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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (2) Show 4 proteins XML

enzymes (2)transporters (2) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015237

Secondary Accession Numbers

HMDB15237

Metabolite Identification

Common Name

Sibutramine

Description

Sibutramine (trade name Meridia in the USA, Reductil in Europe and other countries), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. It is a centrally acting stimulant chemically related to amphetamines. Sibutramine is classified as a Schedule IV controlled substance in the United States. In October 2010, Sibutramine was withdrawn from Canadian and U.S. markets due to concerns that the drug increases the risk of heart attack and stroke in patients with a history of heart disease.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0243547
     RDKit          3D
(R)-Sibutramine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -2.5263    2.0887    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337    0.7458    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1433    0.7449    2.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793    0.1577    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935   -0.1152   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -0.9688   -1.2669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6129   -2.2082   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451   -0.4657   -2.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873   -0.5821   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8898    0.3880    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567    0.1678    1.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286    1.0284    2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    2.1101    1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    3.2337    2.3893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2503    2.3110    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    1.4606   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -1.9616    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520   -2.3869   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6053   -0.9561   -1.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1273    2.0917   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    2.5546   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    2.8065    0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814    0.0599    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205   -0.0621    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    1.6738    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.4936    2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -0.7322    1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4426    0.9195    1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827    0.8896   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7746   -2.2579    0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571   -3.0693   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -2.3992   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -0.9559   -3.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272   -0.7171   -2.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050    0.6259   -2.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355   -0.6974    2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892    0.8365    3.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    3.1913   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0904    1.6280   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -2.0475    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -2.5445    0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1434   -3.1318   -1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -2.7269   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405   -0.8006   -2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.4207   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19  9  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
M  END

1105
  Mrv0541 02231215152D          

 19 20  0  0  1  0            999 V2000
    4.1251   -2.3645    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    1.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 12 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015237

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3

> <INCHI_KEY>
UNAANXDKBXWMLN-UHFFFAOYSA-N

> <FORMULA>
C17H26ClN

> <MOLECULAR_WEIGHT>
279.848

> <EXACT_MASS>
279.175377544

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.9023403046818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}dimethylamine

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
5.201850084

> <ALOGPS_LOGS>
-5.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.774437990168428

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
83.9214

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sibutramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243547
     RDKit          3D
(R)-Sibutramine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -2.5263    2.0887    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337    0.7458    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1433    0.7449    2.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793    0.1577    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935   -0.1152   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -0.9688   -1.2669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6129   -2.2082   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451   -0.4657   -2.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873   -0.5821   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8898    0.3880    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567    0.1678    1.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286    1.0284    2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    2.1101    1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    3.2337    2.3893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2503    2.3110    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    1.4606   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -1.9616    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520   -2.3869   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6053   -0.9561   -1.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1273    2.0917   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    2.5546   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    2.8065    0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814    0.0599    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205   -0.0621    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    1.6738    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.4936    2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -0.7322    1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4426    0.9195    1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827    0.8896   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7746   -2.2579    0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571   -3.0693   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -2.3992   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -0.9559   -3.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272   -0.7171   -2.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050    0.6259   -2.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355   -0.6974    2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892    0.8365    3.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    3.1913   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0904    1.6280   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -2.0475    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -2.5445    0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1434   -3.1318   -1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -2.7269   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405   -0.8006   -2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.4207   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19  9  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1105                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       7.700  -4.414   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       5.390   3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.700   1.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.240   1.746   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.700   3.286   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   1.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   3.286   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.700   0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.390   0.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850   0.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.034  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.366  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.160   4.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -0.921   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   1.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.034  -2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.366  -2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.700  -2.874   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    6   13   14                                                  
CONECT    3    4    5    6    8                                             
CONECT    4    3    7                                                       
CONECT    5    3    7                                                       
CONECT    6    2    3    9                                                  
CONECT    7    4    5                                                       
CONECT    8    3   11   12                                                  
CONECT    9    6   10                                                       
CONECT   10    9   15   16                                                  
CONECT   11    8   17                                                       
CONECT   12    8   18                                                       
CONECT   13    2                                                            
CONECT   14    2                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
CONECT   17   11   19                                                       
CONECT   18   12   19                                                       
CONECT   19    1   17   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0243547
HETATM    1  C1  UNL     1      -2.526   2.089   0.066  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.434   0.746   0.716  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.143   0.745   2.045  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.079   0.158   0.862  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.394  -0.115  -0.473  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.193  -0.969  -1.267  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.613  -2.208  -0.773  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.745  -0.466  -2.460  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.987  -0.582  -0.334  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.890   0.388   0.371  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.257   0.168   1.685  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.129   1.028   2.330  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.621   2.110   1.630  1.00  0.00           C  
HETATM   14 CL1  UNL     1       4.759   3.234   2.389  1.00  0.00          CL  
HETATM   15  C13 UNL     1       3.250   2.311   0.334  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.376   1.461  -0.334  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.305  -1.962   0.104  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.752  -2.387  -1.273  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.605  -0.956  -1.720  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.127   2.092  -0.897  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.569   2.555  -0.194  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.129   2.807   0.701  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.081   0.060   0.017  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.921  -0.062   2.097  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.675   1.674   2.294  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.457   0.494   2.889  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.041  -0.732   1.504  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.443   0.919   1.355  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.383   0.890  -0.979  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.775  -2.258   0.324  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.057  -3.069  -1.137  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.674  -2.399  -1.180  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.252  -0.956  -3.352  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.827  -0.717  -2.568  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.605   0.626  -2.604  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.835  -0.697   2.196  1.00  0.00           H  
HETATM   37  H18 UNL     1       3.389   0.836   3.343  1.00  0.00           H  
HETATM   38  H19 UNL     1       3.666   3.191  -0.207  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.090   1.628  -1.349  1.00  0.00           H  
HETATM   40  H21 UNL     1       2.225  -2.048   0.777  1.00  0.00           H  
HETATM   41  H22 UNL     1       0.524  -2.544   0.577  1.00  0.00           H  
HETATM   42  H23 UNL     1       1.143  -3.132  -1.780  1.00  0.00           H  
HETATM   43  H24 UNL     1       2.819  -2.727  -1.349  1.00  0.00           H  
HETATM   44  H25 UNL     1       0.940  -0.801  -2.547  1.00  0.00           H  
HETATM   45  H26 UNL     1       2.578  -0.421  -1.827  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   23
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6    9   29
CONECT    6    7    8
CONECT    7   30   31   32
CONECT    8   33   34   35
CONECT    9   10   17   19
CONECT   10   11   11   16
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14   15
CONECT   15   16   16   38
CONECT   16   39
CONECT   17   18   40   41
CONECT   18   19   42   43
CONECT   19   44   45
END

