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Duloxetine, sold under the brand name Cymbalta among others,[1] is a medication used to treat major depressive disorder, generalized anxiety disorder, obsessive–compulsive disorder, fibromyalgia, neuropathic pain, central sensitization, and other types of chronic pain.[9][10] It is taken by mouth.[9]
Duloxetine is a serotonin–norepinephrine reuptake inhibitor (SNRI).[11] The precise mechanism for its antidepressant and anxiolytic effects is not known.[9]
Common side effects include dry mouth, nausea, constipation, loss of appetite, drowsiness, sexual problems, and increased sweating.[12] Severe side effects include an increased risk of suicide, serotonin syndrome, mania, and liver problems.[9] Antidepressant withdrawal syndrome may occur if stopped.[9] Use during the later part of pregnancy may increase the risk of bleeding or cause complications for the fetus.[12]
Duloxetine was approved for medical use in the United States[9][13] and the European Union in 2004.[4][6] It is available as a generic medication.[11] In 2023, it was the 31st most commonly prescribed medication in the United States, with more than 18 million prescriptions.[14][15]
Medical uses
The main uses of duloxetine are in major depressive disorder, generalized anxiety disorder, neuropathic pain, chronic musculoskeletal pain, and fibromyalgia.[3][9][16][17]
Duloxetine is recommended as a first-line agent for the treatment of chemotherapy-induced neuropathy by the American Society of Clinical Oncology,[18] as a first-line therapy for fibromyalgia in the presence of mood disorders by the German Interdisciplinary Association for Pain Therapy,[19] as a Grade B recommendation for the treatment of diabetic neuropathy by the American Association for Neurology[20] and as a level A recommendation in certain neuropathic states by the European Federation of Neurological Societies.[21]
Painful diabetic peripheral neuropathy
A 2014 Cochrane review concluded that duloxetine is beneficial in the treatment of diabetic neuropathy and fibromyalgia but that more comparative studies with other medicines are needed.[22] The French medical journal Prescrire concluded that duloxetine is no better than other available agents and has a greater risk of side effects.[23] Whereas duloxetine has shown efficacy in treating painful diabetic peripheral neuropathy by blocking late Nav 1.7 sodium ion channels and increasing norepinephrine, serotonin, and dopamine in the central nervous system (CNS) and while improving mean NPRS scores and achieving a ≥50% pain response in more patients compared to placebo, it has been associated with potentially serious adverse reactions including hepatotoxicity, serotonin syndrome, severe skin reactions, increased risk of bleeding, increased blood pressure and sexual dysfunction.
Duloxetine
Researchers requiring consistent dual SERT/NET inhibition face variable SNRI selectivity that compromises assay reproducibility. Duloxetine delivers a stable 9-fold SERT/NET ratio (Ki: 0.8/7.5 nM) across all doses, validated for transporter binding and functional assays with minimal off-target binding. • Reliable in vivo dual inhibition at 5-10 mg/kg (rat); no dose escalation required • Defined CYP2D6 inhibition profile and drug-drug interaction benchmarks (e.g., ~60% AUC increase with paroxetine) for translational studies • Clinically validated in chemotherapy-induced peripheral neuropathy (2024 RCT), supporting pain signaling and oncology supportive care research
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Technical Parameters
Basic Identity
| Product Name | Duloxetine |
|---|---|
| CAS | 116539-59-4 |
| Synonyms |
Cymbalta, duloxetine, Duloxetine Ethanedioate (1:1), (+-)-isomer – T353987, Duloxetine HCl, duloxetine hydrochloride, duloxetine, (+)-isomer, HCl, Duloxetine, Hydrochloride, Duloxetine, LY 227942, LY 248686, LY-227942, LY-248686, LY227942, LY248686, N-methyl-3-(1-naphthalenyloxy)-2-thiophenepropanamine, N-methyl-3-(1-naphthalenyloxy)-3-(2-thiophene)propanamide
|
| Molecular Formula | C18H19NOS |
| Molecular Weight | 297.4 g/mol |
Structural Identifiers
| SMILES | CNCCC(C1=CC=CS1)OC2=CC=CC3=CC=CC=C32 |
|---|---|
| InChI | InChI=1S/C18H19NOS/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/t17-/m0/s1 |
| InChIKey | ZEUITGRIYCTCEM-KRWDZBQOSA-N |
Commercial & Availability
| Standard Pack Sizes | 5 mg / 10 mg / 25 mg / Bulk Custom |
|---|---|
| Availability | In Stock |
| Custom Synthesis | Available on request |
Handling Information
| Appearance | Solid powder |
|---|---|
| Solubility | 2.96e-03 g/L |
| Storage | Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years). |
Structure & Identifiers
Duloxetine Specification and Classification
Duloxetine is a serotonin-norepinephrine reuptake inhibitor (SNRI) that acts as a dual inhibitor of human serotonin (5-HT) and norepinephrine (NE) transporters with high affinity [1]. Its molecular formula is C18H19NOS, and it is commercially available as the hydrochloride salt for research applications . The compound is extensively used in neuroscience, pharmacology, and drug discovery research focused on mood disorders, neuropathic pain, and transporter pharmacology.
