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Dihydroergocryptine

Dihydroergocryptine

Synopsis, Chemistry

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Also known as: Dihydro-alpha-ergocryptine, 25447-66-9, Alpha-dihydroergocryptine, 9,10-dihydro-alpha-ergocryptine, Alpha-dihydroergocriptine, 12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)-9,10alpha-dihydroergotaman-3',6',18-trione

Molecular Formula

C₃₂H₄₃N₅O₅

Molecular Weight

577.7 g/mol

InChI Key

PBUNVLRHZGSROC-VTIMJTGVSA-N

FDA UNII

202229IR8Y

A 9,10alpha-dihydro derivative of ERGOTAMINE that contains an isopropyl sidechain at the 2' position and an alpha-isobutyl sidechain at 5'alpha position of the molecule.

1 2D Structure

Dihydroergocryptine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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

2.1.2 InChI

InChI=1S/C32H43N5O5/c1-17(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/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1

2.1.3 InChI Key

PBUNVLRHZGSROC-VTIMJTGVSA-N

2.1.4 Canonical SMILES

CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CC5C(CC6=CNC7=CC=CC5=C67)N(C4)C)O

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

202229IR8Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Almirid

2. Cripar

3. Dihydroergocryptine Mesylate

4. Dihydroergocryptine Monomesylate

5. Dihydroergokryptine Mesylate

6. Dihydroergokryptine Monomesylate

7. Mesylate, Dihydroergocryptine

8. Mesylate, Dihydroergokryptine

9. Monomesylate, Dihydroergocryptine

10. Monomesylate, Dihydroergokryptine

2.3.2 Depositor-Supplied Synonyms

1. Dihydro-alpha-ergocryptine

2. 25447-66-9

3. Alpha-dihydroergocryptine

4. 9,10-dihydro-alpha-ergocryptine

5. Alpha-dihydroergocriptine

6. 12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)-9,10alpha-dihydroergotaman-3',6',18-trione

7. Chembl1743263

8. Chebi:59919

9. 202229ir8y

10. Dihydroergocriptine

11. (10alphah)-12'-hydroxy-5'alpha-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)-9,10-dihydroergotaman

12. (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

13. 9,10-dihydroergocryptine

14. Einecs 246-993-6

15. Dihydro-.alpha.-ergocryptine

16. Unii-202229ir8y

17. Ncgc00183332-01

18. Dsstox_cid_28615

19. Dsstox_rid_82885

20. Dsstox_gsid_48689

21. Schembl233373

22. Dtxsid5048689

23. Bdbm81453

24. Zinc3929793

25. Tox21_113078

26. Bdbm50390994

27. Pdsp2_001088

28. Cas_159729

29. Db11274

30. Nsc_159729

31. Ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.,10.alpha.)-

32. Ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha,10alpha)-

33. Cas-25447-66-9

34. D07835

35. Q905717

36. (6ar,9r,10ar)-n-[(1s,2r,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

37. 12'-hydroxy-2'-(1-methylethyl)-5'.alpha.-(2-methylpropyl)-9,10.alpha.-dihydroergotaman-3',6',18-trione

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₄₃N₅O₅
Molecular Weight	577.7 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	577.32641949 g/mol
Monoisotopic Mass	577.32641949 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	1130
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Alpha-dihydroergocryptine has been studied for the early treatment of Parkinson disease as well as for its use in migraine prophylaxis, treatment of low blood pressure and peripheral vascular disorder. To know more about the ergoloid mesylate mixture and its uses please visit [DB01049].

5 Pharmacology and Biochemistry

5.1 Pharmacology

The effect of alpha-dihydroergocryptine in dopamine receptors was tested in PD patients and seem to generate a significant clinical improvement in the tested patients as well as to reduce motor complications and side effects. In long-term clinical trials with Parkinson disease patients, the administration of alpha-dihydroergocryptine and levodopa, the symptoms were reposted to improve or completely vanish in 80% of the tested individuals. All the registered effects of alpha-dihydroergocryptine suggest a potential neuroprotective effect of this drug and some reports have indicated that this activity may be related to the activation of NF-kB. The effect of alpha-dihydroergocryptine in the dopamine D2 receptor also reduces prolactin plasma levels and induce hypotension. To know more about the ergoloid mesylate mixture please visit [DB01049].

5.2 MeSH Pharmacological Classification

Dopamine Agonists

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

Vasodilator Agents

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

5.3 Absorption, Distribution and Excretion

Absorption

Alpha-dihydroergocryptine is rapidly absorbed but it presents a very low bioavailability as it is part of a first-pass hepatic metabolism and thus less of 5% of the administered dose reaches blood circulation. The peak plasma concentration is attained after 30-120 minutes. The absorption of alpha-dihydroergocryptine is not affected by the co-administration with food. When administered in repeated oral doses the Cmax after 1 hour was registered to be 2157 pg/ml. To know more about the ergoloid mesylate mixture please visit [DB01049].

Route of Elimination

Alpha-dihydroergocryptine is eliminated mainly by feces and to present a very low urinary excretion. To know more about the ergoloid mesylate mixture please visit [DB01049].

Volume of Distribution

In preclinical studies, the volume of distribution after intravenous or oral administration was registered to be 11.054 L and 218.630 L respectively. To know more about the ergoloid mesylate mixture please visit [DB01049].

Clearance

In preclinical studies, the clearance rate after intravenous or oral administration was registered to be 1.129 L/h and 25.98 L/h respectively. To know more about the ergoloid mesylate mixture please visit [DB01049].

5.4 Metabolism/Metabolites

Alpha-dihydroergocryptine presents a linear metabolism with the formation of active metabolites and the metabolism kinetics of this compound has no interference with L-dopa. It is highly metabolized with a rate of 2.4 ng/min/mg protein in the microsomal system and a formation of eight different metabolites. the metabolism of alpha-dihydroergocryptine seems to be highly marked by the action of CYP 3A4. To know more about the ergoloid mesylate mixture please visit [DB01049].

5.5 Biological Half-Life

Alpha-dihydroergocryptine has been studied in Parkinson disease models and it has shown a half-life of 12-16 hours. To know more about the ergoloid mesylate mixture please visit [DB01049].

5.6 Mechanism of Action

Alpha-dihydroergocryptine is an established high-affinity ligand to alpha 1 and alpha 2 adrenoreceptors in a number of tissues as well as a dopamine ligand in the brain. It is reported to be a potent agonist of the dopamine D2 receptor and a partial agonist of the dopamine receptors D1 and D3. To know more about the ergoloid mesylate mixture please visit [DB01049] and to know more about the isomer please visit [DB11275].