This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Lypressin
Accession Number
DB14642  (DBSALT002465)
Type
Small Molecule
Groups
Approved
Description
Not Available
Structure
Thumb
Synonyms
  • 8-L-lysinevasopressin
  • Lysine vasopressin
  • Vasopressin pig
  • Vasopressin, 8-L-lysine
International/Other Brands
Diapid (Sandoz)
Categories
UNII
7CZF3L922Y
CAS number
50-57-7
Weight
Average: 1056.23
Monoisotopic: 1055.431706933
Chemical Formula
C46H65N13O12S2
InChI Key
BJFIDCADFRDPIO-DZCXQCEKSA-N
InChI
InChI=1S/C46H65N13O12S2/c47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34/h1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
IUPAC Name
(2S)-6-amino-2-({[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-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]hexanimidic acid
SMILES
[H]N([H])C(=O)C[C@]1([H])NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@@H](N)CSSC[C@H](NC1=O)C(=O)N1CCC[C@H]1C(=O)NC([H])(CCCCN)C(=O)NCC(N)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AVasopressin V1a receptorNot AvailableHumans
AVasopressin V2 receptorNot AvailableHumans
AVasopressin V1b receptorNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
3,5-diiodothyropropionic acidThe therapeutic efficacy of Lypressin can be increased when used in combination with 3,5-diiodothyropropionic acid.
AbaloparatideThe therapeutic efficacy of Lypressin can be increased when used in combination with Abaloparatide.
BenzylthiouracilThe therapeutic efficacy of Lypressin can be increased when used in combination with Benzylthiouracil.
CarbimazoleThe therapeutic efficacy of Lypressin can be increased when used in combination with Carbimazole.
DibromotyrosineThe therapeutic efficacy of Lypressin can be increased when used in combination with Dibromotyrosine.
FollitropinThe therapeutic efficacy of Lypressin can be increased when used in combination with Follitropin.
LevothyroxineThe therapeutic efficacy of Lypressin can be increased when used in combination with Levothyroxine.
LidocaineThe risk or severity of hypertension can be increased when Lypressin is combined with Lidocaine.
LiothyronineThe therapeutic efficacy of Lypressin can be increased when used in combination with Liothyronine.
LiotrixThe therapeutic efficacy of Lypressin can be increased when used in combination with Liotrix.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
559125
ChEBI
94802
ChEMBL
CHEMBL1200690
Wikipedia
Vasopressin
ATC Codes
H01BA03 — Lypressin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0497 mg/mLALOGPS
logP-1.1ALOGPS
logP2.28ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area452.95 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity303.23 m3·mol-1ChemAxon
Polarizability106.45 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Cyclic peptides / Proline and derivatives / Macrolactams / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Pyrrolidinecarboxamides / N-acylpyrrolidines / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / N-acyl amines
show 11 more
Substituents
Alpha-oligopeptide / 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
show 30 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Vasopressin receptor activity
Specific Function
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl-inositol-calcium second messenger system. Has been involved in social behavi...
Gene Name
AVPR1A
Uniprot ID
P37288
Uniprot Name
Vasopressin V1a receptor
Molecular Weight
46799.105 Da
References
  1. Hiroyama M, Wang S, Aoyagi T, Oikawa R, Sanbe A, Takeo S, Tanoue A: Vasopressin promotes cardiomyocyte hypertrophy via the vasopressin V1A receptor in neonatal mice. Eur J Pharmacol. 2007 Mar 22;559(2-3):89-97. Epub 2006 Dec 29. [PubMed:17275806]
  2. Liedman R, Grant L, Igidbashian S, James I, McLeod A, Skillern L, Akerlund M: Intrauterine pressure, ischemia markers, and experienced pain during administration of a vasopressin V1a receptor antagonist in spontaneous and vasopressin-induced dysmenorrhea. Acta Obstet Gynecol Scand. 2006;85(2):207-11. [PubMed:16532916]
  3. Adikesavan NV, Mahmood SS, Stanley N, Xu Z, Wu N, Thibonnier M, Shoham M: A C-terminal segment of the V1R vasopressin receptor is unstructured in the crystal structure of its chimera with the maltose-binding protein. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Apr 1;61(Pt 4):341-5. Epub 2005 Mar 24. [PubMed:16511036]
  4. Hammock EA, Lim MM, Nair HP, Young LJ: Association of vasopressin 1a receptor levels with a regulatory microsatellite and behavior. Genes Brain Behav. 2005 Jul;4(5):289-301. [PubMed:16011575]
  5. Aoyagi T, Birumachi J, Hiroyama M, Fujiwara Y, Sanbe A, Yamauchi J, Tanoue A: Alteration of glucose homeostasis in V1a vasopressin receptor-deficient mice. Endocrinology. 2007 May;148(5):2075-84. Epub 2007 Feb 15. [PubMed:17303660]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Vasopressin receptor activity
Specific Function
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. Involved in renal water reabsorption.
