Carbetocin

Carbetocin: Carbetocin

Systematic (IUPAC) name

(2S)-1-[(3S,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]-
9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-
[(4-hydroxyphenyl)methyl]-16-methyl-5,8,11,14,17-
pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-
3-carbonyl]-N-[(1S)-1-(carbamoylmethylcarbamoyl)-
3-methyl-butyl]pyrrolidine-2-carboxamide

Clinical data

AHFS/Drugs.com Micromedex Detailed Consumer Information

Pregnancy cat. ?

Legal status POM (UK) Not available (U.S.)

Routes Intravenous, intramuscular

Pharmacokinetic data

Bioavailability 80% (IM)

Half-life 40 minutes

Identifiers

CAS number 37025-55-1^Y

ATC code H01BB03

PubChem CID 71715

DrugBank DB01282

ChemSpider 64765^Y

UNII 88TWF8015Y^Y

KEGG D07229^N

Chemical data

Formula C₄₅H₆₉N₁₁O₁₂S

Mol. mass 988.162 g/mol

InChI

InChI=1S/C45H69N11O12S/c1-6-25(4)38-44(67)50-28(15-16-34(46)58)40(63)51-30(21-35(47)59)41(64)53-31(23-69-18-8-10-37(61)55(5)33(43(66)54-38)20-26-11-13-27(57)14-12-26)45(68)56-17-7-9-32(56)42(65)52-29(19-24(2)3)39(62)49-22-36(48)60/h11-14,24-25,28-33,38,57H,6-10,15-23H2,1-5H3,(H2,46,58)(H2,47,59)(H2,48,60)(H,49,62)(H,50,67)(H,51,63)(H,52,65)(H,53,64)(H,54,66)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1^Y
Key:SMMBGKXBHJTULT-DTRKZRJBSA-N^Y

N(what is this?) (verify)

Carbetocin (Duratocin) is an obstetric drug used to control postpartum hemorrhage, bleeding after giving birth.^[1] It is an analogue of oxytocin, and its action is similar to that of oxytocin, such as contraction of the uterus.^[2]^[3]

Carbetocin is available in Canada and the United Kingdom, but not in the United States.

See also

Demoxytocin

Oxytocin

WAY-267,464

References

^ "Carbetocin Versus Syntometrine for the Third Stage of Labour". http://clinicaltrials.gov/ct2/show/NCT00499005.

^ "Carbetocin (Systemic)". http://www.drugs.com/mmx/carbetocin.html.

^ "Carbetocin may be more potent than oxytocin following c-section>". http://www.thedoctorschannel.com/video/3333.html.

External links

Carbetocin - Drugs.com

v · d · eAnxiolytics (N05B)

GABA_A PAMs

Benzodiazepine

Adinazolam • Alprazolam • Bretazenil • Bromazepam • Camazepam • Chlordiazepoxide • Clobazam • Clonazepam • Clorazepate • Clotiazepam • Cloxazolam • Diazepam • Ethyl Loflazepate • Etizolam • Fludiazepam • Halazepam • Imidazenil • Ketazolam • Lorazepam • Medazepam • Nordazepam • Oxazepam • Pinazepam • Prazepam

Carbamates

Emylcamate • Mebutamate • Meprobamate (Carisoprodol, Tybamate) • Phenprobamate • Procymate

Nonbenzodiazepines

Abecarnil • Adipiplon • Alpidem • CGS-8216 • CGS-9896 • CGS-13767 • CGS-20625 • Divaplon • ELB-139 • Fasiplon • GBLD-345 • Gedocarnil • L-838,417 • NS-2664 • NS-2710 • Ocinaplon • Pagoclone • Panadiplon • Pipequaline • RWJ-51204 • SB-205,384 • SL-651,498 • Taniplon • TP-003 • TP-13 • TPA-023 • Y-23684 • ZK-93423

Pyrazolopyridines

Cartazolate • Etazolate • ICI-190,622 • Tracazolate

Others

Chlormezanone • Ethanol (Alcohol) • Etifoxine • Kavalactones (Kava Kava) • Skullcap • Valerenic Acid (Valerian)

α₂δ VDCC Blockers
Gabapentin • Pregabalin

5-HT_1A Agonists
Azapirones: Buspirone • Gepirone • Tandospirone; Others: Flesinoxan • Oxaflozane