HMDB0243547
     RDKit          3D
(R)-Sibutramine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -2.5263    2.0887    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4337    0.7458    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1433    0.7449    2.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793    0.1577    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935   -0.1152   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -0.9688   -1.2669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6129   -2.2082   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451   -0.4657   -2.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873   -0.5821   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8898    0.3880    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567    0.1678    1.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286    1.0284    2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    2.1101    1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    3.2337    2.3893 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2503    2.3110    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    1.4606   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -1.9616    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520   -2.3869   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6053   -0.9561   -1.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1273    2.0917   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694    2.5546   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1291    2.8065    0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814    0.0599    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205   -0.0621    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    1.6738    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.4936    2.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -0.7322    1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4426    0.9195    1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827    0.8896   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7746   -2.2579    0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571   -3.0693   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -2.3992   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -0.9559   -3.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272   -0.7171   -2.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050    0.6259   -2.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355   -0.6974    2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892    0.8365    3.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    3.1913   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0904    1.6280   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -2.0475    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -2.5445    0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1434   -3.1318   -1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -2.7269   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405   -0.8006   -2.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.4207   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19  9  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Butramin	Kegg
Meridia	HMDB
Didesmethylsibutramine	HMDB
Sibutramine hydrochloride	HMDB
Di-desmethylsibutramine	HMDB
mono-Desmethylsibutramine	HMDB
(R)-DDMS	HMDB
N-1-(1-(4-Chlorophenyl)cyclobutyl)-3-methylbutyl-N,N-dimethylamine HCL	HMDB
Reductil	HMDB

Chemical Formula

C₁₇H₂₆ClN

Average Molecular Weight

279.848

Monoisotopic Molecular Weight

279.175377544

IUPAC Name

{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}dimethylamine

Traditional Name

sibutramine

CAS Registry Number

106650-56-0

SMILES

CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3

InChI Key

UNAANXDKBXWMLN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Aralkylamine
Chlorobenzene
Aryl halide
Aryl chloride
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:9137 )
organochlorine compound (CHEBI:9137 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015237)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 - 192 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00094 g/L	Not Available
LogP	5.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	168.0	30932474
[M+H]+	Not Available	167.967	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000851

