(4R,7R)-N-[(2S)-1-hydroxybutan-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: 237
• Molecular Formular: C20H25N3O2
• Molecular Mass: 339.4314
• Monoisotopic Mass: 339.19467706
• SMILES: O=C(N[C@@H](CC)CO)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C
• Canonical SMILES: CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CO
• InChI: InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1
• InChIKey: UNBRKDKAWYKMIV-QWQRMKEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(2S)-1-hydroxybutan-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: methylergonovine
• Brand Name: Basofortina; Metenarin; Methergen; Methergin; Methergine; Norforms; Partergin; Ryegonovin; Spametrin-M
• Synonyms: Methylergometrine; Methylergonovin; Methylergometrin; Methylergobrevin; Methylergobasine; Methylergobasin; methylergonovine maleate; Methylergonovine

Database IDs

• CAS Number: 113-42-8
• PubChem SID: 46507746; 160963700
• PubChem CID: 8226

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.997192
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.80055475
• LogD (pH = 7.4): 0.95344526
• Log P: 1.5932183
• Molar Refractivity: 99.5759 cm^3
• Polarizability: 39.292522 Å^3
• Polar Surface Area: 68.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.74
• LOG S: -3.22
• Solubility (Water): 2.04e-01 g/l

PROPERTIES

Physical Property

• Solubility: 25 mg/mL
• Hydrophobicity(logP): 1.2

DETAILS

DrugBank - DB00353

• Drug Groups: approved
• Description: A homolog of ergonovine containing one more CH2 group. (Merck Index, 11th ed)
• Indication: For the prevention and control of excessive bleeding following vaginal childbirth
• Pharmacology: Methylergonovine is a semisynthetic ergot alkaloid and a derivative of ergonovine and is used for the prevention and control of postpartum and post-abortion hemorrhage. In general, the effects of all the ergot alkaloids appear to results from their actions as partial agonists or antagonists at adrenergic, dopaminergic, and tryptaminergic receptors. The spectrum of effects depends on the agent, dosage, species, tissue, and experimental or physiological conditions. All of the alkaloids of ergot significantly increase the motor activity of the uterus. After small doses contractions are increased in force or frequency, or both, but are followed by a normal degree of relaxation. As the dose is increased, contractions become more forceful and prolonged, resting tonus is markedly increased, and sustained contracture can result.
• Toxicity: Signs and symptoms of overexposure: hypertension, seizures, headache, hypotension, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, with extensive first-pass metabolism.
• Absorption: Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.
• Half Life: 3.39 hours
• Elimination: Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver.
• Distribution: * 56.1 ± 0 L
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com