H₁ Antagonists
Diphenylmethanes: Captodiame • Hydroxyzine; Others: Brompheniramine • Chlorpheniramine • Pheniramine

CRH₁ Antagonists
Antalarmin • CP-154,526 • Pexacerfont • Pivagabine

NK₂ Antagonists
GR-159,897 • Saredutant

MCH₁ antagonists
ATC-0175 • SNAP-94847

mGluR₂_/₃ Agonists
Eglumegad

mGluR5 NAMs
Fenobam

TSPO agonists
DAA-1097 • DAA-1106 • Emapunil • FGIN-127 • FGIN-143

σ₁ agonists
Afobazole • Opipramol

Others
Benzoctamine • Carbetocin • Demoxytocin • Mephenoxalone • Mepiprazole • Oxanamide • Oxytocin • Promoxolane • Tofisopam • Trimetozine • WAY-267,464

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc(eval/thrp), drug(N5A/5B/5C/6A/6B/6D)

v · d · eHypothalamic-pituitary hormones and analogues (H01)

Hypothalamic

GNRH

Agonists: Gonadorelin • Nafarelin • Histrelin
Antagonists: Cetrorelix • Ganirelix

Somatostatin

Agonists: Lanreotide • Octreotide

Anterior pituitary

ACTH

Agonists: Corticotropin • Cosyntropin • Tetracosactide

GH

Agonists: IGF-1 (Mecasermin/Mecasermin rinfabate) • Sermorelin • Somatrem
Antagonists: Pegvisomant

TSH

Agonists: Thyrotropin

Posterior pituitary

Oxytocin

Agonists: Carbetocin • Demoxytocin
Antagonists: Atosiban

Vasopressin

Agonists: Argipressin • Desmopressin • Felypressin • Lypressin • Ornipressin • Terlipressin
Antagonists: Conivaptan • Demeclocycline • Lixivaptan • Mozavaptan • Nelivaptan • Relcovaptan • Satavaptan • Tolvaptan

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

v · d · eUterotonics/labor inducers/oxytocics (G02A)

Cervical ripening

Ergot alkaloids

Ergometrine^# (+oxytocin) • Methylergometrine

Prostaglandins and
analogues

E: Misoprostol/E1^# • Gemeprost/E1 • Dinoprostone/E2 • Sulprostone/E2
F: Dinoprost/F2α • Carboprost/F2α

Contraction induction
Oxytocin^# • Carbetocin • Demoxytocin • WAY-267,464

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: OBS

phys/devp/memb

mthr/fetu/infc, epon

proc, drug(2A/G2C)

v · d · eNeuropeptidergics

Cholecystokinin

CCK_A

Agonists: Cholecystokinin • CCK-4
Antagonists: Asperlicin • Proglumide • Lorglumide • Devazepide • Dexloxiglumide

CCK_B

Agonists: Cholecystokinin • CCK-4 • Gastrin
Antagonists: Proglumide • CI-988

CRH

CRF₁

Agonists: Corticotropin releasing hormone
Antagonists: Antalarmin • CP-154,526 • Pexacerfont

CRF₂

Agonists: Corticotropin releasing hormone

Galanin

GAL₁

Agonists: Galanin • Galanin-like peptide • Galmic • Galnon

GAL₂

Agonists: Galanin • Galanin-like peptide • Galmic • Galnon

GAL₃

Agonists: Galanin • Galmic • Galnon

Ghrelin
Agonists: Ghrelin • Capromorelin • MK-677 • Sermorelin • SM-130,686 • Tabimorelin

MCH

MCH₁

Agonists: Melanin concentrating hormone
Antagonists: ATC-0175 • GW-803,430 • NGD-4715 • SNAP-7941 • SNAP-94847

MCH₂

Agonists: Melanin concentrating hormone

Melanocortin

MC₁

Agonists: alpha-MSH • Afamelanotide • Bremelanotide • Melanotan II
Antagonists: Agouti signalling peptide

MC₂

Agonists: ACTH • Cosyntropin • Tetracosactide

MC₃

Agonists: alpha-MSH • Bremelanotide • Melanotan II

MC₄

Agonists: alpha-MSH • Bremelanotide • Melanotan II • THIQ
Antagonists: Agouti-related peptide

