Find Stiripentol manufacturers, exporters & distributors on PharmaCompass

Stiripentol

ACCESS ALL DATA
Browse all information
CHEMISTRY
Discover Molecule Insights

ACTIVE PHARMA INGREDIENTS

6 API Suppliers, 5 USDMF, 1 EU WC, 3 NDC API, 4 Listed Suppliers, $ API Reference Price

6 API Suppliers
5 USDMF
1 EU WC
3 NDC API
4 Listed Suppliers
$ API Reference Price

DEVELOPMENTS

2 Drugs in Development

2 Drugs in Development

FINISHED DOSAGE FORMULATIONS

19 FDF Dossiers, 4 FDA Orange Book, 8 Europe, 3 Canada, 4 Australia

19 FDF Dossiers
4 FDA Orange Book
8 Europe
3 Canada
4 Australia

DIGITAL CONTENT

8 NEWS #PharmaBuzz

media
8 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions, 4 Finished Drug Prices

globalSalesInformation
1 US Medicaid Prescriptions
4 Finished Drug Prices

MARKET PLACE

2 APIs, 1 FDF Dossiers

marketPlace
2 APIs
1 FDF Dossiers

PATENTS & EXCLUSIVITIES

12 US Exclusivities

patents
12 US Exclusivities

Nuray Stiripentol

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

MARKET PLACE

API

FDF

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

854,407

Annual Reports (USD Million)

Finished Drug Prices

0RELATED EXCIPIENT COMPANIES

0EXCIPIENTS BY APPLICATIONS

Chemistry

Click the arrow to open the dropdown

Click the button for full data set

Also known as: 49763-96-4, Diacomit, Bcx 2600, 1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol, 137767-55-6, Bcx-2600

Molecular Formula

C₁₄H₁₈O₃

Molecular Weight

234.29 g/mol

InChI Key

IBLNKMRFIPWSOY-FNORWQNLSA-N

FDA UNII

R02XOT8V8I

Stiripentol is an anticonvulsant drug used in the treatment of epilepsy as an adjunct therapy along with [DB00349] and [DB00313]. This drug is currently approved in the USA, Canada, and European countries as oral tablets marketed as Diacomit. FDA approval of this drug was granted on August 20, 2018,. Unrelated to other anticonvulsants, stiripentol belongs to the group of aromatic allylic alcohols and may potentiate the effect of other antiepileptic drugs (AEDs) due to pharmacokinetic interactions. It elevates the levels of gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter that regulates electrical activity in the central nervous system.

1 2D Structure

Stiripentol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

2.1.2 InChI

InChI=1S/C14H18O3/c1-14(2,3)13(15)7-5-10-4-6-11-12(8-10)17-9-16-11/h4-8,13,15H,9H2,1-3H3/b7-5+

2.1.3 InChI Key

IBLNKMRFIPWSOY-FNORWQNLSA-N

2.1.4 Canonical SMILES

CC(C)(C)C(C=CC1=CC2=C(C=C1)OCO2)O

2.1.5 Isomeric SMILES

CC(C)(C)C(/C=C/C1=CC2=C(C=C1)OCO2)O

2.2 Other Identifiers

2.2.1 UNII

R02XOT8V8I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. D-306

2. Diacomit

2.3.2 Depositor-Supplied Synonyms

1. 49763-96-4

2. Diacomit

3. Bcx 2600

4. 1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol

5. 137767-55-6

6. Bcx-2600

7. 1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

8. 4,4-dimethyl-1-((3,4-methylenedioxy)phenyl)-1-penten-3-ol

9. (1e)-1-(2h-1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

10. Ncgc00185769-01

11. Estiripentol

12. 1-penten-3-ol, 4,4-dimethyl-1-(3,4-methylenedioxyphenyl)-

13. (e)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

14. 1-penten-3-ol, 1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-

15. Stiripentolum

16. Stiripentol [mi]

17. Stiripentol [inn]

18. Stiripentol [jan]

19. Stiripentol [usan:inn]

20. Stiripentol [usan]

21. Stiripentolum [inn-latin]

22. Estiripentol [inn-spanish]

23. Stiripentol [mart.]

24. 4,4-dimethyl-1-(3,4-methylenedioxyphenyl)-1-penten-3-ol

25. Smr000449279

26. Stiripentol [who-dd]

27. Stiripentol [ema Epar]

28. R02xot8v8i

29. Einecs 256-480-9

30. Mfcd00869310

31. Brn 1313047

32. (e)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

33. Diacomit (tn)

34. Me-2080

35. Cpd000449279

36. Dsstox_cid_28994

37. Dsstox_rid_83259

38. Dsstox_gsid_49068

39. 5-19-02-00640 (beilstein Handbook Reference)

