(4R,7R)-N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

• ChemBase ID: 1122
• Molecular Formular: C19H23N3O2
• Molecular Mass: 325.40482
• Monoisotopic Mass: 325.17902699
• SMILES: O=C(N[C@H](CO)C)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C
• Canonical SMILES: OC[C@@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)C
• InChI: InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
• InChIKey: WVVSZNPYNCNODU-XTQGRXLLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
• IUPAC Traditional name: ergonovine
• Brand Name: Ergotrate
• Synonyms: Ergotrate maleate; Ergometrine; Ergobasine; Ergonovine

Database IDs

• CAS Number: 60-79-7
• PubChem SID: 46506922; 160964585
• PubChem CID: 443884

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.998553
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.3230772
• LogD (pH = 7.4): 0.43092284
• Log P: 1.070696
• Molar Refractivity: 95.0519 cm^3
• Polarizability: 37.447586 Å^3
• Polar Surface Area: 68.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.53
• LOG S: -3.01
• Solubility (Water): 3.21e-01 g/l

PROPERTIES

Physical Property

• Solubility: 2.68 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]
• Hydrophobicity(logP): 0.9

DETAILS

DrugBank - DB01253

• Drug Groups: approved
• Description: An ergot alkaloid with uterine and vascular smooth muscle contractile properties. [PubChem]
• Indication: Used to treat postpartum haemorrhage and postabortion haemorrhage in patients with uterine atony.
• Pharmacology: Ergonovine belongs to the group of medicines known as ergot alkaloids. These medicines are usually given to stop excessive bleeding that sometimes occurs after abortion or a baby is delivered. They work by causing the muscle of the uterus to contract.
• Toxicity: The principal symptoms of overdose are convulsions and gangrene. Other symptoms include bradycardia, confusion, diarrhoea, dizziness, dyspnoea, drowsiness, fast and/or weak pulse, miosis, hypercoagulability, loss of consciousness, nausea and vomiting, numbness and coldness of the extremities, pain in the chest, peripheral vasoconstriction, respiratory depression, rise or fall in blood pressure, severe cramping of the uterus, tachycardia, tingling, and unusual thirst.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Absorption is rapid and complete after oral or intramuscular administration.
• Half Life: t_{1/2 α}=10 minutes; t_{1/2 β}=2 hours
• Elimination: Thought to be eliminated by non-renal mechanisms (i.e. hepatic metabolism, excretion in feces)
• External Links: Wikipedia; Drugs.com