Identification

Name
Oxytocin
Accession Number
DB00107
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.

Type
Biotech
Groups
Approved, Vet approved
Biologic Classification
Protein Based Therapies
Hormones
Protein Structure
Db00107
Protein Chemical Formula
C43H66N12O12S2
Protein Average Weight
1007.187 Da
Sequences
>DB00107 sequence
CYIQNCPLG
Download FASTA Format
Synonyms
  • Oxitocina
  • Oxytocin

Pharmacology

Indication

Used 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.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Indirectly 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 action

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 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.

TargetActionsOrganism
AOxytocin receptor
agonist
Humans
UOxytocin-neurophysin 1
binder
Humans
Absorption

Uterine 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 binding

30%

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 elimination

Biliary and renal (excreted unchanged in the urine)

Half-life

1-6 min, this is decreased in late pregnancy and during lactation.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Oxytocin 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Acebutolol.
AcrivastineThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Ajmaline.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Alfuzosin.
AlimemazineThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Alimemazine.
AmantadineThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amantadine.
AmifampridineThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amifampridine.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amiodarone.
AmisulprideThe risk or severity of QTc prolongation can be increased when Oxytocin is combined with Amisulpride.
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

Products

Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OxytocinInjection, solution30 [USP'U]/500mLIntravenousCantrell Drug Company2011-10-20Not applicableUS flag
OxytocinInjection, solution30 [USP'U]/500mLIntravenousCantrell Drug Company2011-10-20Not applicableUS flag
OxytocinInjection, solution20 [USP'U]/1000mLIntravenousCantrell Drug Company2011-10-202017-12-06US flag
OxytocinInjection, solution10 [USP'U]/1mLIntramuscular; IntravenousFresenius Kabi USA, LLC2000-08-10Not applicableUS flag
OxytocinInjection, solution10 [USP'U]/500mLIntravenousCantrell Drug Company2011-10-202012-11-09US flag
OxytocinInjection, solution30 [USP'U]/1000mLIntravenousCantrell Drug Company2016-03-18Not applicableUS flag
OxytocinInjection10 [USP'U]/1mLIntramuscular; IntravenousHikma Pharmaceuticals USA Inc.1980-04-29Not applicableUS flag
OxytocinInjection10 [USP'U]/1mLIntramuscular; IntravenousBaxter Laboratories1990-09-302013-02-27US flag
OxytocinInjection, solution2 [USP'U]/100mLIntravenousCantrell Drug Company2011-10-20Not applicableUS flag
OxytocinInjection, solution10 [USP'U]/1mLIntramuscular; IntravenousCardinal Health2000-08-10Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OxytocinInjection10 [USP'U]/1mLIntravenousTeva Parenteral Medicines, Inc.2008-01-242011-04-30US flag
OxytocinInjection10 [USP'U]/1mLIntramuscular; IntravenousWest-Ward Pharmaceuticals Corp2013-02-13Not applicableUS flag
OxytocinInjection10 [USP'U]/1mLIntramuscular; IntravenousWest-Ward Pharmaceuticals Corp2013-02-13Not applicableUS flag
OxytocinInjection10 [iU]/1mLIntravenousPar Pharmaceutical2012-06-012015-07-13US flag
OxytocinInjection10 [USP'U]/1mLIntramuscular; IntravenousHikma Farmaceutica2009-08-012014-10-01US flag
OxytocinInjection, solution10 [USP'U]/1mLIntramuscular; IntravenousSagent Pharmaceuticals2018-04-012018-07-19US flag
OxytocinInjection100 [USP'U]/10mLIntravenousTeva Parenteral Medicines, Inc.2008-01-242011-02-28US flag
OxytocinInjection10 [iU]/1mLIntravenousPar Pharmaceutical2012-06-012015-04-30US flag
OxytocinInjection100 [USP'U]/10mLIntramuscular; IntravascularHikma Farmaceutica2009-08-012014-10-01US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bakumokon 5% MinoxidilOxytocin (0.01 mg/100mg) + Dutasteride (0.1 mg/100mg) + Minoxidil (5 mg/100mg)LiquidTopicalDS LABORATORIES, INC.2015-02-092017-10-19US flag
Bakumokon 7% Minoxidil SulfateOxytocin (0.01 mg/100mg) + Dutasteride (0.1 mg/100mg) + Minoxidil sulfate (7 mg/100mg)LiquidTopicalDS LABORATORIES, INC.2015-02-092017-10-11US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
OxytocinOxytocin (10 [USP'U]/500mL)Injection, solutionIntravenousCantrell Drug Company2011-10-202012-11-12US flag
OxytocinOxytocin (20 [USP'U]/1000mL)Injection, solutionIntravenousCantrell Drug Company2011-10-202015-01-14US flag
OxytocinOxytocin (30 [USP'U]/500mL)Injection, solutionIntravenousCantrell Drug Company2011-07-01Not applicableUS flag
OxytocinOxytocin (30 [USP'U]/500mL)Injection, solutionIntravenousCantrell Drug Company2011-10-20Not applicableUS flag
OxytocinOxytocin (10 [USP'U]/1000mL)Injection, solutionIntravenousCantrell Drug Company2012-07-30Not applicableUS flag
OxytocinOxytocin (20 [USP'U]/500mL)Injection, solutionIntravenousCantrell Drug Company2016-03-18Not applicableUS flag
OxytocinOxytocin (30 [USP'U]/500mL)Injection, solutionIntravenousCantrell Drug Company2011-10-20Not applicableUS flag
OxytocinOxytocin (2 [USP'U]/100mL)Injection, solutionIntravenousCantrell Drug Company2011-10-20Not applicableUS flag
OxytocinOxytocin (10 [USP'U]/500mL)Injection, solutionIntravenousCantrell Drug Company2011-10-202012-11-09US flag
OxytocinOxytocin (30 [USP'U]/1000mL)Injection, solutionIntravenousCantrell Drug Company2016-03-18Not applicableUS flag

