(2S)-2-{[(2S)-1-[(3R,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-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide

• ChemBase ID: 1140
• Molecular Formular: C45H69N11O12S
• Molecular Mass: 988.16086
• Monoisotopic Mass: 987.4847877
• SMILES: S1C[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N(C(=O)CCC1)C)Cc1ccc(O)cc1)[C@H](CC)C)CCC(=O)N)CC(=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N
• Canonical SMILES: CC[C@@H]([C@@H]1NC(=O)[C@H](Cc2ccc(cc2)O)N(C)C(=O)CCCSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CC(C)C)C
• 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
• InChIKey: SMMBGKXBHJTULT-DTRKZRJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(3R,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-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(3R,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-pentaazacycloicosane-3-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide; carbetocin
• Brand Name: Duratocin; Duratocin, Pabal, Lonactene
• Synonyms: Carbetocinum [inn-latin]; Carbetocino [inn-spanish]; Carbetocin

Database IDs

• CAS Number: 37025-55-1
• PubChem SID: 160964603
• PubChem CID: 71715
• ATC CODE: H01BB03
• Chemspider ID: 64765
• DrugBank ID: DB01282
• KEGG ID: D07229
• Unique Ingredient Identifier: 88TWF8015Y
• Wikipedia Title: Carbetocin

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.499266
• H Acceptors: 12
• H Donor: 10
• LogD (pH = 5.5): -3.506033
• LogD (pH = 7.4): -3.5094075
• Log P: -3.5059896
• Molar Refractivity: 250.5991 cm^3
• Polarizability: 97.95759 Å^3
• Polar Surface Area: 364.72 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.29
• LOG S: -4.32
• Solubility (Water): 4.69e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2

Pharmacology Properties

• Admin Routes: Intravenous, intramuscular
• Bioavailability: 80% (IM)
• Half Life: 40 minutes
• Legal Status: Not available (U.S.); POM (UK)

DETAILS

DrugBank - DB01282

• Drug Groups: approved
• Description: Carbetocin is a drug used to control postpartum hemorrhage, bleeding after giving birth. It is an analogue of oxytocin, and its action is similar to that of oxytocin -- it causes contraction of the uterus.
• Indication: Used to control postpartum hemorrhage and bleeding after giving birth.
• Pharmacology: Carbetocin is a drug used to control postpartum hemorrhage, bleeding after giving birth. It is sold under the trade name Duratocin. It is an analogue of oxytocin, and its action is similar to that of oxytocin; it causes contraction of the uterus.
• Affected Organisms: Humans and other mammals
• Absorption: Bioavailability is 80% following intramuscular injection.
• Half Life: 40 minutes
• External Links: Wikipedia