Drug/Small Molecule:
oxytocin

Overview

Generic Names: Pitocin; Syntocinon
IUPAC Name: (2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
Trade Names: Oxytocin (BAM Biotech); Pitocin (Parke-Davis); Syntocinon (Sandoz)
PharmGKB Accession Id: PA450760

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.

Indication

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

ATC Therapeutic Category

  • H01BB:Oxytocin and analogues

Pharmacology and Interactions

Mechanism Of Action

Binds the oxytocin receptor which leads to an increase in intracellular calcium levels.

Pharmacology

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.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Protein Binding

30%

Half Life

1-6 min

Chemical Properties

Chemical Formula:

C43H66N12O12S2

SMILES Code:

CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)O)
N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

1007.187 / 1006.4365

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00107
KEGG Compound ID:
C00746
KEGG Drug ID:
D00089
PubChem Compound ID:
439302
PubChem Substance ID:
4008

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
©2001-2010 PharmGKB.