Input interpretation
![fluoxetine](../image_source/307a70550c89ada543dddae5019e6768.png)
fluoxetine
Chemical names and formulas
![formula | C_17H_18F_3NO name | fluoxetine IUPAC name | N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine alternate names | deprex | fluval | prozac mass fractions | C (carbon) 66% | F (fluorine) 18.4% | H (hydrogen) 5.87% | N (nitrogen) 4.53% | O (oxygen) 5.17%](../image_source/5feed2297a53f6a8d695238845fad327.png)
formula | C_17H_18F_3NO name | fluoxetine IUPAC name | N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine alternate names | deprex | fluval | prozac mass fractions | C (carbon) 66% | F (fluorine) 18.4% | H (hydrogen) 5.87% | N (nitrogen) 4.53% | O (oxygen) 5.17%
Lewis structure
![Draw the Lewis structure of fluoxetine. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), fluorine (n_F, val = 7), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms: 17 n_C, val + 3 n_F, val + 18 n_H, val + n_N, val + n_O, val = 118 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), fluorine (n_F, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8): 17 n_C, full + 3 n_F, full + 18 n_H, full + n_N, full + n_O, full = 212 Subtracting these two numbers shows that 212 - 118 = 94 bonding electrons are needed. Each bond has two electrons, so in addition to the 41 bonds already present in the diagram add 6 bonds. To minimize formal charge carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 6 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom rings are aromatic, so that the single and double bonds may be rearranged: Answer: | |](../image_source/b0a52ac596380a4d91f05575d14af5f6.png)
Draw the Lewis structure of fluoxetine. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), fluorine (n_F, val = 7), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms: 17 n_C, val + 3 n_F, val + 18 n_H, val + n_N, val + n_O, val = 118 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), fluorine (n_F, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8): 17 n_C, full + 3 n_F, full + 18 n_H, full + n_N, full + n_O, full = 212 Subtracting these two numbers shows that 212 - 118 = 94 bonding electrons are needed. Each bond has two electrons, so in addition to the 41 bonds already present in the diagram add 6 bonds. To minimize formal charge carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 6 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom rings are aromatic, so that the single and double bonds may be rearranged: Answer: | |
3D structure
![3D structure](../image_source/e32f46e7b6484252d66dc0ab8c837e0d.png)
3D structure
Basic properties
![molar mass | 309.33 g/mol phase | solid (at STP) melting point | 158 °C solubility in water | insoluble](../image_source/bad132e567fab90bb0359c9a6ffba772.png)
molar mass | 309.33 g/mol phase | solid (at STP) melting point | 158 °C solubility in water | insoluble
Units
Hydrophobicity and permeability properties
![experimental LogP hydrophobicity | 4.6 predicted LogP hydrophobicity | 4.1 predicted LogS | -5.26](../image_source/aa6bff4a22be18d2b9ac0bfc017a2059.png)
experimental LogP hydrophobicity | 4.6 predicted LogP hydrophobicity | 4.1 predicted LogS | -5.26
Drug interactions
![acenocoumarol | almotriptan | amitriptyline | amoxapine | amphetamine | anisindione | astemizole | atomoxetine | benzphetamine | carbamazepine | carvedilol | cilostazol | clarithromycin | clomipramine | clozapine | cyclosporin A | cyproheptadine | desipramine | dexfenfluramine | dextroamphetamine | ... (total: 71)](../image_source/f21fd1856df897dcc34d848a9132f10b.png)
acenocoumarol | almotriptan | amitriptyline | amoxapine | amphetamine | anisindione | astemizole | atomoxetine | benzphetamine | carbamazepine | carvedilol | cilostazol | clarithromycin | clomipramine | clozapine | cyclosporin A | cyproheptadine | desipramine | dexfenfluramine | dextroamphetamine | ... (total: 71)
Basic drug properties
![approval status | approved | small molecule indication | depression | obsessive compulsive disorder | bulimia nervosa drug categories | second-generation antidepressant | second-generation antidepressive agent | selective serotonin reuptake inhibitor (SSRI) | serotonin uptake inhibitor dosage forms | oral: capsule | oral: liquid | oral: solution](../image_source/83ff362051e6198086b14934a878e660.png)
approval status | approved | small molecule indication | depression | obsessive compulsive disorder | bulimia nervosa drug categories | second-generation antidepressant | second-generation antidepressive agent | selective serotonin reuptake inhibitor (SSRI) | serotonin uptake inhibitor dosage forms | oral: capsule | oral: liquid | oral: solution
![brand names | adofen | animex-On | deprex | eufor | fluctin | fluoxeren | fluval | fontex | foxetin | portal | prozac | prozac weekly | pulvules | reneuron | sarafem organisms affected | homo sapiens | mammals](../image_source/a1b207b23146624166d967753b237472.png)
brand names | adofen | animex-On | deprex | eufor | fluctin | fluoxeren | fluval | fontex | foxetin | portal | prozac | prozac weekly | pulvules | reneuron | sarafem organisms affected | homo sapiens | mammals
Pharmacodynamics and pharmacokinetics
![absorption | 72% protein binding | 94.5% biological half-life | 48 hours lethal dosage LD_50 | 284 mg/kg (milligrams per kilogram) biotransformation | hepatic](../image_source/02d97a93923a2649db0888c36bad0cc5.png)
absorption | 72% protein binding | 94.5% biological half-life | 48 hours lethal dosage LD_50 | 284 mg/kg (milligrams per kilogram) biotransformation | hepatic
Chemical identifiers
![CAS number | 54910-89-3 Beilstein number | 3991406 PubChem CID number | 3386 PubChem SID number | 181999 SMILES identifier | CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F InChI identifier | InChI=1/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18, 19)20/h2-10, 16, 21H, 11-12H2, 1H3 InChI key | RTHCYVBBDHJXIQ-UHFFFAOYAV RTECS number | DA8326855 NSC number | 283480](../image_source/85cb012d572a1458a328516c0e3bc9e4.png)
CAS number | 54910-89-3 Beilstein number | 3991406 PubChem CID number | 3386 PubChem SID number | 181999 SMILES identifier | CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F InChI identifier | InChI=1/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18, 19)20/h2-10, 16, 21H, 11-12H2, 1H3 InChI key | RTHCYVBBDHJXIQ-UHFFFAOYAV RTECS number | DA8326855 NSC number | 283480
Toxicity properties
![lethal dosage LD_50 | 284 mg/kg (oral dose for mice)](../image_source/c623f4c830100436b545737afaa8e089.png)
lethal dosage LD_50 | 284 mg/kg (oral dose for mice)
![RTECS classes | drug | reproductive effector | human data](../image_source/d946958d154e17f398ebc11b457248ec.png)
RTECS classes | drug | reproductive effector | human data