remestyp | HMDB | TGLVP | HMDB | Glypressin | HMDB | Triglycyl lysine vasopressin | HMDB | Glipressin | HMDB | Terlypressin | HMDB | Triglycyl-(8-lysine)vasopressin | HMDB | (2S)-6-Amino-2-({[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-{[2-({2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxyethylidene]amino}-13-benzyl-6,9,12,15,18-pentahydroxy-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-N-[(C-hydroxycarbonimidoyl)methyl]hexanimidate | HMDB | Gly gly gly 8 lys vasopressin | HMDB | Tri-gly-8-lys- vasopressin | HMDB | Terlipressin | MeSH |
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Chemical Formula | C52H74N16O15S2 |
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Average Molecular Weight | 1227.372 |
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Monoisotopic Molecular Weight | 1226.496097158 |
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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 |
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Traditional Name | terlipressin |
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CAS Registry Number | 14636-12-5 |
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SMILES | 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 |
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InChI Identifier | 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 |
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InChI Key | BENFXAYNYRLAIU-QSVFAHTRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. |
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Kingdom | Organic compounds |
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Super Class | Organic Polymers |
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Class | Polypeptides |
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Sub Class | Not Available |
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Direct Parent | Polypeptides |
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Alternative Parents | |
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Substituents | - Polypeptide
- Cyclic alpha peptide
- Proline or derivatives
- Macrolactam
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- N-acylpyrrolidine
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine-2-carboxamide
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Benzenoid
- Pyrrolidine
- Tertiary carboxylic acid amide
- Secondary carboxylic acid amide
- Organic disulfide
- Amino acid or derivatives
- Primary carboxylic acid amide
- Carboxamide group
- Lactam
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Primary amine
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary aliphatic amine
- Carbonyl group
- Organic nitrogen compound
- Organopnictogen compound
- Amine
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.17 g/L | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 324.552 | 30932474 | DeepCCS | [M-H]- | 322.899 | 30932474 | DeepCCS | [M-2H]- | 356.932 | 30932474 | DeepCCS | [M+Na]+ | 330.709 | 30932474 |
Predicted Kovats Retention IndicesNot Available |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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MS | Mass Spectrum (Electron Ionization) | Not Available | 2022-08-06 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 10V, Positive-QTOF | splash10-000l-9730000000-a8d68dda1eff985cd914 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 20V, Positive-QTOF | splash10-052r-9510000000-891a33e18235006eee81 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 40V, Positive-QTOF | splash10-000i-9100000000-e04b89517b6a7732b095 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 10V, Negative-QTOF | splash10-056r-3890000000-9b92091320e40161e6da | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 20V, Negative-QTOF | splash10-0zml-6970000001-861b801a7476e9e5937d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 40V, Negative-QTOF | splash10-0fdo-9630000010-73ee99640a78fc6019c3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 10V, Positive-QTOF | splash10-004i-6590000000-47d9bd21e8229f357439 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 20V, Positive-QTOF | splash10-0bvi-9510000000-17fabccd2717c964fced | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 40V, Positive-QTOF | splash10-0600-9400000000-66b70375d23a49bfc543 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 10V, Negative-QTOF | splash10-00b9-5970000000-829ad70af249c53ff63b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 20V, Negative-QTOF | splash10-074l-9110000000-b9faa13362605fe7add7 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Terlipressin 40V, Negative-QTOF | splash10-0006-9100000000-e33d93f0810127e18002 | 2021-10-11 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Kam PC, Williams S, Yoong FF: Vasopressin and terlipressin: pharmacology and its clinical relevance. Anaesthesia. 2004 Oct;59(10):993-1001. [PubMed:15488059 ]
- Matok I, Vard A, Efrati O, Rubinshtein M, Vishne T, Leibovitch L, Adam M, Barzilay Z, Paret G: Terlipressin as rescue therapy for intractable hypotension due to septic shock in children. Shock. 2005 Apr;23(4):305-10. [PubMed:15803052 ]
- Leone M, Charvet A, Delmas A, Albanese J, Martin C, Boyle WA: Terlipressin: a new therapeutic for calcium-channel blockers overdose. J Crit Care. 2005 Mar;20(1):114-5. [PubMed:16015526 ]
- Klein M, Weksler N, Borer A, Koyfman L, Kesslin J, Gurman GM: Terlipressin facilitates transport of septic patients treated with norepinephrine. Isr Med Assoc J. 2006 Oct;8(10):691-3. [PubMed:17125115 ]
- Pesaturo AB, Jennings HR, Voils SA: Terlipressin: vasopressin analog and novel drug for septic shock. Ann Pharmacother. 2006 Dec;40(12):2170-7. Epub 2006 Dec 5. [PubMed:17148649 ]
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