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Chemistry

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Also known as: 93413-62-8, O-desmethylvenlafaxine, 4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol, 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol, O-desmethyl venlafaxine, Dvs 233
Molecular Formula
C16H25NO2
Molecular Weight
263.37  g/mol
InChI Key
KYYIDSXMWOZKMP-UHFFFAOYSA-N
FDA UNII
NG99554ANW

Desvenlafaxine Succinate
A cyclohexanol and phenol derivative and metabolite of venlafaxine that functions as a SEROTONIN AND NORADRENALINE REUPTAKE INHIBITOR (SNRI) and is used as an ANTIDEPRESSIVE AGENT.
Desvenlafaxine is a Serotonin and Norepinephrine Reuptake Inhibitor. The mechanism of action of desvenlafaxine is as a Norepinephrine Uptake Inhibitor, and Serotonin Uptake Inhibitor, and Cytochrome P450 2D6 Inhibitor.
1 2D Structure

Desvenlafaxine Succinate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
2.1.2 InChI
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
2.1.3 InChI Key
KYYIDSXMWOZKMP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CC(C1=CC=C(C=C1)O)C2(CCCCC2)O
2.2 Other Identifiers
2.2.1 UNII
NG99554ANW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(1-hydroxycyclohexyl)-2-((4-hydroxyphenyl)ethyl)dimethylammonium 3-carboxypropanoate Monohydrate

2. 4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol

3. 45,233, Wy

4. 45233, Wy

5. Desvenlafaxine Succinate

6. Monohydrate, O-desmethylvenlafaxine Succinate

7. O Desmethylvenlafaxine

8. O Desmethylvenlafaxine Succinate

9. O Desmethylvenlafaxine Succinate Monohydrate

10. O-desmethylvenlafaxine

11. O-desmethylvenlafaxine Succinate

12. O-desmethylvenlafaxine Succinate Monohydrate

13. Pristiq

14. Succinate Monohydrate, O-desmethylvenlafaxine

15. Succinate, Desvenlafaxine

16. Succinate, O-desmethylvenlafaxine

17. Wy 45,233

18. Wy 45233

19. Wy-45,233

20. Wy-45233

21. Wy45,233

22. Wy45233

2.3.2 Depositor-Supplied Synonyms

1. 93413-62-8

2. O-desmethylvenlafaxine

3. 4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol

4. 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol

5. O-desmethyl Venlafaxine

6. Dvs 233

7. Newven

8. D-veniz

9. D,l-o-desmethylvenlafaxine

10. Mdd-xr

11. Desvenlafaxine (inn)

12. Desvenlafaxine [inn]

13. D,l-o-desmethyl Venlafaxine

14. Ng99554anw

15. Chebi:83527

16. 93413-62-8 (free Base)

