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Details

Stereochemistry RACEMIC
Molecular Formula C12H15N
Molecular Weight 173.2546
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BICIFADINE

SMILES

Cc1ccc(cc1)[C@]23C[C@]3([H])CNC2

InChI

InChIKey=OFYVIGTWSQPCLF-NEPJUHHUSA-N
InChI=1S/C12H15N/c1-9-2-4-10(5-3-9)12-6-11(12)7-13-8-12/h2-5,11,13H,6-8H2,1H3/t11-,12+/m1/s1

HIDE SMILES / InChI

Molecular Formula C12H15N
Molecular Weight 173.2546
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Bicifadine (DOV-220075) is not a narcotic and is well-tolerated and, in preclinical studies, has been shown not to act at any opiate receptor, but inhibits monoamine neurotransmitter uptake by recombinant human transporters in vitro with a relative potency of norepinephrine:serotonin:dopamine of 1:2:17. Bicifadine was in Phase II clinical trial for pain caused by diabetic neuropathy, in addition, was in phase III clinical trial to treat Chronic Low Back Pain, but that studies were discontinued

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P23975
Gene ID: 6530.0
Gene Symbol: SLC6A2
Target Organism: Homo sapiens (Human)
5.0 µM [Ki]
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
2.4 µM [Ki]
Target ID: Q01959
Gene ID: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
5.2 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1780 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BICIFADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
34271 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BICIFADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.63 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BICIFADINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2.2%
BICIFADINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
200 mg single, oral (unknown)
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
healthy, ADULT
n = 8
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 8
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
In vitro metabolism of the analgesic bicifadine in the mouse, rat, monkey, and human.
2007 Dec
Patents

Patents

Sample Use Guides

400 mg bid or tid for one year
Route of Administration: Oral
Bicifadine interactions with neurotransmitter transporters, receptors, and ion channels were tested, using the radioligand-receptor binding screen. Bicifadine inhibited [125I]RTI-55 binding to sites on recombinant human 5-HT, NE, and DA transporters with moderate (micromolar) but equivalent affinities (1:2:2, respectively). Subsequent functional tests indicated that bicifadine potently inhibited the uptake of [3H]NE and [3H]5-HT by cell lines expressing recombinant human monoamine transporters (IC50 = 55 and 117 nM, respectively), whereas its potency in blocking [3H]DA uptake was approximately one order of magnitude lower (IC50 = 910 nM) (1:2:17, respectively).
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:36:41 UTC 2021
Edited
by admin
on Fri Jun 25 20:36:41 UTC 2021
Record UNII
B0SV3N7J3H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BICIFADINE
INN  
INN  
Official Name English
(+/-)-1-P-TOLYL-3-AZABICYCLO(3.1.0)HEXANE
Common Name English
3-AZABICYCLO(3.1.0)HEXANE, 1-(4-METHYLPHENYL)-, (+/-)-
Systematic Name English
BICIFADINE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
Code System Code Type Description
INN
4814
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL511099
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
FDA UNII
B0SV3N7J3H
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
MESH
C034438
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
NCI_THESAURUS
C79930
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
EVMPD
SUB05818MIG
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
DRUG BANK
DB04889
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
CAS
71195-57-8
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
WIKIPEDIA
BICIFADINE
Created by admin on Fri Jun 25 20:36:42 UTC 2021 , Edited by admin on Fri Jun 25 20:36:42 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
FECAL; URINE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
Combined with acid metabolite accounted for another 22.4% of the dose
URINE
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
Neither unchanged bicifadine nor M12 were detected in urine or feces
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION