WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H317591
CAS#: 93413-62-8 (free base)
Description: Desvenlafaxine (brand name: Pristiq, Desfax), also known as O-desmethylvenlafaxine, is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class developed and marketed by Wyeth (now part of Pfizer). Desvenlafaxine is a synthetic form of the major active metabolite of venlafaxine (sold under the brand names Effexor and Efexor). It is being targeted as the first non-hormonal based treatment for menopause. Desvenlafaxine is a synthetic phenethylamine bicyclic derivative with antidepressant activity. Desvenlafaxine is a selective reuptake inhibitor of serotonin and norepinephrine due to its high binding affinities to the pre-synaptic serotonin and norepinephrine transporters. By blocking both transporters, this agent prolongs neurotransmitter activities of both serotonin and norepinephrine, thereby alleviating depressive state. (Source: https://en.wikipedia.org/wiki/Desvenlafaxine).
Hodoodo Cat#: H317591
Name: Desvenlafaxine
CAS#: 93413-62-8 (free base)
Chemical Formula: C16H25NO2
Exact Mass: 263.19
Molecular Weight: 263.380
Elemental Analysis: C, 72.96; H, 9.57; N, 5.32; O, 12.15
Related CAS #: 93413-62-8 (free base) 448904-47-0 (succinate) 386750-22-7 (Succinate hydrate) 300827-87-6 (HCl) 93414-04-1 (fumarate) 1147940-37-1 (benzoate),
Synonym: Pristiq; Desfax
IUPAC/Chemical Name: 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
InChi Key: KYYIDSXMWOZKMP-UHFFFAOYSA-N
InChi Code: InChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
SMILES Code: CN(C)CC(C1=CC=C(C=C1)O)C2(CCCCC2)O
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:
| Biological target: | Desvenlafaxine (WY 45233 Succinate) is a serotonin (5-HT) and norepinephrine (NE) reuptake inhibitor with Ki of 40.2 nM and 558.4 nM, respectively. |
| In vitro activity: | The purpose of this study was to characterize a new chemical entity, desvenlafaxine succinate (DVS). Competitive radioligand binding assays were performed using cells expressing either the human serotonin (5-HT) transporter (hSERT) or norepinephrine (NE) transporter (hNET) with K(i) values for DVS of 40.2 +/- 1.6 and 558.4 +/- 121.6 nM, respectively. DVS showed weak binding affinity (62% inhibition at 100 microM) at the human dopamine (DA) transporter. Inhibition of [3H]5-HT or [3H]NE uptake by DVS for the hSERT or hNET produced IC50 values of 47.3 +/- 19.4 and 531.3 +/- 113.0 nM, respectively. DVS (10 microM), examined at a large number of nontransporter targets, showed no significant activity. In conclusion, DVS is a new 5-HT and NE reuptake inhibitor in vitro that demonstrates good brain-to-plasma ratios, suggesting utility in a variety of central nervous system-related disorders. Reference: J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. https://pubmed.ncbi.nlm.nih.gov/16675639/ |
| In vivo activity: | Desvenlafaxine (DVS) was orally administrated to UCMS mice at the dose of 10 mg/kg/day 1 week before they went through a 7week stress procedure and lasted for over 8 weeks before the mice were killed. No significant changes were found for protein markers of neurons and astrocytes in UCMS mice. However, myelin and oligodendrocyte-related proteins were significantly reduced in UCMS mice. DVS prevented the stress-induced injury to white matter and the decrease of phosphorylated 5'-AMP-activated protein kinase and 3-hydroxy-3-methyl-glutaryl-CoA reductase protein expression. DVS increased open arm entries in an elevated plus-maze test, sucrose consumption in the sucrose preference test and decreased immobility in tail suspension and forced swimming tests. These findings suggest that stress induces depression-like behaviors and white matter deficits in UCMS mice. DVS may ameliorate the oligodendrocyte dysfunction by affecting cholesterol synthesis, alleviating the depression-like phenotypes in these mice Reference: J Neurochem. 2014 Oct;131(2):229-38. https://pubmed.ncbi.nlm.nih.gov/24934403/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 37.0 | 140.48 | |
| Ethanol | 3.0 | 11.39 |
The following data is based on the product molecular weight 263.38 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. Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH. Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. doi: 10.1124/jpet.106.103382. Epub 2006 May 4. PMID: 16675639. 2. Asokan A, Ball AR, Laird CD, Hermer L, Ormerod BK. Desvenlafaxine may accelerate neuronal maturation in the dentate gyri of adult male rats. PLoS One. 2014 Jun 4;9(6):e98530. doi: 10.1371/journal.pone.0098530. PMID: 24896246; PMCID: PMC4045676 3. Wang J, Qiao J, Zhang Y, Wang H, Zhu S, Zhang H, Hartle K, Guo H, Guo W, He J, Kong J, Huang Q, Li XM. Desvenlafaxine prevents white matter injury and improves the decreased phosphorylation of the rate-limiting enzyme of cholesterol synthesis in a chronic mouse model of depression. J Neurochem. 2014 Oct;131(2):229-38. doi: 10.1111/jnc.12792. Epub 2014 Jul 8. PMID: 24934403. |
| In vitro protocol: | 1. Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH. Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. doi: 10.1124/jpet.106.103382. Epub 2006 May 4. PMID: 16675639. |
| In vivo protocol: | 1. Asokan A, Ball AR, Laird CD, Hermer L, Ormerod BK. Desvenlafaxine may accelerate neuronal maturation in the dentate gyri of adult male rats. PLoS One. 2014 Jun 4;9(6):e98530. doi: 10.1371/journal.pone.0098530. PMID: 24896246; PMCID: PMC4045676. 2. Wang J, Qiao J, Zhang Y, Wang H, Zhu S, Zhang H, Hartle K, Guo H, Guo W, He J, Kong J, Huang Q, Li XM. Desvenlafaxine prevents white matter injury and improves the decreased phosphorylation of the rate-limiting enzyme of cholesterol synthesis in a chronic mouse model of depression. J Neurochem. 2014 Oct;131(2):229-38. doi: 10.1111/jnc.12792. Epub 2014 Jul 8. PMID: 24934403. |
1: McIntyre RS, Fayyad R, Mackell JA, Boucher M. Effect of metabolic syndrome and thyroid hormone on efficacy of desvenlafaxine 50 and 100 mg/d in major depressive disorder. Curr Med Res Opin. 2015 Dec 28:1-44. [Epub ahead of print] PubMed PMID: 26709542.