17. 1-[2-(dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol

18. Phenol, 4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)-

19. Phenol, 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-

20. Desvenlafaxine [inn:ban]

21. Khedezla

22. Odv

23. Venlafaxine O-desmethyl

24. Unii-ng99554anw

25. O-desvenlafaxine

26. Hsdb 7993

27. Khedezla (tn)

28. O-desmethylvenlafaxine (odv)

29. O-desmethyl-venlafaxine

30. Desvenlafaxine [mi]

31. Ec 700-516-2

32. Chembl1118

33. Schembl34864

34. Mls006010042

35. Desvenlafaxine [vandf]

36. O-desmethylvenlafaxine Solution

37. (s)-desmethyl Venlafaxine D6

38. Gtpl7158

39. Desvenlafaxine [usp-rs]

40. Desvenlafaxine [who-dd]

41. 4-[2-dimethylamino-1-(1-hydroxycyclohexyl)ethyl]phenol

42. R-(-)-o-desmethyl-venlafaxine

43. S-(+)-o-desmethyl-venlafaxine

44. Bdbm86748

45. Dtxsid40869118

46. Hms3652k16

47. Hms3885f05

48. Amy15413

49. Bcp28517

50. D,l-o-desmethyl Venlafaxine-[d6]

51. Hy-b0602

52. Desvenlafaxine [orange Book]

53. Mfcd00871934

54. Pdsp1_001804

55. Pdsp2_001787

56. S4113

57. Desvenlafaxine [usp Monograph]

58. Akos015896311

59. Ccg-267081

60. Db06700

61. Ds-1282

62. Sb17444

63. Nsc_6918664

64. Ncgc00345883-04

65. Ncgc00345883-07

66. Smr004701214

67. O-desmethylvenlafaxine, Analytical Standard

68. Cas_386750-22-7

69. D5598

70. Ft-0654519

71. Ft-0666245

72. Ft-0666246

73. Sw219514-2

74. O-desmethylvenlafaxine 0.1 Mg/ml In Methanol

75. D07793

76. Ab01563022_01

77. 413d628

78. A844583

79. Q2419445

80. Venlafaxine O-desmethyl 100 Microg/ml In Acetonitrile

81. 4-[2-dimethyamino-1-(1-hydroxycyclohexyl)ethyl]phenol

82. 1-[2-dimethylamino-1-(4-hydroxyphenyl)ethyl]cyclohexanol

83. 4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)-ethyl)phenol

84. 4-[2-(dimethylamino)-1-(1-oxidanylcyclohexyl)ethyl]phenol

85. 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol #

86. (rs)-1-[2-(dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol

87. O-desmethylvenlafaxine Solution, 1.0 Mg/ml In Methanol, Certified Reference Material

88. O-desmethylvenlafaxine Solution, 100 Mug/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.3.3 Other Synonyms

1. O-desmethylvenlafaxine

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 263.37 g/mol
Molecular Formula C16H25NO2
XLogP32.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass263.188529040 g/mol
Monoisotopic Mass263.188529040 g/mol
Topological Polar Surface Area43.7 Ų
Heavy Atom Count19
Formal Charge0
Complexity266
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDesvenlafaxine
PubMed HealthDesvenlafaxine (By mouth)
Drug ClassesAntidepressant
Drug LabelKHEDEZLA Extended-release Tablets for oral administration contains desvenlafaxine, a structurally novel SNRI for the treatment of MDD. Desvenlafaxine (O-desmethylvenlafaxine) is the major active metabolite of the antidepressant venlafaxine, a medicat...
Active IngredientDesvenlafaxine; Desvenlafaxine fumarate
Dosage FormTablet, extended release
RouteOral
Strengtheq 100mg base; 100mg; eq 50mg base; 50mg
Market StatusPrescription
CompanyAlembic Pharms; Sun Pharma Global

2 of 2  
Drug NameDesvenlafaxine
PubMed HealthDesvenlafaxine (By mouth)
Drug ClassesAntidepressant
Drug LabelKHEDEZLA Extended-release Tablets for oral administration contains desvenlafaxine, a structurally novel SNRI for the treatment of MDD. Desvenlafaxine (O-desmethylvenlafaxine) is the major active metabolite of the antidepressant venlafaxine, a medicat...
Active IngredientDesvenlafaxine; Desvenlafaxine fumarate
Dosage FormTablet, extended release
RouteOral
Strengtheq 100mg base; 100mg; eq 50mg base; 50mg
Market StatusPrescription
CompanyAlembic Pharms; Sun Pharma Global

4.2 Therapeutic Uses

Antidepressive Agents; Neurotransmitter Uptake Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 2011)


Used to treat major depressive, generalized anxiety, social anxiety and panic disorders /Desvenlafaxine succinate monohydrate/

FDA; RxList. The Internet Drug Index. Top 200 Drugs - US Only. Available from, as of Oct 31, 2011: https://www.rxlist.com/script/main/hp.asp


Like some other selective serotonin and norepinephrine reuptake inhibitors (SNRIs) and selective serotonin-reuptake inhibitors (SSRIs), desvenlafaxine succinate has been studied for the management of vasomotor symptoms in postmenopausal women. /NOT included in US product labeling/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 2352


Desvenlafaxine succinate is used in the treatment of major depressive disorder in adults. /Included in US product labeling/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 2352


Recent reviews have questioned whether the serotonin-norepinephrine reuptake inhibitor (SNRI) desvenlafaxine succinate offers any practical clinical advantages over existing SNRIs. The following case is one instance where it appears that this SNRI offers unique safety and benefit. Presented is a case report of a patient with Gilbert's syndrome, longstanding social phobia, and more recent depressive disorder not otherwise specified, who was found to have elevated liver transaminases when prescribed both duloxetine and venlafaxine. The patient subsequently responded to desvenlafaxine but without liver abnormalities. In this patient with Gilbert's Syndrome, desvenlafaxine's lack of metabolism through the cytochrome P450 (CYP) 2D6 pathway may explain the avoidance of these abnormalities and thus suggests a possible therapeutic role for this SNRI in similarly susceptible patients.

