(S)-Duloxetine HCl | CAS#136434-34-9 | Serotonin-Norepinephrine Reuptake Inhibitor

MedKoo Cat#: 317759 | Name: (S)-Duloxetine HCl

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Description:

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

(S)-Duloxetine HCl is a serotonin and norepinephrine reuptake inhibitor. It is mostly prescribed for major depressive disorder, generalized anxiety disorder, fibromyalgia and neuropathic pain. Duloxetine is sold under the brand name Cymbalta among others. It is also used in the treatment of stress urinary incontinence.

Chemical Structure

(S)-Duloxetine HCl

CAS#136434-34-9

Theoretical Analysis

MedKoo Cat#: 317759

Name: (S)-Duloxetine HCl

CAS#: 136434-34-9

Chemical Formula: C18H20ClNOS

Exact Mass:

Molecular Weight: 333.87

Elemental Analysis: C, 64.75; H, 6.04; Cl, 10.62; N, 4.20; O, 4.79; S, 9.60

Price and Availability

Size	Price	Availability
250mg	USD 250.00	2 weeks
1g	USD 550.00	2 weeks
5g	USD 1,150.00	2 weeks

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Synonym

Duloxetine; Cymbalta; (S)-Duloxetine; Yentreve; LY-227942; LY-248686; LY227942; LY248686; Duloxetine HCl; duloxetine hydrochloride; duloxetine, (+)-isomer; HCl, Duloxetine Hydrochloride, Duloxetine; LY 227942; LY 248686;

IUPAC/Chemical Name

(S)-N-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine hydrochloride

InChi Key

BFFSMCNJSOPUAY-LMOVPXPDSA-N

InChi Code

InChI=1S/C18H19NOS.ClH/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16;/h2-10,13,17,19H,11-12H2,1H3;1H/t17-;/m0./s1

SMILES Code

CNCC[C@H](OC1=CC=CC2=CC=CC=C21)C3=CC=CS3.Cl

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Duloxetine is a serotonin-norepinephrine reuptake inhibitor with a Ki of 4.6 nM, used for treatment of major depressive disorder and generalized anxiety disorder (GAD).

In vitro activity:

This study aimed to investigate the duloxetine-induced neural cytotoxicity effect and its performance in an N2a cell neurite outgrowth model. Duloxetine-induced changes in the N2a cell populations as follows: an increase in the annexin V- and PI-positive cells (Fig.2c); a decrease in the colony-formation ability (Fig.2d); and an increase in the TUNEL-positive cells (Fig.2f), all of which were significant in the 25 μM, 50 μM, and 100 μM groups (Fig.22 e and g). Duloxetine-induced biochemical changes in the N2a cells included increased levels of MDA in the cell lysates (Fig.2h) and LDH (Fig.2i) in the cell culture supernatants and decreases in the protein levels of CYP1A2 (Fig.2j) and CYP2D6 (Fig.2k) in the cell culture supernatants in a dose-dependent manner. The cell viability of the N2a cells was not attenuated after the 24-h duloxetine treatment, but this treatment led to a significant reduction in the last 5 days (Fig.4f). Reference: Neurotox Res. 2020 Dec;38(4):859-870. https://pubmed.ncbi.nlm.nih.gov/32415528/

In vivo activity:

When significant allodynic signs were observed, three different doses of duloxetine (10, 30, and 60 mg/kg, i.p.) were injected into mice. Representative extracellular recording raw trace of WDR neurons to press (Figure 2A) stimulations demonstrated that the neuronal firing rate decreased one hour after duloxetine administration. In addition, the number of spike responses of the WDR neurons to mechanical (brush, press, and pinch) and cold (acetone drop) stimulation were significantly decreased after the injection of duloxetine compared to the responses shown before the injection (Figure 2B). However, the control group (D.W., i.p.) showed no significant change in WDR neuronal responses. These results show that 30 mg/kg of duloxetine treatment significantly reduced the augmented frequency of the WDR neurons in response to cold and mechanical stimulation elicited by oxaliplatin injection. Reference: Int J Mol Sci. 2017 Dec 5;18(12):2626. https://pubmed.ncbi.nlm.nih.gov/29206213/