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00094 g/L	ALOGPS
logP	5.05	ALOGPS
logP	5.2	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.92 m³·mol⁻¹	ChemAxon
Polarizability	32.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	178.552	30932474
DeepCCS	[M-H]-	176.194	30932474
DeepCCS	[M-2H]-	209.08	30932474
DeepCCS	[M+Na]+	184.645	30932474
AllCCS	[M+H]+	167.4	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.4	32859911
AllCCS	[M-H]-	174.6	32859911
AllCCS	[M+Na-2H]-	175.0	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sibutramine	CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1	2311.7	Standard polar	33892256
Sibutramine	CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1	1862.6	Standard non polar	33892256
Sibutramine	CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1	1890.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sibutramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-07bf-9640000000-63dab33ab67c598b8779	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sibutramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sibutramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sibutramine , positive-QTOF	splash10-003r-1930000000-b90a7add9041c09efb5e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sibutramine , positive-QTOF	splash10-005i-1930000000-524395362f2824760185	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sibutramine 35V, Positive-QTOF	splash10-004r-1900000000-f5b2dc8eb6cd3b695581	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 10V, Positive-QTOF	splash10-001i-0090000000-5389ad6755b0b9d3f3b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 20V, Positive-QTOF	splash10-05gr-2290000000-2c27a844d317defb5527	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 40V, Positive-QTOF	splash10-0a4i-9540000000-8a05a19349a6eb1a0852	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 10V, Negative-QTOF	splash10-004i-0090000000-4ddcf8011b3e19977025	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 20V, Negative-QTOF	splash10-004i-0190000000-3b0d542f8a73ec923a94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 40V, Negative-QTOF	splash10-03k9-4980000000-3be05aa6c152cc4a87a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 10V, Negative-QTOF	splash10-004i-0190000000-f6b1e08de10b5f29753d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 20V, Negative-QTOF	splash10-004i-0190000000-d2de1be3a5b498179198	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 40V, Negative-QTOF	splash10-01q9-9700000000-4feca2b9a2fe44fb0adc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 10V, Positive-QTOF	splash10-001i-0590000000-e841763a4ecec6c31d60	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 20V, Positive-QTOF	splash10-014i-2940000000-780b7e85e0bd0df044da	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sibutramine 40V, Positive-QTOF	splash10-014i-3900000000-80359ff0e43a20860a42	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01105	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01105	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01105

