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Identification
NameOxytocin
Accession NumberDB00107  (BTD00016, BIOD00016)
TypeBiotech
GroupsApproved, Vet Approved
DescriptionSynthetic 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
Related Articles
Protein chemical formulaC43H66N12O12S2
Protein average weight1007.187 Da
Sequences
>DB00107 sequence
CYIQNCPLG
Download FASTA Format
Synonyms
Pitocin
Syntocinon
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxytocininjection, solution10 [USP'U]/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-08-10Not applicableUs
Oxytocininjection10 [USP'U]/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1980-04-29Not applicableUs
Oxytocininjection10 [iU]/mLintravenousJHP Pharmaceuticals, LLC2012-06-01Not applicableUs
Oxytocininjection10 [USP'U]/mLintramuscular; intravenousBaxter Healthcare Corporation2009-06-262015-12-29Us
Oxytocininjection10 [USP'U]/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1980-04-29Not applicableUs
Oxytocininjection10 [iU]/mLintravenousJHP Pharmaceuticals, LLC2012-06-01Not applicableUs
Oxytocininjection, solution10 [USP'U]/mLintramuscular; intravenousCardinal Health2000-08-10Not applicableUs
Oxytocin Inj 10unit/ml USPliquid10 unitintramuscular; intravenousLyphomed, Division Of Fujisawa Canada Inc.1988-12-311996-09-10Canada
Oxytocin Injectionsolution10 unitintramuscular; intravenousFresenius Kabi Canada Ltd1996-08-14Not applicableCanada
Oxytocin Injection 10unit/mlsolution10 unitintramuscular; intravenousHospira Healthcare Corporation1981-12-31Not applicableCanada
Pitocininjection10 [iU]/mLintravenousPar Pharmaceutical, Inc.2007-10-01Not applicableUs
Pitocininjection10 [iU]/mLintravenousJHP Pharmaceuticals LLC2012-09-05Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxytocininjection10 [USP'U]/mLintramuscular; intravenousWest ward Pharmaceutical Corp2013-02-13Not applicableUs
Oxytocininjection10 [USP'U]/mLintramuscular; intravenousWest ward Pharmaceutical Corp2013-02-13Not applicableUs
Oxytocininjection, solution10 [USP'U]/mLintramuscular; intravenousSagent Pharmaceuticals2016-04-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxytocininjection, solution30 [USP'U]/500mLintravenousCantrell Drug Company2011-07-01Not applicableUs
Oxytocininjection, solution10 [USP'U]/1000mLintravenousCantrell Drug Company2012-07-30Not applicableUs
Oxytocininjection, solution30 [USP'U]/500mLintravenousCantrell Drug Company2011-10-20Not applicableUs
Oxytocininjection, solution20 [USP'U]/500mLintravenousCantrell Drug Company2016-03-18Not applicableUs
Oxytocininjection, solution2 [USP'U]/100mLintravenousCantrell Drug Company2011-10-20Not applicableUs
Oxytocininjection, solution30 [USP'U]/500mLintravenousCantrell Drug Company2011-10-20Not applicableUs
Oxytocininjection, solution30 [USP'U]/1000mLintravenousCantrell Drug Company2016-03-18Not applicableUs
Oxytocininjection, solution2 [USP'U]/100mLintravenousCantrell Drug Company2011-10-20Not applicableUs
Oxytocininjection, solution2 [USP'U]/100mLintravenousCantrell Drug Company2012-11-12Not applicableUs
Oxytocininjection, solution30 [USP'U]/500mLintravenousCantrell Drug Company2011-10-20Not applicableUs
International Brands
NameCompany
SyntocinonSandoz
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1JQS135EYN
CAS number50-56-6
Taxonomy
DescriptionNot Available
KingdomOrganic Compounds
Super ClassOrganic Acids
ClassCarboxylic Acids and Derivatives
Sub ClassAmino Acids, Peptides, and Analogues
Direct ParentPeptides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot 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.
