[(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate

• ChemBase ID: 581
• Molecular Formular: C24H26BrN3O3
• Molecular Mass: 484.38554
• Monoisotopic Mass: 483.11575371
• SMILES: Brc1cc(C(=O)OC[C@@H]2C[C@@]3(OC)[C@H](N(C2)C)Cc2c4c3cccc4n(c2)C)cnc1
• Canonical SMILES: CO[C@]12C[C@@H](COC(=O)c3cncc(c3)Br)CN([C@@H]1Cc1c3c2cccc3n(c1)C)C
• InChI: InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1
• InChIKey: YSEXMKHXIOCEJA-FVFQAYNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate
• IUPAC Traditional name: nicergoline; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate; [(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate
• Brand Name: MNE; Nargoline; Nicergolin [German]; Nicergolina [Dcit]; Nicergoline [Usan:Ban:Inn:Jan]; Nicergolinum [INN-Latin]; Nicotergoline; Nimergoline; Nimergoline Base; Sermion; Vasospan
• Synonyms: Nicergoline; Nicergoline; Nargoline; Nicotergoline; Nimergoline; Sermion; 5-溴烟酸 10-甲氧基-1,6-二甲基麦角灵-8-甲酯; 尼麦角林

Database IDs

• CAS Number: 27848-84-6
• EC Number: 248-694-6
• MDL Number: MFCD00869626
• PubChem SID: 46508741; 160964044; 24897843
• PubChem CID: 34040

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.1122493
• LogD (pH = 7.4): 2.885367
• Log P: 3.695325
• Molar Refractivity: 123.2974 cm^3
• Polarizability: 48.515564 Å^3
• Polar Surface Area: 56.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.99
• LOG S: -4.58
• Solubility (Water): 1.27e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.3

Safety Information

• RTECS: KE6341000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADRA1A(148)
• Mechanism of Action: a1-Adrenoceptor antagonist; Calcium channel antagonist; Cholinergic; Peripheral vasodilator

Product Information

• Purity: ~97% (TLC)
• Grade: analytical standard, for drug analysis
• Application(s): Cerebroprotective props; Has been used in treatment of senile dementia

DETAILS

DrugBank - DB00699

• Drug Groups: approved
• Description: An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease. [PubChem]
• Indication: For the treatment of senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.
• Pharmacology: Nicergoline is a potent vasodilator (improves brain blood flow). On the cerebral level it prompts a lowering of vascular resistance, an increase in arterial flow and stimulates the use of oxygen and glucose. Nicergoline also improves blood circulation in the lungs and limbs and has been shown to inhibit blood platelet aggregation.
• Affected Organisms: Humans and other mammals
• References: Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - N7889

Biochem/physiol Actions
大脑和周边血管舒张剂
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N7889.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. Pubmed
• Arcari, G. et al., Experientia, 1972, 28, 819
• Bernardi, L. et al., Farmaco, Ed. Sci., 1975, 30, 789, (synth, pharmacol)
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• Arrigo, A. et al., Int. J. Clin. Pharmacol. Res., Suppl. 1, 1982, 11, 33, (use)
• Shintomi, K. et al., J. Pharmacobio-Dyn., 1987, 10, 35, (pharmacol, tox)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7056, (synonyms)
• Takahashi, K. et al., Br. J. Pharmacol., 1990, 100, 705, (pharmacol)
• Banno, K. et al., J. Chromatogr., 1991, 568, 375, (hplc)
• Sioufi, A. et al., Biomed. Chromatogr., 1992, 6, 9, (hplc, metab)
• Fumagalli, M. et al., Contact Dermatitis, 1992, 27, 256
• Carfagna, N. et al., Neurosci. Lett., 1995, 197, 195, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1731
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NDM000