MC₅

Agonists: alpha-MSH • Melanotan II

Neuropeptide S
Agonists: Neuropeptide S
Antagonists: SHA-68

Neuropeptide Y

Y₁

Agonists: Neuropeptide Y • Peptide YY
Antagonists: BIBP-3226

Y₂

Agonists: Neuropeptide Y • Peptide YY
Antagonists: BIIE-0246

Y₄

Agonists: Neuropeptide Y • Pancreatic polypeptide • Peptide YY
Antagonists: UR-AK49

Y₅

Agonists: Neuropeptide Y • Peptide YY
Antagonists: Lu AA-33810

Neurotensin

NTS₁

Agonists: Neurotensin • Neuromedin N
Antagonists: SR-48692 • SR-142,948

NTS₂

Agonists: Neurotensin
Antagonists: Levocabastine • SR-142,948

Opioid
see Template:Opioids

Orexin

OX₁

Agonists: Orexin-A
Antagonists: Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant

OX₂

Agonists: Orexin-A
Antagonists: Almorexant • SB-649,868 • Suvorexant • TCS-OX2-29

Oxytocin
Agonists: Carbetocin • Demoxytocin • Oxytocin • WAY-267,464
Antagonists: Atosiban • Epelsiban • L-371,257 • L-368,899

Tachykinin

NK₁

Agonists: Substance P
Antagonists: Aprepitant • Befetupitant • Casopitant • CI-1021 • CP-96,345 • CP-99,994 • CP-122,721 • Dapitant • Ezlopitant • FK-888 • Fosaprepitant • GR-203,040 • GW-597,599 • HSP-117 • L-733,060 • L-741,671 • L-743,310 • L-758,298 • Lanepitant • LY-306,740 • Maropitant • Netupitant • NKP-608 • Nolpitantium • Orvepitant • RP-67,580 • SDZ NKT 343 • Vestipitant • Vofopitant

NK₂

Agonists: Neurokinin A
Antagonists: GR-159,897 • Ibodutant • Saredutant

NK₃

Agonists: Neurokinin B
Antagonists: Osanetant • Talnetant

Vasopressin

V_1A

Agonists: Desmopressin • Felypressin • Ornipressin • Terlipressin • Vasopressin
Antagonists: Conivaptan • Demeclocycline • Relcovaptan

V_1B

Agonists: Felypressin • Ornipressin • Terlipressin • Vasopressin
Antagonists: Demeclocycline • Nelivaptan

V₂

Agonists: Desmopressin • Ornipressin • Vasopressin
Antagonists: Conivaptan • Demeclocycline • Lixivaptan • Mozavaptan • Satavaptan • Tolvaptan

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Academic Dictionaries and Encyclopedias

Carbetocin

See also

References

External links

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Systematic (IUPAC) name
(2S)-1-[(3S,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]- 9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15- [(4-hydroxyphenyl)methyl]-16-methyl-5,8,11,14,17- pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane- 3-carbonyl]-N-[(1S)-1-(carbamoylmethylcarbamoyl)- 3-methyl-butyl]pyrrolidine-2-carboxamide
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	?
Legal status	POM (UK) Not available (U.S.)
Routes	Intravenous, intramuscular
Pharmacokinetic data
Bioavailability	80% (IM)
Half-life	40 minutes
Identifiers
CAS number	37025-55-1^Y
ATC code	H01BB03
PubChem	CID 71715
DrugBank	DB01282
ChemSpider	64765^Y
UNII	88TWF8015Y^Y
KEGG	D07229^N
Chemical data
Formula	C₄₅H₆₉N₁₁O₁₂S
Mol. mass	988.162 g/mol
InChI InChI=1S/C45H69N11O12S/c1-6-25(4)38-44(67)50-28(15-16-34(46)58)40(63)51-30(21-35(47)59)41(64)53-31(23-69-18-8-10-37(61)55(5)33(43(66)54-38)20-26-11-13-27(57)14-12-26)45(68)56-17-7-9-32(56)42(65)52-29(19-24(2)3)39(62)49-22-36(48)60/h11-14,24-25,28-33,38,57H,6-10,15-23H2,1-5H3,(H2,46,58)(H2,47,59)(H2,48,60)(H,49,62)(H,50,67)(H,51,63)(H,52,65)(H,53,64)(H,54,66)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1^Y Key:SMMBGKXBHJTULT-DTRKZRJBSA-N^Y
N(what is this?) (verify)

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Wikipedia

Carbetocin

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References

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