2: Boyer P, Vialet C, Hwang E, Tourian KA. Efficacy of Desvenlafaxine 50 mg/d Versus Placebo in the Long-Term Treatment of Major Depressive Disorder: A Randomized, Double-Blind Trial. Prim Care Companion CNS Disord. 2015 Aug 27;17(4). doi: 10.4088/PCC.14m01711. eCollection 2015. PubMed PMID: 26693033; PubMed Central PMCID: PMC4664561.
3: McIntyre RS, Fayyad RS, Guico-Pabia CJ, Boucher M. A Post Hoc Analysis of the Effect of Weight on Efficacy in Depressed Patients Treated With Desvenlafaxine 50 mg/d and 100 mg/d. Prim Care Companion CNS Disord. 2015 Jun 4;17(3). doi: 10.4088/PCC.14m01741. eCollection 2015. PubMed PMID: 26644956; PubMed Central PMCID: PMC4578908.
4: Ghosh R, Gupta R, Bhatia MS, Tripathi AK, Gupta LK. Comparison of efficacy, safety and brain derived neurotrophic factor (BDNF) levels in patients of major depressive disorder, treated with fluoxetine and desvenlafaxine. Asian J Psychiatr. 2015 Dec;18:37-41. doi: 10.1016/j.ajp.2015.10.006. Epub 2015 Oct 19. PubMed PMID: 26514447.
5: Rejas Gutiérrez J, Blanca Tamayo M, Gascón Barrachina J, Armada Peláez B. Economic evaluation of desvenlafaxine in the treatment of major depressive disorder in Spain. Rev Psiquiatr Salud Ment. 2015 Oct 13. pii: S1888-9891(15)00141-X. doi: 10.1016/j.rpsm.2015.08.002. [Epub ahead of print] English, Spanish. PubMed PMID: 26475204.
6: Macaluso M, Nichols AI, Preskorn SH. How the Probability and Potential Clinical Significance of Pharmacokinetically Mediated Drug-Drug Interactions Are Assessed in Drug Development: Desvenlafaxine as an Example. Prim Care Companion CNS Disord. 2015 Mar 19;17(2). doi: 10.4088/PCC.14r01710. eCollection 2015. PubMed PMID: 26445693; PubMed Central PMCID: PMC4560193.
7: Sousa CN, Meneses LN, Vasconcelos GS, Silva MC, Silva JC, Macêdo D, de Lucena DF, Vasconcelos SM. Reversal of corticosterone-induced BDNF alterations by the natural antioxidant alpha-lipoic acid alone and combined with desvenlafaxine: Emphasis on the neurotrophic hypothesis of depression. Psychiatry Res. 2015 Dec 15;230(2):211-9. doi: 10.1016/j.psychres.2015.08.042. Epub 2015 Sep 1. PubMed PMID: 26350703.
8: Silva MC, de Sousa CN, Gomes PX, de Oliveira GV, Araújo FY, Ximenes NC, da Silva JC, Vasconcelos GS, Leal LK, Macêdo D, Vasconcelos SM. Evidence for protective effect of lipoic acid and desvenlafaxine on oxidative stress in a model depression in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2016 Jan 4;64:142-8. doi: 10.1016/j.pnpbp.2015.08.002. Epub 2015 Aug 8. PubMed PMID: 26265141.
9: Clayton AH, Hwang E, Kornstein SG, Tourian KA, Cheng RF, Abraham L, Mele L, Boucher M. Effects of 50 and 100 mg desvenlafaxine versus placebo on sexual function in patients with major depressive disorder: a meta-analysis. Int Clin Psychopharmacol. 2015 Nov;30(6):307-15. doi: 10.1097/YIC.0000000000000094. PubMed PMID: 26230270.
10: Chen YX, Du JB, Zhang YF, Chen XY, Zhong DF. [The enantioselective pharmacokinetic study of desvenlafaxine sustained release tablet in Chinese healthy male volunteers after oral administration]. Yao Xue Xue Bao. 2015 Apr;50(4):486-91. Chinese. PubMed PMID: 26223133.
