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Chemistry

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Also known as: Ergoloid mesilates, Co-dergocrine mesylate, Dihydroergotoxine mesilate, Dihydrogenated ergot alkaloids, Chembl2311030, Dihydroergotoxine methanesulfonate

Molecular Formula

C₁₃₄H₁₈₄N₂₀O₃₂S₄

Molecular Weight

2715.3 g/mol

InChI Key

PBKVEOSEPXMKDN-LZHUFOCISA-N

A mixture of three different hydrogenated derivatives of ERGOTAMINE: DIHYDROERGOCORNINE; DIHYDROERGOCRISTINE; and DIHYDROERGOCRYPTINE. Dihydroergotoxine has been proposed to be a neuroprotective agent and a nootropic agent. The mechanism of its therapeutic actions is not clear, but it can act as an alpha-adrenergic antagonist and a dopamine agonist. The methanesulfonate salts of this mixture of alkaloids are called ERGOLOID MESYLATES.

1 2D Structure

Co-Dergocrine Mesilate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-butan-2-yl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(6aR,9R,10aR)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(6aR,9R,10aR)-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;methanesulfonic acid

2.1.2 InChI

InChI=1S/C35H41N5O5.2C32H43N5O5.C31H41N5O5.4CH4O3S/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34;1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20;1-6-18(4)27-29(39)36-12-8-11-25(36)32(41)37(27)30(40)31(42-32,17(2)3)34-28(38)20-13-22-21-9-7-10-23-26(21)19(15-33-23)14-24(22)35(5)16-20;1-16(2)26-28(38)35-11-7-10-24(35)31(40)36(26)29(39)30(41-31,17(3)4)33-27(37)19-12-21-20-8-6-9-22-25(20)18(14-32-22)13-23(21)34(5)15-19;4*1-5(2,3)4/h4-7,9-12,18,20,23,25,27-29,36,44H,8,13-17,19H2,1-3H3,(H,37,41);6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38);7,9-10,15,17-18,20,22,24-25,27,33,41H,6,8,11-14,16H2,1-5H3,(H,34,38);6,8-9,14,16-17,19,21,23-24,26,32,40H,7,10-13,15H2,1-5H3,(H,33,37);4*1H3,(H,2,3,4)/t23-,25-,27-,28+,29+,34-,35+;20-,22-,24-,25+,26+,31-,32+;18?,20-,22-,24-,25+,27+,31-,32+;19-,21-,23-,24+,26+,30-,31+;;;;/m1111..../s1

2.1.3 InChI Key

PBKVEOSEPXMKDN-LZHUFOCISA-N

2.1.4 Canonical SMILES

CCC(C)C1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CC5C(CC6=CNC7=CC=CC5=C67)N(C4)C)O.CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CC5C(CC6=CNC7=CC=CC5=C67)N(C4)C)O.CC(C)C1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CC5C(CC6=CNC7=CC=CC5=C67)N(C4)C)O.CC(C)C1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CC6C(CC7=CNC8=CC=CC6=C78)N(C5)C.CS(=O)(=O)O.CS(=O)(=O)O.CS(=O)(=O)O.CS(=O)(=O)O

2.1.5 Isomeric SMILES

CCC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4C[C@H]5[C@@H](CC6=CNC7=CC=CC5=C67)N(C4)C)O.CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4C[C@H]5[C@@H](CC6=CNC7=CC=CC5=C67)N(C4)C)O.CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4C[C@H]5[C@@H](CC6=CNC7=CC=CC5=C67)N(C4)C)O.CC(C)[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@@H]5C[C@H]6[C@@H](CC7=CNC8=CC=CC6=C78)N(C5)C.CS(=O)(=O)O.CS(=O)(=O)O.CS(=O)(=O)O.CS(=O)(=O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Alkaloids, Hydrogenated Ergot

2. Co-dergocrine

3. Dihydroergotoxin

4. Dihydroergotoxine

5. Ergot Alkaloids, Hydrogenated

6. Circanol

7. Co Dergine Mesylate

8. Co Dergocrine Mesilate

9. Co Dergocrine Mesylate

10. Co-dergine Mesylate

11. Co-dergocrine Mesilate

12. Co-dergocrine Mesylate

13. Dihydroergotoxine Mesylate

14. Dihydroergotoxine Methanesulfonate

15. Dihydroergotoxine Monomethanesulfonate

16. Ergodesit

17. Ergoloid Mesylate

18. Ergoloid Mesylates

19. Ergotoxin, Dihydro-, Monomethasulfonate

20. Hydergine

21. Methanesulfonate, Dihydroergotoxine

22. Monomethanesulfonate, Dihydroergotoxine

23. Redergam

24. Redergin

25. Redergine

2.2.2 Depositor-Supplied Synonyms

1. Ergoloid Mesilates

2. Co-dergocrine Mesylate

3. Dihydroergotoxine Mesilate

4. Dihydrogenated Ergot Alkaloids

5. Chembl2311030

6. Dihydroergotoxine Methanesulfonate

2.3 Create Date

2013-09-23

3 Chemical and Physical Properties

Molecular Formula	C₁₃₄H₁₈₄N₂₀O₃₂S₄
Molecular Weight	2715.3 g/mol
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	36
Rotatable Bond Count	19
Exact Mass	2714.2301933 g/mol
Monoisotopic Mass	2713.2268385 g/mol
Topological Polar Surface Area	724 Å²
Heavy Atom Count	190
Formal Charge	0
Complexity	4690
Isotope Atom Count	0
Defined Atom Stereocenter Count	28
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	8

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Ergoloid mesylates
PubMed Health	Ergoloid Mesylates (By mouth)
Drug Classes	Antimigraine
Drug Label	Each tablet for oral use contains ergoloid mesylates USP; a mixture of the methanesulfonate salt of the following hydrogenated alkaloids:RDihydroergocornine-CH(CH ) 32Dihydroergocristine-CH C H 265Dihydro--ergocryptine-CH CH(CH ) 232Dihydro--ergo...
Active Ingredient	Ergoloid mesylates
Dosage Form	Tablet
Route	Oral
Strength	1mg
Market Status	Prescription
Company	Mutual Pharm

2 of 2
Drug Name	Ergoloid mesylates
PubMed Health	Ergoloid Mesylates (By mouth)
Drug Classes	Antimigraine
Drug Label	Each tablet for oral use contains ergoloid mesylates USP; a mixture of the methanesulfonate salt of the following hydrogenated alkaloids:RDihydroergocornine-CH(CH ) 32Dihydroergocristine-CH C H 265Dihydro--ergocryptine-CH CH(CH ) 232Dihydro--ergo...
Active Ingredient	Ergoloid mesylates
Dosage Form	Tablet
Route	Oral
Strength	1mg
Market Status	Prescription
Company	Mutual Pharm

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Adrenergic alpha-Antagonists

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)

Dopamine Agonists

Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)

Nootropic Agents

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

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