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5021

KEGG Compound ID

C07247

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sibutramine

METLIN ID

Not Available

PubChem Compound

5210

PDB ID

Not Available

ChEBI ID

458192

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [PubMed:18671470 ]
Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [PubMed:19475780 ]
Stock MJ: Sibutramine: a review of the pharmacology of a novel anti-obesity agent. Int J Obes Relat Metab Disord. 1997 Mar;21 Suppl 1:S25-9. [PubMed:9130038 ]
Heal DJ, Aspley S, Prow MR, Jackson HC, Martin KF, Cheetham SC: Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine. Int J Obes Relat Metab Disord. 1998 Aug;22 Suppl 1:S18-28; discussion S29. [PubMed:9758240 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [PubMed:18671470 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [PubMed:19475780 ]
Gomis Barbara R: [Pharmacological treatment of obesity]. Rev Med Univ Navarra. 2004 Apr-Jun;48(2):63-5. [PubMed:15382615 ]
Berke EM, Morden NE: Medical management of obesity. Am Fam Physician. 2000 Jul 15;62(2):419-26. [PubMed:10929704 ]
Nakagawa T, Ukai K, Ohyama T, Gomita Y, Okamura H: Effects of sibutramine on the central dopaminergic system in rodents. Neurotox Res. 2001 Jul;3(3):235-47. [PubMed:15111248 ]
Krahn LE, Moore WR, Altchuler SI: Narcolepsy and obesity: remission of severe cataplexy with sibutramine. Sleep Med. 2001 Jan;2(1):63-65. [PubMed:11152984 ]
Balcioglu A, Wurtman RJ: Sibutramine, a serotonin uptake inhibitor, increases dopamine concentrations in rat striatal and hypothalamic extracellular fluid. Neuropharmacology. 2000 Sep;39(12):2352-9. [PubMed:10974319 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Heusser K, Engeli S, Tank J, Diedrich A, Wiesner S, Janke J, Luft FC, Jordan J: Sympathetic vasomotor tone determines blood pressure response to long-term sibutramine treatment. J Clin Endocrinol Metab. 2007 Apr;92(4):1560-3. Epub 2007 Feb 6. [PubMed:17284621 ]
Jordan J, Scholze J, Matiba B, Wirth A, Hauner H, Sharma AM: Influence of Sibutramine on blood pressure: evidence from placebo-controlled trials. Int J Obes (Lond). 2005 May;29(5):509-16. [PubMed:15685250 ]
Heusser K, Tank J, Diedrich A, Engeli S, Klaua S, Kruger N, Strauss A, Stoffels G, Luft FC, Jordan J: Influence of sibutramine treatment on sympathetic vasomotor tone in obese subjects. Clin Pharmacol Ther. 2006 May;79(5):500-8. [PubMed:16678551 ]
Birkenfeld AL, Schroeder C, Boschmann M, Tank J, Franke G, Luft FC, Biaggioni I, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation. Circulation. 2002 Nov 5;106(19):2459-65. [PubMed:12417543 ]
Birkenfeld AL, Schroeder C, Pischon T, Tank J, Luft FC, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation in obese hypertensive patients--sibutramine and blood pressure. Clin Auton Res. 2005 Jun;15(3):200-6. [PubMed:15944869 ]
Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [PubMed:19475780 ]
Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [PubMed:18671470 ]
Gomis Barbara R: [Pharmacological treatment of obesity]. Rev Med Univ Navarra. 2004 Apr-Jun;48(2):63-5. [PubMed:15382615 ]
Berke EM, Morden NE: Medical management of obesity. Am Fam Physician. 2000 Jul 15;62(2):419-26. [PubMed:10929704 ]
Krahn LE, Moore WR, Altchuler SI: Narcolepsy and obesity: remission of severe cataplexy with sibutramine. Sleep Med. 2001 Jan;2(1):63-65. [PubMed:11152984 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Vazquez Roque MI, Camilleri M, Clark MM, Tepoel DA, Jensen MD, Graszer KM, Kalsy SA, Burton DD, Baxter KL, Zinsmeister AR: Alteration of gastric functions and candidate genes associated with weight reduction in response to sibutramine. Clin Gastroenterol Hepatol. 2007 Jul;5(7):829-37. Epub 2007 Jun 4. [PubMed:17544870 ]
Heusser K, Engeli S, Tank J, Diedrich A, Wiesner S, Janke J, Luft FC, Jordan J: Sympathetic vasomotor tone determines blood pressure response to long-term sibutramine treatment. J Clin Endocrinol Metab. 2007 Apr;92(4):1560-3. Epub 2007 Feb 6. [PubMed:17284621 ]
Jordan J, Scholze J, Matiba B, Wirth A, Hauner H, Sharma AM: Influence of Sibutramine on blood pressure: evidence from placebo-controlled trials. Int J Obes (Lond). 2005 May;29(5):509-16. [PubMed:15685250 ]
Heusser K, Tank J, Diedrich A, Engeli S, Klaua S, Kruger N, Strauss A, Stoffels G, Luft FC, Jordan J: Influence of sibutramine treatment on sympathetic vasomotor tone in obese subjects. Clin Pharmacol Ther. 2006 May;79(5):500-8. [PubMed:16678551 ]
Birkenfeld AL, Schroeder C, Boschmann M, Tank J, Franke G, Luft FC, Biaggioni I, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation. Circulation. 2002 Nov 5;106(19):2459-65. [PubMed:12417543 ]
Birkenfeld AL, Schroeder C, Pischon T, Tank J, Luft FC, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation in obese hypertensive patients--sibutramine and blood pressure. Clin Auton Res. 2005 Jun;15(3):200-6. [PubMed:15944869 ]
Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [PubMed:19475780 ]
Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [PubMed:18671470 ]
Gomis Barbara R: [Pharmacological treatment of obesity]. Rev Med Univ Navarra. 2004 Apr-Jun;48(2):63-5. [PubMed:15382615 ]
Berke EM, Morden NE: Medical management of obesity. Am Fam Physician. 2000 Jul 15;62(2):419-26. [PubMed:10929704 ]
Krahn LE, Moore WR, Altchuler SI: Narcolepsy and obesity: remission of severe cataplexy with sibutramine. Sleep Med. 2001 Jan;2(1):63-65. [PubMed:11152984 ]

Showing metabocard for Sibutramine (HMDB0015237)

MOL for HMDB0015237 (Sibutramine)

3D MOL for HMDB0015237 (Sibutramine)

3D SDF for HMDB0015237 (Sibutramine)

3D-SDF for HMDB0015237 (Sibutramine)

PDB for HMDB0015237 (Sibutramine)

3D PDB for HMDB0015237 (Sibutramine)

SMILES for HMDB0015237 (Sibutramine)

INCHI for HMDB0015237 (Sibutramine)

Structure for HMDB0015237 (Sibutramine)

3D Structure for HMDB0015237 (Sibutramine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References

References