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Identification
NameOxytocin
Accession NumberDB00107  (BIOD00016, BTD00016)
Typebiotech
Groupsapproved
Description

Synthetic 9 residue cyclic peptide. The hormone is prepared synthetically to avoid possible contamination with vasopressin (ADH) and other small polypeptides with biologic activity.

Protein structureNo structure small
Protein chemical formulaC43H66N12O12S2
Protein average weight1007.1870
Sequences
>DB00107 sequence
CYIQNCPLG
Download FASTA Format
Synonyms
SynonymLanguageCode
PitocinNot AvailableNot Available
SyntocinonNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
OxytocinBAM Biotech
PitocinParke-Davis
SyntocinonSandoz
Brand mixturesNot Available
Categories
CAS number50-56-6
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentPeptides
Alternative parentsNot Available
SubstituentsNot Available
Classification descriptionNot Available
Pharmacology
IndicationTo assist in labor, elective labor induction, uterine contraction induction
PharmacodynamicsUsed to induce labor or to enhance uterine contractions during labor. Uterine motility depends on the formation of the contractile protein actomyosin under the influence of the Ca2+-dependent phosphorylating enzyme myosin light-chain kinase. Oxytocin promotes contractions by increasing the intracellular Ca2+, which in turn activates myosins light chain kinase.. Oxytocin has specific receptors in the muscle llining of the uterus and the receptor concentration increases greatly during pregnancy, reaching a maximum in early labor at term.
Mechanism of actionBinds the oxytocin receptor which leads to an increase in intracellular calcium levels. The oxytocin-oxytocin receptor system plays an important role as an inducer of uterine contractions during parturition and of milk ejection.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding30%
Metabolism

hepatic oxytocinases

Route of eliminationBiliary and renal
Half life1-6 min
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Pharmacoeconomics
Manufacturers
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia critical care
  • Teva parenteral medicines inc
  • Abbott laboratories pharmaceutical products div
  • Jhp pharmaceuticals llc
  • Novartis pharmaceuticals corp
Packagers
Dosage forms
FormRouteStrength
SolutionIntramuscular
SolutionIntravenous
Prices
Unit descriptionCostUnit
Oxytocin powder1762.25USDg
Oxytocin 10 unit/ml vial9.84USDvial
Pitocin 10 unit/ml vial1.6USDml
Oxytocin-lr 40 unit/500 ml0.09USDml
Oxytocin-d5w-lr 40 unit/500 ml0.07USDml
Oxytocin-d5lr 30 unit/500 ml0.06USDml
Oxytocin-lr 20 unit/500 ml0.06USDml
Oxytocin-d5w-lr 15 unit/500 ml0.05USDml
Oxytocin-d5w-lr 20 unit/500 ml0.05USDml
Oxytocin-lr 10 unit/500 ml0.05USDml
Oxytocin-d5-1/4ns 15 unit/2500.04USDml
Oxytocin-d5w 40 unit/1000 ml0.04USDml
Oxytocin-d5w-lr 10 unit/500 ml0.04USDml
Oxytocin-d5w 20 unit/1000 ml0.03USDml
Oxytocin-d5w 30 unit/1000 ml0.03USDml
Oxytocin-lr 30 unit/500 ml0.03USDml
Oxytocin-ns 30 unit/1000 ml0.03USDml
Oxytocin-d5w 10 unit/1000 ml0.02USDml
Oxytocin-lr 5 unit/500 ml0.02USDml
Oxytocin-ns 40 unit/1000 ml0.02USDml
Oxytocin-d5-1/2ns 10 unit/10000.01USDml
Oxytocin-d5-1/2ns 20 unit/10000.01USDml
Oxytocin-d5-1/2ns 30 unit/10000.01USDml
Oxytocin-d5-ns 20 unit/1000 ml0.01USDml
Oxytocin-ns 10 unit/1000 ml0.01USDml
Oxytocin-ns 20 unit/1000 ml0.01USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
hydrophobicity-2.7Not Available
isoelectric point5.51Not Available
References
Synthesis Reference

Kerstin Uvnas-Moberg, Thomas Lundeberg, “Use of substances having oxytocin activity for preparation of medicaments for wound healing.” U.S. Patent US6262021, issued August, 1988.