Duloxetine vs Venlafaxine and Milnacipran: Key Differences
Despite belonging to the same SNRI class, duloxetine, venlafaxine, and milnacipran exhibit pronounced differences in transporter binding affinity, selectivity ratios, and dose-response characteristics that preclude experimental interchangeability [1]. Venlafaxine displays a 30-fold selectivity for serotonin over norepinephrine and requires higher doses to achieve dual inhibition, whereas duloxetine maintains a 9-fold selectivity ratio and inhibits both transporters at all doses [2]. Milnacipran exhibits a balanced 1:1 inhibition ratio, a profile distinct from both duloxetine and venlafaxine [3]. These pharmacological divergences translate into different in vivo potency ranges, metabolic pathways, and adverse effect profiles that directly impact experimental design, dose selection, and interpretation of results.
Duloxetine Quantitative Differentiation Evidence
Human NET and SERT Binding Affinity Comparison
In a direct comparative in vitro study, duloxetine inhibited binding to the human norepinephrine (NE) transporter with a Ki of 7.5 nM and to the serotonin (5-HT) transporter with a Ki of 0.8 nM, yielding a Ki ratio (NET/SERT) of 9 [1]. Under identical experimental conditions, venlafaxine exhibited Ki values of 2480 nM and 82 nM for NET and SERT, respectively, with a Ki ratio of 30 [1].
Comparator (Venlafaxine): NET Ki 2480 nM, SERT Ki 82 nM, ratio 30
~310-fold higher NET affinity, ~102-fold higher SERT affinity
In Vivo Transporter Occupancy in Rat Brain
In ex vivo binding studies measuring transporter occupancy in rat brain, duloxetine inhibited binding to 5-HT transporters with an ED50 of 0.03 mg/kg and to NE transporters with an ED50 of 0.7 mg/kg [1]. Venlafaxine required substantially higher doses, with ED50 values of 2 mg/kg for SERT and 54 mg/kg for NET [1].
Comparator: SERT ED50 2 mg/kg, NET ED50 54 mg/kg
~67-fold lower dose for SERT, ~77-fold lower for NET occupancy
Duloxetine (CAS 116539-59-4), also referenced in development literature as LY248686, is a selective serotonin-norepinephrine reuptake inhibitor (SNRI) active pharmaceutical ingredient used as the core therapeutic compound. It is sourced by pharmaceutical manufacturers as a bulk API for formulation into branded and generic prescription medications. The primary application is in the manufacture of delayed-release oral capsules.
These capsules target major depressive disorder, generalized anxiety disorder, and diabetic peripheral neuropathic pain. These are product categories with sustained global generic demand for manufacturers. Contract manufacturers and generic drug developers procure this API to produce enteric-coated pellet formulations. These pellets protect the compound through gastric transit for optimal patient absorption.
Specialty pharma companies also incorporate it into combination or modified-release formats under development. Procurement of this API is subject to ICH Q7 GMP compliance requirements for all suppliers. Supplier qualification and documentation are central purchasing considerations for this material. It is supplied as a white to off-white crystalline powder in bulk quantities suited to commercial-scale manufacturing.
It is available in hydrochloride salt form, which is the standard pharmaceutical grade used in registered drug products. Certificates of Analysis aligned with USP and EP monograph specifications are standard. These documents are expected by qualified buyers to ensure the highest quality standards are met. This ensures the material is suitable for use in finished-dose antidepressant and pain management drug products.
- CAS No.