	Solvent	mg/mL	mM
Solubility
	DMSO	53.0	122.13
	H2O	4.0	9.22

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 333.87 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. Gao W, Chen R, Xie N, Tang D, Zhou B, Wang D. Duloxetine-Induced Neural Cell Death and Promoted Neurite Outgrowth in N2a Cells. Neurotox Res. 2020 Dec;38(4):859-870. doi: 10.1007/s12640-020-00216-x. Epub 2020 May 16. PMID: 32415528; PMCID: PMC7591439. 2. Yamashita T, Yamamoto S, Zhang J, Kometani M, Tomiyama D, Kohno K, Tozaki-Saitoh H, Inoue K, Tsuda M. Duloxetine Inhibits Microglial P2X4 Receptor Function and Alleviates Neuropathic Pain after Peripheral Nerve Injury. PLoS One. 2016 Oct 21;11(10):e0165189. doi: 10.1371/journal.pone.0165189. PMID: 27768754; PMCID: PMC5074465. 3. Moura ECR, da Cunha Leal P, Serra ICPB, de Paulo Ribeiro B, do Nascimento JR, do Nascimento FRF, Sakata RK. Tumor growth activity of duloxetine in Ehrlich carcinoma in mice. BMC Res Notes. 2018 Jul 31;11(1):525. doi: 10.1186/s13104-018-3655-4. PMID: 30064486; PMCID: PMC6069801. 4. . Kim W, Chung Y, Choi S, Min BI, Kim SK. Duloxetine Protects against Oxaliplatin-Induced Neuropathic Pain and Spinal Neuron Hyperexcitability in Rodents. Int J Mol Sci. 2017 Dec 5;18(12):2626. doi: 10.3390/ijms18122626. PMID: 29206213; PMCID: PMC5751229.

In vitro protocol:

In vivo protocol:

1. Moura ECR, da Cunha Leal P, Serra ICPB, de Paulo Ribeiro B, do Nascimento JR, do Nascimento FRF, Sakata RK. Tumor growth activity of duloxetine in Ehrlich carcinoma in mice. BMC Res Notes. 2018 Jul 31;11(1):525. doi: 10.1186/s13104-018-3655-4. PMID: 30064486; PMCID: PMC6069801. 2. Kim W, Chung Y, Choi S, Min BI, Kim SK. Duloxetine Protects against Oxaliplatin-Induced Neuropathic Pain and Spinal Neuron Hyperexcitability in Rodents. Int J Mol Sci. 2017 Dec 5;18(12):2626. doi: 10.3390/ijms18122626. PMID: 29206213; PMCID: PMC5751229

