Demoxytocin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| IUPAC_name = 2-[(1-{[13-(butan-2-yl)-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}pyrrolidin-2-yl)formamido]-N-(carbamoylmethyl)-4-methylpentanamide

| image = Demoxytocin.svg

| width =

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

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| legal_US =

| legal_status = Rx-only

| routes_of_administration = Buccal

| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 113-78-0

| CAS_supplemental =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2N9HM3X95F

| ATC_prefix = H01

| ATC_suffix = BB01

| PubChem = 449224

| DrugBank_Ref =

| DrugBank =

| ChEBI = 135900

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 395815

| C=43 | H=65 | N=11 | O=12 | S=2

| smiles = CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@H](C(=O)N1)Cc2ccc(cc2)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C43H65N11O12S2/c1-5-23(4)36-42(65)49-26(12-13-32(44)56)38(61)50-29(19-33(45)57)39(62)52-30(21-68-67-16-14-35(59)48-28(40(63)53-36)18-24-8-10-25(55)11-9-24)43(66)54-15-6-7-31(54)41(64)51-27(17-22(2)3)37(60)47-20-34(46)58/h8-11,22-23,26-31,36,55H,5-7,12-21H2,1-4H3,(H2,44,56)(H2,45,57)(H2,46,58)(H,47,60)(H,48,59)(H,49,65)(H,50,61)(H,51,64)(H,52,62)(H,53,63)/t23-,26-,27-,28-,29-,30-,31-,36-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GTYWGUNQAMYZPF-QPLNMOKZSA-N

| synonyms = ODA-914;
1-mercaptopropionate-
oxytoxin

}}

Demoxytocin (INN) (brand names Sandopart, Odeax, Sandopral), also known as desaminooxytocin or deaminooxytocin, as well as 1-(3-mercaptopropanoic acid)oxytocin ([Mpa¹]OT), is an oxytocic peptide drug that is used to induce labor, promote lactation, and to prevent and treat puerperal (postpartum) mastitis (breast inflammation).{{cite journal | vauthors = Sternadel Z, Gerkowicz J | title = [Use of deaminooxytocin (Sandopart) in the prevention and treatment of puerperal mastitis] | language = pl | journal = Ginekologia Polska | volume = 50 | issue = 5 | pages = 413–416 | date = May 1979 | pmid = 468056 }} Demoxytocin is a synthetic analogue of oxytocin and has similar activities,{{cite book| vauthors = van Boxtel CJ | chapter = Hormones and Hormone Antagonists | veditors = van Boxtel CJ, Santoso B, Edwards IR |title=Drug Benefits and Risks: International Textbook of Clinical Pharmacology | edition = 2nd | chapter-url = https://books.google.com/books?id=idbvAgAAQBAJ&pg=PA389|date=6 August 2008|publisher=IOS Press|isbn=978-1-60750-345-3|pages=389–}} but is more potent and has a longer half-life in comparison. Unlike oxytocin, which is given via intravenous injection, demoxytocin is administered as a buccal tablet formulation.{{cite book| vauthors = Thiery M | chapter = Stimulation of uterine activity | veditors = Eskes TK, Finster M |title=Drug Therapy During Pregnancy | chapter-url = https://books.google.com/books?id=SAMlBQAAQBAJ&pg=PA185 |date=22 October 2013|publisher=Elsevier|isbn=978-1-4831-6298-0|pages=185–}}

The drug was first synthesized in 1960 and was introduced into clinical practice in 1971 by Sandoz.{{cite book| vauthors = Gross E, Meienhofer J | chapter = The Peptide Bond| veditors = Gross E, Meienhofer J |title=Major Methods of Peptide Bond Formation: The Peptides Analysis, Synthesis, Biology| chapter-url=https://books.google.com/books?id=vz2aBQAAQBAJ&pg=PA53|date=10 May 2014|publisher=Elsevier|isbn=978-1-4832-1796-3|pages=53–}} It is marketed in several European countries, including Italy, Czech Republic, and Poland.{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA301|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=301–}}{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA349|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=349–}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA93|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=93–}} It has the amino acid sequence Mpa-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH₂ (Mpa = β-mercaptopropionic acid),{{cite book| vauthors = Bladon C | chapter = Modifications of Endogenous Peptides and Proteins |title=Pharmaceutical Chemistry: Therapeutic Aspects of Biomacromolecules | chapter-url = https://books.google.com/books?id=y3JTZtHExicC&pg=PA61|date=3 April 2002|publisher=John Wiley & Sons|isbn=978-0-471-49637-3|pages=61–}} and is an analogue of oxytocin wherein the leading cysteine is replaced with β-mercaptopropionic acid.