Deutetrabenazine | Tetrabenazine-d6 | SD809 | CAS#1392826-25-3 | VMAT2 inhibitor

MedKoo Cat#: 326631 | Name: Deutetrabenazine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Deutetrabenazine, also known as SD-809 and Tetrabenazine-d6, is a vesicular monoamine transporter 2 inhibitor which is used for the treatment of chorea associated with Huntington's disease and tardive dyskinesia. Deutetrabenazine acts as a monoamine-depleting agent. Chemically, deutetrabenazine is an isotopic isomer of tetrabenazine in which six hydrogen atoms have been replaced by deuterium atoms. The incorporation of deuterium slows the rate of drug metabolism, allowing less frequent dosing.

Chemical Structure

Deutetrabenazine

CAS#1392826-25-3

Theoretical Analysis

MedKoo Cat#: 326631

Name: Deutetrabenazine

CAS#: 1392826-25-3

Chemical Formula: C19H21D6NO3

Exact Mass: 323.2368

Molecular Weight: 323.47

Elemental Analysis: C, 70.55; H, 10.28; N, 4.33; O, 14.84

Price and Availability

Size	Price	Availability
5mg	USD 90.00	Ready to ship
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship

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Related CAS #

No Data

Synonym

SD809; SD-809; SD 809; GTPL8707; GTPL-8707; GTPL 8707; Deutetrabenazine; Tetrabenazine-d6; Tetrabenazine d6;

IUPAC/Chemical Name

rel-(3R,11bR)-3-isobutyl-9,10-bis(methoxy-d3)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one

InChi Key

MKJIEFSOBYUXJB-VFJJUKLQSA-N

InChi Code

InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3/t14-,16-/m1/s1/i3D3,4D3

SMILES Code

O=C1[C@H](CC(C)C)CN2CCC3=CC(OC([2H])([2H])[2H])=C(OC([2H])([2H])[2H])C=C3[C@@]2([H])C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Deutetrabenazine is a hexahydro-dimethoxybenzoquinolizine derivative and has the following chemical name: (RR, SS)-1, 3, 4, 6, 7, 11b-hexahydro-9, 10-di(methoxy-d3)-3-(2-methylpropyl)2H-benzo[a]quinolizin-2-one. The molecular formula for deutetrabenazine is C19H21D6NO3. Deutetrabenazine is a racemic mixture.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A23T10K19

QC Data

View QC data: current batch, Lot#A23T10K19

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Deutetrabenazine is a deuterium-labled tetrabenazine.

In vitro activity:

To be determined

In vivo activity:

Compared to the tetrabenazine cohort, Huntington’s disease patients treated with deutetrabenazine were more adherent to treatment and had lower discontinuation rates. Reference: Neurol Ther. 2022 Mar;11(1):435-448. https://pubmed.ncbi.nlm.nih.gov/34905160/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.9	10.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 323.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Claassen DO, Ayyagari R, Garcia-Horton V, Zhang S, Alexander J, Leo S. Real-World Adherence to Tetrabenazine or Deutetrabenazine Among Patients With Huntington's Disease: A Retrospective Database Analysis. Neurol Ther. 2022 Mar;11(1):435-448. doi: 10.1007/s40120-021-00309-5. Epub 2021 Dec 14. PMID: 34905160; PMCID: PMC8857359. 2. Dorfman BJ, Jimenez-Shahed J. Deutetrabenazine for treatment of involuntary movements in patients with tardive dyskinesia. Expert Rev Neurother. 2021 Jan;21(1):9-20. doi: 10.1080/14737175.2021.1848548. Epub 2020 Nov 23. PMID: 33174440.

In vitro protocol:

To be determined

In vivo protocol:

