DrugBank: Oxytocin (DB00107)

targets (2) enzymes (1)

Identification

Name

Oxytocin

Accession Number

DB00107 (BIOD00016, BTD00016)

Type

biotech

Groups

approved

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 structure

Protein chemical formula

C₄₃H₆₆N₁₂O₁₂S₂

Protein average weight

1007.1870

Sequences

>DB00107 sequence
CYIQNCPLG

FASTA

Synonyms

Pitocin
Syntocinon

Brand names

Oxytocin (BAM Biotech)
Pitocin (Parke-Davis)
Syntocinon (Sandoz)

Brand name mixtures

Not Available

Categories

Anti-tocolytic Agents
Labor Induction Agents
Oxytocics

CAS number

50-56-6

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

To assist in labor, elective labor induction, uterine contraction induction

Pharmacodynamics

Used 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 action

Binds 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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

30%

Metabolism

hepatic oxytocinases

Route of elimination

Biliary and renal

Half life

1-6 min

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not 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

Form	Route	Strength
Solution	Intramuscular
Solution	Intravenous

Prices

Unit description	Cost	Unit
Oxytocin powder	1762.25 USD	g
Oxytocin 10 unit/ml vial	9.84 USD	vial
Pitocin 10 unit/ml vial	1.6 USD	ml
Oxytocin-lr 40 unit/500 ml	0.09 USD	ml
Oxytocin-d5w-lr 40 unit/500 ml	0.07 USD	ml
Oxytocin-d5lr 30 unit/500 ml	0.06 USD	ml
Oxytocin-lr 20 unit/500 ml	0.06 USD	ml
Oxytocin-d5w-lr 15 unit/500 ml	0.05 USD	ml
Oxytocin-d5w-lr 20 unit/500 ml	0.05 USD	ml
Oxytocin-lr 10 unit/500 ml	0.05 USD	ml
Oxytocin-d5-1/4ns 15 unit/250	0.04 USD	ml
Oxytocin-d5w 40 unit/1000 ml	0.04 USD	ml
Oxytocin-d5w-lr 10 unit/500 ml	0.04 USD	ml
Oxytocin-d5w 20 unit/1000 ml	0.03 USD	ml
Oxytocin-d5w 30 unit/1000 ml	0.03 USD	ml
Oxytocin-lr 30 unit/500 ml	0.03 USD	ml
Oxytocin-ns 30 unit/1000 ml	0.03 USD	ml
Oxytocin-d5w 10 unit/1000 ml	0.02 USD	ml
Oxytocin-lr 5 unit/500 ml	0.02 USD	ml
Oxytocin-ns 40 unit/1000 ml	0.02 USD	ml
Oxytocin-d5-1/2ns 10 unit/1000	0.01 USD	ml
Oxytocin-d5-1/2ns 20 unit/1000	0.01 USD	ml
Oxytocin-d5-1/2ns 30 unit/1000	0.01 USD	ml
Oxytocin-d5-ns 20 unit/1000 ml	0.01 USD	ml
Oxytocin-ns 10 unit/1000 ml	0.01 USD	ml
Oxytocin-ns 20 unit/1000 ml	0.01 USD	ml

Patents

Not Available

Properties

State

liquid

Melting point

Not Available

Experimental Properties

Property	Value	Source
hydrophobicity	-2.7	PhysProp
isoelectric point	5.51	Various sources

References

Synthesis Reference

Not Available

General Reference

Kosfeld M, Heinrichs M, Zak PJ, Fischbacher U, Fehr E: Oxytocin increases trust in humans. Nature. 2005 Jun 2;435(7042):673-6. Pubmed
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
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
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
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

Resource	Link
PharmGKB	PA450760
Drug Product Database	0
RxList	http://www.rxlist.com/cgi/generic3/oxytocin.htm
Drugs.com	http://www.drugs.com/cdi/oxytocin.html
Wikipedia	http://en.wikipedia.org/wiki/Oxytocin

ATC Codes

H01BB01
H01BB02

AHFS Codes

76:00.00

PDB Entries

1NPO

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Oxytocin receptor Pharmacological action: yes Actions: agonist Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol- calcium second messenger system Organism class: human UniProt ID: P30559 Gene: OXTR Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 Gimpl G, Reitz J, Brauer S, Trossen C: Oxytocin receptors: ligand binding, signalling and cholesterol dependence. Prog Brain Res. 2008;170:193-204. Pubmed 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 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 Pharmacological action: unknown Actions: binder Oxytocin causes contraction of the smooth muscle of the uterus and of the mammary gland Organism class: human UniProt ID: P01178 Gene: OXT Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 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

Targets

1. Oxytocin receptor

Pharmacological action: yes
Actions: agonist

Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol- calcium second messenger system

Organism class: human
UniProt ID: P30559 Link_out

Gene: OXTR Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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
Gimpl G, Reitz J, Brauer S, Trossen C: Oxytocin receptors: ligand binding, signalling and cholesterol dependence. Prog Brain Res. 2008;170:193-204. Pubmed
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
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

Pharmacological action: unknown
Actions: binder

Oxytocin causes contraction of the smooth muscle of the uterus and of the mammary gland

Organism class: human
UniProt ID: P01178 Link_out

Gene: OXT

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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
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 Actions: substrate Cleaves peptide bonds on the C-terminal side of prolyl residues within peptides that are up to approximately 30 amino acids long UniProt ID: P48147 Gene: PREP Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Bausback HH, Ward PE: Vascular, post proline cleaving enzyme: metabolism of vasoactive peptides. Adv Exp Med Biol. 1986;198 Pt A:397-404. Pubmed 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

Enzymes

1. Prolyl endopeptidase

Actions: substrate

Cleaves peptide bonds on the C-terminal side of prolyl residues within peptides that are up to approximately 30 amino acids long

UniProt ID: P48147 Link_out

Gene: PREP Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
Bausback HH, Ward PE: Vascular, post proline cleaving enzyme: metabolism of vasoactive peptides. Adv Exp Med Biol. 1986;198 Pt A:397-404. Pubmed
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

Comments

Drug created on June 13, 2005 07:24 / Updated on August 11, 2011 23:18

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.