40. Mls000758313

41. Mls001424144

42. Schembl216436

43. Stiripentol (jan/usan/inn)

44. Gtpl5469

45. Schembl2533815

46. Chembl1983350

47. Chebi:94435

48. Stiripentol, >=98% (hplc)

49. Dtxsid80860609

50. Stiripentol [orange Book]

51. Hms2052k07

52. Hms2232p06

53. Hms3886m17

54. Bcp10434

55. Tox21_113622

56. Bdbm50504273

57. S5266

58. Akos025149123

59. Akos027255159

60. Ccg-101092

61. Ccg-266819

62. Cs-7801

63. Db09118

64. Nc00342

65. Ncgc00185769-02

66. Bs-16863

67. Cas-49763-96-4

68. Hy-103392

69. D05928

70. W10731

71. Bcx2600; Bcx-2600; Bcx 2600

72. 763s964

73. Q412182

74. (1e)-1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol

75. (e)-1-(3,4-methylenedioxyphenyl)-4,4-dimethyl-1-penten-3-ol

76. 131206-47-8

2.4 Create Date

2005-09-13

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₈O₃
Molecular Weight	234.29 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	234.125594432 g/mol
Monoisotopic Mass	234.125594432 g/mol
Topological Polar Surface Area	38.7 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	280
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated for use in conjunction with clobazam and valproate as adjunctive therapy of refractory generalized tonic-clonic seizures in patients with severe myoclonic epilepsy in infancy (SMEI, Dravets syndrome) whose seizures are not adequately controlled with clobazam and valproate.

Diacomit is indicated for use in conjunction with clobazam and valproate as adjunctive therapy of refractory generalized tonic-clonic seizures in patients with severe myoclonic epilepsy in infancy (SMEI, Dravet's syndrome) whose seizures are not adequately controlled with clobazam and valproate.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Stiripentol is an orphan drug that effectively reduces seizure frequency in infantile epilepsy as an adjunct therapy and also exhibits a therapeutic advantage in improving the efficacy of other antiepileptic drugs. It potentiates GABA transmission by elevating the levels of the inhibitory neurotransmitters in the brain. Stiripentol is a positive allosteric modulator of GABA-A receptors in the brain that enhances the opening duration of the channel by binding to a site different than the benzodiazepine binding site. Reduced synaptosomal uptake of GABA and/or inhibition of GABA transaminase may also explain the role of stiripentol in reducing the events of seizure. The anticonvulsant activity of stiripentol is age-dependent, with increased efficacy in younger patients.

5.2 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

5.3 ATC Code

N03AX17

N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AX - Other antiepileptics

N03AX17 - Stiripentol

5.4 Absorption, Distribution and Excretion

Absorption

Absorption of stiripentol is quick with the peak plasma concentration reached within 1.5 hours following oral administration. The systemic exposure increases in a dose-proportional relationship. It is rapidly taken up into the brain and enters the cerebellum and medulla. It displays low bioavailability due to water insolubility and metabolism.

Route of Elimination

Renal elimination is mainly responsible for excretion of stiripentol. About 73% of total administered dose is found in urine as metabolites, while further 13-24% of the total dose is recovered in faeces as unchanged substance.

Volume of Distribution

The average volume of distribution is 1.03 L/kg but does not display a dose-dependent relationship. It is expected to be distributed into the extravascular space and with a high degree of tissue binding.

Clearance

Plasma clearance decreases markedly at high doses; it falls from approximately 40 L/kg/day at the dose of 600 mg/day to about 8 L/kg/day at the dose of 2,400 mg. Decreased clearance is probably explained by inhibition of the cytochrome P450 isoenzymes that catalyzes stiripentol metabolism.

5.5 Metabolism/Metabolites

There are 13 metabolites from extensive metabolism stiripentol that are found in urine. The predominant metabolic pathways involve demethylenation and glucuronidation. Other metabolic pathways are oxidative cleavage of the methylenedioxy ring system, O-methylation of catechol metabolites, hydroxylation of the t-butyl group and conversion of the allylic alcohol side-chain to the isomeric 3-pentanone structure. Based on in vitro studies, phase I metabolism of stiripentol involves enzymatic activity of CYP1A2, CYP2C19 and CYP3A4.

5.6 Biological Half-Life

Elimination half life is approximately ranges from 4.5 to 13 hours, in a dose-dependent manner.

5.7 Mechanism of Action

Stiripentol enhances GABAergic inhibition and prolongs the open duration of GABA-A receptor chloride channels by a barbiturate-like mechanism. It binds to GABA-A receptors containing any of the , , , or -subunits but displays strongest potency when bound to receptors containing 3 or subunits. Stiripentol is an inhibitor of lactate dehydrogenase (LDH), which plays a physiological role in energy metabolism of neurons and regulation of neuronal excitation. It binds to the site separate from lactate and pyruvate binding sites of the enzyme and inhibits both pyruvate-to-lactate conversion and lactate-to-pyruvate conversion. LDH inhibitors including stiripentol as antiepileptic treatments mimic ketogenic diet, where the energy source in the brain is switched from glucose to mainly ketone bodies. The ketone bodies directly regulate neuronal excitation and seizures via ATP-sensitive potassium channels and vesicular glutamate transporters. As a potent inhibitor of hepatic cytochrome P450 enzymes, mainly CYP3A4 and CYP2C19, stiripentol co-administration with other antiepileptic drugs elevates the free unchanged active drugs (such as carbamazepine, sodium valproate, phenytoin, phenobarbital and many benzodiazepines) in the circulation to mediate their therapeutic actions.

API SUPPLIERS