PMID:20394185 Feinberg SS et al; CNS Spectr. 2010 Jan;15(1):53-5 (2010)


4.3 Drug Warning

/BOXED WARNING/ WARNING: SUICIDAL THOUGHTS AND BEHAVIORS. Antidepressants increased the risk of suicidal thoughts and behavior in children, adolescents, and young adults in short-term studies. These studies did not show an increase in the risk of suicidal thoughts and behavior with antidepressant use in patients over age 24; there was a reduction in risk with antidepressant use in patients aged 65 and older. In patients of all ages who are started on antidepressant therapy, monitor closely for worsening, and for emergence of suicidal thoughts and behaviors. Advise families and caregivers of the need for close observation and communication with the prescriber. Pristiq is not approved for use in pediatric patients.

US Natl Inst Health; DailyMed. Current Medication Information for PRISTIQ (desvenlafaxine succinate) tablet, extended release (Updated: March 2015). Available from, as of April 23, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0f43610c-f290-46ea-d186-4f998ed99fce


In patients with moderate or severe renal impairment or end-stage renal disease (ESRD) the clearance of Pristiq was decreased, thus prolonging the elimination half-life of the drug. As a result, there were potentially clinically significant increases in exposures to Pristiq. Dosage adjustment (50 mg every other day) is necessary in patients with severe renal impairment or ESRD. The doses should not be escalated in patients with moderate or severe renal impairment or ESRD.

US Natl Inst Health; DailyMed. Current Medication Information for PRISTIQ (desvenlafaxine succinate) tablet, extended release (January 2011). Available from, as of October 25, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=Desvenlafaxine


Sustained increases in blood pressure have been reported. In controlled studies, sustained hypertension occurred in 0.7-2.3% of patients receiving desvenlafaxine dosages from 50-400 mg daily, with a suggestion of a higher incidence (2.3%) in those receiving 400 mg of the drug daily. In addition, some cases of elevated blood pressure requiring immediate treatment have been reported with desvenlafaxine. Sustained blood pressure increases could have adverse consequences in patients receiving the drug. Therefore, the manufacturer recommends that preexisting hypertension be controlled before initiating desvenlafaxine therapy and that regular blood pressure monitoring be performed in patients receiving the drug. Desvenlafaxine should be used cautiously in patients with preexisting hypertension or other underlying conditions that may be compromised by increases in blood pressure. Dosage reduction or drug discontinuance should be considered in patients who experience a sustained increase in blood pressure during therapy.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 2353


Treatment with selective serotonin-reuptake inhibitors (SSRIs) and selective serotonin and norepinephrine reuptake inhibitor (SNRIs), including desvenlafaxine, may result in hyponatremia.In many cases, hyponatremia appears to be due to the syndrome of inappropriate antidiuretic hormone secretion (SIADH). Cases with serum sodium concentrations lower than 110 mmol/L have been reported. Geriatric individuals and patients receiving diuretics or who are otherwise volume depleted may be at greater risk of developing hyponatremia. Signs and symptoms of hyponatremia include headache, difficulty concentrating, memory impairment, confusion, weakness, and unsteadiness, which may lead to falls; more severe and/or acute cases have been associated with hallucinations, syncope, seizures, coma, respiratory arrest, and death. Initiate appropriate medical intervention and consider drug discontinuance in patients with symptomatic hyponatremia.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 2353


For more Drug Warnings (Complete) data for Desvenlafaxine (20 total), please visit the HSDB record page.