Categories

ATC Codes
G02AC01 — Methylergometrine and oxytocinH01BB02 — Oxytocin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
Not Available
Kingdom
Organic Compounds
Super Class
Organic Acids
Class
Carboxylic Acids and Derivatives
Sub Class
Amino Acids, Peptides, and Analogues
Direct Parent
Peptides
Alternative Parents
Not Available
Substituents
Not Available
Molecular Framework
Not Available
External Descriptors
Not Available

Chemical Identifiers

UNII
1JQS135EYN
CAS number
50-56-6

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]
KEGG Drug
D00089
KEGG Compound
C00746
PubChem Substance
46506775
RxNav
7824
ChEMBL
CHEMBL395429
Therapeutic Targets Database
DAP001156
PharmGKB
PA450760
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxytocin
AHFS Codes
  • 76:00.00 — Oxytocics

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingDiagnosticHyperbilirubinemia in neonates1
4Active Not RecruitingTreatmentHealthy Volunteers1
4CompletedNot AvailableAnxiety Disorders / Post Traumatic Stress Disorder (PTSD) / Reconsolidation1
4CompletedBasic ScienceHealth1
4CompletedBasic ScienceNicotine Dependence / Tobacco Smoking Behavior1
4CompletedBasic SciencePain, Chronic2
4CompletedBasic ScienceSocial Behavior1
4CompletedOtherBMI >30 kg/m2 / Induction of Labour / Oxytocin1
4CompletedPreventionAdverse Reaction to Oxytocin1
4CompletedPreventionBlood Loss / Postpartum Haemorrhage (PPH)1

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
  • APP Pharmaceuticals
  • BAM Biotech
  • Baxter International Inc.
  • Bimeda Inc.
  • Cardinal Health
  • Central Admixture Pharmacy Services
  • Gallipot
  • Gland Pharma Ltd.
  • Hikma Pharmaceuticals
  • JHP Pharmaceuticals LLC
  • Monarch Pharmacy
  • MWI Veterinary Supply Co.
  • Osburn Drug Co.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmakon
  • Pharmedium
  • Teva Pharmaceutical Industries Ltd.
  • Vedco Inc.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
LiquidTopical
Injection, solutionIntramuscular; Intravenous5 iu/ml
SolutionIntravenous10 IU
SolutionIntramuscular; Intravenous10 IU
Injection
InjectionIntramuscular; Intravascular100 [USP'U]/10mL
InjectionIntravenous10 [USP'U]/1mL
InjectionIntravenous10 [iU]/1mL
InjectionIntravenous100 [USP'U]/10mL
Injection, solutionIntramuscular; Intravenous10 [USP'U]/1mL
Injection, solutionIntravenous10 [USP'U]/1000mL
Injection, solutionIntravenous10 [USP'U]/500mL
Injection, solutionIntravenous2 [USP'U]/100mL
Injection, solutionIntravenous20 [USP'U]/500mL
Injection, solutionIntravenous20 [USP'U]/1000mL
Injection, solutionIntravenous30 [USP'U]/1000mL
Injection, solutionIntravenous30 [USP'U]/500mL
LiquidIntramuscular; Intravenous
SolutionIntramuscular; Intravenous
InjectionIntramuscular; Intravenous10 [USP'U]/1mL
InjectionIntravenous10
Injection, solutionIntramuscular; Intravenous5 i.u./ml
Injection, solutionIntramuscular; Intravenous10 [iU]/1mL
Injection, solutionParenteral5 U.I./ML
SolutionIntramuscular; Intravenous5 IU
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.
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
hydrophobicity-2.7Not Available
isoelectric point5.51Not Available

Targets

Details
1. Oxytocin receptor
Kind
Protein
Organism
Humans
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
Uniprot Name
Oxytocin receptor
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
Humans
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
Uniprot Name
Oxytocin-neurophysin 1
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
Humans
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
Uniprot Name
Prolyl endopeptidase
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]

Drug created on June 13, 2005 07:24 / Updated on September 17, 2020 23:29

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