Related Articles
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
Injectionintramuscular; intravenous10 [USP'U]/mL
Injection, solutionintramuscular; intravenous10 [USP'U]/mL
Injection, solutionintravenous10 [USP'U]/1000mL
Injection, solutionintravenous2 [USP'U]/100mL
Injection, solutionintravenous20 [USP'U]/500mL
Injection, solutionintravenous30 [USP'U]/1000mL
Injection, solutionintravenous30 [USP'U]/500mL
Liquidintramuscular; intravenous10 unit
Solutionintramuscular; intravenous10 unit
Injectionintravenous10 [iU]/mL
Prices
Unit descriptionCostUnit
Oxytocin powder1762.25USD g
Oxytocin 10 unit/ml vial9.84USD vial
Pitocin 10 unit/ml vial1.6USD ml
Oxytocin-lr 40 unit/500 ml0.09USD ml
Oxytocin-d5w-lr 40 unit/500 ml0.07USD ml
Oxytocin-d5lr 30 unit/500 ml0.06USD ml
Oxytocin-lr 20 unit/500 ml0.06USD ml
Oxytocin-d5w-lr 15 unit/500 ml0.05USD ml
Oxytocin-d5w-lr 20 unit/500 ml0.05USD ml
Oxytocin-lr 10 unit/500 ml0.05USD ml
Oxytocin-d5-1/4ns 15 unit/2500.04USD ml
Oxytocin-d5w 40 unit/1000 ml0.04USD ml
Oxytocin-d5w-lr 10 unit/500 ml0.04USD ml
Oxytocin-d5w 20 unit/1000 ml0.03USD ml
Oxytocin-d5w 30 unit/1000 ml0.03USD ml
Oxytocin-lr 30 unit/500 ml0.03USD ml
Oxytocin-ns 30 unit/1000 ml0.03USD ml
Oxytocin-d5w 10 unit/1000 ml0.02USD ml
Oxytocin-lr 5 unit/500 ml0.02USD ml
Oxytocin-ns 40 unit/1000 ml0.02USD ml
Oxytocin-d5-1/2ns 10 unit/10000.01USD ml
Oxytocin-d5-1/2ns 20 unit/10000.01USD ml
Oxytocin-d5-1/2ns 30 unit/10000.01USD ml
Oxytocin-d5-ns 20 unit/1000 ml0.01USD ml
Oxytocin-ns 10 unit/1000 ml0.01USD ml
Oxytocin-ns 20 unit/1000 ml0.01USD ml
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 References
  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:15931222 ]
  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:16249339 ]
  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:3782434 ]
  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:12093924 ]
  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:15316117 ]
  6. Link [Link]
External Links
ATC CodesH01BB02G02AC01
AHFS Codes
  • 76:00.00
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmiodaroneOxytocin may increase the QTc-prolonging activities of Amiodarone.
AnagrelideOxytocin may increase the QTc-prolonging activities of Anagrelide.
Arsenic trioxideOxytocin may increase the QTc-prolonging activities of Arsenic trioxide.
ArtemetherOxytocin may increase the QTc-prolonging activities of Artemether.
AsenapineOxytocin may increase the QTc-prolonging activities of Asenapine.
AzithromycinOxytocin may increase the QTc-prolonging activities of Azithromycin.
BedaquilineOxytocin may increase the QTc-prolonging activities of Bedaquiline.
Carboprost TromethamineThe risk or severity of adverse effects can be increased when Carboprost Tromethamine is combined with Oxytocin.
CeritinibOxytocin may increase the QTc-prolonging activities of Ceritinib.
ChloroquineOxytocin may increase the QTc-prolonging activities of Chloroquine.
ChlorpromazineOxytocin may increase the QTc-prolonging activities of Chlorpromazine.
CiprofloxacinOxytocin may increase the QTc-prolonging activities of Ciprofloxacin.
CisaprideOxytocin may increase the QTc-prolonging activities of Cisapride.
CitalopramOxytocin may increase the QTc-prolonging activities of Citalopram.
ClarithromycinOxytocin may increase the QTc-prolonging activities of Clarithromycin.
ClozapineOxytocin may increase the QTc-prolonging activities of Clozapine.
CrizotinibOxytocin may increase the QTc-prolonging activities of Crizotinib.
DinoprostoneThe risk or severity of adverse effects can be increased when Dinoprostone is combined with Oxytocin.
DisopyramideOxytocin may increase the QTc-prolonging activities of Disopyramide.
DofetilideOxytocin may increase the QTc-prolonging activities of Dofetilide.
DolasetronOxytocin may increase the QTc-prolonging activities of Dolasetron.
DomperidoneOxytocin may increase the QTc-prolonging activities of Domperidone.
DronedaroneOxytocin may increase the QTc-prolonging activities of Dronedarone.
DroperidolOxytocin may increase the QTc-prolonging activities of Droperidol.
EliglustatOxytocin may increase the QTc-prolonging activities of Eliglustat.
ErythromycinOxytocin may increase the QTc-prolonging activities of Erythromycin.
EscitalopramOxytocin may increase the QTc-prolonging activities of Escitalopram.
FlecainideOxytocin may increase the QTc-prolonging activities of Flecainide.
FluoxetineOxytocin may increase the QTc-prolonging activities of Fluoxetine.
FlupentixolOxytocin may increase the QTc-prolonging activities of Flupentixol.
Gadobenic acidOxytocin may increase the QTc-prolonging activities of Gadobenic acid.
GemifloxacinOxytocin may increase the QTc-prolonging activities of Gemifloxacin.
GoserelinOxytocin may increase the QTc-prolonging activities of Goserelin.
GranisetronOxytocin may increase the QTc-prolonging activities of Granisetron.
HaloperidolOxytocin may increase the QTc-prolonging activities of Haloperidol.
IbutilideOxytocin may increase the QTc-prolonging activities of Ibutilide.