- 116539-59-4
- Chemical Name:
- Duloxetine
- Synonyms
- DULOXETIN;DULOXETINE HCI;DULOXETINE-D3;(S)-DULOXETINE;(3S)-N-methyl-3-naphthalen-1-yloxy-3-thiophen-2-yl-propan-1-amine;CS-559;DULOXETINE;(+)-Duloxetine;Duloxetine Hcl(S);Duloxetine, >=99%
- CBNumber:
- CB8670379
- Molecular Formula:
- C18H19NOS
- Molecular Weight:
- 297.42
- MDL Number:
- MFCD06801358
- MOL File:
- 116539-59-4.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Product description | Number | Pack Size | Price |
| Duloxetine 99.92% | CS-2885 | 5mg | $43 |
| Duloxetine 99.92% | CS-2885 | 10mg | $65 |
| Duloxetine 99.92% | CS-2885 | 25mg | $104 |
| Duloxetine 99.92% | CS-2885 | 50mg | $151 |
| Duloxetine 99.92% | CS-2885 | 100mg | $214 |
| More product size | |||
| Boiling point | 466.2±40.0 °C(Predicted) |
|---|---|
| Density | 1.158±0.06 g/cm3(Predicted) |
| storage temp. | Store at -20°C |
| solubility | Soluble in DMSO |
| form | Oil |
| pka | 10.02±0.10(Predicted) |
| color | Light brown to yellow |
| BCS Class | 2 |
| InChI | InChI=1/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-;/s3 |
| InChIKey | BFFSMCNJSOPUAY-VOPAOICTNA-N |
| SMILES | C1(=CC=CS1)[C@H](CCNC)OC1=CC=CC2=CC=CC=C12.Cl |&1:5,r| |
| FDA UNII | O5TNM5N07U |
| ATC code | N06AX21 |
| EPA Substance Registry System | 2-Thiophenepropanamine, N-methyl-?-(1-naphthalenyloxy)-, (?S)- (116539-59-4) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319 |
| Precautionary statements | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 |
| Hazardous Substances Data | 116539-59-4(Hazardous Substances Data) |
Duloxetine price More Price(33)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| ChemScene | CS-2885 | Duloxetine 99.92% | 116539-59-4 | 5mg | $43 | 2026-06-04 | Buy |
| ChemScene | CS-2885 | Duloxetine 99.92% | 116539-59-4 | 10mg | $65 | 2026-06-04 | Buy |
| ChemScene | CS-2885 | Duloxetine 99.92% | 116539-59-4 | 25mg | $104 | 2026-06-04 | Buy |
| ChemScene | CS-2885 | Duloxetine 99.92% | 116539-59-4 | 50mg | $151 | 2026-06-04 | Buy |
| ChemScene | CS-2885 | Duloxetine 99.92% | 116539-59-4 | 100mg | $214 | 2026-06-04 | Buy |
Duloxetine Chemical Properties, Uses, Production
History
Duloxetine is a second-generation antidepressant. Its mechanism of action involves inhibiting the reuptake of serotonin and norepinephrine by neurons, thereby increasing the concentration of these two neurotransmitters in the synaptic cleft, thus improving mood and relieving pain.
Initial Approval (2004): Cymbalta was initially approved for the treatment of major depressive disorder (MDD). In the same year, it also received approval for the treatment of diabetic peripheral neuropathy (DPNP), making it a unique drug capable of simultaneously addressing two common and frequently co-occurring conditions: depression and neuropathic pain.
Expansion of Indications: Subsequently, Eli Lilly expanded its indications through clinical trials, making it a multi-functional drug. The most significant expansions include generalized anxiety disorder (GAD) (2007), fibromyalgia (2008), and chronic musculoskeletal pain (2010). The approval of these indications secured Cymbalta a significant position in the pain management market, making it one of Eli Lilly’s blockbuster drugs.
Patent Expiration (2013): In December 2013, Cymbalta’s primary patent in the United States expired, a phenomenon known as the “patent cliff.”
Following the patent expiration, the FDA quickly approved several generic versions (generic name: duloxetine), leading to a significant drop in sales, but also enabling wider use of the drug at a lower price.
Uses
Antidepressant.
Definition
ChEBI: (S)-duloxetine is a duloxetine. It is an enantiomer of a (R)-duloxetine.
brand name
Cymbalta (Lilly).
General Description
Duloxetine (Cymbalta) is a newer antidepressant. It islargely like venlafaxine, which is an SNERI (selective norepinephrinereuptake inhibitor).