Gene Name
AVPR2
Uniprot ID
P30518
Uniprot Name
Vasopressin V2 receptor
Molecular Weight
40278.57 Da
References
  1. Boson WL, Della Manna T, Damiani D, Miranda DM, Gadelha MR, Liberman B, Correa H, Romano-Silva MA, Friedman E, Silva FF, Ribeiro PA, De Marco L: Novel vasopressin type 2 (AVPR2) gene mutations in Brazilian nephrogenic diabetes insipidus patients. Genet Test. 2006 Fall;10(3):157-62. [PubMed:17020465]
  2. Slusarz MJ, Slusarz R, Ciarkowski J: Investigation of mechanism of desmopressin binding in vasopressin V2 receptor versus vasopressin V1a and oxytocin receptors: molecular dynamics simulation of the agonist-bound state in the membrane-aqueous system. Biopolymers. 2006 Apr 5;81(5):321-38. [PubMed:16333859]
  3. Bouley R, Hawthorn G, Russo LM, Lin HY, Ausiello DA, Brown D: Aquaporin 2 (AQP2) and vasopressin type 2 receptor (V2R) endocytosis in kidney epithelial cells: AQP2 is located in 'endocytosis-resistant' membrane domains after vasopressin treatment. Biol Cell. 2006 Apr;98(4):215-32. [PubMed:16563128]
  4. Yi X, Bouley R, Lin HY, Bechoua S, Sun TX, Del Re E, Shioda T, Raychowdhury MK, Lu HA, Abou-Samra AB, Brown D, Ausiello DA: Alix (AIP1) is a vasopressin receptor (V2R)-interacting protein that increases lysosomal degradation of the V2R. Am J Physiol Renal Physiol. 2007 May;292(5):F1303-13. Epub 2007 Feb 6. [PubMed:17287200]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Vasopressin receptor activity
Specific Function
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl-inositol-calcium second messenger system.
Gene Name
AVPR1B
Uniprot ID
P47901
Uniprot Name
Vasopressin V1b receptor
Molecular Weight
46970.345 Da
References
  1. Young WS, Li J, Wersinger SR, Palkovits M: The vasopressin 1b receptor is prominent in the hippocampal area CA2 where it is unaffected by restraint stress or adrenalectomy. Neuroscience. 2006 Dec 28;143(4):1031-9. Epub 2006 Oct 4. [PubMed:17027167]
  2. Volpi S, Liu Y, Aguilera G: Vasopressin increases GAGA binding activity to the V1b receptor promoter through transactivation of the MAP kinase pathway. J Mol Endocrinol. 2006 Jun;36(3):581-90. [PubMed:16720725]
  3. Wersinger SR, Caldwell HK, Christiansen M, Young WS 3rd: Disruption of the vasopressin 1b receptor gene impairs the attack component of aggressive behavior in mice. Genes Brain Behav. 2007 Oct;6(7):653-60. Epub 2006 Dec 20. [PubMed:17284170]
  4. Slusarz MJ, Gieldon A, Slusarz R, Ciarkowski J: Analysis of interactions responsible for vasopressin binding to human neurohypophyseal hormone receptors-molecular dynamics study of the activated receptor-vasopressin-G(alpha) systems. J Pept Sci. 2006 Mar;12(3):180-9. [PubMed:16114100]
  5. Jurkevich A, Berghman LR, Cornett LE, Kuenzel WJ: Characterization and immunohistochemical visualization of the vasotocin VT2 receptor in the pituitary gland of the chicken, Gallus gallus. Gen Comp Endocrinol. 2005 Aug;143(1):82-91. Epub 2005 Mar 23. [PubMed:15993108]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Madon J, Hagenbuch B, Landmann L, Meier PJ, Stieger B: Transport function and hepatocellular localization of mrp6 in rat liver. Mol Pharmacol. 2000 Mar;57(3):634-41. [PubMed:10692506]

Drug created on September 01, 2018 15:13 / Updated on May 23, 2019 16:49