IloperidoneOxytocin may increase the QTc-prolonging activities of Iloperidone.
LenvatinibOxytocin may increase the QTc-prolonging activities of Lenvatinib.
LeuprolideOxytocin may increase the QTc-prolonging activities of Leuprolide.
LevofloxacinOxytocin may increase the QTc-prolonging activities of Levofloxacin.
LopinavirOxytocin may increase the QTc-prolonging activities of Lopinavir.
LumefantrineOxytocin may increase the QTc-prolonging activities of Lumefantrine.
MethadoneOxytocin may increase the QTc-prolonging activities of Methadone.
MifepristoneMifepristone may increase the QTc-prolonging activities of Oxytocin.
MisoprostolThe risk or severity of adverse effects can be increased when Misoprostol is combined with Oxytocin.
MoxifloxacinOxytocin may increase the QTc-prolonging activities of Moxifloxacin.
NilotinibOxytocin may increase the QTc-prolonging activities of Nilotinib.
OfloxacinOxytocin may increase the QTc-prolonging activities of Ofloxacin.
OndansetronOxytocin may increase the QTc-prolonging activities of Ondansetron.
PaliperidoneOxytocin may increase the QTc-prolonging activities of Paliperidone.
PanobinostatOxytocin may increase the QTc-prolonging activities of Panobinostat.
PazopanibOxytocin may increase the QTc-prolonging activities of Pazopanib.
PentamidineOxytocin may increase the QTc-prolonging activities of Pentamidine.
PerflutrenOxytocin may increase the QTc-prolonging activities of Perflutren.
PimozideOxytocin may increase the QTc-prolonging activities of Pimozide.
PrimaquineOxytocin may increase the QTc-prolonging activities of Primaquine.
ProcainamideOxytocin may increase the QTc-prolonging activities of Procainamide.
PromazineOxytocin may increase the QTc-prolonging activities of Promazine.
PropafenoneOxytocin may increase the QTc-prolonging activities of Propafenone.
QuetiapineOxytocin may increase the QTc-prolonging activities of Quetiapine.
QuinidineOxytocin may increase the QTc-prolonging activities of Quinidine.
QuinineOxytocin may increase the QTc-prolonging activities of Quinine.
SaquinavirOxytocin may increase the QTc-prolonging activities of Saquinavir.
SotalolOxytocin may increase the QTc-prolonging activities of Sotalol.
SulfisoxazoleOxytocin may increase the QTc-prolonging activities of Sulfisoxazole.
TelavancinOxytocin may increase the QTc-prolonging activities of Telavancin.
TelithromycinOxytocin may increase the QTc-prolonging activities of Telithromycin.
TetrabenazineOxytocin may increase the QTc-prolonging activities of Tetrabenazine.
ThioridazineOxytocin may increase the QTc-prolonging activities of Thioridazine.
ToremifeneOxytocin may increase the QTc-prolonging activities of Toremifene.
VandetanibOxytocin may increase the QTc-prolonging activities of Vandetanib.
VemurafenibOxytocin may increase the QTc-prolonging activities of Vemurafenib.
ZiprasidoneOxytocin may increase the QTc-prolonging activities of Ziprasidone.
ZuclopenthixolOxytocin may increase the QTc-prolonging activities of Zuclopenthixol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Vasopressin receptor activity
Specific Function:
Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system.
Gene Name:
OXTR
Uniprot ID:
P30559
Molecular Weight:
42770.99 Da
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. doi: 10.1007/s00726-009-0470-1. Epub 2010 Jan 27. [PubMed:20108008 ]
  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. doi: 10.1021/jm901084f. [PubMed:20104850 ]
  3. Gimpl G, Reitz J, Brauer S, Trossen C: Oxytocin receptors: ligand binding, signalling and cholesterol dependence. Prog Brain Res. 2008;170:193-204. doi: 10.1016/S0079-6123(08)00417-2. [PubMed:18655883 ]
  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:15646817 ]
  5. Furman DJ, Chen MC, Gotlib IH: Variant in oxytocin receptor gene is associated with amygdala volume. Psychoneuroendocrinology. 2011 Jul;36(6):891-7. doi: 10.1016/j.psyneuen.2010.12.004. Epub 2011 Jan 3. [PubMed:21208749 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Not Available
Specific Function:
Neurophysin 1 specifically binds oxytocin.Oxytocin causes contraction of the smooth muscle of the uterus and of the mammary gland.
Gene Name:
OXT
Uniprot ID:
P01178
Molecular Weight:
12721.51 Da
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:17016423 ]
  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:6687626 ]
  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:1486803 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Serine-type peptidase activity
Specific Function:
Cleaves peptide bonds on the C-terminal side of prolyl residues within peptides that are up to approximately 30 amino acids long.
Gene Name:
PREP
Uniprot ID:
P48147
Molecular Weight:
80698.945 Da
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:11495689 ]
  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:3544718 ]
  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:6361010 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23