Pharmacokinetics
Duloxetine appears to be fairly well absorbed after oral doses, with peak plasma levels in 6 to 10 hours and linear pharmacokinetics. The drug is extensively metabolized in the liver to active metabolites, with 72% of an oral dose primarily excreted in the urine as conjugated metabolites and up to 15% appearing in the feces.
N-demethylation to an active metabolite (CYP2D6) and hydroxylation of the naphthyl ring (CYP1A2) at either the 4-, 5-, or 6-positions are the main metabolic pathways for duloxetine. Its metabolites are primarily excreted into the urine as glucuronide, sulfate, and O-methylated conjugation products. The major metabolites found in plasma also were found in the urine. Preclinical data for 4-hydroxyduloxetine suggests it has a similar pharmacological profile to duloxetine, with selective inhibition of SERT but less activity at the NET.
Clinical Use
Duloxetine has been approved for the treatment of depression and diabetic peripheral neuropathic pain. It is another analogue in the line of fluoxetine-based products from Lilly, in which the phenyl and phenoxy groups of fluoxetine have been respectively replaced with the benzene isostere, thiophene, and a naphthyloxy group (previously described under fluoxetine). Duloxetine exhibits dual inhibition with high affinity for the SERTs and NETs, with a five times preferential inhibition of the SERT. Duloxetine appears to be a more potent in vitro blocker of SERTs and NETs than venlafaxine. In humans, duloxetine has a low affinity for the other neuroreceptors, suggesting low incidence of unwanted adverse effects.
Synthesis
Reaction of 2-acetylthiophene with paraformaldehyde and dimethylamine in ethanol gives 3-(dimethylamino)-1-(2-thienyl)- 1-propanone, which is enantioselectively reduced with a 2:1 complex of (2R,3S)-4-(dimethylamino)- 3-methyl-1,2-diphenyl-2-butanol and LiAlH4 in toluene to yield (S)-3-(dimethylamino)- 1-(2-thienyl)-1-propanol. The condensation of (S)-3-(dimethylamino)-1-(2- thienyl)-1-propanol with 1-fluoronaphthalene catalyzed by NaH in DMSO affords the corresponding naphthyl ether (S)-N,N-dimethyl-3- (naphthalen-1-yloxy)-3-(thiophen-2-yl)propan- 1-amine, which is finally monodemethylated with 2,2,2-trichloroethyl chloroformate and zinc in toluene and treated with oxalic acid .
Drug interactions
Potentially hazardous interactions with other drugs
Antibacterials: metabolism inhibited by ciprofloxacin – avoid.
Anticoagulants: possibly increased risk of bleeding with dabigatran.
Other CNS medication: enhanced effect.
Antidepressants: avoid with MAOIs, moclobemide, St John’s wort, tryptophan, venlaflaxine, amitriptyline, clomipramine and SSRIs due to increased risk of serotonin syndrome; increased risk of side effects with tricyclic antidepressants; fluvoxamine decreases the clearance of duloxetine by 77% – avoid; possible increased risk of convulsions with vortioxetine.
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Dapoxetine: avoid concomitant use.
Methylthioninium: risk of CNS toxicity – avoid if possible.
Metabolism
Duloxetine is extensively metabolised and the metabolites are excreted principally in urine. Both cytochromes P450-2D6 and 1A2 catalyse the formation of the two major metabolites, glucuronide conjugate of 4-hydroxy duloxetine and sulphate conjugate of 5-hydroxy, 6-methoxy duloxetine. Based upon in vitro studies, the circulating metabolites of duloxetine are considered pharmacologically inactive
Duloxetine Preparation Products And Raw materials
Raw materials
Other Names (Synonyms)
(3S)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine|(S)-Duloxetine|Yentreve|2-Thiophenepropanamine, N-methyl-gamma-(1-naphthalenyloxy)-, (gammaS)-|(3S)-N-methyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine|methyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine|O5TNM5N07U
Functional Monoamine Depletion Blockade
In a functional in vivo model of neurotransmitter depletion, duloxetine blocked p-chloroamphetamine-induced 5-HT depletion with an ED50 of 2.3 mg/kg and 6-hydroxydopamine-induced NE depletion with an ED50 of 12 mg/kg [1]. Venlafaxine exhibited ED50 values of 5.9 mg/kg and 94 mg/kg, respectively [1].
