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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 structureDb00107
Protein chemical formulaC43H66N12O12S2
Protein average weight1007.1870
Sequences
>DB00107 sequence
CYIQNCPLG
Download FASTA Format
Synonyms
SynonymLanguageCode
PitocinNot AvailableNot Available
SID29217903Not AvailableNot Available
SID50111741Not 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
IndicationUsed for labor induction, augmentation of labor, postpartum abbreviation of third stage of labor, postpartum control of uterine bleeding, termination of pregnancy and for the evaluation of fetal respiratory capability. Oxytocin cannot be used for elective induction of labor, there must be a clear medical requirement.
PharmacodynamicsIndirectly stimulates contraction of uterine smooth muscle by increasing the sodium permeability of uterine myofibrils. Increases contraction amplitude and frequency, which tends to decrease cervical activity, produce dilation and effacement of the cervix, and transiently impede uterine blood flow; contractions produced by oxytocin at term are similar to those occurring during spontaneous labor. High estrogen concentrations lower the threshold for uterine response to oxytocin. Uterine response increases with the duration of pregnancy and is greater in labor than when not in labor; only very large doses elicit contractions in early pregnancy. Contracts myoepithelial cells surrounding the alveoli of the breasts, forcing milk from the alveoli into the larger ducts and facilitating milk ejection. Minimal antidiuretic activity relative to vasopressin; water intoxication possible at high doses and/or excessive electrolyte-free fluid.
Mechanism of actionUterine 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 myosin's light chain kinase.. Oxytocin has specific receptors in the muscle lining of the uterus and the receptor concentration increases greatly during pregnancy, reaching a maximum in early labor at term.
AbsorptionUterine response after IV administration is immediate and subsides after 1 hour. Uterine contractions occur 3-5mins after IM administration and decreases within 2-3 hours. When 100-200milliunits is administered IV, contractions of the myoepithelial tissue surrounding the alveoli of the breasts occur within minutes and last for about 20 mins.
Volume of distribution

Distributes throughout the extracellular fluid and crosses the placenta. It is probable that it also distributes into milk in small amounts.

Protein binding30%
Metabolism

Oxytocin is rapidly metabolized in the liver and also in the plasma by oxytocinases. It is also metabolized to a smaller degree by the mammary glands.

Route of eliminationBiliary and renal (excreted unchanged in the urine)
Half life1-6 min, this is decreased in late pregnancy and during lactation.
ClearanceNot Available
ToxicityOxytocin can produce a severe water intoxication due to its antidiuretic effect. Prolonged IV infusions of more 40milliunits/min are usually the cause. Severe water intoxication with convulsions, coma, and death can occur. Some neonatal seizures have also been reported. Consider potential for water intoxication, particularly when administered by IV infusion and patient is receiving oral fluids. Uterine effects: High doses or hypersensitivity to oxytocin may cause uterine hypertonicity, spasm, tetanic contraction, or rupture of the uterus. There have also been reported allergic and anaphylactic reactions to oxytocin but they were rarely fatal.
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
  6. Oxytocin. In DynaMed [database online]. EBSCO Information Services.
    http://search.ebscohost.com/login.aspx?direct=true&site=DynaMed&id=233015. Updated January 18, 2013. Accessed October 1, 2014.
    #Lexicomp. Oxytocin. N.p., 2014. Web. 11 Nov. 2014.
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
Carboprost TromethamineAvoid combination due to enhanced oxytocic effects.
DinoprostoneTherapy modification should be considered because of enhanced oxytocic effects
EpinephrinePossible marked increase of arterial pressure
MifepristoneConsider therapy modification because of potential enhanced effect of Q-Tc prolongation
MisoprostolAvoid combination. Manufacturer advises not to administer concomitantly due to enhanced adverse effects of oxytocin, especially when given within 4 hours of oxytocin initiation.
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 November 10, 2014 20:16