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/FormulaC45H69N11O12S
M.W/Mr.988.2
Sequence[But1-Cys6] But-Tyr(Me)-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2
AppearanceSolid powder
ActivityAgonist
Biological ActivityCarbetocin, 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.
TargetOxytocin Receptor
InChIInChI=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 KeyNSTRIRCPWQHTIA-DTRKZRJBSA-N
Canonical SMILESCCC(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 SMILESCC[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
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