4.4 Drug Indication

Desvenlafaxine is indicated for the treatment of major depressive disorder in adults.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Desvenlafaxine is a selective serotonin and norepinephrine reuptake inhibitor. It lacks significant activity on muscarinic-cholinergic, H1-histaminergic, or α1-adrenergic receptors in vitro. Desvenlafaxine does not appear to exert activity against calcium, chloride, potassium and sodium ion channels and also lacks monoamine oxidase (MAO) inhibitory activity. It was also shown to lack significant activity again the cardiac potassium channel, hERG, in vitro. Compared to other SNRIs, desvenlafaxine undergoes simple metabolism, has a low risk of drug-drug interactions and does not have to be extensively titrated to reach a therapeutic dose.


5.2 MeSH Pharmacological Classification

Serotonin and Noradrenaline Reuptake Inhibitors

Drugs that selectively block or suppress the plasma membrane transport of SEROTONIN and NORADRENALINE into axon terminals and are used as ANTIDEPRESSIVE AGENTS. (See all compounds classified as Serotonin and Noradrenaline Reuptake Inhibitors.)


Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DESVENLAFAXINE
5.3.2 FDA UNII
NG99554ANW
5.3.3 Pharmacological Classes
Norepinephrine Uptake Inhibitors [MoA]; Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Cytochrome P450 2D6 Inhibitors [MoA]
5.4 ATC Code

N06AX23

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448


N06AX23

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448


N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX23 - Desvenlafaxine


5.5 Absorption, Distribution and Excretion

Absorption

Oral bioavailability is approximately 80% and is unaffected by food. Peak plasma concentration is reached in 7.5 hours.


Route of Elimination

Desvenlafaxine is mainly excreted in the urine. 45% of the dose is unchanged in the urine, 19% is excreted as a glucuronide metabolite, and <5% is excreted as N,O-didesmethylvenlafaxine. No dosage adjustment is necessary for gender, ethnicity, food, or combination with other psychotropics.


Volume of Distribution

3.4L/kg.


The plasma protein binding of desvenlafaxine is low (30%) and is independent of drug concentration. The desvenlafaxine volume of distribution at steady-state following intravenous administration is 3.4 L/kg, indicating distribution into nonvascular compartments.

US Natl Inst Health; DailyMed. Current Medication Information for PRISTIQ (desvenlafaxine succinate) tablet, extended release (January 2011). Available from, as of October 25, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=Desvenlafaxine


The absolute oral bioavailability of Pristiq after oral administration is about 80%. Mean time to peak plasma concentrations (Tmax) is about 7.5 hours after oral administration.

US Natl Inst Health; DailyMed. Current Medication Information for PRISTIQ (desvenlafaxine succinate) tablet, extended release (January 2011). Available from, as of October 25, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=Desvenlafaxine


Approximately 45% of desvenlafaxine is excreted unchanged in urine at 72 hours after oral administration. Approximately 19% of the administered dose is excreted as the glucuronide metabolite and < 5% as the oxidative metabolite (N,O-didesmethylvenlafaxine) in urine

US Natl Inst Health; DailyMed. Current Medication Information for PRISTIQ (desvenlafaxine succinate) tablet, extended release (January 2011). Available from, as of October 25, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=Desvenlafaxine


Desvenlafaxine is excreted into human milk.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 2354


For more Absorption, Distribution and Excretion (Complete) data for Desvenlafaxine (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Desvenlafaxine also undergoes oxidative N-demethylation via cytochrome P450 3A4 to a minor extent. CYP2D6 is not involved with the metabolism of desvenlafaxine.


Desvenlafaxine is primarily metabolized by conjugation (mediated by UGT isoforms) and, to a minor extent, through oxidative metabolism. CYP3A4 is the cytochrome P450 isozyme mediating the oxidative metabolism (N-demethylation) of desvenlafaxine. The CYP2D6 metabolic pathway is not involved, and after administration of 100 mg, the pharmacokinetics of desvenlafaxine was similar in subjects with CYP2D6 poor and extensive metabolizer phenotype. ... Approximately 19% of the administered dose is excreted as the glucuronide metabolite and < 5% as the oxidative metabolite (N,O-didesmethylvenlafaxine) in urine

US Natl Inst Health; DailyMed. Current Medication Information for PRISTIQ (desvenlafaxine succinate) tablet, extended release (January 2011). Available from, as of October 25, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=Desvenlafaxine


5.7 Biological Half-Life