Oxytocin and Analogs

OXYTOCIN 20 USP UNITS IN DEXTROSE 5%

Also known as: 50-56-6, Pitocin, Endopituitrina, Ocytocin, Syntocinon, Orasthin

Chemistry

Molecular Formula

C43H66N12O12S2

Molecular Weight

1007.2 g/mol

InChI Key

XNOPRXBHLZRZKH-DSZYJQQASA-N

A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.

Identification

Computed Descriptors

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-pentaoxo-1,2-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

InChI

InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1

InChI Key

XNOPRXBHLZRZKH-DSZYJQQASA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

Isomeric SMILES

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

Synonyms

MeSH Synonyms

• Ocytocin
• Pitocin
• Syntocinon

Depositor-Supplied Synonyms

• 50-56-6
• Pitocin
• Endopituitrina
• Ocytocin
• Syntocinon
• Orasthin
• Oxytocinum
• Oxitocina
• Oxytocine
• (1-hemicystine)oxytocin
• Piton S
• Alpha-hypophamine
• 3-isoleucine-8-leucine Vasopressin
• Oxytocic Hormone
• Chebi:7872
• Chembl395429
• (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-pentaoxo-1,2-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
• Oxystin
• Partocon
• Synthetic Oxytocin
• Oxt
• Ocytocinum
• Ossitocina
• Syntocinone
• Oxetakain
• Oxoject
• Oxtocin
• Presoxin
• Synpitan
• Syntocin
• Utedrin
• Uteracon
• Di-sipidin
• Nobitocin S
• Atonin O
• Oxytocin (syntocinon)
• [3h]oxytocin
• Oxetakain [czech]
• 1-({(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-(4-hydroxybenzyl)-13-[(1s)-1-methylpropyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-l-prolyl-l-leucylglycinamide
• L-cysteinyl-l-tyrosyl-l-isoleucyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-leucylglycinamide Cyclic(1-6)-disulfide
• Ossitocina [dcit]
• Oxytocin 5 Usp Units In Dextrose 5%
• Oxytocin 10 Usp Units In Dextrose 5%
• Oxytocin 20 Usp Units In Dextrose 5%
• Oxytocine [inn-french]
• Oxytocinum [inn-latin]
• Oxitocina [inn-spanish]
• Posterior Pituitary Extract
• Unii-1jqs135eyn
• A-hypophamine
• Intertocine S
• [3h]ot (human, Mouse, Rat)
• Hsdb 2182
• Oxytocin [usp:inn:ban:jan]
• Syntocinon (tn)
• Oxytocin (tn)
• Oxytocin,(s)
• (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
• Einecs 200-048-4
• Pitocin (tn)
• Mfcd00076731
• Brn 3586108
• Vasopressin, 3-l-isoleucine-8-l-leucine-
• 1jqs135eyn
• Schembl29048
• Oxytocin (jp17/usp/inn)
• Gtpl2174
• Gtpl2176
• Dtxsid8048361
• Bcbcmap01_000094
• Tnx1900
• Tta-121
• Amy25364
• Cys-tyr-ile-gln-asn-cys-pro-leu-gly-nh2, Cyclic 1-6 Disulfide
• Tnx-1900
• Bdbm50205990
• Ti-001
• Akos015994657
• Hs-2021
• Ncgc00167132-01
• Ac-28730
• L-cysteinyl-l-tyrosyl-l-isoleucyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-leucylglycinamide Cyclic (1-6)-disulfide
• C00746
• D00089
• 076o731
• A828179
• Q169960
• Sr-01000945111
• Sr-01000945111-1
• W-105951
• Oxytocin, European Pharmacopoeia (ep) Reference Standard
• Oxytocin, United States Pharmacopeia (usp) Reference Standard
• Oxytocin-(leucine-5,5,5-d3, Glycine-2,2-d2) Trifluoroacetate Salt
• Oxytocin, Lyophilized Powder, ~15 Iu/mg Solid (prepared From Synthetic Oxytocin)
• 1-[19-amino-7-(2-amino-2-oxo-ethyl)-10-(3-amino-3-oxo-propyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-sec-butyl-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[1-[(2-amino-1-methyl-2-oxo-ethyl)carbamoyl]-3-methyl-butyl]pyrrolidine
• L-cysteinyl-l-tyrosyl-l-isoleucyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-leucylglycinamide Cyclic (1-->6)-disulfide
• Otx

Create Date

2005-06-24

Chemical and Physical Properties

Drug and Medication Information

Drug Information

Therapeutic Uses

Oxytocin is indicated for the medical rather than the elective induction of labor. Available data and information are inadequate to define the benefits-to-risks considerations in the use of the drug product for elective induction. Elective induction of labor is defined as the initiation of labor for convenience in an individual with a term pregnancy who is free of medical indications. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Oxytocin injection (June 2009). Available from, as of February 10, 2010: https://www.frankenthalerfoundation.org

Oxytocin is indicated for the initiation or improvement of uterine contractions, where this is desirable and considered suitable for reasons of fetal or maternal concern, in order to achieve early vaginal delivery. It is indicated for induction of labor in patients with a medical indication for the initiation of labor, such as Rh problems, maternal diabetes, preeclampsia at or near term, when delivery is in the best interests of mother and fetus or when membranes are prematurely ruptured and delivery is indicated... /Included in US product label/

US Natl Inst Health; Daily