US6262021
General Reference
  1. Kosfeld M, Heinrichs M, Zak PJ, Fischbacher U, Fehr E: Oxytocin increases trust in humans. Nature. 2005 Jun 2;435(7042):673-6. Pubmed
  2. Takayanagi Y, Yoshida M, Bielsky IF, Ross HE, Kawamata M, Onaka T, Yanagisawa T, Kimura T, Matzuk MM, Young LJ, Nishimori K: Pervasive social deficits, but normal parturition, in oxytocin receptor-deficient mice. Proc Natl Acad Sci U S A. 2005 Nov 1;102(44):16096-101. Epub 2005 Oct 25. Pubmed
  3. Carmichael MS, Humbert R, Dixen J, Palmisano G, Greenleaf W, Davidson JM: Plasma oxytocin increases in the human sexual response. J Clin Endocrinol Metab. 1987 Jan;64(1):27-31. Pubmed
  4. Paquin J, Danalache BA, Jankowski M, McCann SM, Gutkowska J: Oxytocin induces differentiation of P19 embryonic stem cells to cardiomyocytes. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9550-5. Epub 2002 Jul 1. Pubmed
  5. Jankowski M, Danalache B, Wang D, Bhat P, Hajjar F, Marcinkiewicz M, Paquin J, McCann SM, Gutkowska J: Oxytocin in cardiac ontogeny. Proc Natl Acad Sci U S A. 2004 Aug 31;101(35):13074-9. Epub 2004 Aug 17. Pubmed
External Links
ResourceLink
PharmGKBPA450760
IUPHAR2174
Guide to Pharmacology2174
RxListhttp://www.rxlist.com/cgi/generic3/oxytocin.htm
Drugs.comhttp://www.drugs.com/cdi/oxytocin.html
WikipediaOxytocin
ATC CodesH01BB01H01BB02
AHFS Codes
  • 76:00.00
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
EpinephrinePossible marked increase of arterial pressure
PhenylephrinePossible marked increase of arterial pressure
Food InteractionsNot Available

Targets

1. Oxytocin receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Oxytocin receptor P30559 Details

References:

  1. Spyranti Z, Fragiadaki M, Magafa V, Borovickova L, Spyroulias GA, Cordopatis P, Slaninova J: In position 7 L- and D-Tic-substituted oxytocin and deamino oxytocin: NMR study and conformational insights. Amino Acids. 2010 Jul;39(2):539-48. Epub 2010 Jan 27. Pubmed
  2. Frantz MC, Rodrigo J, Boudier L, Durroux T, Mouillac B, Hibert M: Subtlety of the structure-affinity and structure-efficacy relationships around a nonpeptide oxytocin receptor agonist. J Med Chem. 2010 Feb 25;53(4):1546-62. Pubmed
  3. Gimpl G, Reitz J, Brauer S, Trossen C: Oxytocin receptors: ligand binding, signalling and cholesterol dependence. Prog Brain Res. 2008;170:193-204. Pubmed
  4. Ahn TG, Han SJ, Cho YS, An TH, Pak SC, Flouret G: In vivo activity of the potent oxytocin antagonist on uterine activity in the rat. In Vivo. 2004 Nov-Dec;18(6):763-6. Pubmed
  5. Furman DJ, Chen MC, Gotlib IH: Variant in oxytocin receptor gene is associated with amygdala volume. Psychoneuroendocrinology. 2011 Jan 3. Pubmed

2. Oxytocin-neurophysin 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Oxytocin-neurophysin 1 P01178 Details

References:

  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  2. Land H, Grez M, Ruppert S, Schmale H, Rehbein M, Richter D, Schutz G: Deduced amino acid sequence from the bovine oxytocin-neurophysin I precursor cDNA. Nature. 1983 Mar 24-30;302(5906):342-4. Pubmed
  3. Rao VV, Loffler C, Battey J, Hansmann I: The human gene for oxytocin-neurophysin I (OXT) is physically mapped to chromosome 20p13 by in situ hybridization. Cytogenet Cell Genet. 1992;61(4):271-3. Pubmed

Enzymes

1. Prolyl endopeptidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Prolyl endopeptidase P48147 Details

References:

  1. Irazusta J, Silveira PF, Gil J, Varona A, Casis L: Effects of hydrosaline treatments on prolyl endopeptidase activity in rat tissues. Regul Pept. 2001 Sep 15;101(1-3):141-7. Pubmed
  2. Bausback HH, Ward PE: Vascular, post proline cleaving enzyme: metabolism of vasoactive peptides. Adv Exp Med Biol. 1986;198 Pt A:397-404. Pubmed
  3. Yoshimoto T, Nishimura T, Kita T, Tsuru D: Post-proline cleaving enzyme (prolyl endopeptidase) from bovine brain. J Biochem. 1983 Oct;94(4):1179-90. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 13, 2013 10:49