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93413-69-5 molecular structure
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1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

ChemBase ID: 170
Molecular Formular: C17H27NO2
Molecular Mass: 277.40178
Monoisotopic Mass: 277.20417911
SMILES and InChIs

SMILES:
OC1(C(CN(C)C)c2ccc(OC)cc2)CCCCC1
Canonical SMILES:
COc1ccc(cc1)C(C1(O)CCCCC1)CN(C)C
InChI:
InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3
InChIKey:
PNVNVHUZROJLTJ-UHFFFAOYSA-N

Cite this record

CBID:170 http://www.chembase.cn/molecule-170.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
IUPAC Traditional name
venlafaxine
Brand Name
Effexor
Effexor XR
Elafax
Synonyms
Venlafaxina [INN-Spanish]
Venlafaxine [INN:Ban]
Venlafaxinum [INN-Latin]
Venlafaxine
1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol
(+/-)-Venlafaxine
Trevilor
Velafax
Venlafaxin
Venlafexine
D,L-Venlafaxine
CAS Number
93413-69-5
PubChem SID
46504593
160963633
PubChem CID
5656
CHEBI ID
9943
ATC CODE
N06AX16
CHEMBL
637
Chemspider ID
5454
DrugBank ID
DB00285
Unique Ingredient Identifier
GRZ5RCB1QG
Wikipedia Title
Venlafaxine

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
V119995 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.420212  H Acceptors
H Donor LogD (pH = 5.5) -0.412785 
LogD (pH = 7.4) 1.221672  Log P 2.7385228 
Molar Refractivity 83.0242 cm3 Polarizability 32.606743 Å3
Polar Surface Area 32.7 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.69  LOG S -3.08 
Solubility (Water) 2.30e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
572 mg/ml (Hydrochloride salt) expand Show data source
Dichloromethane expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
72-74°C expand Show data source
Hydrophobicity(logP)
2.8 expand Show data source
Storage Condition
Refrigerator, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
10-45% expand Show data source
Excretion
Renal expand Show data source
Half Life
4.9 ± 2.4 h (parent compound); 10.3 ± 4.3 h (active metabolite) expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
27% expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
S4 (Australia) expand Show data source
Pregnancy Category
C expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00285 external link
Item Information
Drug Groups approved
Description Venlafaxine (Effexor) is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class first introduced by Wyeth in 1993. It is prescribed for the treatment of clinical depression and anxiety disorders. Due to the pronounced side effects and suspicions that venlafaxine may significantly increase the risk of suicide it is not recommended as a first line treatment of depression. However, it is often effective for depression not responding to SSRIs. Venlafaxine was the sixth most widely-used antidepressant based on the amount of retail prescriptions in the US (17.1 million) in 2006. [Wikipedia]
Indication For the management of major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder (social phobia), panic disorder with or without agoraphobia, and vasomotor symptoms in women with breast cancer and in postmenopausal women.
Pharmacology Venlafaxine, an antidepressant agent structurally and pharmacologically unrelated to other antidepressants and agents used to treat generalized anxiety disorder, is used to treat melancholia, generalized anxiety disorder (GAD), panic disorder, post-traumatic stress disorder, and hot flashes in breast cancer survivors.
Toxicity Most patients overdosing with venlafaxine develop only mild symptoms. However, severe toxicity is reported with the most common symptoms being CNS depression, serotonin toxicity, seizure, or cardiac conduction abnormalities. Venlafaxine's toxicity appears to be higher than other SSRIs, with a fatal toxic dose closer to that of the tricyclic antidepressants than the SSRIs. Doses of 900 mg or more are likely to cause moderate toxicity. Deaths have been reported following large doses.
Affected Organisms
Humans and other mammals
Biotransformation Undergoes extensive first pass metabolism in the liver to its major, active metabolite, ODV, and two minor, less active metabolites, N-desmethylvenlafaxine and N,O-didesmethylvenlafaxine. Formation of ODV is catalyzed by cytochrome P450 (CYP) 2D6, whereas N-demethylation is catalyzed by CYP3A4, 2C19 and 2C9. ODV possesses antidepressant activity that is comparable to that of venlfaxine.
Absorption Bioavailability is 45% following oral administration.
Half Life 5 hours
Protein Binding venlafaxine, 27%; ODV, 30%
Elimination Renal elimination of venlafaxine and its metabolites is the primary route of excretion.
Distribution * 7.5 ± 3.7 L/kg [venlafaxine]
* 5.7 ± 1.8 L/kg [O-desmethylvenlafaxine(active metabolite)]
Clearance * 1.3 +/- 0.6 L/h/kg
References
Golden RN, Nicholas L: Antidepressant efficacy of venlafaxine. Depress Anxiety. 2000;12 Suppl 1:45-9. [Pubmed]
Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. [Pubmed]
Bielski RJ, Ventura D, Chang CC: A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder. J Clin Psychiatry. 2004 Sep;65(9):1190-6. [Pubmed]
Rowbotham MC, Goli V, Kunz NR, Lei D: Venlafaxine extended release in the treatment of painful diabetic neuropathy: a double-blind, placebo-controlled study. Pain. 2004 Aug;110(3):697-706. [Pubmed]
Ozyalcin SN, Talu GK, Kiziltan E, Yucel B, Ertas M, Disci R: The efficacy and safety of venlafaxine in the prophylaxis of migraine. Headache. 2005 Feb;45(2):144-52. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - V119995 external link
A selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Golden RN, Nicholas L: Antidepressant efficacy of venlafaxine. Depress Anxiety. 2000;12 Suppl 1:45-9. Pubmed
  • • Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. Pubmed
  • • Bielski RJ, Ventura D, Chang CC: A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder. J Clin Psychiatry. 2004 Sep;65(9):1190-6. Pubmed
  • • Rowbotham MC, Goli V, Kunz NR, Lei D: Venlafaxine extended release in the treatment of painful diabetic neuropathy: a double-blind, placebo-controlled study. Pain. 2004 Aug;110(3):697-706. Pubmed
  • • Ozyalcin SN, Talu GK, Kiziltan E, Yucel B, Ertas M, Disci R: The efficacy and safety of venlafaxine in the prophylaxis of migraine. Headache. 2005 Feb;45(2):144-52. Pubmed
  • • Klamerus, K. J., et al.: J. Clin. PHarmacol., 32, 716 (1992)
  • • Gelenberg, A.J., et al.: J. Am. Med. Assoc., 283, 3082 (2000)
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PATENTS

PATENTS

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