Carbetocin

Carbetocin

Carbetocin is a long-acting synthetic agonist analogue of human oxytocin, with antihemorrhagic and uterotonic activities. Upon administration, carbetocin targets, binds to and activates peripheral oxytocin receptors that are present on the smooth musculature of the uterus. This causes uterus contractions and prevents excessive bleeding after childbirth, particularly following Cesarean section, and may be used to decrease blood loss during hysteroscopic myomectomy.

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CAT No: R1961

CAS No: 37025-55-1

Synonyms/Alias: Carbetocin;37025-55-1;Pabal;Carbetocino;Carbetocinum;carbetocine;Carbetocina;CHEBI:59204;Carbetocinum [INN-Latin];Carbetocino [INN-Spanish];Duratocin (TN);LV-101;deamino-2-O-methyltyrosine-1-carbaoxytocin;88TWF8015Y;CARBETOCIN [MI];1-butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin;CARBETOCIN [INN];1-Butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocin;CARBETOCIN [USAN];CARBETOCIN [MART.];CARBETOCIN [WHO-DD];Carbetocin [USAN:INN:BAN];UNII-88TWF8015Y;FE 992097;FE-992097;DTXSID90897527;EINECS 253-312-6;1-Carbaoxytocin, 1-butanoic acid-2-(O-methyl-L-tyrosine)-;Carbetocinum (INN-Latin);Carbetocino (INN-Spanish);CARBETOCIN (MART.);(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide;1-Buttersaeure-2-(3-(4-methoxyphenyl)-L-alanin)oxytocin;1-Carboxytocin, 1-butanoic acid-2-(O-methyl-L-tyrosine)-;dcomot;(2S)-2-{[(2S)-1-{[(3R,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl]carbonyl}pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide;1-{[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-(4-methoxybenzyl)-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl]carbonyl}-L-prolyl-L-leucylglycinamide;GLYCINAMIDE, N-(4-MERCAPTO-1-OXOBUTYL)-O-METHYL-L-TYROSYL-L-ISOLEUCYL-L-GLUTAMINYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-LEUCYL-, CYCLIC (1->5)-THIOETHER;O-METHYL-N-(4-SULFANYLBUTANOYL)-L-TYROSYL-L-ISOLEUCYL-L-GLUTAMINYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-LEUCYL-GLYCINAMIDE CYCLIC (1->5)-THIOETHER;Carbetocin?;C45H69N11O12S;(2S)-2-(((2S)-1-(((3R,6S,9S,12S,15S)-12-((2S)-butan-2-yl)-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-((4-methoxyphenyl)methyl)-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl)carbonyl)pyrrolidin-2-yl)formamido)-N-(carbamoylmethyl)-4-methylpentanamide;(2S)-N-((2S)-1-((2-amino-2-oxoethyl)amino)-4-methyl-1-oxopentan-2-yl)-1-((3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-((2S)-butan-2-yl)-15-((4-methoxyphenyl)methyl)-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl)pyrrolidine-2-carboxamide;1-(((3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-((2S)-butan-2-yl)-15-(4-methoxybenzyl)-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl)carbonyl)-L-prolyl-L-leucylglycinamide;MFCD01076600;Duratocin long acting;Carbetocin (Standard);1-deamino-1-monocarba-2-(Tyr(OMe))-oxytocin;SCHEMBL39224;Carbetocin (USAN/INN/BAN);oxytocin, 1-desamino-1-monocarba-(Tyr(OMe))(2)-;CHEMBL3301668;GTPL11169;H01BB03;NSTRIRCPWQHTIA-DTRKZRJBSA-N;DTXCID901326882;oxytocin, 1-desamino-1-monocarba-(tyrosine(O-methyl))(2)-;WHO 5014;BDBM50044677;HY-17573R;AKOS015994647;DB01282;FB19694;HS-2007;NCGC00485451-02;HY-17573;NS00056256;D07229;Carbetocin 100 microg/mL in Acetonitrile:Methanol;Q5037853;1-Deamino-1-monocarba-(0-2-methyltyrosine)-oxytocin;BRD-K56107812-001-01-7;1-Butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin;Deamino-2-O-methyltyrosine-1-carbaoxytocin;Depotocin;Carbetocin;253-312-6;

Chemical Name: (2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide

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M.F/Formula	C45H69N11O12S
M.W/Mr.	988.2
Sequence	[But1-Cys6] But-Tyr(Me)-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2
Appearance	Solid powder
Activity	Agonist
Biological Activity	Carbetocin, an oxytocin (OT) analogue, is an oxytocin receptor agonist with a Ki of 7.1 nM. Carbetocin has high affinity to chimeric N-terminus (E1) of the oxytocin receptor (Ki=1.17 μM). Carbetocin has the potential for postpartum hemorrhage research. Carbetocin can crosse the blood-brain barrier and produces antidepressant-like activity via activation of oxytocin receptors in the CNS.
Target	Oxytocin Receptor

InChI	InChI=1S/C45H69N11O12S/c1-6-25(4)38-44(66)51-28(15-16-34(46)57)40(62)52-31(21-35(47)58)41(63)54-32(23-69-18-8-10-37(60)50-30(42(64)55-38)20-26-11-13-27(68-5)14-12-26)45(67)56-17-7-9-33(56)43(65)53-29(19-24(2)3)39(61)49-22-36(48)59/h11-14,24-25,28-33,38H,6-10,15-23H2,1-5H3,(H2,46,57)(H2,47,58)(H2,48,59)(H,49,61)(H,50,60)(H,51,66)(H,52,62)(H,53,65)(H,54,63)(H,55,64)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1
InChI Key	NSTRIRCPWQHTIA-DTRKZRJBSA-N
Canonical SMILES	CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSCCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OC)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](CSCCCC(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

1. Exosomes-mediated Transfer of miR-125a/b in Cell-to-cell Communication: A Novel Mechanism of Genetic Exchange in the Intestinal Microenvironment

2. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line

3. Effect of Probiotic Lactobacillus plantarum on Streptococcus mutans and Candida albicans Clinical Isolates from Children with Early Childhood Caries

4. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum

5. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes

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