1: Jankovic J, Coffey B, Claassen DO, Jimenez-Shahed J, Gertz BJ, Garofalo EA, Stamler DA, Wieman M, Savola JM, Harary E, Alexander J, Barkay H, Gordon MF. Safety and Efficacy of Long-Term Deutetrabenazine Use in Children and Adolescents with Tics Associated with Tourette Syndrome: An Open-Label Extension Study. Mov Disord Clin Pract. 2023 Aug 24;10(9):1388-1398. doi: 10.1002/mdc3.13849. PMID: 37772282; PMCID: PMC10525047. 2: Pudukodu HS, Radhakrishnan V, Rosen JH. Polypharmacologic Toxicity Involving Deutetrabenazine in a Patient With Renal Insufficiency. J Acad Consult Liaison Psychiatry. 2023 Aug 14:S2667-2960(23)00111-8. doi: 10.1016/j.jaclp.2023.08.004. Epub ahead of print. PMID: 37586640. 3: Curtis K, Sung V. Real-World Experience With Deutetrabenazine for Huntington Disease Chorea. J Clin Pharmacol. 2023 Aug 11. doi: 10.1002/jcph.2336. Epub ahead of print. PMID: 37565322. 4: Patel NJ, Jankovic J. NKX2-1-Related Disorders. 2014 Feb 20 [updated 2023 Jun 29]. In: Adam MP, Mirzaa GM, Pagon RA, Wallace SE, Bean LJH, Gripp KW, Amemiya A, editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993–2023. PMID: 24555207. 5: Makhoul K, Jankovic J. Real-world experience with VMAT2 inhibitors in Tourette syndrome. J Neurol. 2023 Sep;270(9):4518-4522. doi: 10.1007/s00415-023-11769-0. Epub 2023 Jun 11. PMID: 37301806. 6: Di Martino RMC, Maxwell BD, Pirali T. Deuterium in drug discovery: progress, opportunities and challenges. Nat Rev Drug Discov. 2023 Jul;22(7):562-584. doi: 10.1038/s41573-023-00703-8. Epub 2023 Jun 5. PMID: 37277503; PMCID: PMC10241557. 7: Chandra Mouli HM, Vinod A, Kumari S, Tiwari AK, Kathiravan MK, Ravichandiran V, Peraman R. Deuterated driven new chemical entities: An optimistic way to improve therapeutic efficacy. Bioorg Chem. 2023 Jun;135:106490. doi: 10.1016/j.bioorg.2023.106490. Epub 2023 Mar 22. PMID: 37001472. 8: Bhat SA, Ahamad S, Dar NJ, Siddique YH, Nazir A. The Emerging Landscape of Natural Small-molecule Therapeutics for Huntington's Disease. Curr Neuropharmacol. 2023;21(4):867-889. doi: 10.2174/1570159X21666230216104621. PMID: 36797612; PMCID: PMC10227909. 9: Brar S, Vijan A, Scott FL, Jimenez R, Zhang H, Grigoriadis DE, Loewen G. Pharmacokinetic and Pharmacologic Characterization of the Dihydrotetrabenazine Isomers of Deutetrabenazine and Valbenazine. Clin Pharmacol Drug Dev. 2023 Apr;12(4):447-456. doi: 10.1002/cpdd.1205. Epub 2022 Dec 18. PMID: 36530055. 10: Frank S, Testa C, Edmondson MC, Goldstein J, Kayson E, Leavitt BR, Oakes D, O'Neill C, Vaughan C, Whaley J, Gross N, Gordon MF, Savola JM; Huntington Study Group/ARC-HD Investigators and Coordinators. The Safety of Deutetrabenazine for Chorea in Huntington Disease: An Open-Label Extension Study. CNS Drugs. 2022 Nov;36(11):1207-1216. doi: 10.1007/s40263-022-00956-8. Epub 2022 Oct 15. PMID: 36242718; PMCID: PMC9653309. 11: Belete TM. Recent Updates on the Development of Deuterium-Containing Drugs for the Treatment of Cancer. Drug Des Devel Ther. 2022 Oct 4;16:3465-3472. doi: 10.2147/DDDT.S379496. PMID: 36217450; PMCID: PMC9547620. 12: Ilyas U, Umar Z, Lin D. Group A Beta-Hemolytic Streptococcus-Induced Tic- Like Movement Disorder in an Adult: A Case Report. Cureus. 2022 Aug 26;14(8):e28451. doi: 10.7759/cureus.28451. PMID: 36176823; PMCID: PMC9510048. 13: Schneider F, Darpo B, Loupe PS, Xue H, Knebel H, Gutierrez M, Gordon MF, Rabinovich-Guilatt L. Evaluation of Deutetrabenazine's Potential to Delay Cardiac Repolarization Using Concentration-QTc Analysis. Clin Pharmacol Drug Dev. 2023 Jan;12(1):94-106. doi: 10.1002/cpdd.1161. Epub 2022 Sep 13. PMID: 36098670; PMCID: PMC10086964. 14: Gupta H, Perkins W, Stark C, Kikkeri S, Kakazu J, Kaye A, Kaye A. deutetrabenazine for the treatment of chorea associated with Huntington's disease. Health Psychol Res. 2022 Jun 28;10(3):36040. doi: 10.52965/001c.36040. PMID: 35774908; PMCID: PMC9239349. 15: Jastrzębska-Więsek M, Wesołowska A, Kołaczkowski M, Varney MA, Newman- Tancredi A, Depoortere R. The selective 5-HT 1A receptor agonist, NLX-112, overcomes tetrabenazine-induced catalepsy and depression-like behavior in the rat. Behav Pharmacol. 2022 Aug 1;33(5):333-341. doi: 10.1097/FBP.0000000000000681. Epub 2022 Jun 9. PMID: 35695543. 16: Salles PA, Liao J, Shuaib U, Mata IF, Fernandez HH. A Review on Response to Device-Aided Therapies Used in Monogenic Parkinsonism and GBA Variants Carriers: A Need for Guidelines and Comparative Studies. J Parkinsons Dis. 2022;12(6):1703-1725. doi: 10.3233/JPD-212986. PMID: 35662127; PMCID: PMC9535575. 17: Hauser RA, Barkay H, Wilhelm A, Wieman M, Savola JM, Gordon MF. Minimal clinically important change in Abnormal Involuntary Movement Scale score in tardive dyskinesia as assessed in pivotal trials of deutetrabenazine. Parkinsonism Relat Disord. 2022 Apr;97:47-51. doi: 10.1016/j.parkreldis.2022.02.017. Epub 2022 Mar 2. PMID: 35299070. 18: Hauser RA, Barkay H, Fernandez HH, Factor SA, Jimenez-Shahed J, Gross N, Marinelli L, Wilhelm A, Alexander J, Gordon MF, Savola JM, Anderson KE. Long- Term Deutetrabenazine Treatment for Tardive Dyskinesia Is Associated With Sustained Benefits and Safety: A 3-Year, Open-Label Extension Study. Front Neurol. 2022 Feb 23;13:773999. doi: 10.3389/fneur.2022.773999. PMID: 35280262; PMCID: PMC8906841. 19: Molnar MJ, Molnar V, Fedor M, Csehi R, Acsai K, Borsos B, Grosz Z. Improving Mood and Cognitive Symptoms in Huntington's Disease With Cariprazine Treatment. Front Psychiatry. 2022 Feb 10;12:825532. doi: 10.3389/fpsyt.2021.825532. PMID: 35222108; PMCID: PMC8866559. 20: Devadiga SJ, Bharate SS. Recent developments in the management of Huntington's disease. Bioorg Chem. 2022 Mar;120:105642. doi: 10.1016/j.bioorg.2022.105642. Epub 2022 Jan 30. PMID: 35121553.