1: Schukro RP, Oehmke MJ, Geroldinger A, Heinze G, Kress HG, Pramhas S. Efficacy of Duloxetine in Chronic Low Back Pain with a Neuropathic Component: A Randomized, Double-blind, Placebo-controlled Crossover Trial. Anesthesiology. 2016 Jan;124(1):150-8. doi: 10.1097/ALN.0000000000000902. PubMed PMID: 26517858. 2: Bellows BK, Nelson RE, Oderda GM, LaFleur J. Long-term cost-effectiveness of initiating treatment for painful diabetic neuropathy with pregabalin, duloxetine, gabapentin, or desipramine. Pain. 2016 Jan;157(1):203-13. doi: 10.1097/j.pain.0000000000000350. PubMed PMID: 26397932. 3: Paulzen M, Gründer G, Veselinovic T, Wolf B, Hiemke C, Lammertz SE. Duloxetine enters the brain - But why is it not found in the cerebrospinal fluid. J Affect Disord. 2016 Jan 1;189:159-63. doi: 10.1016/j.jad.2015.08.073. Epub 2015 Sep 25. PubMed PMID: 26437230. 4: Castro-Alves LJ, Oliveira de Medeiros AC, Neves SP, Carneiro de Albuquerque CL, Modolo NS, De Azevedo VL, De Oliveira GS Jr. Perioperative Duloxetine to Improve Postoperative Recovery After Abdominal Hysterectomy: A Prospective, Randomized, Double-Blinded, Placebo-Controlled Study. Anesth Analg. 2016 Jan;122(1):98-104. doi: 10.1213/ANE.0000000000000971. PubMed PMID: 26421810. 5: Hossain SM, Hussain SM, Ekram AR. Duloxetine in Painful Diabetic Neuropathy: A Systematic Review. Clin J Pain. 2015 Dec 24. [Epub ahead of print] PubMed PMID: 26710221. 6: Scanlon KA, Stoppacher R, Blum LM, Starkey SJ. Comprehensive Duloxetine Analysis in a Fatal Overdose. J Anal Toxicol. 2015 Dec 10. pii: bkv134. [Epub ahead of print] PubMed PMID: 26662354. 7: Wang CF, Russell G, Wang SY, Strichartz GR, Wang GK. R-Duloxetine and N-Methyl Duloxetine as Novel Analgesics Against Experimental Postincisional Pain. Anesth Analg. 2015 Dec 7. [Epub ahead of print] PubMed PMID: 26646348. 8: Kim YI, Pradhan R, Paudel BK, Choi JY, Im HT, Kim JO. Preparation and evaluation of enteric-coated delayed-release pellets of duloxetine hydrochloride using a fluidized bed coater. Arch Pharm Res. 2015 Dec;38(12):2163-71. doi: 10.1007/s12272-015-0590-y. Epub 2015 Jul 17. PubMed PMID: 26183280. 9: Smith EM, Pang H, Ye C, Cirrincione C, Fleishman S, Paskett ED, Ahles T, Bressler LR, Le-Lindqwister N, Fadul CE, Loprinzi C, Shapiro CL; Alliance for Clinical Trials in Oncology. Predictors of duloxetine response in patients with oxaliplatin-induced painful chemotherapy-induced peripheral neuropathy (CIPN): a secondary analysis of randomised controlled trial - CALGB/alliance 170601. Eur J Cancer Care (Engl). 2015 Nov 25. doi: 10.1111/ecc.12421. [Epub ahead of print] PubMed PMID: 26603828. 10: Maciukiewicz M, Marshe VS, Tiwari AK, Fonseka TM, Freeman N, Rotzinger S, Foster JA, Kennedy JL, Kennedy SH, Müller DJ. Genetic variation in IL-1β, IL-2, IL-6, TSPO and BDNF and response to duloxetine or placebo treatment in major depressive disorder. Pharmacogenomics. 2015 Nov;16(17):1919-29. doi: 10.2217/pgs.15.136. Epub 2015 Nov 10. PubMed PMID: 26556688. 11: Choi HS, Park JH, Ahn JH, Hong S, Cho JH, Won MH, Lee CH. The anti-inflammatory activity of duloxetine, a serotonin/norepinephrine reuptake inhibitor, prevents kainic acid-induced hippocampal neuronal death in mice. J Neurol Sci. 2015 Nov 15;358(1-2):390-7. doi: 10.1016/j.jns.2015.10.001. Epub 2015 Oct 3. PubMed PMID: 26453128. 12: Lin ND, Norman H, Regev A, Perahia DG, Li H, Chang CL, Dore DD. Hepatic outcomes among adults taking duloxetine: a retrospective cohort study in a US health care claims database. BMC Gastroenterol. 2015 Oct 14;15:134. doi: 10.1186/s12876-015-0373-4. PubMed PMID: 26467777; PubMed Central PMCID: PMC4607169. 13: Lassen D, Ennis ZN, Damkier P. First-Trimester Pregnancy Exposure to Venlafaxine or Duloxetine and Risk of Major Congenital Malformations: A Systematic Review. Basic Clin Pharmacol Toxicol. 2015 Oct 5. doi: 10.1111/bcpt.12497. [Epub ahead of print] Review. PubMed PMID: 26435496. 14: Harada E, Kato M, Fujikoshi S, Wohlreich MM, Berggren L, Tokuoka H. Changes in energy during treatment of depression: an analysis of duloxetine in double-blind placebo-controlled trials. Int J Clin Pract. 2015 Oct;69(10):1139-48. doi: 10.1111/ijcp.12658. Epub 2015 May 16. PubMed PMID: 25980552; PubMed Central PMCID: PMC4682452. 15: Hirayama Y, Ishitani K, Sato Y, Iyama S, Takada K, Murase K, Kuroda H, Nagamachi Y, Konuma Y, Fujimi A, Sagawa T, Ono K, Horiguchi H, Terui T, Koike K, Kusakabe T, Sato T, Takimoto R, Kobune M, Kato J. Effect of duloxetine in Japanese patients with chemotherapy-induced peripheral neuropathy: a pilot randomized trial. Int J Clin Oncol. 2015 Oct;20(5):866-71. doi: 10.1007/s10147-015-0810-y. Epub 2015 Mar 12. PubMed PMID: 25762165. 16: Carlos F, Espejel L, Novick D, López R, Flores D. Duloxetine for the treatment of painful diabetic peripheral neuropathy in Venezuela: economic evaluation. Medwave. 2015 Sep 25;15(8):e6265. doi: 10.5867/medwave.2015.08.6265. English, Spanish. PubMed PMID: 26460688. 17: Bicer T, Kosker M, Celikay O, Gurdal C. A case of retrobulbar optic neuritis caused by duloxetine. Cutan Ocul Toxicol. 2015 Sep 11:1-3. [Epub ahead of print] PubMed PMID: 26362493. 18: Gao Y, Guo X, Han P, Li Q, Yang G, Qu S, Yue L, Wang CN, Skljarevski V, Dueñas H, Raskin J, Gu L. Treatment of patients with diabetic peripheral neuropathic pain in China: a double-blind randomised trial of duloxetine vs. placebo. Int J Clin Pract. 2015 Sep;69(9):957-66. doi: 10.1111/ijcp.12641. Epub 2015 May 4. PubMed PMID: 25939897; PubMed Central PMCID: PMC4682474. 19: Ball SG, Lipsius S, Escobar R. Validation of the geriatric anxiety inventory in a duloxetine clinical trial for elderly adults with generalized anxiety disorder. Int Psychogeriatr. 2015 Sep;27(9):1533-9. doi: 10.1017/S1041610215000381. Epub 2015 Apr 30. PubMed PMID: 25925598. 20: Miyazato M, Kitta T, Kaiho Y, Oshiro T, Saito S, Chancellor MB, de Groat WC, Yoshimura N. Effects of Duloxetine on Urethral Continence Reflex and Bladder Activity in Rats with Cerebral Infarction. J Urol. 2015 Sep;194(3):842-7. doi: 10.1016/j.juro.2015.03.091. Epub 2015 Mar 21. PubMed PMID: 25804088.