Comparator: 5-HT ED50 5.9 mg/kg, NE ED50 94 mg/kg
2.6-fold lower for 5-HT, 7.8-fold lower for NE blockade
CYP2D6 Inhibition Profile
Duloxetine is classified as a moderate inhibitor of CYP2D6 [1]. Concomitant administration of duloxetine (40 mg once daily) with paroxetine (20 mg once daily) increased duloxetine AUC by approximately 60% [2]. In contrast, paroxetine and fluoxetine are potent CYP2D6 inhibitors [3].
Potent inhibitors: paroxetine, fluoxetine
Pharmacokinetics in Hepatic Impairment
In a study comparing six cirrhotic subjects (Child-Pugh class B) with six healthy controls following a single 20 mg oral dose, duloxetine elimination half-life was significantly prolonged in cirrhosis (47.8 hours vs 13.5 hours, p < 0.05) [1]. Apparent clearance was markedly reduced (24 L/h vs 160 L/h, p < 0.05) [1].
3.5-fold half-life extension, 6.7-fold clearance reduction
Efficacy in Taxane-Induced Neuropathy
A 2024 randomized clinical trial compared duloxetine and venlafaxine in breast cancer patients with acute symptomatic taxane-induced neuropathy [1]. Both groups exhibited decreased neuropathic pain, and the study concluded that both drugs effectively treat neuropathic symptoms such as paresthesia, tingling, and itching, with no statistically significant difference between interventions on any variables measured [1].
Duloxetine Research and Industrial Applications
In Vitro Transporter Assay and Reference Compound
Duloxetine serves as a high-affinity reference ligand for serotonin (SERT) and norepinephrine (NET) transporter binding and functional assays. Its well-characterized Ki values (SERT Ki = 0.8 nM; NET Ki = 7.5 nM) and 9-fold selectivity ratio make it suitable for assay validation, competitive binding studies, and as a positive control in transporter inhibition screens [1]. Its minimal off-target binding to dopaminergic, adrenergic, cholinergic, and other receptor systems ensures assay specificity [2].
In Vivo Neuropharmacology in Rodent Models
The in vivo potency profile of duloxetine—with ex vivo SERT ED50 of 0.03 mg/kg and NET ED50 of 0.7 mg/kg in rats—enables precise dose selection for behavioral and neurochemical studies [1]. Researchers can confidently achieve dual transporter inhibition at doses as low as 5-10 mg/kg (oral or intraperitoneal), avoiding the dose-escalation complexities associated with venlafaxine, which requires >50 mg/kg for equivalent NET occupancy [1]. This makes duloxetine particularly suitable for chronic dosing paradigms and studies requiring sustained dual transporter inhibition.
Drug Metabolism and CYP2D6 Inhibition
Duloxetine is extensively metabolized by CYP1A2 and CYP2D6, with over 96% plasma protein binding [1]. Its moderate CYP2D6 inhibition profile provides a useful comparator to potent inhibitors like paroxetine and fluoxetine [2]. Known drug interaction magnitudes (e.g., ~60% AUC increase with paroxetine 20 mg; ~6-fold AUC increase with fluvoxamine 100 mg) offer quantitative benchmarks for designing and interpreting drug-drug interaction studies [3].
Taxane-Induced Neuropathic Pain Model
A 2024 head-to-head randomized trial confirmed that duloxetine is effective in managing taxane-induced neuropathic symptoms in breast cancer patients, with efficacy comparable to venlafaxine [1]. This clinical validation positions duloxetine as a viable compound for preclinical and translational research investigating chemotherapy-induced peripheral neuropathy, pain signaling pathways, and adjunctive therapies in oncology supportive care.
Technical Documentation Hub
Structured technical reading across foundational, methodological, troubleshooting, and validation/comparative pathways. Use the hub when you need more detail before procurement.
Duloxetine’s Mechanism of Action in Neuropathic Pain: A Technical Guide
Unveiling the Off-Target Landscape of Duloxetine: A Technical Guide for Researchers
The Effect of Duloxetine on Dopamine in the Prefrontal Cortex: A Technical Whitepaper
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Jul 27, 2026 · Duloxetine (CAS 116539-59-4) information, including chemical properties, structure, melting point, boiling point, …
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Boiling point: 466.2±40.0 °C (Predicted)
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solubility: Soluble in DMSO
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Density: 1.158±0.06 g/cm3 (Predicted)
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storage temp.: Store at -20°C
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